Home Vacation Rentals By Owner In Siesta Key, FL

Showing 1720 Of 2077 Vacation Rentals
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Exceptional(13)

$1201.17

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Private Vacation Home

5 Star LUXURY RETREAT on BEACH ROAD, SIESTA KEY BEACH, New POOL

Siesta Key, Florida, United States

One of the nicest homes on Siesta Key Beach with two units. Please note This listing's pricing is to rent one 3-bedroom unit. Both units are beautifully furnished. We have the highest 5 star rating on Siesta Key. See Vrbo 802548 for more reviews of this home. Stunning and spacious on Beach Road right across the street from Beach Access 10 (ranked number one Beach in US.) brbrThe front-facing unit (pictures 1, 7 - 14) offers a spacious Open-Concept Kitchen & Living Area with Sunset Lanai. It has 3 beautiful bedrooms and 2.5 baths. It sleeps 8. Two spacious bedrooms also offer large walk-in closets. The bathrooms are also spacious. brbrWhen you enter this unit, you step into a bright, open living space where clean design and everyday comfort come together. At the center is a modern white kitchen with sleek lacquer cabinetry, quartz countertops, and everything you need for easy cooking and entertaining. The kitchen flows into a spacious living and dining area, perfect for relaxing or hosting guests.brbrGlass doors open to a private lanai with comfortable seating—just the place to enjoy a quiet evening and watch the sunset or continue the party - with partial water and beach views. The balcony has a dining table and beautiful upscale outdoors furniture.brbrThe rear unit, See pictures (15 - 18.) 555B has 3 beautiful bedrooms and 2 baths and an outdoor balcony and dining table that overlooks the resort pool area. All three bedrooms are similar in size. Two of the bedrooms have king beds and the third offers a queen. Sleeps 6 in beds. We also have new air mattresses. Inside on the main floor is a lovely living, dining, and kitchen area with a new appliances and a new 50 Flat Screen Hi Def TV. New ceiling fans throughout.brbrThe units can also be rented together as one large property with 6 bedrooms and 4.5 baths. Our stunning home comes with all the amenities: beach chairs, beach caddies, umbrellas, beach toys, fine linens, beach towels, and so much more. brbr555 Beach is the perfect vacation home. It's larger, more spacious, and offers more room for entertaining than the majority of homes on Siesta Key. The backyard and private pool area are new with new outdoor decor and dining areas. The heated 25-foot pool and paver brick back yard satisfy the discerning traveler.brbrBoth units also have new washer/dryers and high def TVs throughout.br brAs mentioned, the two units also work well together, and when available, create one of the most spacious 6-bedroom 5-baths on Siesta Key! Please see pictures for more details. We offer high speed internet and have new high definition flat screens throughout. BBQ Grill in a brand new paver brick pool area. We also have two heated outdoor showers. brbrThe property is located right across the street from Siesta Key Beach Access 10. This is a major benefit. There are many homes on Beach Road that don't offer such convenient beach access.brbrI'm also a graduate of Cornell's School of Hotel Administration. To understand more about our commitment to you and hospitality, please see more reviews. See VRBO Listing #802548 Most often we rent both units together.
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Bath 2

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Sleep 8

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Exceptional(47)

$268.61

/ Nightly
Condo

COZY UNIT ON THE BEACH, ACCESS TO 3 POOLS. Very clean and newly remodeled!

Siesta Key, Florida, United States

PLEASE NOTE: ONE WEEK MINIMUM STAY REQUIRED DURING THE PRIME SEASON, AND 4 NIGHT MINIMUM STAY OFF SEASON.br*Banyan Tree Beach Resort requires a signed contract WITHIN ONE WEEK OF BOOKING to confirm.*brOn location, you can pick from the three pools, play shuffleboard, walk on the beach, or you may want to take a short walk to Siesta Key Public Beach Pavilion (by the beach or sidewalk) where there are Tennis courts, Pickleball courts, Volleyball and much more. You are less than a mile to the Village, where there are restaurants, banks, grocery stores, drug stores, gift shops, ice cream shops, bars, and nightclubs, banks, salons, coffee shops. You can rent bikes, Segways, boats, scooters, snorkel, fish, dive go parasailing, to name a few. We have several malls and outlet malls, movie theaters. You may also want to attend a play, musicals, fine dining, Sarasota Opera, The Players Theatre, Golden Apple Dinner Theater, Florida West Coast Symphony, Historic Spanish Point, Sarasota Jungle Gardens, John & Mable Ringling Museum, Mote Marine Laboratory, South Florida Museum Bishop Planetarium, Marie Selby Botanical Gardens, G-Wiz science museum, Van Wezel Performing Arts, Myakka River State Park, Oscar Scherer state park, Sarasota Ballet, Large fishing head boats or private charters, sailing, scuba diving, Golfing, or go to a professional ball game.brbrPlease note: Sleeper sofa will accommodate only one adult or two children.
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Bath 1

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Sleep 4

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Exceptional(22)

$234.62

/ Nightly
Condo

Newly Renovated Siesta Key Waterfront Condo, Fishing Pier, Large Pool - Short Walk to Turtle Beach!

Siesta Key, Florida, United States

Beautifully renovated 2 bedroom, 2.5 bath waterfront townhouse on Blind Pass Lagoon in Siesta Key just a short 3-5 minute walk from Turtle Beach. Relax and enjoy peaceful surroundings, fish from the docks, take a dip in the pool and watch kayaks paddling past on the waterway. Bring your boat, or rent one from nearby Turtles Marina (docking is free for residents).brbrRecent renovations include a new kitchen with custom cabinetry, granite counters, appliances, and the entire townhouse was repainted. On the first level is the large living room, large updated kitchen, dining area and half bathroom. Living room leads out to the main balcony. 2 bedrooms and 2 bathrooms are on the second level, and another balcony is accessible from the master bedroom. Sleeps 6 with a king in the master & 2 full beds in the guest bedroom plus new queen sleeper sofa in the living room. Full size Maytag washer & dryer are in the unit. TV's are in the living room & both bedrooms. Free WiFi & cable, plus all of your beach gear is provided. Covered, assigned parking garage.brbrThe Cozy Cove community located on the quieter southern end of Siesta Key and is comprised of six intimate units. It is the perfect spot for a relaxing tropical experience.brbrTurtle Beach is a just short walk with Picnic areas, playground, and volleyball court. Several restaurants, including Turtle's Restaurant and Ophelia's on the Bay, are both within a 5 minute walk and you can dine on the water. Turtle Beach Marina is nearby if you want to rent a boat or kayak. Free trolley service is provided from one end of the island to the other, which is a great option to explore Siesta Key Village and Crescent Beach.
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Bath 2

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Exceptional(9)

$372.13

/ Nightly
Private Vacation Home

Canal-Front Home with Dock, Pool, and Dog-Friendly - Sunset Cove

Siesta Key, Florida, United States

Sunset Cove by Siesta Key Luxury Rental Properties br brWelcome to Sunset Cove, a stunning four-bedroom, three and a half-bath oasis overlooking the tranquil Heron Lagoon! This luxurious retreat features a private dock for exploring the lagoon, a spacious screened-in patio with a private pool, and direct access to nature’s beauty. Perfectly situated just one mile from Siesta Key Beach and close to Turtle Beach and Siesta Key Village, this home offers effortless access to sun, sand, shopping, and dining. Whether seeking restful lakeside serenity or outdoor adventures, Sunset Cove delivers an unmatched vacation experience. brbrHighlights br• Canal front with private dock br• 4 Bedroom / 3.5 Bathroom br• 2 Kings, 1 Queen, 2 Twin beds br• Private pool and screened-in lounge  br• Outdoor bar area  br• Beach chairs provided br• 1 mile to Siesta Key Beach’s br• Washer and dryer br• Dog friendly br• 4 Parking spaces br brEnjoy the outdoor resort-like ambiance with your private pool and a built-in bar for poolside drinks. The screened-in pool area invites relaxing afternoons or lively gatherings, while the dock provides easy access to explore the lagoon. Inside, the open concept living spaces with coastal accents make entertaining simple, and the fully equipped kitchen is perfect for large family meals or casual snacks. br brThe seamless flow between the living room, kitchen, and formal dining area creates a social hub, great for family fun or gatherings with friends. The living space features charming coastal decor, comfortable seating, and a smart TV. The kitchen boasts a full range of appliances, dishware, and a walk-in pantry with laundry facilities, ensuring both convenience and style. br brUnwind in the primary suite, which offers French doors opening to a balcony overlooking the lagoon, with spectacular pool and water views. The suite includes a king-sized bed, walk-in closet, and a luxurious bath with a soaking tub, double vanities, and a walk-in shower. The remaining guest rooms include a second king bed, a queen bed, and two twin beds in the fourth bedroom, all decorated with upscale furnishings and equipped with TVs. The two guest bathrooms feature a shower-tub combo, blending style with practicality. brbrRoom Details br• Primary Bedroom: King bed, balcony, ensuite with walk-in shower and soaking tub  br• Second Bedroom: King bed  br• Third Bedroom: Queen bed  br• Fourth Bedroom: Two twin beds br brGuests will enjoy a washer and dryer, outdoor dry bar, pet-friendly policies, and proximity to Turtle Beach and Siesta Key Village. The lush backyard with a private pool and dock offers endless opportunities for outdoor relaxation and water adventures. Located in the sought after Siesta Key area, this home is your perfect escape for a luxurious Gulf Coast vacation.br brBook your stay at Sunset Cove today and indulge in a luxury vacation surrounded by stunning water views, outdoor amenities, and island charm. Whether lounging poolside, kayaking the lagoon, or exploring local shops and eateries, this home provides everything for a memorable getaway. Reserve your dates now and start creating lifelong memories in paradise! br brbr- brThis home is managed by Siesta Key Luxury Rental Properties.  brbrThis home requires a minimum 30-night stay in accordance with local city regulations, and shorter stays are not permitted.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.  brbrKids playhouse not for guest use. 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.  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.
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Sleep 8

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$296.11

/ Nightly
Condo

Harbor Towers 628 - Tropical Sands Accommodations

Siesta Key, Florida, United States

Harbor Towers 628 by Tropical Sands AccommodationsbrbrWelcome to Harbor Towers 628, a beautifully appointed three-bedroom, three-bathroom Siesta Key vacation rental located on Midnight Pass Road. Perfect for extended stay guests with a 13-night minimum, this spacious condo offers comfortable coastal living just minutes from world famous Siesta Key Beach and Siesta Key Village. With serene views, generous living space, and access to one of the most amenity rich communities on the island, this residence is ideal for seasonal stays, remote work escapes, or long term coastal retreats.brbrHighlightsbr• 3 Bedrooms / 3 Bathroomsbr• 1 King, 1 Queen, 2 Twinsbr• 13-night minimum stay communitybr• Located on Midnight Pass Rdbr• Short drive to Siesta Key Beachbr• Two heated community poolsbr• Three Har-Tru tennis courtsbr• 40-slip marinabr• Gated waterfront communitybr• In-unit washer and dryerbrbrHarbor Towers is one of Siesta Key’s most desirable gated waterfront communities. Guests enjoy access to two heated pools surrounded by tropical landscaping, three tennis courts, and a private 40-slip marina. The beautifully maintained grounds and waterfront setting create a peaceful atmosphere perfect for extended stays. Whether you are enjoying a morning swim, an afternoon tennis match, or simply relaxing by the water, this community elevates your Siesta Key experience.brbrThe open living and dining area is bright and welcoming, with comfortable seating and large windows that allow natural light to fill the space. The layout flows seamlessly into the fully equipped kitchen, featuring granite countertops, modern appliances, and ample cabinet space. A breakfast bar provides additional seating, while the dining table offers the perfect setting for shared meals, remote work, or evening gatherings after a day at the beach.brbrThe primary bedroom serves as a peaceful retreat with a king-sized bed and an ensuite bathroom designed for comfort and privacy. Natural light and coastal tones create a calm, relaxing atmosphere ideal for restful nights. The second bedroom features a queen bed and convenient access to a nearby bathroom. The third bedroom offers two twin beds, making it perfect for guests or visiting family members. A shared hallway bathroom provides additional convenience for the home. Each bedroom is thoughtfully arranged to ensure comfort for longer stays.brbrRoom Detailsbr• Primary Bedroom: King bed with ensuite bathroombr• Second Bedroom: Queen bedbr• Third Bedroom: Two twin bedsbr• Shared hallway bathroombrbrThis Siesta Key condo includes an in unit washer and dryer, central air conditioning, elevator access within the building, and secure gated entry. The 14-night minimum stay requirement makes this residence especially well suited for snowbirds, seasonal visitors, and extended coastal escapes.brbrIf you are searching for a spacious, amenity rich Siesta Key vacation rental designed for longer stays, Harbor Towers 628 offers the perfect blend of comfort, location, and community features. Secure your dates and experience waterfront living at Harbor Towers on Siesta Key today.
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Bath 3

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Sleep 6

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Exceptional(6)

$834.77

/ Nightly
Private Vacation Home

Sunburst Courtyard | Pet Friendly Waterfront Home w/ Pool, Walk to Siesta Key Beach & Village!

Siesta Key, Florida, United States

Welcome to Sunburst Courtyard, your waterfront paradise located on the tropical island of Siesta Key! This exceptional 4-bedroom, 3-bathroom rental home offers all the amenities you need for a memorable stay, and its prime location provides easy access to the world-famous Siesta Key Beach, just a 15-minute walk away.brbrAs you enter Sunburst Courtyard, you'll be greeted by the mother-in-law suite, providing a private and comfortable space for guests or extended family members. Moving through the property, you'll discover the centerpiece of this home - the spacious screened-in courtyard, featuring a sparkling private heated pool & spa and ample lounging areas. Spend your days swimming, relaxing poolside, or grilling out and enjoying delicious BBQ meals in the warm island breeze.brbrThe main house of Sunburst Courtyard features two bedrooms and two baths, offering a comfortable and inviting space to unwind. The bright and elegant design creates a welcoming atmosphere, while the private casita adjacent to the courtyard provides two additional generously sized bedrooms, ensuring privacy and space for everyone in your group.brbrInside the main living quarters, the fully equipped gourmet kitchen is a chef's dream, featuring top-of-the-line appliances, sleek countertops, wood cabinets, and ample space to create culinary masterpieces. Whether you're whipping up a quick breakfast or preparing a gourmet feast, this kitchen has everything you need.brbrAdjacent to the kitchen is the inviting living area, complete with comfortable seating and a pool table for hours of entertainment and friendly competition. The living room features a screened-in balcony, perfect for those looking to unwind in the shade while still taking in the breathtaking water views.brbrAs you make your way to the backyard, you'll find a tranquil retreat where you can soak up the sun, sip your favorite beverage, and take in the picturesque surroundings. From the comfort of your own backyard, you can marvel at the beauty of the water and immerse yourself in the peacefulness of the outdoors.brbrSunburst Courtyard is ideally located, allowing you to experience the best of Siesta Key. Take a leisurely 10-minute walk to Siesta Key Village, where you can explore a variety of dining options, indulge in some retail therapy, and immerse yourself in the vibrant local entertainment scene. For beach lovers, a scenic 15-minute stroll will lead you to the pristine white sands and crystal-clear waters of Siesta Key Beach, consistently ranked among the top beaches in the world.brbrExclusive Amenities Include:br• Private Screened Heated Pool & Spabr• Pool Tablebr• 10 Minute Walk to Siesta Key Villagebr• 15 Minute Walk to Siesta Key Beachbr• Canal Front Homebr• 2 Bedroom Detached Private Guest Quartersbr• 4 Bedrooms, 3 Full Bathsbr• 2 King Beds, 1 Queen Bed, 1 Twin Bed w/ Trundle Bed (convertible to a King), 1 Queen Sleeper Sofa, 2 Rollaway Twin Beds (Sleeps 12) with Linens Providedbr• Private Courtyard Lounge Areabr• Private 2 Car Garagebr• Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials Providedbr• Starter Pack of Toiletry Essentials Included - Shampoo, Conditioner, Hand / Face Soap, Body Lotion, & Makeup Wipesbr• Starter Pack of Home Essentials Included - Dish Soap, Dish Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipesbr• Beach Towels, Chairs, Cooler, & Caddy Providedbr• Free WiFi & Multiple HDTV'sbr• Gas Grillbr• Enhanced Cleaning Protocols Provided By Our CottageClean Teambr• Island Shuttle Transportation Availablebr​​​​​​​• Dog-Friendly with a Fee (1 dog up to 25lbs)brbrSunburst Courtyard can accommodate up to 12 guest with a bedding configuration as follows:brbrMain Cottage:br• Bedroom # 1: King Bed (1) - Sleeps: 2br• Bedroom # 2: Queen Bed (1) - Sleeps: 2brbrPrivate Guest Quarters:br• Bedroom # 3: King Bed (1) - Sleeps: 2br• Bedroom # 4: Twin Bed w/ Trundle Bed (convertible to a King) (1) - Sleeps: 2br• Common Space: Queen Sleeper Sofa (1) - Sleeps: 2br• Extra: Twin Rollaway Beds (2) - Sleeps 2brbrWe go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol within our CottageClean Program. After our six hour in-depth cleaning of your home, we complete a 35 point property inspection to ensure that you feel tremendously safe and happy with this amazing home. This allows you to vacation worry free regarding the cleanliness of your home and truly relax as soon as you arrive. Our goal is to have you feel like you are walking into a brand new vacation home that no one has ever stayed at before!brbrPLEASE NOTE: There is a 1 rental per 30 day period, per Sarasota, FL ordinance, contact us for more information. Reservation must follow under the accordance of the Sarasota County code regulations. This pool is heated from November 15th to April 15th.
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Exceptional(4)

$332.73

/ Nightly
Private Vacation Home

Newly Updated, Walk to Siesta Key Beach, Tennis, Heated Pool

Siesta Key, Florida, United States

Just steps away from Florida's top rated Siesta Key beach, this beautifully decorated and newly renovated coastal retreat is located directly across from the main Siesta Key Beach access and Siesta Key Pavilion with plenty of parking and tons of amenities. We provide all the beach essentials you need including bicycles, sand-resistant Turkish beach towels that double as a wrap, beach umbrellas, beach chairs, and a beach wagon for an easy and convenient walk to Siesta Key. Back at the condo enjoy resort-style amenities with two tennis courts, a heated pool, and a private balcony overlooking a small lake. Inside, you'll find super comfy beds with high-quality linens, and plenty of fresh clean plush bath towels for a relaxing stay. This vacation townhouse offers everything you need for a memorable and relaxing Siesta Key getaway. With its spacious layout, resort-style amenities, and unbeatable location across from the island’s top beach, it’s the perfect place to call home while you soak up the sun!brbrUnbeatable Location:br• Situated directly across the street from the main public access to world-famous Siesta Key Beach and Pavilion br• Walking distance to the powdery white sands and turquoise waters of the Gulf Coast with unbeatable sunsets brbrSpacious, Bi-Level Townhouse:br• Thoughtfully designed layout with two levels of comfortable and beautifully decorated living spacebr• Ideal for families or groups looking for both privacy and shared gathering areasbr• Spacious living room, dining room, and large kitchen all with balcony access and views brbrPrimary Bedroom Suite:br• Located on the main level with a king-size bed, Roku TV, and large en-suite bathroom stocked with fresh plush bath towels br• Opens up to the outdoor private patio with seating overlooking the quiet lake – perfect for a morning coffee or sunset viewbrbrCharming Upstairs Beachy Bedroom:br• Two comfy twin beds, a Smart TV for streaming and movie nights br• Adjacent full bathroom makes it a great space for kids or guestsbrbrRelaxing Living Room:br• Comfortable and roomy with plenty of seating, including two twin pullout couches with bedding and linens provided for your guests br• Smart TV for streaming and entertainment and a balcony overlooking the lake with table and chairs to enjoy the Gulf breezebr• A great place to unwind after a day at the beach or pool or to watch the sunset from the patio brbrFully Equipped Dine-In Kitchen:br• Stocked with all the kitchen essentials you need to prepare meals at homebr• Overlooks a beautifully decorated large dining area perfect for family dinners and gatherings br• Features a small kitchen table perfect for a quick snack or breakfast at home br• Stocked with plenty of cookware, and both a drip and Keurig coffee makerbrbrResort-Style Amenities at Our House at the Beach:br• Swimming pool with plenty of loungers - ideal for relaxing in the Florida sunbr• Covered cabana area with grills and outdoor dining tables for cookouts and al fresco mealsbr• Two tennis courts for friendly matches or a game of pickleball brbrExtras for a Hassle-Free Stay:br• Super comfy beds, high-quality linens, and plush bath towelsbr• Vacation and beach essentials provided for your stay including bikes, umbrellas, beach chairs and a wagon so you’re ready to hit the sand right awaybrbrThe Beauty of Siesta KeybrSiesta Key is a barrier island positioned between the Gulf of Mexico and intracoastal waterway. The powdery white sandy beaches are world renowned and stretch over 8 miles along the southwest coast of Florida. Siesta Key is a water-lovers paradise offering crystal clear turquoise water, sailing, fishing, swimming and so much more. Play in the gentle waves and shallow waters, gather unique seashells, or build a sandcastle with your kids or grandkids. brbrThe Siesta Key Village offers a wide selection of shops, cafes, top restaurants, and live music for both its residents and guests. From local oyster bars to waterside dining, Siesta Key has something for every palate. Trolley transportation is available around the island and throughout Sarasota.
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Exceptional(6)

$1620.57

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Private Vacation Home

Beautiful 4 Bedroom/ 4 Bath Beach House-Directly on Beach!

Siesta Key, Florida, United States

Experience the breathtaking views of this beachfront home! Located directly on Sunset Beach on Siesta Key, this 4-bedroom 4-bathroom home is a must. Inside, this home is beautifully decorated and can comfortably sleep up to 12 guests. This home comes equipped with a full kitchen, a dining area, and a spacious living room for you to enjoy time with your family and friends. Watch the spectacular sunsets from one of your multiple balconies located on each floor, or walk out your front door to the sugary white sand of our world-famous beaches. This unit also includes a very convenient outdoor shower and the use of the pool at the Siesta Key Beachside Villas just a block away. Even better still, this unit is only a short stroll into Siesta Key Village, where you can experience many of the wonderful shops and restaurants the island has to offer! With views like this, this vacation home is sure to be your choice returning year after year!br*This unit is stairs only. All guests must have the ability to use stairsbrbrBedroom 1 – KingbrBedroom 2 – King and Queen Sleeper SofabrBedroom 3 – Queen brBedroom 4 – King brLiving 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 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
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Bath 4

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Home Most popular vacation rentals in Siesta Key