Home 5+ Bedroom Vacation Rentals In Siesta Key, FL

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Exceptional(6)

$918.17

/ Nightly
Private Vacation Home

Shore Thing | Luxe Pool Oasis, Hot Tub, Siesta Key Beach

Siesta Key, Florida, United States

Imagine waking up in your own private coastal retreat. At Shore Thing, island serenity meets modern luxury—your dream Siesta Key escape begins here.brbrWelcome to Shore Thing—your private slice of paradise in the heart of Siesta Key. This newly renovated home was thoughtfully curated for your comfort where upscale comfort meets laid-back beach living, Your just a 5-minute drive to the world-famous Siesta Key Beach.brbrAs you step into the backyard, prepare to be transported. A sprawling resort-style pool shimmers under the Florida sun, bordered by lush tropical landscaping and swaying palms. Whether you're floating in the crystal-clear water, enjoying the soothing spillover hot tub, or sipping cocktails by the fire pit, this outdoor oasis was designed for unforgettable moments.brbrEvenings are best spent under the stars, sharing laughter around the propane fire feature or enjoying a sunset dinner on the covered patio. The backyard seamlessly connects to the interior, offering a true indoor-outdoor living experience.brbrInside, Shore Thing offers the ideal layout for families or groups traveling together:br• Three private master suites, each with spa-inspired en-suite bathrooms and direct access to the outdoor area.br• A fourth bedroom with a private lounge area behind sliding glass doors—perfect for quiet reading or morning yoga.br• A fifth bedroom with a twin-over-full bunk setup—ideal for kids or teens.brbrAt the heart of the home is a chef-ready kitchen with modern appliances and everything you need to cook, dine, and entertain. Start your day with coffee from either the classic drip machine or Keurig, then enjoy a breezy breakfast outdoors as the palms rustle overhead.brbrEach bedroom—aside from the bunk room—is equipped with a large Smart TV, making it easy to unwind after beach days or poolside lounging.brbrExplore the charm of Siesta Key Village, just minutes away, where you'll find boutique shops, waterfront dining, and lively coastal nightlife. Whether you seek adventure, relaxation, or quality time with loved ones, Shore Thing delivers the full island experience.brDon't miss your chance to stay at one of Siesta Key's most captivating private homes. Book your stay at Shore Thing today and create lasting memories in your own tropical paradise—steps from the beach and a world away from ordinary.brShore Thing Siesta Key | 5BR home w/ pool, hot tub & fire pit. Book your luxury island escape today!brbrShore Thing can accommodate up to 10 guest with a bedding configuration as follows:brBedroom #1: Queen Bed (1) sleeps 2brBedroom #2: King Bed (1) sleeps 2brBedroom #3: King Bed (1) sleeps 2brBedroom #4: Queen Bed (1) sleeps 2brBedroom #5: Twin bed (1) and a Full Bed (1) sleeps 3brbrWe go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol within our CottageClean Program. After our six hour in-depth cleaning of your home, we complete a 35 point property inspection to ensure that you feel tremendously safe and happy with this amazing home. This allows you to vacation worry free regarding the cleanliness of your home and truly relax as soon as you arrive. Our goal is to have you feel like you are walking into a brand new vacation home that no one has ever stayed at before!brbrPLEASE NOTE: The Spa is heated from November 15th to April 15th. This property is registered as a vacation rental within the City of Sarasota with the Registration Number VR25-00056. Due to the City of Sarasota vacation rental code, this property can only be rented once during a seven (7) day period and has a maximum occupancy of 10 guests.
Bed 5

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Bath 4

Bath

Sleep 10

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$5026.18

/ Nightly
Private Vacation Home

Beach Rd, 300ft to Beach Access & 500ft to Village, Large Condo Complex

Siesta Key, Florida, United States

Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village walkability, we are confident that this space will cultivate unforgettable memories.brbrOne of the closest rentals to the beach in Siesta Key Dream’s portfolio features 9 units, totaling 12-bedrooms, 12-baths, 19-beds and can accommodate up to 35 guests. This rental is perfect for family and friend gatherings and is truly unique in location and ability to host a high quantity of traveling friends and/or family. On the first floor of the three buildings, you’ll have three 1-bed and 1-bath condos connecting to a living room and full kitchen with an island. On the second floors, you’ll have three 2-bed and 2-bath condos with spacious floor plans that connect welcoming living rooms with dining rooms that have walk-out balconies! The dining room contains a large sliding doors that lead out to private balconies, all facing Beach Road and the ocean. The balconies are perfect for your morning coffee. On the third floors, you’ll find studio-suites fitted with a bathroom, living space, and kitchen. Two of the balconies on the third floor feature partial ocean views. Siesta Key Dreams is happy to provide free, high-speed internet & Wi-Fi, HD Televisions equipped with live sports & extension channel options via free streaming services, and electric appliances so you will not miss a beat.brbrOn the ground floor you will have private outdoor spaces which include patios, lounge chairs, and grills. A perfect area for relaxation in the shade and a festive BBQ. The ground area is fenced and covered with greenery, providing full coverage and privacy from neighbors. This outdoor space is perfect for relaxing or gatherings with friends and family!brbrSiesta Key Dreams always shows our exact address in our listings, so our guests know exactly how close they truly are to the beach and village. Unplug and explore your surroundings, such as the Siesta Village which is less than a 5-minute walk away down Beach road! From cafes to fine dining, local shopping and entertainment, you will certainly find what you need. brbrIf you’re looking to soak up the sun and clear waters, the beach access point is a mere 100 steps away from this property. Easily slip on your sandals and take a 2-minute stroll to experience the brilliant 99% white quartz sand. brbr-brIn addition to the stunning, white quartz sand, the beaches of Siesta Keys offer picnic areas, concession stands, and volleyball courts. The shallow, crystal water and year-round lifeguard protection makes each beach a safe and relaxing escape. Having your property mere minutes away from the ocean means that you will certainly witness breathtaking sunsets. A 3-minute walk from the beach reveals Siesta Village, which offers a wide-range of dining and entertainment options from gourmet donuts, coffee, and seafood to award-winning steakhouses. brbrWe recognize that parking can be difficult at times to locate, which is why our rentals come with private, reserved spaces at no additional cost to you. Alternatively, we offer an exclusive upgrade which includes a golf cart rental for easy travel and access to all the top tourist spots around town. The Siesta Key Breeze Trolley also operates on the main roads outside your rental, which is free for all riders and operates 8 AM - 10 PM, seven days a week!brbrSiesta Key Dreams wishes to provide you with Unreasonable Hospitality” – service at the highest caliber, well above your expectations. As soon as you secure your vacation rental, our team will provide you with clear expectations to help prepare for your stay. If you experience any issues upon arrival, a Guest Experience Manager who lives within the Siesta Keys area will be available at a moment’s notice to assist you. Siesta Key Dreams takes pride in providing professional and personalized services to ensure that your stay is unforgettable.brbrIncluded within your reservation and rental cost are complimentary bathroom toiletries (shampoo, conditioner, soap), coffee & a Keurig-pods, and your choice of either a bottle of wine, champagne, or sparkling grape juice. To prep for the numerous beach trips, we provide you with towels, beach chairs, umbrellas, and carts to transport your items easily! Traveling with your children We offer complementary cribs and highchairs available per request! brbrShortly after you secure your vacation rental, you will receive a link where you can book local services experiences provided by vendors throughout the island. Siesta Key Dreams provides golf-carts to rent and mid-stay services such as cleanings, and linen changes.brbrWhen available, guests can request flexible booking with early check-in or late check out options. Siesta Key Dreams also offers baggage drop-off prior to your check-in time. You will be able to indicate your preferences in the link you will receive prior to check-in. brbrGuests will receive a Rental Agreement via email that provides common details about our terms and conditions, such as our no-smoking policy. An electronic signature prior to the stay allows for us to provide contactless check-in and check-out!brCheck Out: 10AMbrCheck In: 3pmbrQuiet Hours: 10pm - 7AM brNo smokingbrLarge Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key Dreams (entire building rentals are available)brPets: Pet Friendly & Non-Pet Units are designated during the reservation process. Pets are not allowed unless explicitly listed on the unit listing. Pet Friendly units require deposit or waiver and additional cleaning/pet charge.brAdditional Details: See Vacation Rental Agreement for all details
Bed 12

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Bath 12

Bath

Sleep 35

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Exceptional(11)

$1893.33

/ Nightly
Private Vacation Home

7 Bedroom Luxury Home with Private Pool on Siesta Key!

Siesta Key, Florida, United States

Welcome to Las Palmas! This gorgeous new home on Siesta Key offers luxury around every turn. Stay with up to 16 guests in this 7-bedroom, 7.5-bathroom home, complete with a private pool and spa area, fenced in yard, large full kitchen, dining room, two living spaces with a game room, and much more! Spend time outside by the pool, featuring a kid’s slide, rain curtain, pool fountains, and hot tub, all conveniently position by the patio lounge area with a BBQ grill, Mini Fridge and plenty of space for everyone to relax. Located around the corner form Siesta Key Village, this home sits across the street from beach access numbers 8 and 9. Guests can gaze out at the ocean and enjoy beautiful sunset skies from the rooftop patio or take the short walk into the Village for the many wonder shops and restaurants Siesta Key has to offer. Capture your piece of paradise with this fabulous new home. brbrThe Space:brBedroom 1 – King, w/ TVbrBedroom 2 – King, w/ TVbrBedroom 3 – King, w/ TVbrBedroom 4 – King, w/ TVbrBedroom 5 – King, w/ TVbrBedroom 6 – King, w/ TVbrBedroom 7 – Double Twin Bunk Beds,br2 Livings Rooms, Private Kitchen, Dining Room, Game Room, 4 Balconies, Private Pool, Hot Tub, Large Outdoor Patio with BBQ Grill and Dining SpacebrbrThe Location: br- Less than 400 Feet to entrance of Public Beach Access #8 and 9br- 0.4 Miles to Siesta Key Villagebr- 2.3 Miles to Crescent Villagebr- 0.4 Miles to Pool Access br- Less than 300 Feet to local free trolley stop.brSiesta Key has 13 beach access points and a free trolley system making all of Siesta Key easily accessible no matter where you are on the island!brbrImportant things to note:br- Check-in is located at our office. Address will be shared with check-in instructions.br- This home is Pet Friendly. An additional charge of $39 Per Pet, Per Night will be applied. Please speak with a member of our team to confirm breed and weight restrictions.br- Events are possible upon request. Please speak with management for details.brbrAdded Amenities Included in Your Stay:br- Free Wifibr- Beach Chairs, Beach Towels, Beach Wagon, and Beach Cooler,br- Partner Property Pool/Hot tub Access,br- Complimentary Bicycles Rentals located at Partner Property,br- 7-days a week, Beachside Management office is open for your convenience and guest needs with after-hours support!
Bed 7

Bed

Bath 7

Bath

Sleep 16

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Exceptional(1)

$2157.13

/ Nightly
Private Vacation Home

Siesta Key Village, Heated Pool, Beach Access 4 min Walk, 8bdr

Siesta Key, Florida, United States

Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village walkability, we are confident that this space will cultivate unforgettable memories.brbrThis listing by Siesta Key Dream, is our closest to the Siesta Key Village and it combines all four units within this unique fourplex. This Mediterranean style building includes two one-bedroom condos and two 3-bedroom townhouses. By combining all four units, guests will have 8 spacious bedrooms which can accommodate up to 28 guests.brbrThe ground level is where the two one-bedroom condos are located, each having a bedroom with an king bed, a living room with a queen sofa bed, dining area, and a kitchen.brbrOn the second floor, you’ll find the two three-bedroom townhouses which provide and additional six bedrooms, four full-bathrooms, and two half-bathrooms. The two main-bedrooms contain sliding-door balconies that overlook Siesta Key Village. This location provides free WiFi internet, multiple HDTVs equipped with live sports & extension channel options via DirecTV Stream, and electric appliances (fridges, ovens, dishwashers, Keurig-pods, washers/dryers) so you will not miss a beat.brbrWith this vacation rental, you gain access to a fully PRIVATE, heated pool and an outdoor space that is perfect to bask in the Florida sun and enjoy a quiet pool day or festive BBQ! The 18 x 26 ft pool is surrounded by an array of palm trees and tropical plants, providing full coverage and privacy from neighbors. On the pool deck, you’ll find multiple lounge chairs, large umbrellas for shade, dining tables, and two grills. This outdoor space is perfect for relaxing or gatherings with friends and family!brbrSiesta Key Dreams always shows our exact address in our listings, so our guests know exactly how close they truly are to the beach and village. Unplug and explore your surroundings, such as the Siesta Village which is a mere ten steps across the street from you – it is so close, you can often hear live music playing! From cafes to fine dining, local shopping and entertainment, you will certainly find what you need. If you’re looking to soak up the sun and clear waters, the beach access point is less than a 5-minute walk from this property. Easily slip on your sandals and take a brief stroll to experience the brilliant 99% white quartz sand.brbrIn addition to the stunning, white quartz sand, the beaches of Siesta Keys offer picnic areas, concession stands, and volleyball courts. The shallow, crystal water and year-round lifeguard protection makes each beach a safe and relaxing escape. Having your property mere minutes away from the ocean means that you will certainly witness breathtaking sunsets. Across the street from your condo, the Siesta Key Village, offers a wide-range of dining and entertainment options from gourmet donuts, coffee, and seafood to award-winning steakhouses. brbrParking on Siesta Key is a challenge, which is why our rentals come with SIX reserved spaces at no additional cost to you. Additionally, we offer golf cart rental; a fun way for easy travel and access to all the top tourist spots around town. The Siesta Key Breeze Trolley also operates on the main roads outside your rental, it is free for all riders and operates 8AM - 10PM, seven days a week!brbrSiesta Key Dreams wishes to provide you with `Unreasonable Hospitality” – service at the highest caliber, well above your expectations. As soon as you secure your vacation rental, our team will provide you with clear expectations to help prepare for your stay. If you experience any issues upon arrival, a Guest Experience Manager who lives within the Siesta Keys area will be available at a moment’s notice to assist you. Siesta Key Dreams takes pride in providing professional and personalized services to ensure that your stay is unforgettable.brbrYour reservation includes: bathroom toiletries (shampoo, body wash, conditioner, soap), coffee & a Keurig-pods, and your choice of either a bottle of sparkling wine, or sparkling grape juice. To prep for the numerous beach trips, we provide you with towels, beach chairs, umbrellas, beach blankets, coolers!brbrTraveling with your children We offer complementary cribs, highchairs, toys, silverware, and baby-monitors! brbrShortly after you secure your vacation rental, you will receive a link where you can book local services and experiences provided by vendors throughout the island. Siesta Key Dreams provides golf-carts for rent and mid-stay services such as cleanings, and linen changes for an additional charge.brbrWhen available, guests can request flexible booking with early check-in or late check out options. Siesta Key Dreams also offers baggage drop-off prior to your check-in time. You will be able to indicate your preferences in the link you will receive prior to check-in. brbrGuests will receive a Rental Agreement via email that provides common details about our terms and conditions, such as our no-smoking policy. Before you check-in, and just after booking, we require guest verification. You will receive information after booking and the process only takes a couple minutes. All of this allows us to provide a safe location for our guests, neighbors, and employees.brCheck Out: 10AMbrCheck In: 3PMbrQuiet Hours: 11PM - 7AM brNo smokingbrParking: 6 spaces (6 vehicle max)brLarge Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key Dreams (entire building rentals are available)brPets: Allowed for additional fee per petbrAdditional Details: See Vacation Rental Agreement for all details
Bed 8

Bed

Bath 7

Bath

Sleep 28

Sleeps

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$1778.57

/ Nightly
Private Vacation Home

Exclusive complex - Private Heated Pool - 100 Steps to Beach - Village 5 minute walk

Siesta Key, Florida, United States

Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village walkability, we are confident that this space will cultivate unforgettable memories.brbrOffering some of the best backyard experiences of Siesta Key Dream’s portfolio, this location contains 3 units, totaling 5 bedrooms and 4.5 bathrooms. This rental is perfect for family and friend gatherings and can accommodate up to 18 guests. Two units feature 1 bedroom spaces complete with a living room, kitchen and associated appliances, king sized beds, queen size pull-out sofa-beds and separate bathroom. The last unit contains 3 bedrooms and 2.5 bathrooms, holding a large, spacious floor plan that connects a living room, a dining room that seats 8, and a modernized kitchen featuring stainless steel appliances. Next to this living room, you’ll find a private, enclosed lanai with comfortable seating that is perfect for shaded, outdoor entertainment. In the third bedroom you’ll find a bunk+trundle bed and a twin bed, totaling 4 mattresses, perfect for families with children! To accommodate larger groups, the sofa turns into a queen bed and there is an additional queen air mattress on site. Siesta Key Dreams is happy to provide free, high-speed internet & Wi-Fi, HD Televisions equipped with live sports & extension channel options via free streaming services, and electric appliances so you will not miss a beat.brbrBeyond the enclosed deck, you’ll see a PRIVATE heated pool and outdoor space that is perfect to bask in the Florida sun and enjoy a quiet pool day or festive BBQ! Next to the pool, you’ll see a rare cabana fitted with fans and comfortable seating to relax in between swims. On the pool deck, there are numerous lounge chairs, large umbrellas for shade, dining table, and a grill. This outdoor space is perfect for relaxing or gatherings with friends and family!brbrSiesta Key Dreams always shows our exact address in our listings, so our guests know exactly how close they truly are to the beach and village. Unplug and explore your surroundings, such as the Siesta Village which is less than a 5-minute walk away! From cafes to fine dining, local shopping and entertainment, you will certainly find what you need. brbrIf you’re looking to soak up the sun and clear waters, the beach access point is a mere 100 steps away from this property. Easily slip on your sandals and take a 2-minute stroll to experience the brilliant 99% white quartz sand. brbrIn addition to the stunning, white quartz sand, the beaches of Siesta Keys offer picnic areas, concession stands, and volleyball courts. The shallow, crystal water and year-round lifeguard protection makes each beach a safe and relaxing escape. Having your property mere minutes away from the ocean means that you will certainly witness breathtaking sunsets. A 3-minute walk from the beach reveals Siesta Village, which offers a wide-range of dining and entertainment options from gourmet donuts, coffee, and seafood to award-winning steakhouses. brbrWe recognize that parking can be difficult at times to locate, which is why this rental comes with SIX private, reserved spaces at no additional cost to you. Alternatively, we offer an exclusive upgrade which includes a golf cart rental for easy travel and access to all the top tourist spots around town. The Siesta Key Breeze Trolley also operates on the main roads outside your rental, which is free for all riders and operates 8 AM - 10 PM, seven days a week!brbrSiesta Key Dreams wishes to provide you with `Unreasonable Hospitality” – service at the highest caliber, well above your expectations. As soon as you secure your vacation rental, our team will provide you with clear expectations to help prepare for your stay. If you experience any issues upon arrival, a Guest Experience Manager who lives within the Siesta Keys area will be available at a moment’s notice to assist you. Siesta Key Dreams takes pride in providing professional and personalized services to ensure that your stay is unforgettable.brbrIncluded within your reservation and rental cost are complimentary bathroom toiletries (shampoo, conditioner, soap), coffee & a Keurig-pods, and your choice of either a bottle of sparkling wine or sparkling grape juice. To prep for the numerous beach trips, we provide you with towels, beach chairs, umbrellas, blankets, coolers and carts to transport your items easily! Traveling with your children We offer complementary cribs, highchairs, toys, silverware, and baby-monitors available per request! brbrShortly after you secure your vacation rental, you will receive a link where you can book local services experiences provided by vendors throughout the island. Siesta Key Dreams provides golf-carts to rent and mid-stay services such as cleanings, and linen changes.brbrWhen available, guests can request flexible booking with early check-in or late check out options. Siesta Key Dreams also offers baggage drop-off prior to your check-in time. You will be able to indicate your preferences in the link you will receive prior to check-in. brbrGuests will receive a Rental Agreement via email that provides common details about our terms and conditions, such as our no-smoking policy. Before you check-in, and just after booking, we require guest verification. You will receive information after booking and the process only takes a couple minutes. This allows us to provide a safe location for our guests, neighbors, and employees.brCheck Out: 10AMbrCheck In: 3pmbrQuiet Hours: 10pm - 7AM brNo smokingbrLarge Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key Dreams (entire building rentals are available)brPets: Pet Friendly & Non-Pet Units are designated during the reservation process. Pets are not allowed unless explicitly listed on the unit listing. Pet Friendly units require deposit or waiver and additional cleaning/pet charge.brAdditional Details: See Vacation Rental Agreement for all details
Bed 5

Bed

Bath 4

Bath

Sleep 18

Sleeps

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Exceptional(3)

$1594.41

/ Nightly
Condo

Lulu's Key House: Private Heated Pool, Steps to Siesta Key Beach & Perfectly Located in the Village!

Siesta Key, Florida, United States

Welcome to Lulu’s Key House—your ideal group getaway on Siesta Key! brbr brbrPerfect for large families or groups, this rare 4-unit Siesta Key property offers the ideal setup—stay close together while enjoying the privacy of separate updated units. Just a 2-minute walk to Siesta Key Beach and steps from the Village, this 6-bedroom, 6-bath coastal compound sleeps up to 20 guests comfortably. Book the entire property for the ultimate group getaway with shared outdoor spaces and private retreats for downtime! brbr brbrLOCATION HIGHLIGHTS: brbr- Located directly in Siesta Key Village – Walk to shops, dining, and nightlife brbr- 2-minute walk to Siesta Key Beach – Powdery white sand and turquoise water brbr- Island shuttle transportation available – No need for a car once you arrive brbr- Steps to entertainment but tucked just enough for privacy brbr brbrPROPERTY FEATURES: brbr- 4 private units combined into one group stay experience brbr- 6 bedrooms, 6 full bathrooms – 4 master suites for comfort brbr- Sleeps up to 20 guests brbr- Private entrances for each unit – Perfect for families and friends traveling together brbr- Coastal décor and upgraded finishes throughout brbr- 4 fully stocked kitchens and 2 balcony spaces for lounging brbr- 10 HDTVs and free WiFi included brbr- 2 washers and 2 dryers on-site brbr brbrOUTDOOR SPACES: brbr- Private heated courtyard pool – Open year-round brbr- Outdoor lounge seating and café umbrellas brbr- Gas grill with dining area for casual island meals brbr brbrKITCHEN & DINING: brbr- 4 modern kitchens with full appliances brbr- Regular and Keurig coffee makers provided brbr- Dishwashers, cookware, utensils, and dining essentials included brbr- Indoor and outdoor dining options for group gatherings brbr brbrBEDROOMS AND BATHROOMS: brbr- 4 master bedrooms with en-suite bathrooms brbr- 2 King bedrooms and 4 Queen bedrooms brbr- 4 Queen sleeper sofas with linens provided brbr brbrEXTRA PERKS: brbr- Beach towels, chairs, umbrellas and caddy ready to go brbr- Starter pack of toiletries available brbr brbrLOCAL FAVORITES: brbr- Siesta Key Beach for sunsets, shelling, and swimming brbr- Siesta Village nightlife, live music, seafood spots, and coffee shops brbr- Easy access to kayak rentals, parasailing, and island tours brbr- Bike and scooter rentals just around the corner brbr brbrIMPORTANT INFO: brbr- No smoking and no pets permitted brbr- Pool depth is 5 ft at deep end brbr- 6 parking spots included with stay brbr brbrEXPERIENCE COMFORT, CONVENIENCE, AND A GETAWAY LIKE NO OTHER! BOOK YOUR STAY TODAY!brbrWe help make the most of your vacation by providing Xplorie's Free Admission to some of the area’s top attractions each and every day including a choice of a free bike rental, kayak rental, a dolphin cruise tour, or admission to the Ringling Museum ! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA with advance reservation. The fare is free but please tip the driver. Limited to one activity for just one person each day (other members of the group can partake but will need to pay). Create exciting memories, have more fun, and truly experience the Beaches of Sarasota! Book now for an amazing vacation experience! Activities are subject to change and based on availability; non-cumulative and non-transferrable.brbrbrbrimg src=https://admin.itrip.net/upload/360/marketingimageitripsarasota.1718820503.jpg alt=marketing /brbrbrbrFeel free to book for a month or longer but Xplorie is not available for booking 25 days or longer.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.
Bed 6

Bed

Bath 6

Bath

Sleep 20

Sleeps

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Exceptional(4)

$1602.66

/ Nightly
Private Vacation Home

Beach Dream | Home w/ Ocean Views, 2 Private Pools, Rooftop Lookout and Steps to Siesta Key Beach!

Siesta Key, Florida, United States

Beach Dream | 6BR with Rooftop Patio, Two Private Heated Pools, and a 2-Min Walk to Siesta Key Beachbrbr Why You'll Love This HomebrWelcome to Beach Dream, a luxurious 6-bedroom entire duplex offering dual private pools, a rooftop lookout, and a prime location to Siesta Key Beach just across the street. With modern interiors, sleeping for up to 22 guests, it's the perfect space for reunions, retreats, and unforgettable coastal gatherings.brbr ‍ ‍ Perfect ForbrIdeal for large families, multi-generational groups, wedding parties, or friends traveling together—Beach Dream gives you the privacy of two units with the shared benefits of rooftop sunsets and unbeatable walkability to the beach and village.brbr ️ Imagine ThisbrWake up just steps from the sand, where two fully private heated pools await your crew's morning splash. Each part of this stylish duplex boasts its own modern living space, full kitchen, and designer bedrooms, giving your group the ability to gather together while also spreading out when needed. Prepare meals in either sleek kitchen, or host a group dinner al fresco on the patios. Spend afternoons lounging in one of the two fenced backyards or sipping cocktails on the shared rooftop lookout, with panoramic views of Siesta Key's shimmering Gulf waters. With dual laundry rooms and TVs in every bedroom, Beach Dream is both functional and fabulous for group living. As night falls, retreat to one of six beautifully appointed bedrooms, including four with king beds and two expansive bunk rooms that sleep up to 14 combined. Whether you're planning lazy beach days or lively evenings in Siesta Key Village, Beach Dream is the elevated group escape you've been dreaming of.brbr Where You'll SleepbrCrystal Sands:br• Bedroom 1: King Bed, Ensuite Bath, 2nd Floor, TVbr• Bedroom 2: King Bed, Shared Bath, 2nd Floor, TVbr• Bedroom 3: Full Over Full Bunk Bed & Full Bed, Shared Bath, 2nd Floor, TVbrbrSilver Shorebr• Bedroom 4: King Bed, Ensuite Bath, 4th Floor, TVbr• Bedroom 5: King Bed, Shared Bath, 4th Floor, TVbr• Bedroom 6: Two Full Over Full Bunk Beds, Shared Bath, 4th Floor, TVbrbr Explore the Areabr• 0.1 miles to Siesta Key Public Beach Accessbr• 0.6 miles to Siesta Key Village – a short walk to dining, boutiques, and nightlifebr• Rent kayaks, paddle boards, and bikes nearbybr• Enjoy local cafés, sunset bars, and family activities all within easy reachbrbr Your Siesta Key Escape AwaitsbrA rare find for large groups, Beach Dream offers two duplex homes, two pools, and a rooftop deck just a 2-minute walk to the beach. Your stay includes our trusted CottageClean™ program—a deep, 6-hour clean and 35-point inspection before every guest. Now is the time to book your dream group getaway!brbrNeed to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free High-Speed WiFi. Both pools are heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. Stairs: Both units have stairs. Contact us if any guest has mobility concerns. Duplex Note: This listing includes both duplex units. Guests will have access to the entire unit, including both private pools and backyards. brbrRelated Units: Prefer to book just one part of the duplex View individual listings:br • 3 Bedroom Option: Crystal Sandsbr • 3 Bedroom Option: Silver Shore
Bed 6

Bed

Bath 5

Bath

Sleep 22

Sleeps

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Exceptional(11)

$1915.16

/ Nightly
Private Vacation Home

Siesta Key Village Heated pool

Siesta Key, Florida, United States

Summary:brbrEscape to Oasis on the Key, a stunning villa in the heart of Siesta Key Village. This elegant home offers a private heated pool and is steps away from the beach and vibrant village life. Perfect for families, it comfortably accommodates up to 14 guests, offering a luxurious and convenient vacation experience.brbrbrbrThe Space:brbrThis charming Siesta Key vacation rental home is a unique combination of two units: “Baybreeze” and “Pinacolada” (3200 sq. ft. total). Each unit features a 3BR/2.5BA configuration, each with their very own common space to include a kitchen, dining area, living room and outdoor patio area. When booked together, Coconut Grove offers a private heated pool (when booked separately, the pool is shared between the two units). This home has every amenity you could fathom at an absolutely location in the HEART of Siesta Key Village and just a 4 minute walk to the #1 beach in the USA!brbrbrbrGuest Access:brbrThis charming Siesta Key vacation rental home is a unique combination of two units: “Sea La Vie” and “Endless Summer” (3200 sq. ft. total). Each unit features a 3BR/2.5BA configuration, each with its very own common space to include a kitchen, dining area, living room and outdoor patio area. When booked together, Oasis on the key offers a private heated pool (when booked separately, the pool is shared between the two units). This home has every amenity you could fathom at an absolute location in the HEART of Siesta Key Village and just a 2-minute walk to the #1 beach in the USA! brbrbrbrCoconut Grove can accommodate up to 16 guests with a bedding configuration as follows:brbrbrbrEndless Summer can accommodate up to 8 guests with a bedding configuration as follows:brbrbrbr• Bedroom # 1: King Bed (1) - Sleeps: 2brbr• Bedroom # 2: Queen Bed (1) - Sleeps: 2brbr• Bedroom # 3: Queen Bed (2) - Sleeps: 4brbrbrbrSea La Vie can accommodate up to 8 guests with a bedding configuration as follows:brbrbrbr• Bedroom # 1: King Bed (1) - Sleeps: 2brbr• Bedroom # 2: Queen Bed (1) - Sleeps: 2brbr• Bedroom # 3: Queen Bed (2) - Sleeps: 4brbrbrbrExclusive Amenities Include:brbrbrbr• Private Heated Pool (when rented separately, the pool is shared between both units)brbr• Linens Providedbrbr• Regular Coffee Makersbrbr• Kitchen Essentials Providedbrbr• Flat Screen HDTVs (in every bedroom + each living room)brbr• Beach Towelsbrbr• Beach Caddy (2)brbr• Coolers (2)brbr• Beach Chairsbrbr• Outdoor Lounge Areabrbr• Gas Grillbrbr• Views of Siesta Key Villagebrbr• 2 Minute Walk to Siesta Key Beach (when using beach access #5)brbr• Outdoor Showerbrbr• Washer/Dryer (in unit)brbr• Secure Parking in Lotbrbr• Free WiFIbrbrbrbrbrbrThis property hasbrbrBedroom #1: King Bed (1)brbrBedroom #2: Queen Bed (1)brbrBedroom #3: Queen Bed (2)brbrBedroom #4: King Bed (1)brbrBedroom #5: Queen Bed (1)brbrBedroom #6: Queen Bed (2)brbrbrbrThe Neighborhood:brbrSiesta Key, Florida is very proud of our sand. In fact, we have the “World’s Finest Whitest Sand”. You’ll find beautiful seashells on Siesta’s white sands, and you’ll find the finest beach-front vacation rentals and showcase homes on the Key, too. What else can you find on the sands of Siesta Key brbrbrbrYou are sure to see and hear our wild parrots and the friendly pelicans while you stroll the breathtaking 8-mile long barrier island that is Siesta Key. Siesta Village is famous for its wild parrots up in the swaying palm trees as well as many other shorebirds including terns, plovers, ibis, spoonbills, and storks. Bird watching is one of the favourite activities of residents and visitors alike. The many varieties of wading birds, like the beautiful snowy egret, and the great heron are just a few of the different types on our beaches and in our village. Keep an eye out for our 4 to 5 foot tall Florida Sand Hill Cranes with their bright red heads and distinctive calling sounds. You will often see two walking side by side since they mate for life. Our birds seem to live comfortably among the people of Siesta Key.brbrbrbrGetting Around:brbrGetting around Siesta Key is a breeze! While exploring the Village and beach is easy on foot, you'll find convenient access to various transportation options. Public transportation, including local buses, is available for trips to Sarasota and surrounding areas. For those arriving by air, Sarasota Bradenton International Airport (SRQ) is a short drive away, approximately 20 minutes depending on traffic. Ample parking is available at the property, ensuring a hassle-free stay for you and your guests. Explore the beauty of Siesta Key and the wider region with ease, knowing you have convenient travel options at your fingertips.brbrbrbrOther Things to Note:brbrAttractions brbrBay brbrCoin LaundrybrbrHealth Beauty SpabrbrMarinabrbrMuseumsbrbrParksbrbrWater ParksbrbrWinery ToursbrbrZoobrbrbrbrEntertainmentbrbrSatellite / CablebrbrTelevisionbrbrFeaturesbrbrAir ConditioningbrbrCentral HeatbrbrClothes DryerbrbrHair DryerbrbrHeatingbrbrInternet - Hi SpeedbrbrInternet - WirelessbrbrIron and BoardbrbrLinens ProvidedbrbrLiving RoombrbrParkingbrbrTowels ProvidedbrbrWashing MachinebrbrKitchenbrbrCoffee MakerbrbrCookwarebrbrDining AreabrbrDining SpicesbrbrDishes & UtensilsbrbrDishwasherbrbrKitchenbrbrMicrowavebrbrOvenbrbrRefrigeratorbrbrStovebrbrToasterbrbrLeisurebrbrAntiquingbrbrBird WatchingbrbrBoatingbrbrEco TourismbrbrGamblingbrbrOutlet ShoppingbrbrPaddle BoatbrbrShoppingbrbrWater SportsbrbrWildlife ViewingbrbrbrbrLocalbrbrHospitalbrbrLaundromatbrbrLocationbrbrBeachbrbrNear OceanbrbrVillagebrbrOutdoorbrbrDeck/PatiobrbrGas GrillbrbrPoolbrbrHeated PoolbrbrPrivate PoolbrbrSportsbrbrBasketball CourtbrbrBikingbrbrDeep Sea FishingbrbrFishingbrbrFishing BaybrbrFishing FlybrbrFishing SurfbrbrGolf OptionalbrbrGolfingbrbrHikingbrbrJet SkiingbrbrKayakingbrbrParaglidingbrbrParasailingbrbrPier FishingbrbrRoller BladingbrbrSailingbrbrScuba or SnorkelingbrbrSnorkelingbrbrSurfingbrbrSwimmingbrbrWater SkiingbrbrWater TubingbrbrWind SurfingbrbrThemesbrbrFamilybrbrLuxurybrbrbrbrCancellation; Non-Refundable Transaction Fee VRBO BOOKING.COM ONLY In the event of any cancellation,or, or termination, of a booking for any reason whatsoever, the 3.9% transaction processing fee assessed at the time of payment shall be strictly non-refundable. This fee represents payment processing costs incurred and is earned immediately upon receipt of funds. Under no circumstances shall the 3.9% transaction fee be returned, credited, or otherwise reimbursed, including but not limited to cancellations made within any stated refund period, force major events, or cancellations initiated by the Guest. Any applicable refund shall be calculated net of the 3.9% transaction processing fee.brbrbrbrInteraction with Guests:brbrI am available throughout your stay to assist with any questions or needs. You can reach me anytime via the booking platform messaging system. I strive to respond as quickly as possible.brbrbrbrCancellation; Non-Refundable Transaction Fee VRBO BOOKING.COM ONLY In the event of any cancellation,or, or termination, of a booking for any reason whatsoever, the 3.9% transaction processing fee assessed at the time of payment shall be strictly non-refundable. This fee represents payment processing costs incurred and is earned immediately upon receipt of funds. Under no circumstances shall the 3.9% transaction fee be returned, credited, or otherwise reimbursed, including but not limited to cancellations made within any stated refund period, force majeure events, or cancellations initiated by the Guest. Any applicable refund shall be calculated net of the 3.9% transaction processing fee.
Bed 6

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Bath 5

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Sleep 14

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Exceptional(17)

$2522.03

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Apartment

Gertrude's Siesta | 100% Private, 8-steps to Beach Path! 4-min Dining & Music! Snorkeling, Sunsets!

Siesta Key, Florida, United States

The Coral Cabanas InnbrJust 8-steps to path of Siesta Key Beach, the world's best beach! 100% private 8BR including 5 units. 4-minute walk to bars, entertainment, shopping, dining and live music! Communal lounging, alfresco dining, snorkeling, sunsets, and hammocks. Listing includes two side-by-side units including a 1BR and 2BR (total 3BR). Book your groups Siesta Key vacation rental getaway now!brbrWhat Guests Lovebr∙ Separate Units – 5 units deliver space and privacy, perfect for large gatheringsbr∙ Beaches – 12-step walk to Siesta Key's award winning beaches, calm shallow and clearbr∙ Relaxing –secluded spot with hammocks, alfresco-lounging, westerly facing deckbr∙ Reef Snorkeling – 60-yard walk to Point of Rocks, free snorkel gear providedbr∙ The Food –12 restaurants within 0.5 miles, 3 waterfront restaurants within 4 milesbr∙ Activities – Boat bike jet-ski & sport-fishing tours, marina and rentals 7-min awaybr∙ Sunsets –walk 30-seconds to best sunsets on Siesta Key and whatever comes nextbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - 4-min walk to South Village and live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – access Siesta Key's top attractions and beaches guaranteed fun for allbr∙ Price - this Siesta Key vacation rental listing is direct with the manager and is the guaranteed lowest costbrbrThe BeachbrSkip the crowds and commercial feel. Coral Cabanas offers Siesta Key-style charm and beach access #13—quieter, more private, and just across the street. With no public parking nearby, this cove is one of Siesta's most exclusive beaches. The white quartz sand, tide pools, and calm, clear water are perfect for relaxing. A livelier scene with food, drinks, and the weekend drum circle is just a short beach walk north. Point of Rocks reef is only 60 yards south.brbrThe LocationbrNo car needed. Nestled on a quiet street with no traffic, businesses, or public parking. Walk 7 minutes to Siesta's top eco-adventures—boat, bike, jet-ski, and fishing tours. Prefer to relax Sunbathe on the balcony, nap in a hammock, or enjoy Siesta's top-rated seafood, ice cream, and waterfront dining. Just a short stroll to favorites like Daiquiri Deck, Sniki-Tiki, Crescent Club, and Orange Octopus.brbrReef SnorkelingbrSiesta Key is already paradise—now add one of the Gulf Coast's best snorkeling spots! Just 60 yards south, Point of Rocks offers safe, shallow waters filled with tide pools, colorful marine life, and shelling treasures. Most days you'll spot chameleons, sponges, mother-of-pearl shells, conch, and maybe even dolphins or turtles. Ideal for exploring by foot, snorkel, paddleboard, or kayak.brbrBedroom DetailsbrListing includes three 2BR and two 1BR units (8BR total). One 2BR unit is ground level, other units are one flight up. The 1BR units have a large queen bedroom and a queen sleeper in the living room. Two of the 2BR units have a large queen BR, a room with two doubles, and a sleeper sofa. The ground floor 2BR unit has two queen bedrooms and a queen sleeper sofa in the living room. The property can sleep up to 31 family style. Need more space We can get you an additional unit nearby.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, snorkel equipment, and umbrellas. There are also a few paddle boards available on a first come first serve basis and any other gear can be found for sale or rental nearby! brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrSiesta Key is a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.
Bed 8

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Bath 5

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Sleep 32

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$762.19

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Private Vacation Home

Large Pool Home- Blocks from Siesta Key Beach

Siesta Key, Florida, United States

Summary:brWelcome to Ocean Breeze Cottage, brbrThis beautiful 5 bedroom 3 bath home is perfect for a family vacation to Siesta Key Beach. Ocean Breeze Cottage is a quick block and a half stroll or bike ride up the street from The Nation’s Number One Beach; where you can enjoy Siesta Key’s famous white sand, swim in the Gulf of Mexico and take in a technicolor sunset. Looking to do some shopping, grab a bite to eat, or just enjoy live music and some drinks then you will enjoy Siesta Village.brbrThe Space:brWelcome to Ocean Breeze Cottage where you can enjoy all the best elements of the perfect Island vacation. brbrWhat the Ocean Breeze Cottage has to offer:brThe home's interior is spacious with five bedrooms and three newly updated baths, accommodating ten. The second floor has an open living and dining space. Three of the bedrooms are on this floor. The first floor is home to two additional bedrooms, a bathroom and comfy TV room and Foosball table. (Please note that the main living, dining and master bedroom are located on the second floor only accessible by stairs, NO elevator)brbrBedroom 1 features:brLocated on the upper main living level.br1-King bed, All bed linens, ceiling fan, walk-in closet, dresser, smart TVbrbrBedroom 2 features:brLocated on the upper main living levelbr1-Queen bed, All bed linens, ceiling fan, closet, dresser, smart TVbrbrBedroom 3 features:brLocated on the upper main living levelbr2-Twin beds, ceiling fan, closet, dresser, smart TV brbrBedroom 4 features:brLocated on lower levelbr1-King bed, All bed linens, ceiling fan, walk-in closet, dresser, smart TVbrbrBedroom 5 features:brLocated on lower levelbr1-Queen bed, All bed linens, ceiling fan, dresser, smart TVbrbrKitchen features:brLocated on upper main living level, features granite counter-tops, stainless steel appliances, and is fully equipped, allowing you to enjoy anything from a quiet lunch together to preparing a feast for your family!brDinnerware for inside and outsidebrDrinkware, Coffee cups, Wine glassesbrCutlery and Kitchen gadgetsbrToaster, Blender, KettlebrCoffee Maker- Dual Style both drip and podbrPots, Pans, BakewarebrbrDining Options:br6-person dining room table insidebr10-person dining table on upper balcony overlooking poolbr8-person dining table on lower pool deckbrbrLiving Room:brOffers comfy seating with a couch, loveseat and chair brFree WI-FIbr75” Smart TVbrbr3-Bathrooms: (2 located on upper main living level and 1 on lower level)brEn-suite bathroom features walk-in showerbrUpper and lower guest bathrooms features tub/shower combobrBath towels/wash clothsbrHairdryerbrbrLaundry Area:br2 Full Sized Stacked Washer and DryerbrIron and Ironing BoardbrbrOutdoor Space:brThe partially fenced private backyard has a screen lanai and heated saltwater pool (heated from January 1st to March 31st, other times upon request and additional fee of 25.00 per day).brThe pool gets serviced weekly by an outside company. Please note that, after it rains, there may be some debris that washes off the screen and into the pool between cleanings due to unpredictable weather conditions in Florida - this is normal. We provide a pool skimmer that you may use to remove light debris throughout your stay.br4-Loungersbr2-Outdoor Dining Tables (10 person and 8 person)brSeating area with couch brSmart 70” TVbrGas Grill available for the times you want to eat in.brCorn Hole BoardsbrbrBeach Items:br8-Beach ChairsbrBeach/Pool TowelsbrCoolerbrBeach WagonbrbrSupplies:brA complimentary starter supply includes:br1-Roll of Paper Towelbr1- Small Bottle of Dish Soapbr5- Dishwasher Podsbr10- Trash Bagsbr10-Laundry Detergent Podsbr2- Rolls of toilet paper, per bathroombrFor extended stays, please be prepared to bring any additional supplies that you will need.brbrPet Policy:brMax number 2 pets Limited to dog(s) all other pets are strictly prohibited.brGuest must have pet listed on reservation at the time of booking and pay required pet fee of 200.00 (any unauthorized pets found on property will be charged a 500.00 fee.brGuest must complete and sign pet addendum brPets are not allowed in pool. brAll pets must comply with the following specifications.brMay not exceed 50 lbs. without prior approval.brMust be up-to-date on rabies vaccinations and all other vaccinations required for boarding. Guest must be able to provide documentation from an accredited veterinarian upon requestbrbrNoise/Good Neighbor Policy:brThis is a private residence in a residential neighborhood. Quite times are 9pm to 8am and we always follow strict noise regulations and ask you to be respectful and considerate. Strictly no parties or gatherings are to be held at this property. Any breach of these regulations may result in eviction without a refund of the remaining funds or deposit.brbrAge Limit:brWe do not accept reservations for groups with travelers under the age of 26 years unless a specific exception has been approved. Travelers under the age of 26 that are traveling with a family group with a parent are more than welcome to stay with us.brbrRegistered Guests:brONLY the registered guests are allowed to stay at the property!brUnless discussed and agreed with us otherwise, this includes inviting groups over during the day/night beyond the number of persons you have booked for.brbrCheck in is from 4pm and check out is at 10am.brbrGuest Access:brThe whole housebrbrThe Neighborhood:brOcean Breeze Cottage is a quick 2 block stroll up the street from The Nation’s Number One Beach; where you can enjoy Siesta Key’s famous white sand, swim in the Gulf of Mexico and take in a technicolor sunset. Looking to do some shopping, grab a bite to eat, or just enjoy live music and some drinks then you will enjoy Siesta Village which is just a mile away.brbrGetting Around:brThere are free ride shuttles available to take you anywhere on the key, as public parking can be challenging during peak season.brbrOther Things to Note:brPLEASE NOTE:brThere is a 1 rental per 30 day period, per Sarasota, FL ordinance, contact us for more information.brReservation must follow under the accordance of the Sarasota County code regulations.brbrInteraction with Guests:brRest assure there will always be someone available to answer any questions or concerns
Bed 5

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Bath 3

Bath

Sleep 10

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$458.78

/ Nightly
Private Vacation Home

#1 Beach House Siesta Key

Siesta Key, Florida, United States

Luxury Siesta Key Retreat – 5 Bedrooms | Walk to the Beach | Game Room | Bikes IncludedbrbrExperience the best of Siesta Key from this stunning 5-bedroom, 5-bathroom coastal retreat, perfectly designed for families and groups looking for space, comfort, and unforgettable beach memories.brbrLocated within walking distance to the world-famous Siesta Key Beach, you can start your mornings with a peaceful stroll to the powder-white sand and end your evenings watching the breathtaking Gulf Coast sunsets.brbrStep inside to a bright and welcoming home where modern comfort meets relaxed island living. The spacious layout offers multiple gathering areas perfect for entertaining, relaxing after the beach, or enjoying quality time with family and friends.brbrEach bedroom is thoughtfully designed to provide a peaceful and private escape, while the five full bathrooms ensure everyone has plenty of space to get ready for the day or unwind after sunset. The bathrooms feature spa-like showers with luxurious rainfall showerheads, creating a relaxing retreat after a long day in the sun.brbrKids and adults alike will love the dedicated game room with arcade games, making it the perfect spot for entertainment, laughter, and friendly competition.brbrFor exploring the island, bikes are included, making it easy to cruise around Siesta Key, ride to the beach, or explore the nearby restaurants and shops in Siesta Key Village.brbrAfter a day at the beach, rinse off in the convenient outdoor shower, then relax in the tranquil atmosphere of your private retreat.brbrWhether you're planning a family vacation, group getaway, or special celebration, this home offers the perfect balance of location, comfort, luxury, and fun.brbrCome experience the magic of Siesta Key living — where unforgettable memories are made.
Bed 5

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Bath 5

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Sleep 10

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Exceptional(5)

$1368.14

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Private Vacation Home

Siesta Key Beach 3 Condos in One Building, half a block to Point of Rocks

Siesta Key, Florida, United States

Siesta Key Beachside Tri-Plexbr3 Private Condos | 6 Bedrooms | 6 Bathrooms | Point of RocksbrbrWelcome to your private Siesta Key oasis. A one-of-a-kind beachside tri-plex offering the comfort of three separate condos within one exclusive property. Nestled in the peaceful Point of Rocks neighborhood, this unique retreat is perfect for large families, multiple families traveling together, or groups seeking both shared gathering spaces and private accommodations.brbrWith approximately 3,700 square feet of living space spread across two levels, this property comfortably accommodates up to 12 guests while providing privacy, comfort, and easy access to world famous Siesta Key Beach.brbrThe Three Private CondosbrCondo 1 – Ground FloorbrbrThis cozy ground floor condo features:brbr1 bedroom with a king bedbr1 bathroombrFully equipped kitchenbrComfortable living spacebrbrPerfect for couples or guests seeking easy access and privacy.brbrCondo 2 – Second FloorbrbrThis spacious second floor condo includes:brbr2 bedroomsbrPrimary bedroom with king bedbrGuest bedroom with two twin bedsbr2 bathroomsbrFully equipped kitchenbrOpen living and dining areabrbrIdeal for families or smaller groups.brbrCondo 3 – second floor with a spiral staircase to the master suite in the Crow’s NestbrbrThe largest condo offers:brbr3 bedroomsbrCrow’s nest primary suite with king bed, ensuite bathroombrOne guest bedroom with queen bedbrOne guest bedroom with two twin bedsbr2 additional bathrooms for conveniencebrFully equipped kitchenbrSpacious living areas and balconiesbrbrThe crow’s nest suite creates a truly memorable coastal retreat with added privacy.brbrProperty HighlightsbrMultiple Living Spaces, patios and outdoor seatingbrbrEnjoy spacious gathering areas balanced with private retreats throughout the property. Beautiful coastal inspired interiors create a relaxed and beachy atmosphere that reflects the charm of Siesta Key.brbrFully Equipped KitchensbrbrEach condo includes its own full kitchen, making meal preparation simple whether you are cooking for the entire group or enjoying quiet meals separately.brbrOutdoor Living & Heated PoolbrbrRelax by the shared heated pool surrounded by tropical landscaping, or enjoy the multiple balconies offering views of the pool.brbrPrime Siesta Key LocationbrSteps to the Beach brbrLocated just half a block from Beach Access 13, you are only steps away from the powdery white sands and crystal-clear waters of Siesta Key Beach.brbrExplore the IslandbrbrEnjoy nearby restaurants, shopping, snorkeling, paddleboarding, and local attractions throughout Siesta Key Village and beyond.brbrConvenient Island TransportationbrbrEasy access to the Siesta Key Trolley makes exploring the island simple and convenient without needing a car.brbrThis exclusive Siesta Key tri-plex offers the perfect combination of privacy, flexibility, and close to the beach living. ideal for creating unforgettable memories with family and friends in one of Florida’s most beautiful coastal destinations.brbrAdditional Amenities:br- Washer and Dryer - in each unitbr- Beach Supplies - chairs, umbrellas, cooler, beach cart, towelsbr- Pool Toysbr- Linens and Towelsbrbr**Minimum Age 25: All Reservations must be booked by and accompanied by an adult who is 25 years of age or older. Valid photo I.D. may be required at the time of booking. br**Your inquiry on our property will be responded directly to your personal email. Please keep a lookout for our response so we may best serve your request
Bed 6

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Bath 6

Bath

Sleep 14

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Exceptional(9)

$1467.77

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Private Vacation Home

Luxury 6 Bedroom near the Village

Siesta Key, Florida, United States

Escape to unparalleled luxury at this brand-new, exquisitely built vacation rental, completed in June 2025, and ideally situated just steps from the vibrant Siesta Key Village. This magnificent retreat boasts 6 spacious bedrooms, each with its own en-suite bathroom, plus an additional half-bath for ultimate convenience, comfortably accommodating large families or groups. Experience effortless living with a private elevator servicing all levels. The heart of the home is a state-of-the-art gourmet kitchen, fully equipped with top-of-the-line appliances and ample counter space, perfect for culinary enthusiasts. Indulge in the ultimate outdoor oasis featuring an expansive, heated pool and a luxurious hot tub, surrounded by extensive outdoor living areas designed for relaxation and entertainment. A dedicated outdoor kitchen allows for seamless al fresco dining. Ascend to the spectacular rooftop deck for breathtaking panoramic views, ideal for savoring Siesta Key`s famous sunsets. This premier vacation home comes fully stocked with essential beach equipment, ensuring you`re ready for days on the world-renowned Siesta Beach, just a short stroll away. With its impeccable design, unparalleled amenities, and prime location close to Siesta Key Village`s dining, shopping, and entertainment, this newly constructed masterpiece promises an unforgettable, luxurious escape to paradise.
Bed 6

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Bath 6

Bath

Sleep 14

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Exceptional(13)

$2131.6

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Private Vacation Home

16 Guest Pool house walk to the beach and village

Siesta Key, Florida, United States

Combination Duplex 3 Bedroom 2 Bath per unit brWith a balcony overlooking the pool area and canal road , this 6-bedroom home is within strolling distance of the island’s best beaches, dining, shopping, and entertainment. Vaulted ceilings, an open multilevel floor plan, and breezy beach décor contribute to the space’s fresh, serene feel.br​brUpon entry, immediately ascend to the main (second) floor. In the master bedroom, located on this main floor, you will find a king-sized bed with quality linens. An updated full bath is conveniently situated next to the master bedroom. Also on the main floor, the kitchen is equipped with modern cabinets, granite countertops with a sleek tile backsplash, and stainless steel appliances. Adjoining the kitchen is the dining area, which comfortably seats six and opens up to the great room. This spacious living area features sliding glass doors that open up to the balcony and 20-foot ceilings with ceiling fans. The flatscreen TV features cable with upgraded sports packages and a dvd player. Stairs lead up to the top floor, where there are two more well-appointed rooms—one with a king-size bed and the other with two queen-size beds. Between the rooms is a full bathroom with a tub/shower combo. brbrThis beach house is located along a quiet, meandering street dotted with palm trees, and is just 300 steps or approximately a 3 minute walk to Siesta Key’s Beach Access #7 and a short 3-4 minute stroll to the village for shopping, dining, and entertainment. With attractions within easy walking distance and the local airport an affordable cab drive away, a rental car is not necessary, although convenient driveway parking for is offered. There are 2 parking spaces for the unit and you can fit up to 4 cars if you double park. brbrA paved walk borders the driveway and leads to the home’s private entrance, as well as the entrance to the adjoining unit. Continue following the path to access the secluded, pool area where each unit has a private cabana, it's own dining table and chairs, and barbecue grill.brbrThe distinctive combination of open concept interior and expansive outdoor gathering area makes this home ideal for families and groups of friends looking for a relaxing beach getaway.
Bed 6

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Bath 4

Bath

Sleep 16

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Exceptional(1)

$1229.48

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Private Vacation Home

Entire Building, Sundeck w/ Ocean view, 20ft to Beach Access, 500ft from Village

Siesta Key, Florida, United States

Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village walkability, we are confident that this space will cultivate unforgettable memories.brbrSiesta Key Dream’s flagship vacation rental features TWO-CONDOS in a single building, totaling 6-bedrooms, 14 beds, and 4 bathrooms. This rental is perfect for family and friend gatherings and can accommodate up to 20 guests (16 adults and 4 children). With this reservation, the ENTIRE building is yours, as there is no other condos in the building, besides the two that are included in this listing.brbrBoth units contain large, spacious floor plans that connect welcoming living rooms, dining rooms that seat 8 or more, and a modernized kitchens. Next to both living rooms, you’ll find a private, enclosed balcony that has partial ocean views and has comfortable seating that is perfect for shaded, outdoor entertainment.brbrPenthouse Condo has the following bedrooms:br - Main bedroom: King bed, HDTV w/ DirecTV Stream, partial Gulf of Mexico View, ensuite bathroom, walk-in closet, and walk-out to the enclosed balconybr- Bedroom #2: King bed & HDTV w/ DirecTV Streambr- Bedroom #3: Bunk bed that has two twin mattresses + one trundle bed that pulls out from under the bunk bed, Queen size Futon, & HDTV w/ DirecTV StreambrbrThe 2nd Level Condo has the following bedrooms:br - Main bedroom: King bed, HDTV w/ DirecTV Stream, partial Gulf of Mexico View, ensuite bathroom, walk-in closet, and walk-out to the enclosed balconybr- Bedroom #5 (2nd bedroom in condo): King bedbr- Bedroom #6 (3rd bedroom in condo): Bunk bed that has two twin mattresses + one trundle bed that pulls out from under the bunk bedbrbrThere are a total of three roll-away-twin sized mattresses for the common spaces. brbrSiesta Key Dreams is happy to provide free high-speed WiFi internet, HDTV equipped with live sports & extension channel options via DirecTV Stream, and electric appliances so you will not miss a beat.brbrOn the rooftop of the building, you’ll see a PRIVATE sundeck and outdoor space that provides partial ocean and beach views – some of the best in Siesta Key Dream’s portfolio! On the rooftop you will have sun-loungers and a couch, perfect for tanning and hanging out in the Florida sun. brbrSiesta Key Dreams always shows our exact address in our listings, so our guests know exactly how close they truly are to the beach and village. Unplug and explore your surroundings, such as the Siesta Village which is less than a 5-minute walk away down Beach Road! From cafes to fine dining, local shopping, live music and entertainment, you will certainly find what you need. brbrIf you’re looking to soak up the sun and clear waters, you will be given PRIVATE beach access with a gated key, which provides you with a direct path to the beach access point within a mere 20 steps. Easily slip on your sandals and take a stroll on the private beach entrance point to experience the brilliant 99% white quartz sand.brbrNote: During peak rain months (June to Aug) there is a chance the private path to the beach is flooded, the alternative path is Beach Access #5, which is only a few feet away and the total walk to the sand is the same.brbrIn addition to the stunning, white quartz sand, the beaches of Siesta Keys offer picnic areas, concession stands, and volleyball courts. The shallow, crystal water and year-round lifeguard protection makes each beach a safe and relaxing escape. Having your property mere minutes away from the ocean means that you will certainly witness breathtaking sunsets. A 3-minute walk from the beach reveals Siesta Village, which offers a wide-range of dining and entertainment options from live-music to gourmet donuts, coffee, and seafood to award-winning steakhouses. brbrWe recognize that parking can be difficult, which is why our rentals come with FIVE private-reserved spaces at no additional cost to you (five vehicle max). We also offer golf cart rental for easy travel and access to all the top tourist spots around town, you can book the golf-cart via the `boarding pass` we send after you make your reservation.brbrThe Siesta Key Breeze Trolley also operates on Beach Road, just outside your rental, which is free for all riders and operates 8AM - 10PM, seven days a week!brbrSiesta Key Dreams wishes to provide you with `Unreasonable Hospitality” – service at the highest caliber, well above your expectations. As soon as you secure your vacation rental, our team will provide you with clear expectations to help prepare for your stay. If you experience any issues upon arrival, a Guest Experience Manager who lives within the Siesta Keys area will be available at a moment’s notice to assist you. Siesta Key Dreams takes pride in providing professional and personalized services to ensure that your stay is unforgettable.brbrIncluded within your reservation are complimentary bathroom toiletries (shampoo, conditioner, body wash, soap), coffee & a Keurig-pods, and your choice of either a bottle of sparkling wine or sparkling grape juice. To prep for the numerous beach trips, we provide you with towels, beach chairs, umbrellas, blankets, coolers and carts to transport your items easily! Traveling with your children We offer complementary cribs, highchairs, toys, silverware, and baby-monitors available per request! brbrShortly after you secure your vacation rental, you will receive a link where you can book local services or experiences provided by vendors throughout the island. Siesta Key Dreams provides golf-carts to rent and mid-stay services such as cleanings, and linen changes for an additional charge.brbrWhen available, guests can request flexible booking with early check-in or late check out options. Siesta Key Dreams also offers baggage drop-off prior to your check-in time. You will be able to indicate your preferences in the link you will receive prior to check-in. brbrLeading up to the check-in date, guests are supported via email & SMS.brbrGuests will receive an electronic Rental Agreement that provides common details about our terms and conditions, such as our no-smoking policy. Before you check-in, and just after booking, we require guest verification. You will receive information after booking and the process only takes a couple minutes. This allows us to provide a safe location for our guests, neighbors, and employees.brbrPayment: 50% at time of booking, 50% 7-days before check-inbrCheck Out: 10AMbrCheck In: 3PMbrSmoking: No smokingbrQuiet Hours: 12PM - 7AM brParking: 5 reserved parking spaces (5 vehicle max)brLarge Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key Dreams brPets: No PetsbrSee Vacation Rental Agreement for all details
Bed 6

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Bath 4

Bath

Sleep 20

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Exceptional(18)

$2181.04

/ Nightly
Private Vacation Home

Nearly Beachfront, One house from the beach! Pool and Game Room - Ocean Overlook

Siesta Key, Florida, United States

Ocean Overlook by Siesta Key Luxury Rental Properties brbrOcean Overlook by Siesta Key Luxury Rental Properties is an exceptional eight bedroom, eight bathroom coastal retreat with two additional half baths, thoughtfully designed for large families and large group getaways seeking luxury coastal living. Located just a three-minute walk to Siesta Key Beach, this four-story Siesta Key luxury rental offers sweeping Gulf views, large balconies, and a private outdoor oasis. Guests are also a short nine-minute walk to Siesta Key Village, where dining, boutiques, and island nightlife await. With an elevator to all levels, multiple living spaces, and parking for up to five vehicles, Ocean Overlook delivers effortless comfort in one of Sarasota’s most desirable beach locations. brbrHighlights br• 3-minute walk to Siesta Key Beach br• 8 Bedrooms / 8 Full Bathrooms / 2 Half Bathrooms br• 6 King beds, 1 Queen bed, 1 Full over Full bunk bed br• Private pool with in-ground spa br• Balconies with Gulf views br• Game room with foosball and gaming systems br• Elevator for guest use br• Outdoor dining, BBQ grill, and entertainment space br• Beach chairs, wagon, and cooler provided br• Dog Friendly with host approval and additional fee br• Parking for up to 5 vehicles br• 9-minute walk to Siesta Key Village brbrThis Siesta Key vacation home with pool is centered around an inviting backyard retreat designed for relaxation and entertainment. The private pool features tranquil water elements, lush landscaping, and a connected spa, creating a peaceful setting for afternoons in the sun or evenings under the stars. Nearby, the outdoor kitchen and BBQ area includes a grill, island with built in refrigerator, and multiple dining tables, making it easy to gather for casual meals or celebratory dinners. A shaded outdoor dining bar with seating and a TV adds another layer of comfort, while the outdoor shower and provided beach gear make transitioning from the Gulf to the pool seamless. brbrThe main living level showcases a bright, open concept design with expansive windows framing Gulf views. A spacious living area with comfortable seating and a large TV flows into a fully equipped gourmet kitchen featuring high end appliances, generous counter space, and bar top seating ideal for group cooking and conversation. The formal dining table comfortably accommodates large meals together. Step onto the balcony to enjoy ocean breezes and dine outdoors with stunning views of the Gulf. On the third floor, the game room offers an additional gathering space complete with a wet bar, bar seating, a living area, and a TV. Entertainment continues with a foosball table, PlayStation, and vintage Nintendo console, plus balcony access. brbrOcean Overlook offers a collection of thoughtfully designed bedrooms, many functioning as private primary style suites. King bedrooms feature plush bedding, ample closet space, and elegant ensuite bathrooms with walk-in showers, double vanities, and select soaking tubs. Several suites include private balconies, offering quiet spaces to unwind with Gulf views. The Queen bedroom and bunk bedroom each include charming ensuite bathrooms with shower and tub combinations, ideal for families traveling together. Two half baths and conveniently located laundry facilities enhance comfort throughout the home. brbrRoom Details br• Primary Bedroom (3rd Floor): King bed, balcony, ensuite bathroom with double vanity and walk-in shower br• Second Bedroom (3rd Floor): King bed, ensuite bathroom with double vanity, walk-in shower, and soaking tub br• Third Bedroom (3rd Floor): King bed, ensuite bathroom with walk-in shower br• Fourth Bedroom (2nd Floor): King bed, ensuite bathroom with walk-in shower br• Fifth Bedroom (2nd Floor): King bed, balcony, ensuite bathroom with double vanity and walk-in shower br• Sixth Bedroom (2nd Floor): King bed, balcony, ensuite bathroom with walk-in shower br• Seventh Bedroom (2nd Floor): Queen bed, ensuite bathroom with shower and tub combo br• Eighth Bedroom (2nd Floor): Full-over-Full bunk bed, ensuite bathroom with shower and tub combo brbrOcean Overlook is ideally positioned along Beach Road, placing guests just minutes from Siesta Key Beach and within a short nine minute walk to Siesta Key Village, home to popular restaurants, beach bars, and boutique shopping. This Siesta Key vacation rental includes an in-home washer and dryer, elevator access to all levels, and parking for up to five vehicles, making extended stays and large group travel effortless. brbrFrom sunrise coffee overlooking the Gulf to evenings spent poolside with family and friends, Ocean Overlook by Siesta Key Luxury Rental Properties offers an elevated beach getaway designed for unforgettable moments. With walkable beach access, luxurious indoor and outdoor spaces, and proximity to Siesta Key Village, this home delivers the perfect balance of relaxation and island adventure. Book your stay at Ocean Overlook today and experience the best of Siesta Key luxury living! brbr- brWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Siesta Key Luxury Rental Properties Rental Policies for full details. brbr5 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrPlease see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrThis home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.
Bed 8

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Bath 9

Bath

Sleep 18

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Exceptional(2)

$2193.2

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Private Vacation Home

Seashell Esta – Luxe Siesta Key Escape

Siesta Key, Florida, United States

Summary:brbrSeashell Esta is a 7BR/7.5BA luxury Siesta Key retreat just 2 minutes from the beach ️. Enjoy a heated pool, spa, waterslide, rooftop deck, elevator, and stunning Gulf views . With king suites, bunk room, balconies, and walkable access to Siesta Key Village dining and shopping, this resort-style home is perfect for unforgettable coastal vacations ✨.brbrbrbrThe Space:brbr Seashell Esta – Luxe Siesta Key Escape brbrbrbr89 Avenida Messina | Siesta KeybrbrbrbrWelcome to Seashell Esta, a spectacular 7-bedroom, 7.5-bath luxury retreat just steps from the world-famous Siesta Key Beach ️. Spanning three stunning levels with an elevator, private balconies, and a show-stopping rooftop deck, this newly built home offers breathtaking Gulf views, glowing sunsets, and a private resort-style backyard designed for unforgettable island living.brbrbrbrThe expansive great room is perfect for gathering, with plush seating, coastal elegance, and seamless flow into the gourmet kitchen ️. Featuring state-of-the-art appliances, a large island, and abundant prep space, the kitchen is ideal for everything from quick breakfasts to celebratory dinners. Open the doors to the balcony and enjoy dining with warm Gulf breezes and sunset skies .brbrbrbrOutside, your private oasis awaits . Lounge beside the heated lagoon-style pool, slide into fun on the waterslide, or unwind in the spa. Fire up the grill for poolside meals, relax under the covered patio, and enjoy movie nights on the outdoor TV. Upstairs, the rooftop deck delivers panoramic views that make every sunset unforgettable .brbrbrbr✨ Highlights ✨brbrbrbr• ️ 2-minute walk to Siesta Key Beachbrbr• Heated pool, spa & waterslidebrbr• Rooftop deck with Gulf viewsbrbr• Elevator access to all floorsbrbr• Private balconies & outdoor diningbrbr• Outdoor TV & lounge areabrbr• ️ Near Siesta Key Village dining & boutiquesbrbrbrbr Bedrooms brbrbrbr• Primary Bedroom (3rd Floor): King bed, private balcony, ensuite bath with standalone tub & walk-in showerbrbr• Second Bedroom (3rd Floor): King bed, balcony, ensuite with walk-in showerbrbr• Third Bedroom (3rd Floor): King bed, balcony, ensuite with walk-in showerbrbr• Fourth Bedroom (2nd Floor): King bed, ensuite with walk-in showerbrbr• Fifth Bedroom (2nd Floor): King bed, balcony, ensuite with walk-in showerbrbr• Sixth Bedroom (2nd Floor): King bed, balcony, ensuite with walk-in showerbrbr• Seventh Bedroom: Full-over-Full bunk bed, ensuite with tub/shower combobrbrbrbrAdditional Sleeping:brbr• Living Room – Queen sleeper sofabrbr• Club Room – Queen sleeper sofabrbrbrbrGuest Access:brbrGuests have full access to the entire home, including a private heated pool/spa and a fully fenced backyard—perfect for relaxing, entertaining, and enjoying your own secluded space.☀️brbrbrbrOther Things to Note:brbr ️ Beach-Ready Convenience brbrTo make your stay effortless, the home is fully stocked with beach chairs, a beach cart, and a beach umbrella, plus all bath towels, beach towels, and linens—just pack your bags and enjoy island time ☀️ brbrbrbr Parking InformationbrbrParking is available for up to 4 vehicles maximum. Please plan ahead and coordinate with your group accordingly.brbrbrbr Friendly Island ReminderbrbrThis home is located in a residential neighborhood. We kindly ask guests to be respectful of our neighbors by keeping noise at a considerate level day and night. Thank you for helping preserve the peaceful island atmosphere brbrbrbrInteraction with Guests:brbrIf you need anything during your stay, I’m always here to help! You can call or text me directly on my cell anytime. I’m available 24/7 to answer questions, share local tips ️, or assist with anything that comes up. Your comfort and peace of mind are my top priority! ✨
Bed 7

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Bath 7

Bath

Sleep 20

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Exceptional(1)

$1886.03

/ Nightly
Private Vacation Home

Island House – Walk to Siesta Key Beach!

Siesta Key, Florida, United States

Summary:brbrIsland House is a 7BR/6BA Siesta Key retreat just a 4-minute walk to the beach ️. Enjoy a private pool with waterslide, hot tub, BBQ area, and separate guest suite. With king bedrooms, bunk rooms, pet-friendly options, and walkable access to Siesta Key Village dining and shops, this home is perfect for unforgettable family vacations ✨brbrbrbrThe Space:brbr Island House – Your Private Siesta Key Oasis brbr 344 Canal Rd, Siesta Key, FL 34242brbrbrbrWelcome to Island House, a spacious and family-friendly 7-bedroom, 6-bathroom retreat just a 4-minute walk to world-famous Siesta Beach ️. Designed for unforgettable group getaways, this coastal escape features a private pool with waterslide, relaxing hot tub, and a separate guest suite—perfect for multi-family vacations or traveling with grandparents.brbrbrbrAfter a day at the beach, retreat to your private backyard paradise . Splash into the sparkling pool, race down the waterslide, rinse off in the outdoor shower, then gather around the grill for alfresco dinners under the island sky . Inside, the open living space invites everyone to relax together, while the fully equipped kitchen with coastal finishes makes meal prep a breeze.brbrbrbrWith thoughtful sleeping arrangements, plenty of space to spread out, and a walkable location near Siesta Key Village’s shops and dining, Island House delivers the perfect blend of comfort, convenience, and island fun .brbrbrbr✨ Highlights ✨brbrbrbr• ️ 4-minute walk to Siesta Beachbrbr• Private pool, hot tub & waterslidebrbr• Pet-friendly (host approval & fee)brbr• BBQ grill & outdoor diningbrbr• Outdoor showerbrbr• Separate private guest suitebrbr• ️ Walk to Siesta Key Villagebrbr• ️ Sleeps a crowd comfortablybrbr• 4 parking spacesbrbr• Washer & dryerbrbr• ️ Professional linen programbrbrbrbr Bedrooms & Sleeping Arrangements brbrbrbr• Primary Bedroom (2nd Floor): King bed, ensuite bath with shower/tub combobrbr• Second Bedroom (2nd Floor): King bed, ensuite bath with shower/tub combobrbr• Third Bedroom (2nd Floor): King bed, ensuite bath with walk-in showerbrbr• Fourth Bedroom (2nd Floor): Twin-over-twin bunk with twin trundle, ensuite bathbrbr• Fifth Bedroom (2nd Floor): Full-over-full bunk bedbrbr• Sixth Bedroom (1st Floor): King bed, shared hall bath with walk-in showerbrbr• Seventh Bedroom – Private Suite: King bed, TV, mini fridge, ensuite bath with shower/tub combobrbrbrbrAdditional Sleeping:brbr• Living Room: Full sleeper sofabrbrbrbrGuest Access:brbrGuests have full access to the entire home, including a private heated pool/spa and a fully fenced backyard—perfect for relaxing, entertaining, and enjoying your own secluded space.☀️brbrbrbrOther Things to Note:brbr ️ Beach-Ready Convenience brbrTo make your stay effortless, the home is fully stocked with beach chairs, a beach cart, and a beach umbrella, plus all bath towels, beach towels, and linens—just pack your bags and enjoy island time ☀️ brbrbrbr Parking InformationbrbrParking is available for up to 4 vehicles maximum. Please plan ahead and coordinate with your group accordingly.brbrbrbr Friendly Island ReminderbrbrThis home is located in a residential neighborhood. We kindly ask guests to be respectful of our neighbors by keeping noise at a considerate level day and night. Thank you for helping preserve the peaceful island atmosphere brbrbrbrInteraction with Guests:brbrIf you need anything during your stay, I’m always here to help! You can call or text me directly on my cell anytime. I’m available 24/7 to answer questions, share local tips ️, or assist with anything that comes up. Your comfort and peace of mind are my top priority! ✨
Bed 7

Bed

Bath 6

Bath

Sleep 19

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Exceptional(17)

$1547.43

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Private Vacation Home

Beautiful 5 Bedroom Home Directly on Siesta Key Beach!!

Siesta Key, Florida, United States

Experience the breathtaking views of this beachfront home! Located directly on Sunset Beach on Siesta Key, this 5-bedroom 4-bathroom home is a must. Inside, this home is beautifully decorated and can comfortably sleep up to 14 guests. This home comes equipped with a full kitchen, a dining area, and a spacious living room for you to enjoy time with your family and friends. Watch the spectacular sunsets from one of your multiple balconies located on each floor, or walk out your front door to the sugary white sand of our world-famous beaches. This unit also includes a very convenient outdoor shower and the use of the pool at the Siesta Key Beachside Villas just a block away. Even better still, this unit is only a short stroll into Siesta Key Village, where you can experience many of the wonderful shops and restaurants the island has to offer! With views like this, this vacation home is sure to be your choice returning year after year!br*This unit is stairs only. All guests must have the ability to use stairsbr*There is no garage parking.brbrBedroom 1 – KingbrBedroom 2 – King brBedroom 3 – King brBedroom 4 – King brBedroom 5 – Full Bunk BedbrLiving Room- Sleeper SofabrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles Rentals,brOne Complimentary Parking Space,brWifi,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool/Hot tub Access,brAccess to Siesta Beach Pickleball Courts,brSiesta Key Trolley - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 25br*To book a Beachside Managed Property Between February 1st and April 15th, the booker must be 27 years old or older. br*Security Authorization Hold taken upon check-in. Amount: $1,500
Bed 5

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Bath 4

Bath

Sleep 14

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