Home Vacation Rentals By Owner In Siesta Key, FL

Showing 1620 Of 2077 Vacation Rentals
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$459.45

/ Nightly
Apartment

Siesta Cool : Only Minutes Walk to Siesta Beach!

Siesta Key, Florida, United States

Light, bright and cozy in the HEART of Siesta Key Village! Open floor plan including queen-sized murphy bed, Smart TVs, &Strong WIFI. Amazing balcony for the best people watching on Ocean Blvd. Quick & easy three minute walk will put you on the #1 Beach in the USA, Siesta Beach! This beautifully appointed apt. is perfect for those who will not mind the buzz and energy of our busy little Village. No need for a car to get around. You are where everyone wants to be already. Very walkable!brbrThe spacebrVery unique because of it’s proximity to the beach and the heart of Siesta Key VillagebrbrGuest accessbrAccess through a locked gate and up a set of stairs. There is also partial access to an elevator that is used primarily for the cool store downstairs but can be accessed if absolutely necessary. Amazing people watching from the very private and cool balconybrbrOther things to notebrRental age restrictions:br-This property has a minimum primary renter age requirement of 25.br- Upon booking, a signed rental agreement and government issued photo identification are required prior to receiving an electronic access code to the property.br- Pets are welcome, however, we do charge a $150 non-refundable fee per pet*.br*Due to online booking policies, some payments may need to be submitted after the booking is reserved and confirmed. Please let us know if you have questions about the policies prior to booking.br-Parking: There is only one space for parking.br- Island Sewer System: Our Island sewer system is very fragile. Please do not flush anything except toilet paper. No Wipes! Please discard in the trash.br- Towels may not be hung over the balcony railing at any time.br-Stays in excess of three weeks shall incur an additional cleaning fee.brbrPlease remember that you're staying in an apartment, not a hotel. Please treat the space with respect. If any problems arise, we will do our best to take action ASAP, but there is no one living on-site 24/7. Thank you for your understanding.
Bed 2

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Bath 1

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Sleep 3

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Exceptional(3)

$327.99

/ Nightly
Condo

Fully renovated Villa on Siesta Key, Heated Pool, Walk to Siesta and Crescent Beaches!

Siesta Key, Florida, United States

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Moonmist Circle-Steps to Heated Pool! brbr brbrEscape to this updated villa in peaceful Polynesian Gardens, just a 12-minute walk from Crescent Beach on Siesta Key. Enjoy Gulf sunsets, mornings fishing off the private pier, and a large outdoor patio with BBQ and dining area. With plenty of parking and a heated community pool just steps away, it’s the perfect beach getaway. brbr brbrLOCATION HIGHLIGHTS: brbr- Peaceful Polynesian Gardens neighborhood brbr- 12-minute walk to Crescent Beach brbr- Steps from heated community pool brbr- Short drive to Sarasota attractions, shopping, and dining brbr- Private community fishing pier brbr brbrPROPERTY FEATURES: brbr- 2 bedrooms, 2 bathroom villa (1120 sq ft) brbr- Private washer & dryer brbr- Ample parking: carport plus additional pad space brbr- Dedicated WIFI and cable brbr- Exterior security cameras (no cameras inside) brbr- Central AC with ceiling fans brbr brbrLIVING ROOM: brbr- Spacious living area, 65 Smart TV brbr- Sunroom with views of lush landscaping brbr brbrKITCHEN AND DINING: brbr- Fully equipped kitchen with stainless appliances brbr- Dining table seats 4 brbr- Dining area on large outdoor patio brbr- BBQ available for outdoor meals brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom; queen bed, access to lanai, ensuite bathroom brbr- Master ensuite bathroom: vanity with walk-in shower, glass doors brbr- Guest bedroom with twin beds brbr- Guest bathroom: tub/shower combo, spacious vanity brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: a couple of beach chairs, beach umbrella, and beach towels brbr brbrIMPORTANT INFO: brbr- No smoking or vaping brbr- No pets allowed brbr brbrLOCK IN YOUR BEACH GETAWAY NOWbrbrWe 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.brbrThis property does not allow Emotional Support Animals in addition to their no pet policy.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.
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Bath 2

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Sleep 4

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Exceptional(10)

$435.52

/ Nightly
Private Vacation Home

Stunning 3 Bedroom Townhome With Rooftop Sun Deck Steps From Siesta Key Beach!

Siesta Key, Florida, United States

Welcome to Surfside Swank! Where you will experience beautiful Siesta Key Living! This 3-Bedroom, 2.5-bathroom home sleeps up to 6. Relax on the spacious rooftop sun deck and take in the amazing sweeping views of our world-famous beach, Siesta Key. Inside, on the first living level, you will find a large, open living area, a half bathroom, a nice sized balcony for enjoying that island breeze, and a large kitchen with plenty of space to cook in. The second living level has 3 bedrooms, 2 full baths, a washer and dryer, and another balcony off the bedrooms. Up one more flight of stairs is the large rooftop sun deck, perfect for watching gorgeous sunsets all year round. This home is equipped with 2 parking spaces: 1 in the drive way and 1 carport space in the rear. For your convenience, there is an onsite beach access path that will lead you to the sugary sands and crystal-clear waters. This home is just a short stroll to the Siesta Key Village with a large variety of dining and shopping options. Capture your piece of paradise with this fabulous Siesta Key townhome.br*Stairs only. All guests must have the ability to use stairs.br*Pool and Hot Tub access located off site. There is no pool or hot tub on property.brbrBedroom 1: KingbrBedroom 2: KingbrBedroom 3: Twin 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: 27br*Security Authorization Hold taken upon check-in. Amount: $1,000
Bed 3

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Bath 2

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Sleep 8

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Exceptional(15)

$750.19

/ Nightly
Private Vacation Home

Perfect location Walk to the village and beach Private Balcony Heated Pool

Siesta Key, Florida, United States

Facing a stretch of Siesta Key’s Grand Canal, this 3-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.brbrUpon 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. brbrA paved walk borders the driveway and leads to the home’s entrance, . Continue following the path to access the secluded shared pool, private cabana, dining table and chairs, and barbecue grill.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 .brbrThe distinctive combination of open concept interior and expansive outdoor gathering area makes this home ideal for families brLocated on Canal road this beautiful home has all the features to make your stay wonderful. Location is between the Beach and the Village . Weather you like the fun in the village, sunset on the beach this location covers both!
Bed 3

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Bath 2

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Sleep 8

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Exceptional(6)

$509.68

/ Nightly
Private Vacation Home

Siesta Key Village, Pool, Beach Access 4-min. Walk, 3bdr

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 two-story townhouse style location, Siesta Key Dream’s closest unit to the Village, includes 3 spacious bedrooms that are perfect for up to 10 guests. On the first floor, you’ll experience an open floor plan connecting a welcoming living room, a dining room that seats 6, and kitchen featuring stainless steel appliances. On the second floor, you’ll find three bedrooms and two bathrooms. The main bedroom has an ensuite bathroom, tub with jets, and a walkout balcony perfect for a coffee and a read. In the guest room, you’ll see a Juliet balcony that provides fantastic view of the pool below, the keys greenery, and surrounding neighborhoods. This location provides free, high-speed internet & Wi-Fi, three HD Televisions 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. If needed, this rental can accommodate up to seven beds, which includes a queen sofa bed on the first floor & a fold-away bed on the second floor.brbrOutside, you’ll have a shared, heated pool and 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 sun loungers, large umbrellas for shade, dining tables, 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 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, Public Beach Access Point #5 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. The Siesta Village offers a wide-range of dining and entertainment options from live music, gourmet donuts, coffee, and seafood to award-winning steakhouses. brbrWe recognize that parking can be difficult to locate, which is why this vacation rental has TWO private-reserved parking 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 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, 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 beach towels, beach chairs, a beach blanket, a cooler, an umbrella, and a cart to transport your items easily! Traveling with your children We offer many baby items, including complementary cribs and highchairs.brbrShortly after you secure your vacation rental, you will receive a link where you can book local experiences provided by vendors throughout the island. For an additional charge, 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 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.brbrLooking for a larger space Siesta Key Dreams offers the entire complex to rent.brbrPayment: 50% at time of booking, 50% 7-days prior to reservation datebrParking: Two reserved parking spaces (2 vehicle max)brCheck Out: 10AMbrCheck In: 3PMbrQuiet Hours: 10PM - 7AM brPool/Backyard Hours: 8AM - 10PMbrNo smokingbrLarge Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key Dreams brPets: Allowed for additional charges, guests are required to notify Siesta Key Dreams of pet during the booking process. Pets are not allowed in shared spaces (Ie: shared pools, BBQ areas, patios). Other pets, besides dogs require approval by Siesta Key DreamsbrAdditional Details: See Vacation Rental Agreement for all details
Bed 3

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Bath 2

Bath

Sleep 10

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Exceptional(4)

$439.53

/ Nightly
Private Vacation Home

Siesta Key Village, Pool, Beach Access 4-min. Walk, 3bdr

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 two-story townhouse style location, Siesta Key Dream’s closest unit to the Village, includes 3 spacious bedrooms that are perfect for up to 10 guests. On the first floor, you’ll experience an open floor plan connecting a welcoming living room, a dining room that seats 6, and kitchen featuring stainless steel appliances. On the second floor, you’ll find three bedrooms and two bathrooms. The main bedroom has an ensuite bathroom, tub with jets, and a walkout balcony perfect for a coffee and a read. In the guest room, you’ll see a Juliet balcony that provides fantastic view of the pool below, the keys greenery, and surrounding neighborhoods. This location provides free, high-speed internet & Wi-Fi, three HD Televisions 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. If needed, this rental can accommodate up to seven beds, which includes a queen sofa bed on the first floor & a fold-away bed on the second floor.brbrOutside, you’ll have a shared, heated pool and 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 sun loungers, large umbrellas for shade, dining tables, 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 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, Public Beach Access Point #5 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. The Siesta Village offers a wide-range of dining and entertainment options from live music, gourmet donuts, coffee, and seafood to award-winning steakhouses. brbrWe recognize that parking can be difficult to locate, which is why this vacation rental has TWO private-reserved parking 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 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, 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 beach towels, beach chairs, a beach blanket, a cooler, an umbrella, and a cart to transport your items easily! Traveling with your children We offer many baby items, including complementary cribs and highchairs.brbrShortly after you secure your vacation rental, you will receive a link where you can book local experiences provided by vendors throughout the island. For an additional charge, 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 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.brbrLooking for a larger space Siesta Key Dreams offers the entire complex to rent.brbrPayment: 50% at time of booking, 50% 7-days prior to reservation datebrParking: Two reserved parking spaces (2 vehicle max)brCheck Out: 10AMbrCheck In: 3PMbrQuiet Hours: 10PM - 7AM brPool/Backyard Hours: 8AM - 10PMbrNo smokingbrLarge Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key Dreams brPets: Allowed for additional charges, guests are required to notify Siesta Key Dreams of pet during the booking process. Pets are not allowed in shared spaces (Ie: shared pools, BBQ areas, patios). Other pets, besides dogs require approval by Siesta Key DreamsbrAdditional Details: See Vacation Rental Agreement for all details
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Bath 2

Bath

Sleep 10

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Exceptional(10)

$273.49

/ Nightly
Condo

Siesta Key Village, Pool, Beach Access 4-min. Walk, 1bdr

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.brbrOn the ground floor of a three-story townhouse style location, this condo is Siesta Key Dream’s closest unit to the Village. It includes a bright, welcoming 1-bedroom unit with a full bathroom, kitchen, & living room. A king bed is in the bedroom, and in the living room a pull-out couch turns into a queen mattress. This location provides free, high-speed internet & WiFi, an HD Television equipped with live sports & extension channel options via free DirecTV Stream, and electric appliances (fridge, oven, dishwasher, Keurig-pods, washer/dryer) so you will not miss a beat.brbrOutside, you’ll find a shared, heated pool and 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 chaise lounge chairs, large umbrellas for shade, dining tables, and a BBQ for use. This outdoor space is perfect for relaxing or a night in with 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. brbrIf you’re looking to soak up the sun and clear waters, the beaches of Siesta Keys 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. 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 ONE private, reserved space 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, umbrella, blanket, cooler and a cart 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.brbrLooking for a larger space Siesta Key Dreams offers a 3 bedroom and or combine the units for 4 or 8-bedrooms! Contact us to learn more.brbrCheck 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: Allowed for additional charges, guests are required to notify Siesta Key Dreams of pet during the booking process. Pets are not allowed in shared spaces (Ie: shared pools, bbq areas, patios). Other pets, besides dogs require approval by Siesta Key DreamsbrAdditional Details: See Vacation Rental Agreement for all details
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Bath 1

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Sleep 4

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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

Bed

Bath 9

Bath

Sleep 18

Sleeps

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$358.09

/ Nightly
Condo

Beachfront View and Lovely Sunsets - A210, Free Boat Docks & WiFi

Siesta Key, Florida, United States

Bright, airy, comfortable vacation rental located on the second floor with easy elevator access and beautiful beach views. The condo boasts three large flat screen televisions, full size washer and dryer, along with a king master bed, two twin guest room beds and a queen sleep sofa which has been upgraded with a memory foam mattress. br brThe kitchen provides all the comforts of home with ample storage and counter space. Fully equipped, you will be able to create delicious meals, scrumptious desserts or simple snacks. Three comfortable bar stools invite family or friends to join you in conversation at the large granite counter peninsula. br brIn the family room, enjoy watching the 55 inch HD flat screen television while you settle in for a relaxing evening. A reclining club chair and rocking club chair also provide you with maximum comfort. The family room couch is fitted with a queen pull out bed. The bed has been upgraded with a memory foam mattress which will afford you with a pleasant nights rest. brbrOn the lanai there is a gracious dining table which seats up to six people. There is a side table provided for food, beverage or dinnerware overflow. Enjoy the beautiful sunset around the table with family and friends…where some of the best memories are made! brbrThe master bedroom is located on the Gulf side of the condo. Open the window to enjoy the night’s breeze and lapping sound of the waves while you rest in the king bed. You can also enjoy watching the large HD flat screen TV that is mounted directly across from the bed. There is an abundance of storage space in the walk-in closet and double sized dresser. brbrA full capacity high efficiency washer and dryer is located off the master bedroom. brThe master bathroom includes a shower-bathtub combo with sliding privacy doors. There is plenty of storage area in the bathroom vanity cabinet and drawers.brbrThe second bedroom offers two comfortable twin beds, large flat screen TV, and a generous amount of storage. There is a full closet and tall chest of drawers to help you organize and settle in. Enjoy the relaxing, enjoyable feel of this room after a long day in the sun. brbrThe second bathroom is adjacent to the second bedroom. It boasts a large walk in shower that is fitted with sliding glass privacy doors. brbrPlease, be our guest! Make yourself comfortable in your vacation home away from home! brbrFisherman’s Cove, Siesta Key Gulf Front! Sandwiched between the Gulf and Blind Pass Lagoon which leads to Sarasota Bay, you can enjoy sunning or fishing from the Gulf or Lagoon or kayaking and paddle boarding. Our Siesta Key location on the island’s south end features the best shelling on the island as well. The Gulf waters are only 150 feet from your beachfront lanai. Enjoy romantic sunsets from the comfort of your apartment’s private terrace or directly on the beach. brbrYou can walk south along our beachfront and enjoy at least one mile of undeveloped property. Continue on if you wish for many miles of serenity to Casey Key.br brBring your boat or rent one for a day as the boat docks are free! Your boat trailer must be kept off property and the on-site office can provide a list of places in the area for storage. brbrDine at several excellent restaurants within walking distance, or drive to Crescent Beach approximately 2.5 miles north where there is a grocery and other stores and restaurant options. The Siesta Key Village is approximately 7 miles distance on the island. Off island trips bring you to diverse neighborhoods and shopping and dining areas within a 15 to 30 minute drive.brbrFisherman’s Cove, Siesta Key, is adjacent to Turtle Beach with picnic area, grills and boat ramp. You will drive through Turtle Beach Park to our gated community – leaving the traffic behind. Our south end of Siesta Key is known as the quieter end of the island and has a laid back feel. The action on the northern end is available via free trolley service or thru one of the free ride services that work for tips.brbrbrSleeping Arrangements - Comfortable sleeping options make this unit ideal for families or groups.brPrimary Bedroom: King bed, private en-suite bathbrGuest Bedroom: Two Twin bedsbrLiving Room; Sleeper Sofa
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

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$353.07

/ Nightly
Condo

Relax with Panoramic Gulf Views

Siesta Key, Florida, United States

Location, location, location ~ and a beautiful view from the 3rd floor corner unit that overlooks Turtle Beach.brbrNo other property on Siesta Key is built this close to the Gulf where you can hear the waves from your lanai and master bedroom windows.brbrNew updates include new king bed, new queen bed and new twin bed, and all new mattresses as well as new top bedding, includes onsite coin laundry.brbrBring your boat or rent one for a day as the boat docks are free! Your boat trailer must be kept off property and the on-site office can provide a list of places in the area for storage. brbrEach unit features cable television, wireless internet access, fully equipped kitchen, a heated community pool, boat slips, kayak launching and assigned parking. brbrNO Pets allowed. brbrThe on-site office staff is there to be of service. Please Note: For your convenience, the rental program provides a starter supply of paper products, including two rolls of toilet paper per bathroom and one roll of paper towels in the kitchen. Guests are responsible for providing any additional paper products needed during their stay.brbrDine at several excellent restaurants within walking distance, or drive to Crescent Beach approximately 2.5 miles north where there is a grocery and other stores and restaurant options. The Siesta Key Village is approximately 7 miles distance on the island. Off island trips bring you to diverse neighborhoods and shopping and dining areas within a 15 to 30 minute drive.brbrFisherman’s Cove, Siesta Key, is adjacent to Turtle Beach with picnic area, grills and boat ramp. You will drive through Turtle Beach Park to our gated community – leaving the traffic behind. Our south end of Siesta Key is known as the quieter end of the island and has a laid back feel. The action on the northern end is available via free trolley service or thru one of the free ride services that work for tips.brbrWhile you are here, you will want to visit Siesta Key Public Beach and put your toes in the world famous white sand which consists of 99% pure quartz, ultimately derived from the southern Appalachians. Over millennia, rivers carried the grains of sand into the Gulf and south along Florida’s coast. Those quartz grains are fine, without any coral or shell fragments, which results in sand with a soft, flour-like texture.brbrSleeping Arrangements - Comfortable sleeping options make this unit ideal for families or groups.brPrimary Bedroom: King bed, private en-suite bathbrGuest Bedroom: One Queen and One Twin bedbrLiving Room; Sleeper Sofa
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

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$374.65

/ Nightly
Condo

Gulf-Front Condo – Perfect Siesta Key Stay

Siesta Key, Florida, United States

Location, location, location ~ and a beautiful view from the 3rd floor corner unit that overlooks Turtle Beach.brbrNo other property on Siesta Key is built this close to the Gulf where you can hear the waves from your lanai and master bedroom windows.brbr2024 updates include new king bed, new queen bed and new twin bed, and all new mattresses as well as new top bedding.brbrBring your boat or rent one for a day as the boat docks are free! Your boat trailer must be kept off property and the on-site office can provide a list of places in the area for storage. brbrEach unit features cable television, wireless internet access, fully equipped kitchen, a heated community pool, boat slips, kayak launching and assigned parking. brbrNO Pets allowed. brbrThe on-site office staff is there to be of service. Please Note: For your convenience, the rental program provides a starter supply of paper products, including two rolls of toilet paper per bathroom and one roll of paper towels in the kitchen. Guests are responsible for providing any additional paper products needed during their stay.brbrDine at several excellent restaurants within walking distance, or drive to Crescent Beach approximately 2.5 miles north where there is a grocery and other stores and restaurant options. The Siesta Key Village is approximately 7 miles distance on the island. Off island trips bring you to diverse neighborhoods and shopping and dining areas within a 15 to 30 minute drive.brbrFisherman’s Cove, Siesta Key, is adjacent to Turtle Beach with picnic area, grills and boat ramp. You will drive through Turtle Beach Park to our gated community – leaving the traffic behind. Our south end of Siesta Key is known as the quieter end of the island and has a laid back feel. The action on the northern end is available via free trolley service or thru one of the free ride services that work for tips.brbrWhile you are here, you will want to visit Siesta Key Public Beach and put your toes in the world famous white sand which consists of 99% pure quartz, ultimately derived from the southern Appalachians. Over millennia, rivers carried the grains of sand into the Gulf of America and south along Florida’s coast. Those quartz grains are fine, without any coral or shell fragments, which results in sand with a soft, flour-like texture.brbrSleeping Arrangements - Comfortable sleeping options make this unit ideal for families or groups.brPrimary Bedroom: King bed, private en-suite bathbrGuest Bedroom: One Queen and One TwinbrLiving Room; Sleeper Sofa
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

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Exceptional(1)

$325.87

/ Nightly
Condo

Escape to the Gulf – Prime Beachfront Location

Siesta Key, Florida, United States

Come enjoy the amazing view from this one bedroom unit on the 3rd floor of our A Building - the closest to Turtle Beach. The unit has been completely updated from top to bottom including new lanai windows. You will certainly enjoy the waves and Gulf breeze. The new kitchen with granite counter, bar stools, and new appliances is well-stocked for any chef. The new coastal style furnishings throughout the unit include a sleep sofa for an extra guest or children.brbrBeach chairs, cooler and a beach umbrella are provided. brbrThe unit also provides a full sized washer and dryer and gorgeous tile throughout.brJust bring your groceries and you are ready for a relaxing week on our amazing beach. Turtle Beach is the quiet end of Siesta Key. Local vendors can deliver bikes and kayaks for you to enjoy and Siesta Key has free shuttles and a trolley to experience the island. Siesta Key Village (approx 7 miles north) is known for it's many wonderful restaurants, shopping and bars with great local live talent. brbrThis unit sleeps 4 guests. Seven night minimum and No pets.brbrFisherman’s Cove, Siesta Key Gulf Front! Sandwiched between the Gulf and Blind Pass Lagoon which leads to Sarasota Bay, you can enjoy sunning or fishing from the Gulf or Lagoon or kayaking and paddle boarding. Our Siesta Key location on the island’s south end features the best shelling on the island as well. The Gulf waters are only 150 feet from your beachfront lanai. Enjoy romantic sunsets from the comfort of your apartment’s private terrace or directly on the beach. brbrYou can walk south along our beachfront and enjoy at least one mile of undeveloped property. Continue on if you wish for many miles of serenity to Casey Key. brbrBring your boat or rent one for a day as the boat docks are free! Your boat trailer must be kept off property and the on-site office can provide a list of places in the area for storage.brbrbrEach unit features cable television, high speed internet, fully equipped kitchen, a heated community pool, a clubhouse with library, shuffleboard court, boat slips, kayak launching and assigned parking. brbrNO Pets allowed. brbrThe on-site office staff is there to be of service. Please Note: For your convenience, the rental program provides a starter supply of paper products, including two rolls of toilet paper per bathroom and one roll of paper towels in the kitchen. Guests are responsible for providing any additional paper products needed during their stay.brbrbrFisherman’s Cove, Siesta Key, is adjacent to Turtle Beach with picnic area, grills and boat ramp. You will drive through Turtle Beach Park to our gated community – leaving the traffic behind. Our south end of Siesta Key is known as the quieter end of the island and has a laid back feel. The action on the northern end is available via free trolley service or thru one of the free ride services that work for tips.brbrSleeping Arrangements - Comfortable sleeping options make this unit ideal for families or groups.brPrimary Bedroom: King bed, private en-suite bathbrLiving Room; Sleeper Sofa
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

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$374.65

/ Nightly
Condo

Breathtaking Gulf Views – Book Your Stay

Siesta Key, Florida, United States

A-204 is a beautifully remodeled unit with spectacular gulf views from the 2nd floor lanai. Our lanai is furnished with a new deep seat sofa, table and chairs for dining, and motorized floor to ceiling solar screens. brbrThe unit is tiled throughout, with a new fully equipped kitchen featuring granite counters and stainless appliances. brbrThe living room has a new fabric queen sleeper sofa and reclining love seat, Blu-ray, DVD and flat screen SMART TV (to watch your Netflix or other internet accounts, there is a dedicated internet line for this device). brbrThe master bedroom has a king sized bed, the second bedroom has one Queen bed and one Twin bed and both bedrooms have flat screen TVs. brbrWe have a new washer/dryer for your convenience, as well as new beach chairs, umbrellas, cooler, toys, beach towels and fishing gear. br brWe have tried to provide all you need for an enjoyable and relaxing vacation. Hope you love it as much as we dobrbrThough we require a Saturday to Saturday pattern in peak seasons (Mid January thru April; and June thru Mid August) we can be flexible at other times. Please callfor any other pattern of stay.brbrFisherman’s Cove is a waterfront property – sandwiched between the Gulf and Blind Pass Lagoon which leads to Sarasota Bay. Fishing from the Gulf or Lagoon is one of the main attractions. Our location is also perfect for kayaking and paddleboards. Enjoy romantic sunsets from the comfort of your apartment’s private terrace or directly on the beach. brbrBring your boat or rent one for a day as the docks are free! Your boat trailer must be kept off property and the on-site office can provide a list of places in the area for storage. brEach unit features cable television, wireless internet access, fully equipped kitchen, a heated community pool, a clubhouse with library, shuffleboard court, boat slips, kayak launching and assigned parking. NO Pets allowed. brbrDine at several excellent restaurants within walking distance or drive to Crescent Beach approximately 2.5 miles north where there is a grocery and other stores and restaurant options. The Siesta Key Village is approximately 7 miles distance on the island. Off island trips bring you to diverse neighborhoods and shopping and dining areas within a 15 to 30 minute drive.brbrSarasota is known as the Cultural Center of Florida with many live theaters and art galleries. Definitely worth a visit is the Ringling Campus with the State Art Museum of Florida, the Circus Museum and Ca’ d’Zan Mansion on Sarasota Bay. Marie Selby Botanical Gardens is another very special attraction in Sarasota for both adults and children. brbrTurtle Beach is known for swimming, shelling, and sunning. Fisherman’s Cove is adjacent to Turtle Beach with picnic area, grills and boat ramp. You will drive through Turtle Beach to our gated community – leaving the traffic behind. Our south end of Siesta Key is known as the quieter end of the island. brbrWhile you are here, you will want to visit Siesta Beach and put your toes in the world famous white sand which consists of 99% pure quartz, ultimately derived from the southern Appalachians. Over millennia, rivers carried the grains of sand into the Gulf and south along Florida’s coast. Those quartz grains are fine, without any coral or shell fragments, which results in sand with a soft, flour-like texture.brbrSleeping Arrangements - Comfortable sleeping options make this unit ideal for families or groups.brPrimary Bedroom: King bed, private en-suite bath with walk-in shower. brGuest Bedroom: One Queen bed and One twin bed brLiving Room; Sleeper Sofa
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

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$358.09

/ Nightly
Condo

Endless Gulf Views, Endless Relaxation

Siesta Key, Florida, United States

This 2nd floor unit has been completely remodeled with sophistication. Spend your vacation with a superb Gulf View while reclining on new leather and wicker furnishings and watching the large flat screen wall mounted TV. Gorgeous tile throughout and a brand new kitchen with stainless appliances and a washer and dryer. Unit features a king bed in the master and a guest bedroom with two twin beds. There is a sleeper sofa in the living room with Blu-Ray DVD Player and Nintendo Wii included for your enjoyment. brbrThough we require a Saturday to Saturday.brbrFisherman’s Cove, Siesta Key Gulf Front! Sandwiched between the Gulf and Blind Pass Lagoon which leads to Sarasota Bay, you can enjoy sunning or fishing from the Gulf or Lagoon or kayaking and paddle boarding. Our Siesta Key location on the island’s south end features the best shelling on the island as well. The Gulf waters are only 150 feet from your beachfront lanai. Enjoy romantic sunsets from the comfort of your apartment’s private terrace or directly on the beach. brbrYou can walk south along our beachfront and enjoy at least one mile of undeveloped property. Continue on if you wish for many miles of serenity to Casey Key.br brBring your boat or rent one for a day as the boat docks are free! Your boat trailer must be kept off property and the on-site office can provide a list of places in the area for storage. brbrEach unit features cable television, wireless internet access, fully equipped kitchen, a heated community pool, a clubhouse with library, shuffleboard court, boat slips, kayak launching and assigned parking. brbrNO Pets allowed. brbrThe on-site office staff is there to be of service.brbrDine at several excellent restaurants within walking distance, or drive to Crescent Beach approximately 2.5 miles north where there is a grocery and other stores and restaurant options. The Siesta Key Village is approximately 7 miles distance on the island. Off island trips bring you to diverse neighborhoods and shopping and dining areas within a 15 to 30 minute drive.brbrFisherman’s Cove, Siesta Key, is adjacent to Turtle Beach with picnic area, grills and boat ramp. You will drive through Turtle Beach Park to our gated community – leaving the traffic behind. Our south end of Siesta Key is known as the quieter end of the island and has a laid back feel. The action on the northern end is available via free trolley service or thru one of the free ride services that work for tips.brbrWhile you are here, you will want to visit Siesta Key Public Beach and put your toes in the world famous white sand which consists of 99% pure quartz, ultimately derived from the southern Appalachians. Over millennia, rivers carried the grains of sand into the Gulf of Mexico and south along Florida’s coast. Those quartz grains are fine, without any coral or shell fragments, which results in sand with a soft, flour-like texture.br brSarasota is known as the Cultural Center of Florida with many live theaters and art galleries. Definitely worth a visit is the Ringling Campus with the State Art Museum of Florida, the Circus Museum and Ca’ d’Zan Mansion on Sarasota Bay. Marie Selby Botanical Gardens is another very special attraction in Sarasota for both adults and children.brbrbrSleeping Arrangements - Comfortable sleeping options make this unit ideal for families or groups.brPrimary Bedroom: King bed, private en-suite bathbrGuest Bedroom: Two TwinsbrLiving Room; Sleeper Sofa
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

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$378.5

/ Nightly
Condo

Front-Row Gulf Views & Coastal Comfort

Siesta Key, Florida, United States

Enjoy breathtaking Gulf sunsets and the soothing sounds of the surf from your second-floor beachfront condo—just one easy flight of stairs or a convenient elevator ride away. Unit A205 offers the perfect setting to take in the beauty of the sea and sky from sunrise to sunset.brbrOn the Gulf side, a spacious lanai provides unobstructed 180-degree views. Watch dolphins and manatees glide by while boats pass along the horizon. On the inland side, enjoy views of Blind Pass Lagoon and your private boat dock, with direct access to the bird sanctuary, Little Sarasota Bay, and the Gulf.brbrA205 is designed for relaxed coastal living—light-filled, airy, and comfortably appointed. Recent updates include a new king bed in the master bedroom and two Twin beds in the second bedroom, There is ceramic tile flooring in both bedrooms, a lanai dining set for four, and a large flat-screen TV in the living room, perfectly positioned for easy viewing from the lanai.brbrPerfectly situated between the Gulf and Blind Pass Lagoon, you can enjoy sunbathing, fishing, kayaking, or paddleboarding right outside your door. Located on the quieter south end of Siesta Key, this area is known for some of the island’s best shelling and peaceful, uncrowded beaches. The Gulf shoreline is just steps—approximately 150 feet—from your lanai.brbrTake a leisurely walk south along more than a mile of undeveloped beachfront, or continue for miles of natural beauty all the way toward Casey Key.brbrBring your boat or rent one locally—complimentary boat docks are available on-site. (Please note: boat trailers must be stored off property; the office can provide local storage options.)brbrCommunity amenities include:brbrHeated poolbrClubhouse with librarybrShuffleboard courtbrBoat slips and kayak launchbrAssigned parkingbrCable TV and high-speed Wi-FibrFully equipped kitchenbrbrPlease note: No pets allowed.brbrThe on-site office staff is available to assist during your stay, ensuring a smooth and enjoyable experience.brbrYou’ll find several excellent restaurants within walking distance, or take a short drive (about 2.5 miles) to Crescent Beach for groceries, dining, and shopping. Siesta Key Village is approximately 7 miles north, offering vibrant nightlife, boutiques, and waterfront dining.brbrFisherman’s Cove is located adjacent to Turtle Beach Park, featuring picnic areas, grills, and a public boat ramp. Access to the property is through this quiet, scenic area, creating a peaceful, tucked-away feel far from the island’s busier areas.brbrWhile you're here, don’t miss Siesta Key Public Beach, famous for its powdery white sand made of 99% pure quartz—cool to the touch and unlike any other beach in the world.brbrSarasota, known as Florida’s Cultural Coast, offers a rich variety of attractions including live theater, art galleries, and renowned destinations such as The Ringling Museum, Ca’ d’Zan Mansion, and Marie Selby Botanical Gardens.brbrSleeping Arrangements - Comfortable sleeping options make this unit ideal for families or groups.brPrimary Bedroom: King bed, private en-suite bathbrGuest Bedroom: One Queen and One TwinbrLiving Room; Sleeper Sofa
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

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Exceptional(2)

$1175.74

/ Nightly
Private Vacation Home

Siesta Sunset Sanctuary: Incredible Sunset Views!

Siesta Key, Florida, United States

Siesta Sunset Sanctuary by Siesta Key Luxury Rental Properties brbrWelcome to Siesta Sunset Sanctuary, an architecturally stunning waterfront retreat designed by award-winning Sarasota architect Guy Peterson. This elevated four bedroom, five and a half bath luxury home blends modern coastal elegance with serene water views, offering the perfect escape just a short walk to Siesta Village and nearby Siesta Key Beach access. With a private pool and spa, stylish suites, and exceptional outdoor living spaces, this home is ideal for families and groups seeking an elevated Siesta Key getaway. brbrHighlights br• Waterfront home with private seawall for fishing br• 4 Bedrooms, 5.5 Bathrooms br• 3 King Beds, 1 Queen Bed br• Architect-designed residence by Guy Peterson br• Walk to Siesta Key Village and nearby beach access br• Private Pool and Spa with Waterfall Feature br• Elevator (for luggage use only) br• Fenced Backyard with Outdoor Dining and Lounge Areas br• Beach Cart and Beach Chairs Included br• Pet friendly with host approval and additional fee br• 4 Parking Spaces brbrThis contemporary coastal home is designed to maximize the beauty of its waterfront setting. The private pool and spa feature a relaxing cascading waterfall surrounded by tropical landscaping, while the fenced backyard offers inviting outdoor dining and lounge areas perfect for unwinding after a day at the beach. Guests can fish directly from the private seawall, making it easy to enjoy the water from the comfort of home. With stylish architecture, thoughtful outdoor design, and seamless indoor-outdoor living, Siesta Sunset Sanctuary offers a peaceful and luxurious retreat. brbrInside, the open concept living room, dining area, and gourmet kitchen create an airy and sophisticated main living level, complete with premium appliances and a spacious island ideal for gathering and entertaining. Multiple lounge areas throughout the home ensure that everyone has room to relax, whether spending quality time together or enjoying quiet moments overlooking the water. brbrThe home features three private ensuite bedrooms, each designed as a comfortable and peaceful retreat. The primary suite on the fourth floor offers a king bed, double vanities, walk-in shower, and standalone soaking tub. A second king suite on the third floor also features a soaking tub and walk-in shower. The third king suite provides a spa-inspired bathroom with a walk-in shower. Finally, the fourth-floor bedroom features a queen bed and its own ensuite bathroom with a walk-in shower, providing comfortable and flexible accommodations for guests. brbrA full bathroom is conveniently located near the pool, and a half bath sits just off the main living area, providing added ease for groups. brbrRoom Details br-Primary Suite (4th Floor): King bed, ensuite bathroom with double vanity, walk-in shower, standalone soaking tub br-Second Bedroom (3rd Floor): King bed, ensuite bathroom with walk-in shower and standalone soaking tub br- Third Bedroom (3rd Floor): King bed, ensuite bathroom with walk-in shower br- Fourth Bedroom (4th Floor Queen bed, ensuite bathroom with walk-in shower br- Fifth Bathroom (1st Floor): Full bathroom with walk-in shower, located near pool br-Half Bathroom (2nd Floor): Located off the main living level brbrSiesta Sunset Sanctuary includes a fenced backyard, beach chairs, a beach cart, WiFi, multiple lounge areas, and reserved parking for four vehicles. Its prime location allows guests to walk easily to Siesta Village, where restaurants, boutiques, cafes, ice cream shops, and live music create the perfect island atmosphere. Beach access is also nearby, allowing you to enjoy Siesta Key’s famous white quartz sand within minutes. Dogs are welcome with prior approval and applicable fees. brbrWith its modern architectural design, private pool and spa, elegant interior spaces, and unbeatable proximity to Siesta Village and Siesta Key Beach, Siesta Sunset Sanctuary by Siesta Key Luxury Rental Properties offers the ideal coastal retreat for guests seeking luxury, comfort, and convenience. brbrBook your stay at Siesta Sunset Sanctuary today and discover the best of Siesta Key! brbr- brPlease Note: br-The elevator is for luggage use only. br-The garage is not for guest use. brThis property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated; see our Siesta Key Luxury Rental Policies for full details. br4 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. brWe 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. brPlease 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 4

Bed

Bath 5

Bath

Sleep 8

Sleeps

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Exceptional(46)

$423.42

/ Nightly
Condo

Siesta Key Beach Front Condo! Breathtaking view!

Siesta Key, Florida, United States

brThis beautiful 2 bedroom, 2 full bath condo sleeps 6 and is located directly on one of the TOP 10 BEACHES IN THE WORLD! brbrSiesta Key has been a family favorite place for many years and once you stay here you will want to come back! Crescent Arms is a gated community, and this unit is literally steps to the sugary white sand. It is in a great location with a short walk to restaurants, a marina, an ice cream shop, grocery store, a liquor store and bars, live music, shops, and more! Another great adventure won’t cost you a thing! This unit is a short walk to the point of rocks where you can find beautiful shells and sea treasures. brbrYou will be very comfortable in every room with all updated beds, living and dining area furniture & comfortable new lanai furniture. The master bedroom has a king size bed, flat screen tv, and plenty of storage. The second bedroom offers 2 full size beds, flat screen tv and great storage as well. The brand-new kitchen offers a refrigerator/freezer with ice maker, stove, oven, dishwasher, and microwave. There are two all updated full baths, one with a tub/shower and one with a walk-in shower. The living and dining areas are very open with beautiful views of the beach and the screened lanai is the perfect place for relaxing any time of day! brbrMake wonderful memories and book your next vacation with us!! Let us know if we can answer any questions for you. Thank You!
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

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Exceptional(2)

$2193.2

/ Nightly
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

Bed

Bath 7

Bath

Sleep 20

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