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2026-11-07
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Holiday Homes in Sarasota

Boho Bungalow

3466 Winton Avenue, Sarasota, United States Show map

The 3-bedroom Boho Bungalow Sarasota offers swift access to various city sites, such as Green Bean Coffee House, situated nearly 5 minutes' walk away. Providing guests with Wi-Fi and a car park, this… More

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Hot Tub Retreat With Big Private Fenced Yard By Beach

5622 South Lockwood Ridge Road, Sarasota, United States Show map

The 3-bedroom Hot Tub Retreat With Big Private Fenced Yard By Beach Sarasota villa is located 3.6 km from Crescent Arms and provides a Jacuzzi. The holiday home hosts up to 8 guests and provides them… More

From US$ 581 Book Now

The Aquarium

5780 Midnight Pass Road Unit 701, Sarasota, United States Show map

Located a mere 5 minutes' walk from Jamaica Royale, The Aquarium Villa Sarasota is suitable for 8 guests and provides a hot tub and a sauna for a truly relaxing stay. This 3-bedroom villa features… More

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Downtown Oasis Poolside Condo Patio Gym

1703 North Tamiami Trail, Sarasota, United States Show map

Along with proximity to Marietta Museum of Art and Whimsy, located just a 9-minute stroll away, Downtown Oasis Poolside Condo Patio Gym Sarasota villa provides access to a fitness suite. Offering Wi… More

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Lulu'S Crescent Cottage #2

1121 Crescent St, Sarasota, United States Show map

Featuring a swimming pool, the 2-bedroom Lulu'S Crescent Cottage #2 Sarasota is suitable for up to 6 people and is located 3.3 km from Turtle Beach. Providing guests with Wi-Fi and a car park, the… More

From US$ 177 Book Now

*Downtown Home 10Min. Drive To Beach; Walk Dt*

1853 4Th Street, Sarasota, United States Show map

*Downtown Home 10Min. Drive To Beach; Walk Dt* Sarasota provides easy access to various city attractions, such as The Artful Giraffe Gallery, situated around 5 minutes' walk away. Located a mere 1.1… More

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Blue Cottage

3321 Williamsburg Street, Sarasota, United States Show map

Situated 2.9 km from the friendly Edson Keith Estate Park, Blue Cottage Sarasota entices guests to explore various tourist attractions in the area. More

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Sarasota Coastal Retreat

2345 Temple Street, Sarasota, United States Show map

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Mova Poolside Escape

1768 Mova St, Sarasota, United States Show map

Featuring a heated pool, Mova Poolside Escape Villa Sarasota is suitable for up to 4 people and is located about a 25-minute walk from Westfield Sarasota Square. Providing guests with Wi-Fi and a car… More

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Renovated Siesta Key Vacation Rental W/ Heated Pool Walking Distance To Beach

1015 Crescent Street, Sarasota, United States Show map

Located around a 5-minute walk from Crescent Beach, the 1-bedroom Renovated Siesta Key Vacation Rental W/ Heated Pool Walking Distance To Beach Sarasota villa provides a heated pool for guests'… More

From US$ 144 Book Now

Beach, Restaurants, Fun! Very Walkable Location

2411 Gulf Gate Drive, Sarasota, United States Show map

Overlooking the garden, Beach, Restaurants, Fun! Very Walkable Location Sarasota villa enjoys a convenient setting approximately a 5-minute walk from Saint Thomas More Catholic Church. Located 2.7 km… More

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Modern Retro Oasis Private Yard Driveway Downtown

3817 Villa Franca Ave, Sarasota, United States Show map

With the capacity to host 7 guests, the 2-bedroom Modern Retro Oasis Private Yard Driveway Downtown Villa Sarasota is located 4.3 km from such significant cultural landmarks as Towles Court Artist… More

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Cozy Coastal Paradise On Siesta Key 7 Mins To Beach

2108 Jo An Drive, Sarasota, United States Show map

The 3-bedroom Cozy Coastal Paradise On Siesta Key 7 Mins To Beach Sarasota villa offers proximity to nearby tourist spots, such as Escape Countdown, situated just 9 minutes' walk away. With a maximum… More

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Sunstone Retreat 5 Bed/ 3 Bath Heated Pool.

4430 Riverwood Avenue, Sarasota, United States Show map

Situated 4.9 km from Payne Park, Sunstone Retreat 5 Bed/ 3 Bath Heated Pool. Villa Sarasota is suitable for 8 guests and provides a year-round outdoor swimming pool for additional relaxation. More

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Mid-Term Stay In Sarasota! Home W/ Pool & Hot Tub

4534 N Lake Dr, Sarasota, United States Show map

Offering access to entertainment venues such as Forest Lakes Golf Club, situated approximately 10 minutes away by car, the 3-bedroom Mid-Term Stay In Sarasota! Home W/ Pool & Hot Tub can host up to 6… More

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Peaceful Oasis With Pool Near Downtown And Beaches

2667 Cheryle Ln, Sarasota, United States Show map

Located approximately a 10-minute drive from the kid - focused Children's Garden, the 3-bedroom Peaceful Oasis With Pool Near Downtown And Beaches Sarasota villa has a year-round outdoor swimming… More

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Palmetto House

2189 Hillview Street, Sarasota, United States Show map

The 1-bedroom Palmetto House Villa Sarasota is situated only a 5-minute stroll from Gulf Gate Mall, featuring such comforts as Wi-Fi and private car parking. The Sarasota holiday home features a… More

From US$ 387 Book Now

Tranquil Sarasota Retreat Near Beaches, Pool & Nature Escape - Timberwood Villa #183 - Roelens

7893 Timberwood Cir #183, Sarasota, United States Show map

The 2-bedroom Tranquil Sarasota Retreat Near Beaches, Pool & Nature Escape - Timberwood Villa #183 - Roelens accommodates up to 4 guests and offers a prime location merely 11 minutes' stroll from… More

From US$ 90 Book Now

Heated Salt Water Pool & Fire Pit Retreat In Sarasota

3843 Chapel Drive, Sarasota, United States Show map

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Beach Break

161 Tyler Drive, Sarasota, United States Show map

The 5-bedroom Beach Break Sarasota villa, located nearly a 5-minute walk from Coolidge Park, entices guests with a heated pool as well as a Jacuzzi to relax in. Hosting up to 16 guests, the property… More

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Gulf Front 104 - Beach Days & Happy Stays | Free Cancellation

6154 Midnight Pass Rd, Sarasota, United States Show map

Offering a heated pool, the 2-bedroom Gulf Front 104 - Beach Days & Happy Stays | Free Cancellation Sarasota villa is located merely 0.7 km from Crescent Arms and is ideal for up to 5 guests. More

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Magnificent 2 Bedroom Lakefront Condo In Heritage Oaks - Tranquil Waters

5301 Mahogany Run Avenue, Sarasota, United States Show map

Located approximately 25 minutes' walk from Bent Tree Country Club, the 1-bedroom Magnificent 2 Bedroom Lakefront Condo In Heritage Oaks - Tranquil Waters Sarasota villa has an outdoor swimming pool… More

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The Palm

409 N Washington Dr, Sarasota, United States Show map

Located only a 6-minute walk from the upscale Saint Armands Circle Outdoor Mall, the 2-bedroom The Palm Villa Sarasota is suitable for 6 guests and provides a swimming pool to relax in. This holiday… More

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1225 Gulf And Bay Bayside

1225 Siesta Bayside Dr, Sarasota, United States Show map

Located merely a 9-minute walk from Edson Keith Estate Park, the 3-bedroom 1225 Gulf And Bay Bayside Villa Sarasota boasts a swimming pool and can accommodate up to 6. This 2-bathroom villa features… More

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Sarasota Home: Near Beaches & Downtown!

5020 Swift Rd, Sarasota, United States Show map

Staying at the 2-bedroom Sarasota Home: Near Beaches & Downtown!, guests can easily reach Nontando, located approximately a 25-minute walk away. This Sarasota holiday home is suitable for up to 4… More

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Lagoon View Condo With 2 Bedrooms And Resort Pool

1400 Cove II Place, Sarasota, United States Show map

Situated only 9 minutes' stroll from Crescent Arms, the 2-bedroom Lagoon View Condo With 2 Bedrooms And Resort Pool Sarasota villa can welcome up to 6 guests and boasts a Jacuzzi for a relaxing… More

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Whispering Sands 1105

19 Whispering Sands Dr, 1105, Sarasota, United States Show map

Whispering Sands 1105 Sarasota villa offers quick access to such city attractions as Beach Club, located nearly 5 minutes' walk away. More

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Near Siesta Beach Heated Pool, Billiard

2815 Olympic Street, Sarasota, United States Show map

Situated 3.8 km from the shaped Crescent Beach, the 3-bedroom Near Siesta Beach Heated Pool, Billiard Sarasota villa is suitable for 6 guests and provides a swimming pool for additional relaxation. More

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Siesta Key Paradise, Vacation Pool Home, Near Beach, Restaurants And More

1020 Glebe Lane, Sarasota, United States Show map

Located just 5 minutes' walk from Siesta Key Village, the 4-bedroom Siesta Key Paradise, Vacation Pool Home, Near Beach, Restaurants And More Sarasota features an outdoor swimming pool and can… More

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Gorgeous 2Br Townhouse Minutes To Lido Beach

800 South Boulevard Of The Presidents, Sarasota, United States Show map

At the 2-bedroom Gorgeous 2Br Townhouse Minutes To Lido Beach Sarasota villa, guests can enjoy diving, bowling, and mini golf as well as a location just 7 minutes' walk from Bayfront Park. Offering… More

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Lido Rondy Home

1224 Westway Drive, Sarasota, United States Show map

Located approximately 7 km from The Ringling Museum, the 4-bedroom Lido Rondy Home Sarasota has a swimming pool and is ideal for up to 8 guests. Featuring fitness classes, as well as a fitness room… More

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3-Bedroom House In Fabulous Sarasota With Ac

5316 Altoona Street, Sarasota, United States Show map

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Siesta Beachfront Paradise - Infinity Pool & Spa

322 Beach Road, Sarasota, United States Show map

The 8-bedroom Siesta Beachfront Paradise - Infinity Pool & Spa Sarasota villa, located approximately 5 minutes' walk from Sarasota Beach, entices guests with an outdoor swimming pool as well as a hot… More

From US$ 6080 Book Now

Lido Palms - 148

148 Coolidge Dr, Sarasota, United States Show map

Situated approximately a 5-minute stroll from Lido Key Sandy Beach, the 5-bedroom Lido Palms - 148 Villa Sarasota ensures a great leisure experience by offering snorkelling, horseback riding, and… More

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Luxury Condo Living On Sarasota Bay, Minutes From Downtown - Admirals Watch

1703 North Tamiami Trail, Sarasota, United States Show map

The 1-bedroom Luxury Condo Living On Sarasota Bay, Minutes From Downtown - Admirals Watch villa entices active guests with access to a fitness area and is located nearly a 25-minute stroll from… More

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Contemporary Single Family 3 Bedroom Property

United States, Sarasota, United States Show map

Situated merely a 5-minute walk from Green Bean Coffee House, Contemporary Single Family 3 Bedroom Property Sarasota villa entices guests with views of the garden. The 3-bedroom holiday home features… More

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Gulf Gate Getaway 2Br 2Ba With Htd Pool Pet Friendly

2723 Gulf Gate Drive, Sarasota, United States Show map

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Helene'S Coastal Escape

3979 Helene St, Sarasota, United States Show map

Helene'S Coastal Escape Villa Sarasota is located around 7 km from Sarasota Farmers Market, giving access to various tourist spots nearby. More

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Sunny Sarasota Oasis W/ Private Screened Lanai

7461 W Country Club Dr N 102, Sarasota, United States Show map

With the capacity to host 4 guests, the 2-bedroom Sunny Sarasota Oasis W/ Private Screened Lanai villa is located within 7 km of such significant cultural landmarks as The Ringling Museum. Providing… More

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Gulf Front 103 - The Siesta Seaside Escape | Free Cancellation

6154 Midnight Pass Rd, Sarasota, United States Show map

Offering a heated pool, the 1-bedroom Gulf Front 103 - The Siesta Seaside Escape | Free Cancellation* Sarasota villa is located only 9 minutes' walk from Crescent Arms and is ideal for up to 2 guests… More

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Gulf Gate Poolside Retreat

2301 Cass St, Sarasota, United States Show map

The 3-bedroom Gulf Gate Poolside Retreat Villa Sarasota can host up to 10 guests and is situated approximately a 10-minute ride from family venues such as Livingston's Amusements. Providing guests… More

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1200-402 - Premium

1200 Peppertree Lane #402, Sarasota, United States Show map

The 2-bedroom 1200-402 - Premium Villa Sarasota is located around a 20-minute walk from Siesta Key Drum Circle and provides an outdoor swimming pool, ensuring a relaxing stay. This 2-bathroom villa… More

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