Vacation Rentals By Owner In Siesta Key, FL

Showing 1360 Of 2077 Vacation Rentals

$561.89

Villa 52N - Premium - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Villa 52N at Aloha Kai offers the perfect escape for your next beach vacation, featuring three comfortable bedrooms plus a murphy bed and the convenience of an in-unit washer and dryer. Located on Siesta Key—a popular barrier island along Florida’s breathtaking West Coast—this villa is part of Aloha Kai, a family-friendly, gated resort community nestled in the heart of Crescent Beach, consistently ranked the number one beach in the continental United States. Renowned for its powdery white quartz sand and emerald-green waters, Siesta Key is one of Florida’s most sought-after vacation destinations. The stunning three-mile stretch of Crescent Beach and the crystal-clear waters of the Gulf of Mexico create an unforgettable backdrop for peaceful walks and magnificent sunsets. Whether you prefer lounging under shaded beach pavilions or unwinding by the largest pool on Siesta Key, Aloha Kai provides the ideal setting for a relaxed, sun-soaked getaway. The top balcony is closed off due to damages.

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Bath

Sleeps

$380.26

/ Nightly

Villa

Villa 50 - Premium - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Early risers and night owls can live in harmony at Villa 50 at Aloha Kai, where the thoughtful layout features bedrooms upstairs and a convenient bathroom downstairs. This beautifully renovated villa boasts new flooring, an updated kitchen with stainless steel appliances, granite countertops, and modern bathrooms. Whether you're enjoying a meal in the spacious dining room or dining al fresco on the back patio, comfort and style surround you. Located on Siesta Key—a beloved barrier island on Florida’s West Coast—Aloha Kai is a family-friendly, gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States. Renowned for its powdery white quartz sand and emerald-green waters, Siesta Key is one of Florida’s top vacation destinations. The breathtaking three-mile stretch of Crescent Beach and the sparkling Gulf of Mexico offer soul-soothing walks and unforgettable sunsets. Aloha Kai provides the perfect setting for a laid-back beach vacation, with shaded beach pavilions and the largest pool on Siesta Key waiting for you to unwind and relax.

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Bath

Sleeps

$360.89

/ Nightly

Villa

Villa 48 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

New photos coming soon! Villa 48 at Aloha Kai offers the perfect setting for your next beach escape. Located on Siesta Key—a popular barrier island on Florida’s West Coast—this family-friendly, gated resort community is nestled in the heart of Crescent Beach, the number one rated beach in the continental United States. Known for its powdery white quartz sand and emerald-green waters, Siesta Key is one of Florida’s premier vacation destinations. The breathtaking three-mile stretch of Crescent Beach and the crystal-clear Gulf of Mexico waters impress even the most seasoned travelers, offering peaceful walks and unforgettable sunsets. Aloha Kai invites you to enjoy a laid-back coastal lifestyle, whether you're lounging beneath shaded beach pavilions or relaxing by the largest pool on Siesta Key.

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Bath

Sleeps

$354.56

/ Nightly

Villa

Villa 41 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Sun, sand, and sea await you at Villa 41 at Aloha Kai, the perfect setting for your next beach getaway. This beautifully updated villa features an open floor plan, comfortable furnishings, a walk-in shower, and a well-equipped kitchen, offering everything you need for a relaxed and enjoyable stay. With a washer and dryer conveniently included, all you have to bring is your toothbrush, bathing suit, flip-flops, and a good book or two. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach—the number one rated beach in the continental United States. Renowned for its bright white quartz sand and emerald-green waters, Siesta Key is one of Florida’s premier vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you’ll ever see. Aloha Kai provides the perfect backdrop for a laid-back beach vacation, inviting you to lounge under shaded beach pavilions or relax by the largest pool on Siesta Key.

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Bath

Sleeps

$438.96

/ Nightly

Villa

Villa 39 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Paradise is found at Villa 39 at Aloha Kai! Meticulously renovated, this villa stands out with its beamed ceilings and open floor plan, creating a cozy and inviting atmosphere from the moment you step inside this exceptional beach retreat. The primary bedroom features relaxing coastal decor and a spa-like private bath, while guests will feel equally comfortable in the thoughtfully designed living spaces. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach—the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald green waters, Siesta Key is one of Florida’s premier vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you will ever see. Aloha Kai is the perfect location for a laid-back beach vacation, inviting you to lounge under shaded beach pavilions or relax by the largest pool on Siesta Key.

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Bath

Sleeps

$401.12

/ Nightly

Villa

Villa 45 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Villa 45 at Aloha Kai is a newly renovated, light-filled coastal retreat featuring an updated white kitchen that perfectly complements its bright, beachy furnishings, with a 5-night minimum stay required. Whether you prefer a refreshing swim in the Gulf of Mexico or a relaxing afternoon by the pool, the choice is yours. With a king in the main bedroom and one twin and one double in the guest bedroom, this villa comfortably accommodates guests, making it ideal for a family visit. The front porch and back patio extend your living space, offering the perfect spots to unwind and soak in the island atmosphere. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly, gated resort community nestled in the heart of Crescent Beach—rated the number one beach in the continental United States. Known for its powdery white quartz sand and emerald-green waters, Siesta Key is one of Florida’s premier vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico enchant even the most seasoned travelers, providing the perfect backdrop for soul-soothing walks and breathtaking sunsets. Aloha Kai invites you to embrace the laid-back beach lifestyle—whether you’re lounging under shaded pavilions or enjoying the largest pool on Siesta Key.

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Bath

Sleeps

$426.58

/ Nightly

Villa

Villa 38 - Premium - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Villa 38 at Aloha Kai is a fully renovated retreat offering a spacious living area that opens onto an enclosed porch—perfect for enjoying your morning coffee, with a 5-night minimum stay required. Its unique design features beamed ceilings and eclectic furnishings, creating a charming beach bungalow atmosphere. The fully equipped kitchen has everything you need to prepare meals to enjoy on the patio, and a convenient walk-in shower adds to your comfort. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach—the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald green waters, Siesta Key is one of Florida’s premier vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico impress even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you’ll ever see. Aloha Kai is the perfect setting for a laid-back beach vacation, inviting you to relax under shaded beach pavilions or by the largest pool on Siesta Key.

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Bath

Sleeps

$343.97

/ Nightly

Villa

Villa 35 - Premium - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Toes in the sand and sunshine on your shoulder—welcome home to the spacious one-bedroom Villa 35 at Aloha Kai. This beautifully updated villa features granite countertops in both the kitchen and bath, while the bedroom offers ample space and a large closet. The open-concept layout extends to a front porch enclosed with windows and blinds, providing additional living space and privacy. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach—the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald-green waters, Siesta Key is one of Florida’s premier vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you’ll ever see. Aloha Kai is the perfect setting for a laid-back beach vacation, inviting you to lounge under shaded beach pavilions or relax by the largest pool on Siesta Key.

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Bath

Sleeps

Exceptional(1)

$340.99

/ Nightly

Villa

Villa 32 - Premium - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Villa 32 at Aloha Kai is ideally located on Siesta Key, a beloved barrier island along Florida’s beautiful West Coast. This cozy unit features 1 bedroom, 1 bathroom, and includes the convenience of an in-unit washer and dryer. Aloha Kai is a family-friendly, gated resort community nestled in the heart of Crescent Beach—consistently ranked the number one beach in the continental United States. Known for its powdery white quartz sand and shimmering emerald-green waters, Siesta Key is one of Florida’s premier vacation destinations. The breathtaking three-mile stretch of Crescent Beach and the crystal-clear waters of the Gulf of Mexico offer a stunning backdrop for peaceful walks and unforgettable sunsets. Aloha Kai enhances the experience with shaded beach pavilions and the largest pool on Siesta Key, creating the perfect setting for a relaxed, sun-filled beach vacation.

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Bath

Sleeps

Exceptional(1)

$366.14

/ Nightly

Villa

Villa 30 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Renew your spirit and indulge in a beach getaway that celebrates the simple pleasures of life at Villa 30 at Aloha Kai. Unplug, put your feet up, and embrace the tranquility—whether it’s a leisurely walk on the beach, a refreshing swim in the pool, reading on the front porch, or grilling on the back patio. Your only task is to enjoy the day exactly as you please. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States. Known for its bright white quartz beaches and emerald green waters, Siesta Key is one of Florida’s premier vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and some of the most breathtaking sunsets you’ll ever see. Aloha Kai provides the perfect setting for a laid-back beach vacation, inviting you to lounge under shaded beach pavilions or relax by the largest pool on Siesta Key.

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Bath

Sleeps

$366.14

/ Nightly

Villa

Villa 29 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

If the beach is calling your name, Villa 29 at Aloha Kai is the perfect retreat. Whether you’re grabbing a towel and heading to the shore or curling up with a good book by the pool, you’ll find plenty of sunshine and tranquility to enjoy. Unwind on your screened porch or sink into the comfort of a king-size bed as you rest and recharge. For your convenience, this villa also includes a washer and dryer. Located on Siesta Key, a beloved barrier island on Florida’s West Coast, Aloha Kai is a family-friendly, gated resort community nestled in the heart of Crescent Beach—consistently ranked the number one beach in the continental United States. Renowned for its powdery white quartz sand and emerald-green waters, Siesta Key is one of Florida’s top vacation destinations. The breathtaking three-mile stretch of Crescent Beach and the crystal-clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and unforgettable sunsets. Aloha Kai completes the experience with shaded beach pavilions and the largest pool on Siesta Key, making it the ideal setting for a relaxed and memorable beach vacation.

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Bath

Sleeps

$547.37

/ Nightly

Villa

Villa 27 - Premium Plus - W&D Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Welcome to Villa #27, your home away from home on beautiful Crescent Beach, Siesta Key. As one of Aloha Kai’s closest villas to the Gulf of Mexico, you are just steps away from the top-rated beach in the United States. The villa’s décor is comfy and casual, featuring two sofas, a dining table that seats six, and an open kitchen—perfect for relaxing evenings in. Kick back and enjoy a late-night movie with all your favorite channels and streaming apps available on the TV. Villa #27 offers two bedrooms, two bathrooms, and a spacious family room larger than most at Aloha Kai. The fully equipped kitchen and washer/dryer add to the convenience. One bedroom has a king-size bed, while the second features a queen bed with a twin trundle and a pull-out sofa, comfortably accommodating up to five guests. Outside, you’ll find a private outdoor shower, a charcoal grill, and a small front patio with two Adirondack chairs—ideal for savoring an evening cocktail. The villa includes one parking space, with room for a second car in the driveway if needed. We hope you enjoy your unforgettable vacation on Siesta Key!

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Sleeps

$701.94

/ Nightly

Villa

Villa 22 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Villa 22 at Aloha Kai is where memories are made while spending time at the beach with family and friends, offering the perfect spacious setting. Its open floor plan fosters conversation and connection, encouraging moments away from screens. After a day of sunshine and sandy toes, gather in the updated kitchen, featuring a casual dining bar designed to invite everyone to join in meal preparation. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach—the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald-green waters, Siesta Key is one of Florida’s premier vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you’ll ever see. Aloha Kai is the ideal location for a laid-back beach vacation, inviting you to lounge under shaded beach pavilions or relax by the largest pool on Siesta Key.

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Bath

Sleeps

$340.99

/ Nightly

Villa

Villa 36 - Premium - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Villa 36 at Aloha Kai is a newly renovated retreat perfectly situated on Siesta Key, a popular barrier island on Florida’s West Coast, with a 5-night minimum stay required. Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald-green waters, Siesta Key ranks among Florida’s top vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you’ll ever see. Aloha Kai provides the ideal setting for a laid-back beach vacation, inviting you to relax under shaded beach pavilions or by the largest pool on Siesta Key.

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Bath

Sleeps

Exceptional(1)

$466.04

/ Nightly

Villa

Villa 31 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

You’ll love the light, bright coastal décor of the beautifully appointed and inviting Villa 31 at Aloha Kai. This little piece of paradise offers effortless living and a stay so enjoyable, leaving feels impossible. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach—the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald-green waters, Siesta Key ranks among Florida’s top vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you’ll ever see. Aloha Kai provides the perfect setting for a laid-back beach vacation, inviting you to relax under shaded beach pavilions or unwind by the largest pool on Siesta Key.

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Bath

Sleeps

$400.42

/ Nightly

Villa

Villa 15 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

The welcoming beach decor of Villa 15 at Aloha Kai invites you to leave your worries behind and unwind in comfort. This two-bedroom, one-bath unit features an extended living area with a private front porch enclosed with windows and blinds, as well as an open-air patio in the back for your enjoyment. The kitchen is bright and airy, showcasing white cabinetry, quartz countertops, and a cozy dining area. Convenience is enhanced with a washer and dryer located within the unit. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach—the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald-green waters, Siesta Key stands as one of Florida’s premier vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you’ll ever see. Aloha Kai is the perfect setting for a laid-back beach vacation, inviting you to lounge under shaded beach pavilions or relax by the largest pool on Siesta Key.

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Bath

Sleeps

$327.74

/ Nightly

Villa

Villa 14A - Premium - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

New photos coming soon! A wonderful beach vacation awaits you at Villa 14A at Aloha Kai, an updated villa just steps from the beach. Featuring two double beds, it’s an ideal spot for a girlfriend getaway. Start your day with a leisurely walk along the shore, then spend the afternoon relaxing on the front porch or back patio. For a perfect evening, visit a local waterfront restaurant to enjoy a sunset cocktail and dinner. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach—the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald-green waters, Siesta Key is one of Florida’s top vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you’ll ever see. Aloha Kai is the perfect location for a laid-back beach vacation, inviting you to lounge under shaded beach pavilions or relax by the largest pool on Siesta Key.

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Sleeps

$399.68

/ Nightly

Villa

Villa 14 - Premium Plus - W&D Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Villa 14 at Aloha Kai invites you to kick back and enjoy the simple pleasures of beachside living—whether it’s a leisurely stroll along the shore to add to your seashell collection or a quiet afternoon spent lounging poolside with a good book. This light and bright villa features a charming front porch and a private back patio, offering peaceful spaces to relax and unwind at any time of day. For your convenience, the unit also includes a washer and dryer. Located on Siesta Key, a beloved barrier island on Florida’s West Coast, Aloha Kai is a family-friendly, gated resort community situated in the heart of Crescent Beach—ranked the number one beach in the continental United States. Famous for its powdery white quartz sand and emerald-green waters, Siesta Key stands out as one of Florida’s top vacation destinations. The breathtaking three-mile stretch of Crescent Beach and the crystal-clear waters of the Gulf of Mexico create the perfect backdrop for soul-soothing walks and unforgettable sunsets. Aloha Kai completes your ideal beach getaway with shaded beach pavilions and the largest pool on Siesta Key, all designed for a truly laid-back and memorable vacation experience.

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Bath

Sleeps

$379.8

/ Nightly

Villa

Villa 12 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

This beautifully updated Villa 12 at Aloha Kai is ready to offer the perfect beach getaway. Just steps from the villa, you can stroll along the beach with your morning coffee and return in time for a breathtaking sunset. The screened porch provides a lovely spot to enjoy the balmy afternoon breezes in comfort. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach—the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald-green waters, Siesta Key is one of Florida’s top vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico impress even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you’ll ever see. Aloha Kai is the perfect setting for a laid-back beach vacation, inviting you to lounge under shaded beach pavilions or relax by the largest pool on Siesta Key.

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Bath

Sleeps

$384.8

/ Nightly

Villa

Villa 11 - Premium - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Feel the sun on your shoulders and sand between your toes when you choose the updated Villa 11 at Aloha Kai. With a spacious front porch and a back patio, this villa offers plenty of opportunities to make the most of your beach getaway. Just steps from the pool and private beach, it’s an ideal retreat for sun lovers. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach—the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald-green waters, Siesta Key is one of Florida’s premier vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you’ll ever see. Aloha Kai is the perfect setting for a laid-back beach vacation, inviting you to relax under shaded beach pavilions or by the largest pool on Siesta Key.

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Bath

Sleeps

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Most popular vacation rentals in Siesta Key

$2522.03

/ Nightly

Apartment

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

Siesta Key, Florida, United States

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Bath

Sleeps

$2135.02

/ Nightly

Private vacation home

Southern Exposure~2 Homes from Beach! Heated Pool!

Siesta Key, Florida, United States

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Bath

Sleeps

$2157.13

/ Nightly

Private vacation home

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

Siesta Key, Florida, United States

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Bath

Sleeps

$2193.20

/ Nightly

Private vacation home

Seashell Esta – Luxe Siesta Key Escape

Siesta Key, Florida, United States

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Bath

Sleeps

$2342.88

/ Nightly

Private vacation home

Luxe Lagoon | Located in SK Village! Private Pool & Spa, Rooftop, Pet Friendly ?️☀️?

Siesta Key, Florida, United States

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Bath

Sleeps

$2445.50

/ Nightly

Private vacation home

Siesta Key Luxe w/ Pool, Rooftop & Steps to Beach

Siesta Key, Florida, United States

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Bath

Sleeps

$2479.18

/ Nightly

Private vacation home

Steps to Beach/Siesta Village-Resort Pool w/Slide

Siesta Key, Florida, United States

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Bath

Sleeps

$3229.57

/ Nightly

Private vacation home

Entire Resort on Heron Lagoon, the Siesta Key Bungalows

Siesta Key, Florida, United States

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Bath

Sleeps

$3133.33

/ Nightly

Private vacation home

Sunset Gazers Paradise - Resort Pool - Mini Golf

Siesta Key, Florida, United States

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Bath

Sleeps

$3110.58

/ Nightly

Private vacation home

Beachfront Luxury - Resort Pool - Steps to Village

Siesta Key, Florida, United States

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Sleeps

Vacation Rentals By Owner In Siesta Key, FL

$561.89

$380.26

$360.89

$354.56

$438.96

$401.12

$426.58

$343.97

$340.99

$366.14

$366.14

$547.37

$701.94

$340.99

$466.04

$400.42

$327.74

$399.68

$379.8

$384.8

Rent a place that suits your needs

Most popular vacation rentals in Siesta Key

$2522.03

$2135.02

$2157.13

$2193.20

$2342.88

$2445.50

$2479.18

$3229.57

$3133.33

$3110.58

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