Home Vacation Home Rentals By Owner In Siesta Key, FL

Showing 480 Of 517 Vacation Rentals
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Exceptional(2)

$372.74

/ Nightly
Private Vacation Home

Cozy Home Near the Beach - Aloha Kai #37 - Roelens

Siesta Key, Florida, United States

Aloha Kai #37brbrA Siesta Key Beachside Bliss Awaits!brbrEscape to the sun-kissed shores of Siesta Key and immerse yourself in the laid-back luxury of Aloha Kai #37. This charming beach 2-bedroom house is your perfect retreat, where the soothing sounds of the Gulf of Mexico and the vibrant energy of Crescent Beach create an unforgettable vacation. Maximizing comfort in a cozy layout, Aloha Kai #37 invites you to kick off your shoes, sip morning coffee on your private patio, and dive into a world of relaxation and adventure. Here's what makes this home so special:brbrBedding Arrangement:br2 Bedrooms:brMaster Bedroom with King-size bed, Smart TV and Ensuite BathroombrGuest Bedroom 1 with 2 Twin-size beds, Smart TVbrAdditional Sleep: Sleep Sofa in the living area.brTop Features:brSleeps 6brLargest Pool on Siesta Key: Dive into the expansive, sparkling pool surrounded by a large lounging deck with plenty of poolside lounges, tables, and chairs for ultimate relaxation.brDirect Beach Access: Steps away from the powdery white sands of Crescent Beach, rated the #1 beach in the U.S., with shaded pavilions and lounge chairs for your comfort.brFront Screened Porch and Back Patio: Sip coffee in the mornings in your screened porch or curl up with a good book. Enjoy balmy evenings at home on the back patio to relax and unwind after an eventful day.brCommunity Amenities: Enjoy shuffleboard, ping pong, and a poolside community room, plus complimentary beach toys and floats for fun in the sun.brPerfect Home Base Location: Plenty of things to do and unique places to visit. Stroll to nearby restaurants, ice cream parlors, and bars, or hop on the Siesta Key trolley for easy island exploration. There are plenty of activities for children of all ages, thrill seekers and those who want to experience the natural wonders of the region.brNestled within the gated, family-friendly Aloha Kai resort, Aloha Kai #37 places you in the heart of Siesta Key's Crescent Beach, famous for its dazzling quartz sand and emerald waters. Whether you're lounging under a shaded beach pavilion, taking a soul-soothing walk along the 3-mile shoreline, or marveling at breathtaking Gulf sunsets, this little gem offers the perfect blend of tranquility and convenience. With friendly staff, 24-hour support, and daily trash removal, your stay will be seamless and stress-free. Book your Siesta Key escape at Aloha Kai #37 today and create memories that will last a lifetime!brbrRoelens Vacations is proud to partner with the city to promote recycling and make our community more sustainable and greener. Thank you for your cooperation and for being part of a more sustainable future!brDISCLAIMERS: br**10% deposit is due at time of booking, final payment is due 60 days out. Any reservations made within 60 days require full payment. No refunds will be given on deposits.**brThis home does not allow pets. brThis home has a minimum age requirement of 25 to book. Smoking is not allowed on the property.brEvery Villa has ONE designated parking space and parking pass. Additional vehicles and guests must register in the front office for a separate parking pass.
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

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Exceptional(3)

$296.9

/ Nightly
Private Vacation Home

Unveiling Joyful Beachside Moments – Aloha Kai #62 - Roelens

Siesta Key, Florida, United States

Aloha Kai #62brbrA Siesta Key Beachside Bliss Awaits!brbrEscape to the sun-kissed shores of Siesta Key and immerse yourself in the laid-back luxury of Aloha Kai #62. This adorable 1 bedroom, 1 bath unit is your perfect retreat, where the soothing sounds of the Gulf of Mexico and the vibrant energy of Crescent Beach create an unforgettable vacation. Unveiling boundless joy in a snug sanctuary, Aloha Kai #62 invites you to kick off your shoes, sip morning coffee on your private patio, and dive into a world of relaxation and adventure. Here's what makes this home so special:brbrBedding Arrangement:br1 Bedroom:brMaster Suite: King-size bed and Smart TVbrAdditional Sleep: Queen-size sleep sofa in the lounge areabrTop Features:brSleeps 4brLargest Pool on Siesta Key: Dive into the expansive, sparkling pool surrounded by a large lounging deck with plenty of poolside lounges, tables, and chairs for ultimate relaxation.brDirect Beach Access: Steps away from the powdery white sands of Crescent Beach, rated the #1 beach in the U.S., with shaded pavilions and lounge chairs for your comfort.brFront Screened Porch and Back Patio: Sip coffee in the mornings in your screened porch or curl up with a good book. Enjoy balmy evenings at home on the back patio to relax and unwind after an eventful day.brCommunity Amenities: Enjoy shuffleboard, ping pong, and a poolside community room, plus complimentary beach toys and floats for fun in the sun.brPerfect Home Base Location: Plenty of things to do and unique places to visit. Stroll to nearby restaurants, ice cream parlors, and bars, or hop on the Siesta Key trolley for easy island exploration. There are plenty of activities for children of all ages, thrill seekers and those who want to experience the natural wonders of the region.brNestled within the gated, family-friendly Aloha Kai resort, Aloha Kai #62 places you in the heart of Siesta Key's Crescent Beach, famous for its dazzling quartz sand and emerald waters. Whether you're lounging under a shaded beach pavilion, taking a soul-soothing walk along the 3-mile shoreline, or marveling at breathtaking Gulf sunsets, this little gem offers the perfect blend of tranquility and convenience. With friendly staff, 24-hour support, and daily trash removal, your stay will be seamless and stress-free. Book your Siesta Key escape at Aloha Kai #62 today and create memories that will last a lifetime!brbrRoelens Vacations is proud to partner with the city to promote recycling and make our community more sustainable and greener. Thank you for your cooperation and for being part of a more sustainable future!brbrDISCLAIMERS: br**10% deposit is due at time of booking, final payment is due 60 days out. Any reservations made within 60 days require full payment. No refunds will be given on deposits.**brThis home does not allow pets. brThis home has a minimum age requirement of 25 to book. Smoking is not allowed on the property.brEvery Villa has ONE designated parking space and parking pass. Additional vehicles and guests must register in the front office for a separate parking pass.
Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps

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Exceptional(23)

$349.72

/ Nightly
Private Vacation Home

Walkable to Siesta Key Village, Saltwater Pool/Spa, BBQ, Pond Views, Bike to Beach in 6 mins

Siesta Key, Florida, United States

Welcome to Ocean Beach Gleason Home! brbr brbrNewly renovated and furnished! New pics to come! brbr brbrThis beautiful 4-bedroom, 2-bathroom home on Siesta Key is perfect for families or groups looking for a luxurious and relaxing getaway. With over 1,900 square feet of heated space and a total of 2,500 square feet, this single-level home offers plenty of room to spread out. The property features a private saltwater pool and spa, with optional heating, overlooking a serene lake, providing a picturesque backdrop for your stay. brbr brbrLOCATION HIGHLIGHTS: brbr- 6-minute bike ride to Siesta Key Beach brbr- Close to Siesta Key Village dining and shops brbr- Peaceful lakefront setting brbr- Quiet residential neighborhood brbr- Easy access to island hotspots brbr brbrPROPERTY FEATURES: brbr- 4 bedrooms, 2 bathrooms pool home brbr- Private saltwater pool and spa (pool heat extra) brbr- Lake views from pool and patio brbr- Outdoor seating, loungers, and BBQ grill brbr- Pet-friendly for approved dog only (fee required) brbr- Dedicated WIFI and cable brbr- Self check in, keyless door lock brbr- Separate private washer and dryer room brbr brbrLIVING ROOM: brbr- Large flat-screen TV, comfortable seating for group lounging brbr- Sliding doors to pool area brbr- Open and bright layout brbr brbrKITCHEN AND DINING: brbr- High-end appliances with stone countertops and breakfast nook brbr- Dining table seats eight brbr- Open flow to patio and pool area brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom with king bed, custom closet, and ensuite bath brbr- Master ensuite bathroom: Step-in shower, large mirror, updated vanity brbr- Second bedroom with queen bed and Smart TV brbr- Third bedroom with king bed and Smart TV brbr- Fourth bedroom with king and pool access brbr- Guest bathroom: double vanity, tub/shower combo brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: a couple of beach chairs, a beach umbrella, and beach towels. brbr brbrLOCAL FAVORITES: brbr- Siesta Key Beach for powdery white sand brbr- Siesta Key Village for restaurants and nightlife brbr- Scenic bike rides around the island brbr- Waterfront dining options nearby brbr brbrIMPORTANT INFO: brbr- Pool heating available for an extra fee brbr- Dog allowed with prior approval and fee (no cats) brbr- No smoking inside or on patio brbr- Respect residential area and quiet hours brbr brbrCLICK BOOK NOW AND GET CLOSER TO THE COASTLINEbrbrAll pets must be approved so reach out to us first. Certain properties have weight and breed restrictions. For approved pets, there is an a nonrefundable pet fee of $300 plus taxes and processing fee per pet. Make sure to pick up after your dogs.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.
Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps

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Exceptional(1)

$604.61

/ Nightly
Private Vacation Home

Sunrise - Perfect Couples Retreat!

Siesta Key, Florida, United States

Sunrise by Siesta Key Luxury Rental PropertiesbrbrWelcome to Sunrise, a recently refreshed two-bedroom, one-bath vacation rental located on the east side of the Sunshine on Siesta property. Designed for small families or couples, this inviting retreat offers private beach access and a peaceful island setting just moments from the sand.brbrSunrise places guests close to Siesta Key Village, where local restaurants, shops, and island attractions are all within easy reach, creating a convenient and relaxing home base for your stay.brbrHighlightsbr• Private beach accessbr• 2 Bedrooms / 1 Bathroombr• 1 King bed and 2 Twin bedsbr• Recently refreshed homebr• Shared pool with neighboring condominiumbr• Beach chairs and beach cartbr• Shared laundry br• Pets allowed with host approval br• Shared firepitbr• 1 Parking Spotbr• Convenient Siesta Key location near dining and shoppingbrbrGuests at Sunrise enjoy access to shared amenities that enhance the Siesta Key experience. The shared pool is a short two-minute walk away at the Calini Beach Club, which also offers private beach access approximately five minutes from the home. A centrally located shared laundry area is positioned between the duplex units. The shared backyard features a BBQ grill and a firepit seating area, creating a welcoming outdoor space to relax.brbrThe living area is welcoming and comfortable, offering a cozy space to unwind after a day outdoors. The kitchen is designed for simple meal preparation, allowing guests to enjoy breakfasts at home or relaxed dinners before heading out for evening activities.brbrThe primary bedroom features a king bed and a calm, coastal atmosphere that promotes restful nights. The second bedroom includes two twin beds, ideal for children or additional guests. The bathroom features a walk-in shower and is easily accessible from both bedrooms.brbrRoom Detailsbr• Primary Bedroom: King bedbr• Second Bedroom: Two twin bedsbr• Bathroom: Walk-in showerbrbrSunrise by Siesta Key Luxury Rental Properties offers a comfortable and well located retreat with private beach access and shared pool amenities. Whether you are planning a quiet getaway or an island adventure, this home is ready to welcome you. Book your stay today and enjoy the best of Siesta Key living.brbrTraveling with a larger group Reserve both Sunrise and Sunset together as Sunshine on Siesta – the Super Unit, giving your group more space and a seamless stay.brbr-brThis home is managed by Siesta Key Luxury Rental Properties. brbrWith 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. brbr1 car 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. brbrWe 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. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. 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 3

Bed

Bath 1

Bath

Sleep 6

Sleeps

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Exceptional(1)

$487.15

/ Nightly
Private Vacation Home

Sunshine on Siesta - Refreshed Duplex!

Siesta Key, Florida, United States

Sunshine on Siesta – by Siesta Key Luxury Rental PropertiesbrbrWelcome to Sunshine on Siesta, a recently refreshed four-bedroom, two-bath Super Unit designed for families and groups who want to vacation together while enjoying space, comfort, and an unbeatable Siesta Key location. By combining both the Sunrise and Sunset residences, this home offers a unique opportunity to book the entire property at once, making it ideal for multi-generational families or friends traveling as a group.brbrLocated just steps from the Gulf, Sunshine on Siesta provides private beach access and a relaxed coastal setting close to Siesta Key Village, local dining, and shopping. This thoughtfully arranged home allows guests to enjoy shared experiences while still having room to spread out and unwind.brbrHighlightsbr• Private beach access – 5 minute walkbr• 4 Bedrooms / 2 Bathroomsbr• 2 King beds and 4 Twin bedsbr• Recently refreshed homebr• Shared pool with neighboring condominium – 2 minute walk br• Beach chairs and beach cartbr• Shared firepitbr• Washer and dryerbr• Pets allowed with host approval br• 2 Parking spotsbr• Convenient Siesta Key location near dining and shoppingbrbrSunshine on Siesta offers convenient access to shared amenities designed for relaxed island living. The shared pool is located just a two-minute walk from the home at the Calini Beach Club, which also provides private beach access about five minutes away. A shared laundry area sits between the two duplex residences, making it easy for guests booking the full Super Unit to use. The shared backyard includes a BBQ grill and a cozy firepit seating area, perfect for unwinding after a day at the beach.brbrThe Super Unit features two comfortable living areas, making it easy for larger groups to relax without feeling crowded. Each side of the home includes inviting seating and a television, perfect for movie nights or quiet evenings in. The kitchens are equipped for everyday cooking, making it easy to prepare meals, snacks, or beach-day essentials while enjoying time together indoors.brbrEach side of the home includes a primary bedroom with a king bed, offering a calm and comfortable retreat at the end of the day. The additional bedrooms feature twin beds, making them ideal for children or additional guests. Bathrooms are conveniently located and feature walk-in showers, providing easy access for everyone in the group.brbrRoom Detailsbr• Primary Bedroom 1: King bedbr• Primary Bedroom 2: King bedbr• Bedroom 3: Two twin bedsbr• Bedroom 4: Two twin bedsbrbrSunshine on Siesta by Siesta Key Luxury Rental Properties delivers the space of a private compound with the ease of private beach access and shared outdoor amenities. Whether you are planning a family reunion or a group getaway, this Super Unit offers comfort, location, and a true Siesta Key experience. Secure your dates today and start planning your coastal escape.brbr-brThis home is managed by Siesta Key Luxury Rental Properties. brbrWith 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. brbr2 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. brbrWe 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. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. 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 5

Bed

Bath 2

Bath

Sleep 12

Sleeps

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Exceptional(17)

$1951.83

/ Nightly
Private Vacation Home

#1 Rooftop Deck w/ Gulf Views - Steps to Beach

Siesta Key, Florida, United States

Summary:brbrVunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result Unmatched value for travelers who expect more from their getaway.brbrbrbrThe Space:brbrThis house is spectacular, and the rooftop deck (elevator access) is unreal with what it offers and the 360-degree views that it provides! With an outdoor kitchen area that includes ice maker, beverage refrigerators, and grill (natural gas), there is no better view for the chef on all of Siesta Key. There are multiple dining options including a banquet table for 12. There are also sunning and lounging chairs overlooking the Gulf, and a rear turf space with all sorts of games, seating, and a large TV for movies on the lawn'. It's really a remarkable space! The heated saltwater pool and spa features a waterslide, two sun-shelf areas perfect for lounging or for the kids to play, and two water curtains that rain down from the ceiling into the pool and create a wonderful ambiance. The covered patio space includes 2 large smart TVs, multiple seating and dining options, ping pong and putt putt! These spaces are all within the fenced backyard for privacy and security making it family friendly and perfect for the home's pet friendly policy (fees and restrictions apply). As you go up in this home, you'll find multiple balconies with seating and amazing views on all levels, ending at the gigantic roof top deck that features wide open Gulf of Mexico and Siesta Key views.This nearly 4,000 square foot home has soaring 10-foot ceilings, so it feels open and spacious throughout! The floor plan is so inviting for a family or travel group. There are great views and balconies on all levels. This home has an elevator with service to all floors, including the rooftop deck. This home provides 6 bedrooms (6 with en suite baths), and 6 full baths. There are 5 king beds and a custom full-over queen bunk bed. It comfortably sleeps 14 people in beds. The great room is on the top floor and that provides the best views for everyone to enjoy. It is set up as the perfect gathering space that includes the kitchen, living, and dining areas of the home with access to a balcony with great views. The kitchen is fully stocked, and we mean that because we know how important it is to you, our valued guests! Not only is it stocked, but it's also stocked with the products and manufacturers you trust. This home also offers a club room or secondary living space. The club room is on the first living level.This Siesta Key luxury vacation rental features Smart TVs with cable and streaming services, as well as Free Wi-Fi throughout the property - including the outside areas for complete coverage for all of your work or personal needs. TVs in all bedrooms.Accessibility - in addition to the home's elevator access to all levels, most doorways and walkways are 30 inches or larger, and walk-in showers in Baths 1-5. Please see the Photos, 3D Tour, & Video for this home.brbrbrbrFloor Plan Description (by level):brbrbrbrGround Level:brbrFree parking for up to 6 vehicles (2 covered spaces, and 4 spaces in the driveway). On this ground level you'll find the fully fenced pool and backyard area (pet friendly - fees and restrictions apply), including the covered patio space and putt putt. As we already shared, the pool and covered patio areas are great spaces! In addition to all the details already shared, there are ceiling fans throughout the space for added comfort and an outdoor grill (natural gas). The home's beach equipment can be found here, which includes 2 beach wagons, 2 coolers, 6 beach chairs, and 4 bikes. We include a full refrigerator and freezer (with ice maker) here as well so your beach prep and breakdown, and your use of the home and pool is that much easier. These appliances can also be used to support your pool days and time at home as well. You'll also access the home's main entrance foyer with elevator and stair access to the home's two (2) living levels and rooftop deck above.brbrbrbrThe First Level of Living (2nd Floor):brbrFeatures a club room with a living area with large TV, Nintendo Switch gaming console and a balcony. There are 4 Bedrooms including the home's luxurious master bedroom on this floor. The master bedroom features balcony access, king bed, large walk-in closet, and an en suite bathroom with double vanity, oversized soaking tub and walk-in shower. Bedroom 2 features a set of custom full over queen bunk beds, a workspace, and an en suite bathroom with vanity and shower/bathtub combination. Bedroom 3 & 4 both feature a king bed, and an en suite bath with an oversized vanity (double vanity in bathroom 4) and walk-in shower. Bedroom 3's bathroom is also accessed from the hallway and supports the club room space. There is a stackable washer/dryer on this level.brbrbrbrThe Second Level of Living (3rd Floor):brbrThis level features a great room with the fully stocked kitchen that includes a full range and cooktop with hood vent, full sized refrigerator (with ice maker) and freezer, double trash and recycling storage, double dishwasher, microwave, toaster, coffee maker, and is very well appointed with cookware, bakeware, dish ware, cutlery, and specialty items like crockpots, blenders, and more. If you have any questions on kitchen supplies, our reservationists would be happy to provide more details. The living area is very comfortably appointed with smart TV and Gulf views. The dining area here seats 19 people comfortably via a 10-person dining table, 5-person kitchen island bar top, and 4 additional high top bar seats. The main balcony off the great room has additional seating, and sunset and Gulf views. There are 2 bedrooms on this floor. Bedroom 5 & 6 both feature a king bed, and an en suite bath with an oversized vanity (double vanity in bathroom 6) and walk-in shower. Bedroom 5's bathroom is also accessed from the hallway and supports the living room space. There is a half bath and stackable washer/dryer on this level.brbrbrbrThe Rooftop Deck:brbrThis rooftop space is an elevated outdoor living space that really can't be rivaled! As we shared, the outdoor kitchen, dining and seating options, and turf area with games and TV are incredible. The sunrise and sunset experience here is supported so well by the amenities of the space, and trust us, you'll want to be up here throughout the day too. It is perfect for enjoying sunrise over Siesta and greater Sarasota, or sunset over the Gulf of Mexico. So, be sure to grab a book, a coffee or cocktail, and enjoy the sea breeze and Florida sun from this amazing elevated outdoor living space that overlooks all of Siesta Key.brbrbrbrGetting Around:brbrThis home is located about a 5min walk from the Siesta Key Village. South Siesta village entertainment districts and all the restaurants, entertainment, shopping, grocers, and more on the Key can be accessed by bike, golf cart, car, or free trolley. If you want to explore further, without the hassle of driving, you’ll find multiple stops nearby for the free trolley that provides transportation service to the entirety of Siesta Key. You’re also just a quick drive or Uber/Lyft (10-15 minutes) to downtown Sarasota for access to the amazing Sarasota Performing Arts scene, and numerous fantastic restaurants, shops, marinas, bars and entertainment, and more. And, day trips to Lido Key and Anna Maria Island are just 30 minutes away, as well as the amazing theme parks of Tampa and Orlando that are all just 1-2 hours away!brbrbrbrOther Things to Note:brbrThis Siesta Key luxury vacation rental features Smart TVs with cable and streaming services, as well as Free Wi-Fi throughout the property - including the outside areas for complete coverage for all your work or personal needs. TVs in all bedrooms.brbrbrbrAccessibility - in addition to the home’s elevator access to all levels, most doorways and walkways are 30 inches or larger and walk-in showers featured in most bathrooms. Please see the Photos, 3D Tour, & Video for this home for exact information.brbrbrbr*Don't forget to check out our Matterport 3D Tour for this home* And, if you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team of professional reservationists and we will be happy to assist you. We want you to fully understand what you are booking, and yes, an actual human team member is available to help! You are just a couple of clicks away from paradise!brbrbrbrInteraction with Guests:brbrPersonal service and attention to detail define the Vunique Difference. We want your vacation to fit your schedule, which is why we offer flexible bookings starting at just 3 nights for most of the year and any-day arrivals. Our homes are spacious and thoughtfully designed, made for connection as much as comfort. Here, luxury isn’t an upgrade – it’s the standard. Within our portfolio of branded residences, you have every amenity that you need for an unforgettable stay - waterslides, movie rooms, resort-style pools, sport courts, golf simulators, climbing walls, putt-putt courses, zip lines, gaming systems, rooftop decks, biked and beach equipment and more. Our proactive maintenance team ensures everything is in top shape before your arrival, and each property has a dedicated manager who welcomes you personally and stays available throughout your stay should you need anything. Transparency is at the core of everything we do. What you see is what you pay – no hidden fees for pool heat (up to 86 degrees), bikes, propane, or any of the extras that should already be included. Why settle, when you can stay somewhere extraordinary
Bed 6

Bed

Bath 6

Bath

Sleep 14

Sleeps

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Exceptional(12)

$878.98

/ Nightly
Private Vacation Home

NEWLY REMODELED Private Lakefront Bungalow, New Pool Bar,Heated Pool & Hot Tub

Siesta Key, Florida, United States

Newly Remodeled Lakefront Bungalow with Heated Pool, Hot Tub, and Pool Bar – Steps from Siesta Key BeachbrbrEscape to our stunning 2,300 sq. ft. lakefront ranch home, freshly remodeled and just ¾ mile from Siesta Key’s world-famous beach and vibrant Village. This chic, professionally decorated BOHO-style retreat sleeps up to 10, offering the perfect blend of luxury, relaxation, and convenience for families, groups, or couples.brbrOutdoor Oasis: Dive into the brand-new heated pool with a built-in hot tub and a baja sun shelf, ideal for kids’ play or adult lounging. Sip cocktails at the covered Pool Bar, featuring a 10-foot granite bar seating eight, a 75 smart TV for sports and movies, and serene views of spring-fed Lake Nancy, where cranes and birds create a tranquil backdrop for morning coffee or sunset drinks.brbrSpacious & Modern Interior: The open floor plan ensures privacy with a Master Wing (king bed, en-suite bath) on one side and guest bedrooms on the other. Guest Bedroom #1 (king bed), Guest Bedroom #2 (king bed), and the Bunk Room (full bed + two twins) all feature new foam mattresses and 50+ smart TVs. A 75 TV in the living area is perfect for group gatherings. Three brand-new bathrooms with walk-in showers and a fully stocked kitchen with white quartz countertops and new appliances make meal prep a breeze. The laundry room includes a large-capacity LG washer/dryer and an extra fridge for convenience.brbrThoughtful Amenities: Enjoy complimentary beach chairs, an umbrella, beach towels, and a cooler for your Siesta Key adventures. High-speed Wi-Fi, smart TVs, and a relaxed BOHO vibe create a home-away-from-home experience.brbrPrime Location: Just minutes from Siesta Key Village’s dining and shops, with easy access to the North Bridge for downtown Sarasota’s restaurants, cultural attractions, and the airport.brbrGood to Know: Only one reservation is permitted per 30-day period, ensuring an exclusive experience. Book now for an unforgettable Siesta Key getaway!
Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps

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Exceptional(1)

$336.02

/ Nightly
Private Vacation Home

Oceanside Retreat - Recently Refreshed!

Siesta Key, Florida, United States

Oceanside Retreat by Tropical Sands AccommodationsbrbrOceanside Retreat is a recently refreshed three-bedroom, three-bath ground floor vacation rental on Siesta Key, ideal for families and small groups who want a comfortable home base close to the island’s famous beaches, dining, and laid back coastal vibe. After a day on the sand, come home to bright, beachy interiors, plenty of space to spread out, and fun extras that make nights in just as enjoyable as days out exploring Siesta Key.brbrHighlightsbr• 3 Bedrooms / 3 Bathroomsbr• 1 King, 1 Queen, Twin over Full bunk bed with Twin trundlebr• Recently refreshed home on Siesta Keybr• Pool table for indoor funbr• Beach chairs and beach cart providedbr• Washer and dryer in homebr• Pet friendly with host approval br• 3 parking spots br• Convenient access to Siesta Key beaches, restaurants, and shoppingbrbrThis home is built for easy vacation living. Start your mornings with coffee and sunshine, then load up the beach cart with the provided beach chairs and head out for a classic Siesta Key beach day. When you are ready to wind down, the pool table sets the tone for relaxed evenings and friendly competition. With thoughtful touches throughout and a layout that works well for groups, Oceanside Retreat keeps everyone comfortable while still feeling like a true getaway.brbrThe main living area is open, bright, and inviting, with comfortable seating and a large television that makes it easy to gather for movie nights or a break from the sun. The kitchen is fully equipped with modern appliances, generous counter space, and the essentials you need for everything from quick breakfasts to family style dinners. Nearby dining space gives your group a dedicated spot for meals, games, or planning tomorrow’s Siesta Key adventures.brbrThe primary bedroom is a relaxing retreat with a king bed and a private ensuite bathroom featuring a walk-in shower and a standalone soaking tub, perfect for resetting after a day at the beach. The second bedroom offers a queen bed and its own ensuite bathroom with a walk-in shower, giving another couple or set of guests extra privacy. The third bedroom is a great setup for kids or additional guests, featuring a twin over full bunk bed with a twin trundle. A hallway bathroom with a shower and tub combination is conveniently located for this room and the main living spaces.brbrRoom Detailsbr• Primary Bedroom: King bed, ensuite bathroom with walk-in shower and standalone tubbr• Second Bedroom: Queen bed, ensuite bathroom with walk-in showerbr• Third Bedroom: Twin over Full bunk bed with Twin trundlebr• Hall Bathroom: Shower and tub combinationbrbrTo keep your stay simple and stress free, Oceanside Retreat includes an in-home washer and dryer so beach towels and vacation outfits stay fresh throughout the week. Beach gear is also provided, so you can spend less time packing and more time enjoying Siesta Key.brbrIf you are looking for a refreshed Siesta Key vacation rental with a comfortable layout, family friendly sleeping options, and beach gear plus at home entertainment, Oceanside Retreat is ready for you. Book your stay with Tropical Sands Accommodations and start counting down to your Siesta Key escape.brbr-brThis home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. brbrThis home requires a minimum 30-night stay in accordance with local city regulations, and shorter stays are not permitted.brbrThis home has a security camera located by the entrance. brbrWith 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 Tropical Sands Accommodations Rental Policies for full details. brbrWe 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. Please see our Tropical Sands Accommodations Rental Policies for full details. brbr3 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 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 3

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Bath 3

Bath

Sleep 7

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Exceptional(2)

$303.3

/ Nightly
Private Vacation Home

Beachside Bliss Awaits - Aloha Kai #55- Roelens

Siesta Key, Florida, United States

Aloha Kai #55brbrA Siesta Key Beachside Bliss Awaits!brbrEscape to the sun-kissed shores of Siesta Key and immerse yourself in the laid-back luxury of Aloha Kai #55. This charming beach villa is your perfect retreat, where the soothing sounds of the Gulf of Mexico and the vibrant energy of Crescent Beach create an unforgettable vacation. Designed with coastal elegance, Aloha Kai #55 invites you to kick off your shoes, sip morning coffee on your private patio, and dive into a world of relaxation and adventure. Here s what makes this home so special:brbrBedding Arrangement:br1 Bedroom:brMaster Suite: King-size bed and Smart TVbrAdditional Sleep: Queen-size sleep sofa in the lounge areabrTop Features:brSleeps 4brLargest Pool on Siesta Key: Dive into the expansive, sparkling pool surrounded by a large lounging deck with plenty of poolside lounges, tables, and chairs for ultimate relaxation.brDirect Beach Access: Steps away from the powdery white sands of Crescent Beach, rated the #1 beach in the U.S., with shaded pavilions and lounge chairs for your comfort.brCommunity Amenities: Enjoy shuffleboard, ping pong, and a poolside community room, plus complimentary beach toys and floats for fun in the sun.brPerfect Home Base Plenty of things to do and unique places to visit. Stroll to nearby restaurants, ice cream parlors, and bars, or hop on the Siesta Key trolley for easy island exploration. There are plenty of activities for children of all ages, thrill seekers and those who want to experience the natural wonders of the region.brNestled within the gated, family-friendly Aloha Kai resort, Aloha Kai #55 places you in the heart of Siesta Key's Crescent Beach, famous for its dazzling quartz sand and emerald waters. Whether you re lounging under a shaded beach pavilion, taking a soul-soothing walk along the 3-mile shoreline, or marveling at breathtaking Gulf sunsets, this villa offers the perfect blend of tranquility and convenience. With friendly staff, 24-hour support, and daily trash removal, your stay will be seamless and stress-free. Book your Siesta Key escape at Aloha Kai #55 today and create memories that will last a lifetime!brRoelens Vacations is proud to partner with the city to promote recycling and make our community more sustainable and greener. Thank you for your cooperation and for being part of a more sustainable future!brDISCLAIMERS:br**10% deposit is due at time of booking, final payment is due 60 days out. Any reservations made within 60 days require full payment. No refunds will be given on deposits.**brThis home does not allow pets.brThis home has a minimum age requirement of 25 to book. Smoking is not allowed on the property.brEvery Villa has ONE designated parking space and parking pass. Additional vehicles and guests must register in the front office for a separate parking pass.
Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps

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Exceptional(10)

$526.38

/ Nightly
Private Vacation Home

Beautiful 3 Bed/2.5 bath With Roof Top Pool on Siesta Key!

Siesta Key, Florida, United States

Siesta Key beach Residence: This must-see, rare, and beautiful home on Siesta Key offers a much sought after modern and contemporary design. This unit, located on the 2nd floor above the garage, has 3 bedroom, 2/5 bathrooms and can sleep up to 9 guests. This home is perfectly located 0.1 miles from beach access #11, offering quick access to the #1 rated Siesta Beach! Enjoy the breathtaking view from the incredible rooftop pool and relax knowing your vacation home awaits!br*THIS PROPERTY IS STAIRS ONLY! ALL GUESTS MUST HAVE THE ABILITY TO CLIMB STAIRS.br*No garage parking. Driveway parking only.brbrBedroom 1: King brBedroom 2: KingbrBedroom 3: Queen BunkbrLiving room: Queen 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 Trolly - 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: $1,500brbr*Pets are allowed, dogs only. Our pet fee is $39 per day/ per pet. Restrictions may apply on weight and breed, please check when making reservation.
Bed 3

Bed

Bath 2

Bath

Sleep 10

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Exceptional(8)

$541.05

/ Nightly
Private Vacation Home

Stunning 3 Bedroom Home with Roof-Top Pool on Siesta Key!

Siesta Key, Florida, United States

Siesta Key beach Residence: This must-see, rare, and beautiful home on Siesta Key offers a much sought after modern and contemporary design. This unit, located on the 1st floor above the garage, has 3 bedroom, 2/5 bathrooms and can sleep up to 10 guests. This home is perfectly located 0.1 miles from beach access #11, offering quick access to the #1 rated Siesta Beach! Enjoy the breathtaking view from the incredible rooftop pool and relax knowing your vacation home awaits!br*This property is stairs only; all guest must have the ability to climb stairs.br*No garage parking. Driveway parking only.brbrBedroom 1: King brBedroom 2: KingbrBedroom 3: Queen BunkbrLiving room: Queen 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 Trolly - 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: $1,500brbr*Pets are allowed, dogs only. Our pet fee is $39 per day/ per pet. Restrictions may apply on weight and breed, please check when making reservation.
Bed 3

Bed

Bath 2

Bath

Sleep 10

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Exceptional(6)

$848.99

/ Nightly
Private Vacation Home

Luxurious 4 Bedroom Home on Siesta Key, Steps From Siesta Beach!

Siesta Key, Florida, United States

SIESTA KEY BEACH RESIDENCE: This must-see, rare, and beautiful home on Siesta Key offers a much sought after modern and contemporary design. With 4 bedrooms, 4 full bathrooms and 2 half bathrooms, this private home offers enough sleeping space for 10 guests. Experience the luxuries this stunning building has to offer with quartz counters, high-end appliances, en-suite bathrooms throughout, walk-in closets, a heated private lap pool and park BBQ grill. Best of all, this home has floor to ceiling glass, highlighting both the Gulf and Siesta Beach. To top it all off, you can relax on the roof top deck with the best view to watch the gorgeous sunsets. Located just 0.1 miles from beach access, you’ll struggle to decide between taking the short walk to the beach, or taking a trip to Siesta Key Village to experience the great restaurants, shops, and entertainment the island has to offer. Your vacation home awaits you!br*This property is stairs only; all guest must have the ability to climb stairs.br*No garage parkingbrbrBedroom 1- KingbrBedroom 2- QueenbrBedroom 3- QueenbrBedroom 4- QueenbrLiving Room- Two Full Sleeper Sofa.brbrAdded 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 4

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Bath 5

Bath

Sleep 10

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$275.52

/ Nightly
Private Vacation Home

House of the Sun | Cheerful Island Bungalow, Walk to Siesta Village & Beach!

Siesta Key, Florida, United States

Imagine a place where the warm sunshine beckons you to relax, unwind, and truly escape the everyday. Welcome to House of the Sun, a delightful 3-bedroom, 2-bathroom island bungalow meticulously designed for your ultimate Siesta Key retreat, perfectly located just a leisurely stroll from the vibrant Siesta Key Village (packed with shops, restaurants, and entertainment!) and a short walk to the world-famous Siesta Key Beach, consistently ranked #1 in the USA! From the moment you step inside, you'll be embraced by a cozy, comfortable atmosphere and tasteful coastal decor, instantly making you feel at home in your personal island paradise. The updated kitchen is fully equipped for making meals or entertaining, and the formal dining room offers serene views of the tropical backyard where you can dine al fresco or simply soak up the sun in this quiet, family-oriented haven. With a comfortable Queen bed in the primary, two Twin/Single beds in the second bedroom, and a versatile Daybed Sofa in the third, there's space for everyone. This is the tranquil, sun-kissed escape you've been longing for, a perfect place to create unforgettable memories – your Siesta Key adventure awaits!brbrGood to Know for Your Stay:br• Property Management: This property is professionally managed by Ascendia Group, ensuring a seamless and enjoyable stay.br• Beach Equipment: We want your beach days to be effortless! This property comes equipped with beach chairs, a cooler, a wagon, and beach towels for your enjoyment.br• Pet Policy: For the comfort of all our guests, pets are not permitted at this property.br• A Message from Ascendia Group: We're dedicated to ensuring your time at our property is relaxing, enjoyable, and full of unforgettable experiences. Our local team is always available 7 days a week during your stay if you have any questions or need recommendations on what to do and see in the area!
Bed 3

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Bath 2

Bath

Sleep 6

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Exceptional(1)

$314.55

/ Nightly
Private Vacation Home

Siesta Dreamin’ - Canal Front Home with Private Pool and Dock!

Siesta Key, Florida, United States

Siesta Dreamin’ by Tropical Sands AccommodationsbrbrWelcome to Siesta Dreamin’, a stylish and inviting 4-bedroom, 3-bath canal front home with a private dock, perfect for extended stays on Siesta Key. Located just a 12-minute walk to Siesta Key Beach, this comfortable retreat offers a peaceful waterfront setting while still being close to local shops, restaurants, and entertainment. With a private pool, high end kitchen, dedicated office, and relaxing outdoor spaces, this home delivers comfort, convenience, and the relaxed island charm that Siesta Key vacation rentals are known for. brbrHighlights br• 12-minute walk to Siesta Key Beach br• 4 bedrooms / 3 bathrooms br• 1 king, 3 queens, twin daybed with twin trundle br• Private heated pool br• Private dock br• 50-amp EV charging outlet br• Outdoor seating and dining area br• BBQ grill and outdoor shower br• Dedicated office space br• Beach chairs and cart included br• Washer and dryer br• 4 parking spaces brbrSiesta Dreamin’ offers a beautiful outdoor living experience where guests can enjoy quiet mornings by the private heated pool, breezy afternoons on the deck, or dinner under the charming dining pergola. This outdoor space feels private, with comfortable seating for lounging, sunbathing, or reading a book by the water. The home sits along the peaceful canal and includes a private dock, perfect for fishing or launching kayaks and paddleboards. An outdoor shower and BBQ grill make beach days and relaxed nights even more enjoyable, creating a true coastal retreat for long stays. brbrInside, the spacious great room includes a large, comfortable sectional couch and a large TV, making it an ideal spot for movie nights. A bright indoor dining table sits just off the living area, offering a welcoming space for shared meals with views of the pool and garden. Sliding glass doors open directly to the pool and outdoor oasis, creating a bright and seamless indoor outdoor flow. The gourmet kitchen is beautifully updated with custom cabinetry, high end appliances, and striking stone countertops. A Summit dual-zone wine cellar adds a luxurious touch, making this a perfect space for cooking, entertaining, and family meals. A dedicated office area provides an excellent workspace for remote professionals, complete with a twin daybed and twin trundle for flexible guest accommodations. brbrThe primary bedroom offers a peaceful retreat with a luxurious king bed, a spacious walk-in closet, and an ensuite bathroom featuring a double vanity, walk-in shower, and separate soaking tub. Three additional bedrooms each offer comfortable queen beds, creating inviting spaces for family members or extended stay guests. A shared hallway bathroom includes a shower and tub combination, while an additional full bathroom with a walk-in shower provides added comfort and convenience for the group.brbrRoom Details br-Primary Bedroom: King bed, ensuite bathroom with walk-in shower, soaking tub, and double vanity br-Second Bedroom: Queen bed br-Third Bedroom: Queen bed br-Fourth Bedroom: Queen bed br-Bonus Sleeping Space: Office with twin daybed and twin trundle brbrWith its convenient location, guests are just minutes from Siesta Key Beach, local restaurants, and the charm of island living. Siesta Dreamin’ also offers beach chairs, a beach cart, a washer and dryer, and a 50-amp EV outlet to make longer stays comfortable and easy. Whether you prefer peaceful mornings by the water or exploring Sarasota’s coastal attractions, this home offers everything needed for a relaxing extended stay. brbrExperience the ease of coastal living at Siesta Dreamin’ by Tropical Sands Accommodations. With a canal front setting, private pool, high end kitchen, and beautiful outdoor areas, this home is perfect for extended stays on Siesta Key. Book your dream getaway today! brbr- brThis home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. brbrThis home requires a minimum 30-night stay in accordance with local city regulations, and shorter stays are not permitted.brbrBoat Lift is for owner use only. brbrThis property does not allow pets of any kind. brbrWe 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. Please see our Tropical Sands Accommodations Rental Policies for full details. brbr4 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 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 2

Bath

Sleep 8

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$1171.67

/ Nightly
Private Vacation Home

Siesta Key 6Br Beachfront Suites Retreat, Gulfview

Siesta Key, Florida, United States

Beachfront Suites Compound: Surfside, Serenity, and Dreamview Condos on Siesta KeybrbrWelcome to your ultimate beachfront retreat on Siesta Key, where the serene beauty of the Gulf of Mexico meets unparalleled comfort in our exclusive Beachfront Suites compound. Comprising three distinct condos - Surfside, Serenity, and Dreamview - each offering unique features and amenities, this stand-alone triplex delivers a personalized beach getaway experience directly on the world-famous Siesta Key Beach. Whether you seek a family adventure, a tranquil escape, or a romantic rendezvous, our Beachfront Suites cater to every desire.brbrProperty Features:brbr-Surfside Condo (1st Floor): A family-friendly 3-bedroom haven with immediate beach access, a newly renovated bathroom, and a private patio. It's perfect for beach days or relaxing with a book in the large shared backyard.br• Primary Bedroom: King Bedbr• Guest Bedroom 1: Queen Bedbr• Guest Bedroom 2: Twin BedsbrbrSerenity Condo (2nd Floor): Offers a peaceful 2-bedroom escape with stunning Gulf views from a private balcony. Its calming aesthetic and fully stocked kitchen provide a zen-like atmosphere for a truly serene vacation.br• Primary Bedroom: King Bedbr• Guest Bedroom: Queen Bedbr• Pull Out SofabrbrDreamview Condo (3rd Floor): This 1-bedroom suite boasts the best views on Siesta Key, featuring a large Jacuzzi bathtub, plush king bed, and private balcony for unforgettable sunsets. Ideal for romantic getaways or small families.br• Primary Bedroom: King Bedbr• Futon SofabrbrShared Amenities for All Guests:br- Immediate access to Siesta Key Beachbr- Breathtaking views of the Gulf of Mexicobr- HD Smart TVs, outdoor firepit, picnic area, propane & charcoal grillbr- Outdoor and board games, beach suppliesbr- Large shared backyard for ultimate relaxation and funbrbrPet Policy: Each condo welcomes your furry friends with a pet-friendly policy for dogs up to 50 lbs or two dogs with a combined weight of 50 lbs, ensuring no family member is left behind.brbrLocal Area:br- Just .25 miles to Siesta Key Public Beach and .5 miles to Siesta Key Village for dining, shopping, and entertainment. Downtown Sarasota is a short drive away, offering cultural attractions and more.brbrExclusive Compound Advantage:brRenting the Beachfront Suites compound provides an exclusive beachside experience for larger groups or families, offering a blend of privacy, luxury, and shared outdoor spaces. It's an ideal setting for creating lasting memories together on Siesta Key.brbrExperience the best of Siesta Key in one of our beachfront condos, where every stay is tailored to your preferences, whether it's soaking up the sun on the beach, enjoying backyard barbecues, or simply unwinding to the soothing sound of the waves.
Bed 6

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Bath 3

Bath

Sleep 14

Sleeps

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