Vacation Villa Rentals By Owner In Siesta Key, FL

Showing 130 Of 130 Vacation Rentals

$253.38

Siesta Sands 202

Siesta Key, Florida, United States

Villa 202 at Siesta Sands is a bright and comfortable coastal escape, perfect for enjoying the relaxed lifestyle of Siesta Key. Thoughtfully designed with an open layout and plenty of natural light, this inviting villa offers a calm, beach-inspired atmosphere that makes it easy to unwind and feel at home. The well-equipped kitchen and welcoming living areas provide a great space for casual meals, conversation, and downtime. Enjoy the simple pleasures of island living, start your mornings outside, relax by the pool in the sunshine, or take a short stroll to the beach just moments away. Located within the gated, family-friendly Siesta Sands community, Villa 202 offers convenient access to the soft white sands and clear Gulf waters of Crescent Beach. Renowned for its peaceful setting and stunning sunsets, this beautiful shoreline is ideal for leisurely walks and soaking in the coastal views. With access to a private beach and a location that blends tranquility with everyday convenience, Siesta Sands offers the perfect backdrop for your next getaway. Whether you’re planning a quiet retreat or a fun-filled beach vacation, Villa 202 provides a welcoming space to relax and create lasting memories.

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Bath

Sleeps

$272.64

/ Nightly

Villa

Siesta Sands 203

Siesta Key, Florida, United States

Villa 203 at Siesta Sands is an inviting island retreat designed for comfort, ease, and time well spent. Light and airy, this charming villa features an open-concept layout and a soft coastal style that creates a calm, welcoming atmosphere from the moment you arrive. The well-equipped kitchen and comfortable living spaces make it easy to enjoy unhurried mornings and relaxed evenings. Ease into the rhythm of Siesta Key, spend time outdoors, enjoy sunny afternoons by the pool, or take a leisurely walk to the beach just minutes away. Located within the gated, family-friendly Siesta Sands community, Villa 203 places you close to the sugar-white sands and clear Gulf waters of Crescent Beach. Known for its natural beauty and memorable sunsets, this iconic shoreline is perfect for peaceful strolls and quiet moments by the water. With access to a private beach and a location that balances serenity with convenience, Siesta Sands provides an ideal setting for your next escape. Whether you’re seeking a restful getaway or a classic beach vacation, Villa 203 offers a comfortable and welcoming place to relax and make lasting memories.

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Bath

Sleeps

Exceptional(20)

$375.79

/ Nightly

Villa

Island House Beach Resort V10B

Siesta Key, Florida, United States

Island House Beach Resort - Siesta Key Florida - Crescent Beach. brbrThis inviting 2 bedroom, 1 bathroom villa duplex offers 1,000 sq. ft. of comfortable living space. The primary bedroom includes a king-size bed, while the second bedroom features two twin beds. A sleeper sofa provides additional accommodations. This unit features a spacious living room, dining area, and a fully equipped kitchen with all major appliances. Enjoy the added convenience three large flat-screen TVs, central heating and air conditioning, as well as a relaxing lanai.br brLocated on the second floor, this unit sits directly across from our large, heated swimming pool—perfect for easy access and a great place to unwind during your stay.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

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Bath

Sleeps

Exceptional(24)

$392.54

/ Nightly

Villa

Island House Beach Resort V1

Siesta Key, Florida, United States

Island House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrThis beautifully appointed 2-bedroom, 2-bathroom villa offers comfort, style, and privacy just steps from the beach. The primary ensuite features a king-size bed, while the guest bedroom includes two twin beds, making it ideal for families or friends traveling together.brbrEnjoy the spacious living and dining areas, a fully equipped kitchen with granite countertops and modern appliances, and a private screened lanai perfect for relaxing after a day in the sun.brbrFor your convenience, the villa includes three large flat-screen TVs, central heating and air conditioning, and all the amenities you need for a comfortable stay.brbrExperience the privacy and ease of your own standalone villa, while being part of the beautiful Island House Beach Resort community. Just a short walk through the resort brings you to the powdery white sands and turquoise waters of the Gulf of Mexico—perfect for relaxing in the sun, sand, and surf.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

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Bath

Sleeps

Exceptional(17)

$407.76

/ Nightly

Villa

Island House Beach Resort V11

Siesta Key, Florida, United States

Beautifully Appointed 2-Bedroom, 2-Bathroom Villa – Island House Beach Resort, Siesta KeybrbrThis beautifully appointed 2-bedroom, 2-bathroom villa offers the perfect blend of comfort and coastal charm. The primary suite features a king-size bed and private ensuite bathroom, while the guest bedroom includes two twin beds—ideal for family or friends. A sofa bed in the spacious living area provides additional sleeping accommodations.brbrEnjoy an open-concept living and dining area, a fully equipped kitchen with modern appliances and granite countertops, and a private lanai—perfect for relaxing and taking in the island breeze. The villa also includes three large flat-screen TVs, central heating and air conditioning, and all the conveniences of home.brbrExperience the best of Siesta Key with the space, comfort, and privacy of your own beachfront villa—just steps away from the white sands of Crescent Beach.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

Bed

Bath

Sleeps

Exceptional(18)

$398.36

/ Nightly

Villa

Island House Beach Resort V32

Siesta Key, Florida, United States

Island House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrThis beautifully appointed 2-bedroom, 2-bathroom villa offers comfort, style, and privacy just steps from the beach. The primary ensuite features a king-size bed, while the guest bedroom includes 2 twin beds and a sleeper sofa in the living area, making it ideal for families or friends traveling together.brbrEnjoy the spacious living and dining areas, a fully equipped kitchen with updated countertops, modern appliances, and a private screened lanai perfect for relaxing after a day in the sun.brbrFor your convenience, the villa includes three large flat-screen TVs, central heating and air conditioning, and all the amenities you need for a comfortable stay.brbrExperience the privacy and ease of your own standalone villa, while being part of the beautiful Island House Beach Resort community. Just a short walk through the resort brings you to the powdery white sands and turquoise waters of the Gulf of Mexico—perfect for relaxing in the sun, sand, and surf.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

Bed

Bath

Sleeps

Exceptional(21)

$402.05

/ Nightly

Villa

Island House Beach Resort V28

Siesta Key, Florida, United States

Island House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrThis beautifully appointed 2-bedroom, 2-bathroom villa offers comfort, style, and privacy just steps from the beach. The primary ensuite features a king-size bed, while the guest bedroom includes 2 twins and a sofa bed in the living area, making it ideal for families or friends traveling together.brbrEnjoy the spacious living and dining areas, a fully equipped kitchen with updated countertops, modern appliances, and a private screened lanai perfect for relaxing after a day in the sun.brbrFor your convenience, the villa includes three large flat-screen TVs, central heating and air conditioning, and all the amenities you need for a comfortable stay.brbrExperience the privacy and ease of your own standalone villa, while being part of the beautiful Island House Beach Resort community. Just a short walk through the resort brings you to the powdery white sands and turquoise waters of the Gulf of Mexico—perfect for relaxing in the sun, sand, and surf.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

Bed

Bath

Sleeps

Exceptional(25)

$421.22

/ Nightly

Villa

Steps to the beach! Island House Beach Resort V19

Siesta Key, Florida, United States

Island House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrThis beautifully appointed 2 bedroom, 2 bathroom villa features a spacious primary ensuite with a king bed, while the guest room offers one double bed and one twin bed. The villa includes a large living area, a dedicated dining space, and a fully equipped kitchen with all major appliances. A private screened lanai is perfect for relaxing after a day in the sun. For your comfort and entertainment, the villa is equipped with three large flat-screen TVs as well as central heating and air conditioning.brbrExperience the privacy and ease of your own standalone villa, while being part of the beautiful Island House Beach Resort community. Just a short walk through the resort brings you to the powdery white sands and turquoise waters of the Gulf of Mexico—perfect for relaxing in the sun, sand, and surf.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

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Bath

Sleeps

$620.27

/ Nightly

Villa

Crescent Arms Villa 15 Siesta Key Florida

Siesta Key, Florida, United States

THIS unit has been completely remodeled however it is no longer accepting new reservations at this time. CA V15 Welcome to Crescent Arms on beautiful siesta key Florida. If you are looking for your vacation to be on the best beach and have the most beautiful sunsets, then you are in luck.brThis unit Features:brBeach front property! No loading up a car or crossing streets just walk out of the building onto the sand! 2 Bedroom 2 bathroom. Sleeps up to 6 people. Full kitchen, dining area, Tv in each room with free Wi-Fi. brShared resort amenities:brHeated pool, Private Beach, BBQ area with gas grills. Beach chairs provided. Beach personnel you can rent an umbrella from. Beach towels included. Bed linens and bath towels included. We do not have a linen service if you would like fresh linen you will have to wash them. Coin operated laundry in the tower buildings. Villas have washers and dryers in the garage. brNO GOLF CARTS, Trailers, motorcycles, mopeds, boats If you want to enjoy the sugar-white sand of Crescent Beach, shop or just relax by the pool, located directly on the beach side of Midnight Pass Road, we offer something for everyone: Wi-Fi, cable television, generous closet space, a lanai or glassed-in porch and a fully furnished kitchen. brCrescent Arms features: Easy access on and off the Island! Fully Furnished, Gated Condominiums Private Beach Access with Chairs No smoking and no pets, please! brThere is a seven-night minimum stay Saturday to Saturday. Check in: 4 PM Check out: 10 AM We strongly encourage you to get rental insurance in case of any problems that may occur. Your Florida Vacation Awaits You.

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Exceptional(7)

$285.73

/ Nightly

Villa

Completely remodeled villa next to famous Siesta Key Beach in Sarasota

Siesta Key, Florida, United States

Totally rehabbed 1 Bedroom 1.5 Bathroom ground unit with private patio area, and covered carport parking directly outside your front door. About 100 yards to private resort beach. 3 Swimming Pools to choose from. Fully equipped kitchen. Washer and dryer in unit.brJamaica Royale is located directly on the Gulf of Mexico along the white sands of world-famous Siesta Key Beach in Sarasota, Florida. A barrier island on Florida’s West coast, considered the most beautiful of Florida’s barrier islands, Siesta Key’s beach boasts “the world’s finest and whitest sand”.brJamaica Royale is located on a private lane that leads directly to the beach… no through traffic and no streets to cross ~ just stroll to the famed white sands of Siesta Key Beach.

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Most popular vacation rentals in Siesta Key

Exceptional(7)

$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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Exceptional(7)

$2135.02

/ Nightly

Private vacation home

Southern Exposure~2 Homes from Beach! Heated Pool!

Siesta Key, Florida, United States

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Bath

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Exceptional(7)

$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

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Exceptional(7)

$2193.20

/ Nightly

Private vacation home

Seashell Esta – Luxe Siesta Key Escape

Siesta Key, Florida, United States

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Bath

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Exceptional(7)

$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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Exceptional(7)

$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

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Exceptional(7)

$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

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Exceptional(7)

$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

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Exceptional(7)

$3133.33

/ Nightly

Private vacation home

Sunset Gazers Paradise - Resort Pool - Mini Golf

Siesta Key, Florida, United States

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Bath

Sleeps

Exceptional(7)

$3110.58

/ Nightly

Private vacation home

Beachfront Luxury - Resort Pool - Steps to Village

Siesta Key, Florida, United States

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Vacation Villa Rentals By Owner In Siesta Key, FL

$253.38

$272.64

$375.79

$392.54

$407.76

$398.36

$402.05

$421.22

$620.27

$285.73

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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