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2026-11-07
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Holiday Homes in Sarasota

Tropical Fruit Garden

4001 Groveland Ave, Sarasota, United States Show map

Located nearly a 15-minute ride from Sarasota Farmers Market, the 2-bedroom Tropical Fruit Garden Villa Sarasota boasts an outdoor swimming pool with a pool cover. More

From US$ 237 Book Now

Updated Unit With Easy Beach Access On Siesta Key

1101 Crescent Street, Sarasota, United States Show map

Updated Unit With Easy Beach Access On Siesta Key Sarasota villa is situated within a 400-metre distance of Crescent Beach and hosts up to 4 travellers. More

From US$ 118 Book Now

Beach Downtown-Family & Pet Friendly-Balcony & Garage-10 Acre Park With Pickleball, Tennis & Basketball-Lido Beach-Opera-Symphony-St Armands Circle

635 North Osprey Avenue, Sarasota, United States Show map

Located in the Central Sarasota district, within a 500-metre distance of The Artful Giraffe Gallery, Beach Downtown-Family & Pet Friendly-Balcony & Garage-10 Acre Park With Pickleball, Tennis &… More

From US$ 479 Book Now

Fully Renovated Beachside Getaway With Heated Pool - Walk To Restaurants

1011 Crescent Street, Sarasota, United States Show map

The 2-bedroom Fully Renovated Beachside Getaway With Heated Pool - Walk To Restaurants Sarasota villa is situated around 5 minutes' walk from Crescent Beach and hosts up to 6 travellers. Providing… More

From US$ 159 Book Now

Private Backyard Oasis! Hot Tub & Salt Water Pool!

5363 Foxwood Drive, Sarasota, United States Show map

Featuring an outdoor swimming pool, the 3-bedroom Private Backyard Oasis! Hot Tub & Salt Water Pool! Villa Sarasota is suitable for up to 8 people and is located nearly 20 minutes' walk from Colonial… More

From US$ 831 Book Now

Private Cozy Sarasota Home Home

1821 Ivanhoe Street, Sarasota, United States Show map

The 3-bedroom Private Cozy Sarasota Home Home offers quick access to such city attractions as Trader Joe's, located merely 6 minutes' walk away. Providing guests with Wi-Fi and a car park, this… More

From US$ 410 Book Now

Poolside Paradise Near Siesta Key Beach

5153 Honore Avenue, Sarasota, United States Show map

Offering a location 3.3 km from Bee Ridge Park, Poolside Paradise Near Siesta Key Beach Sarasota villa gives access to various tourist spots in the area. The 3-bedroom holiday home hosts up to 11… More

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Modern Vacation Home Near Siesta Key & Downtown

3940 Brookside Drive, Sarasota, United States Show map

Staying at Modern Vacation Home Near Siesta Key & Downtown Sarasota, guests can easily reach Sarasota Square, located just 1.3 km away. More

From US$ 259 Book Now

House Of The Sun Siesta Key Crescent Beach

6518 Midnight Pass Rd, Sarasota, United States Show map

Located only a 7-minute stroll from Siesta Key Marina, the 2-bedroom House Of The Sun Siesta Key Crescent Beach Sarasota villa provides a swimming pool as well as snorkelling, cycling, and fisheries… More

From US$ 526 Book Now

Gulfview Lido Key Gem - Walk To Beach & Shops

313 Benjamin Franklin Dr Unit B, Sarasota, United States Show map

The 2-bedroom Gulfview Lido Key Gem - Walk To Beach & Shops Sarasota villa hosts up to 4 guests and provides proximity to Lido Key Sandy Beach, situated about a 5-minute stroll away. Providing guests… More

From US$ 308 Book Now

Sarasota Vacation Rental W/ Private Pool & Lanai!

310 Buena Vista Ave, Sarasota, United States Show map

The 3-bedroom Sarasota Vacation Rental W/ Private Pool & Lanai! villa can host up to 6 guests and is situated within a 6-km distance of family venues such as Sarasota Jungle Gardens. Providing guests… More

From US$ 303 Book Now

Sunny Sarasota Abode W/ Yard ~ 1 Mi To Dtwn!

2225 Bahia Vista St, Sarasota, United States Show map

Staying at the 4-bedroom Sunny Sarasota Abode W/ Yard ~ 1 Mi To Dtwn! Villa, guests can visit Eloise Werlin Park, which is nearly a 25-minute walk away. The welcoming holiday home is suitable for up… More

From US$ 240 Book Now

Casa Stellata Downtown Sarasota 3 Blocks To Bay

1345 12Th Street, Sarasota, United States Show map

Offering access to entertainment venues such as the highly regarded nonprofit community theater "Players Theatre", situated only 0.7 km away, the 3-bedroom Casa Stellata Downtown Sarasota 3 Blocks To… More

From US$ 174 Book Now

Renovated Condo With Easy Beach Access On Siesta

1103 Crescent Street, Sarasota, United States Show map

The 2-bedroom Renovated Condo With Easy Beach Access On Siesta Sarasota villa is situated around a 5-minute walk from Crescent Beach and hosts up to 4 travellers. More

From US$ 239 Book Now

Near Downtown + Ocean: Sarasota Getaway

2375 Bahia Vista St, Sarasota, United States Show map

Situated approximately a 25-minute walk from Colonial Village Shopping Center, the welcoming Near Downtown + Ocean: Sarasota Getaway Villa provides access to numerous tourist attractions in the area.… More

From US$ 174 Book Now

Siesta Key Condo W/ Heated Pool < 1 Mi To Beach

6703 Midnight Pass Rd Unit 213, Sarasota, United States Show map

Up to 6 guests can stay at Siesta Key Condo W/ Heated Pool 1 Mi To Beach Sarasota villa and enjoy Green Turtle Shell & Gift City, located about a 5-minute walk away. Located merely 0.8 km from… More

From US$ 542 Book Now

Sarasota Home W/ Heated Pool: 3 Mi To Airport!

520 Saturn Ave, Sarasota, United States Show map

Featuring a heated pool, the welcoming Sarasota Home W/ Heated Pool: 3 Mi To Airport! is suitable for up to 8 people and is located around 3 km from The Ringling Museum. Providing guests with Wi-Fi… More

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Lovely Cottage Near The Beach And Downtown Sarasota

Liberty Avenue, Sarasota, United States Show map

Situated a 6-minute walk from Sarasota Square, Lovely Cottage Near The Beach And Downtown Sarasota entices guests with views of the garden. Located 4.5 km from Unconditional Surrender Sculpture… More

From US$ 263 Book Now

Sarasota Escape ~ 4 Mi To Siesta Key Beach!

3459 Clark Rd 258, Sarasota, United States Show map

Located approximately a 10-minute ride from Sarasota Square, the 3-bedroom Sarasota Escape ~ 4 Mi To Siesta Key Beach! villa has a swimming pool and is ideal for up to 6 guests. More

From US$ 186 Book Now

The Julia Place Carriage House

404 Julia Place, Sarasota, United States Show map

The 1-bedroom The Julia Place Carriage House Sarasota villa is situated about a 5-minute walk from Museum of Asian Art, featuring such comforts as Wi-Fi and private car parking. This accommodation… More

From US$ 236 Book Now

Pinecraft Tiny Home 'Green Parrot '

3100 Hawthorne Street, Sarasota, United States Show map

Staying at Pinecraft Tiny Home 'Green Parrot ' Sarasota, guests can easily reach Museum of Asian Art, located approximately a 10-minute drive away. More

From US$ 247 Book Now

Mermaid House With Pool Jacuzzi Steps To Siesta Key Beach

5228 Calle Menorca, Sarasota, United States Show map

Mermaid House With Pool Jacuzzi Steps To Siesta Key Beach Sarasota villa is nestled a 9-minute walk from Siesta Key Beach Access 2 and can accommodate up to 12 guests. More

From US$ 1296 Book Now

Cozy Tropical Bungalow With Heated Pool

1144 Crescent Street, Sarasota, United States Show map

Cozy Tropical Bungalow With Heated Pool Villa Sarasota is located approximately 25 minutes' walk from Jamaica Royale, giving access to various tourist spots nearby. More

From US$ 227 Book Now

Coastal Sarasota Condo: Minutes To Beach!

3712 Iroquois Ave, Sarasota, United States Show map

The 2-bedroom Coastal Sarasota Condo: Minutes To Beach! villa hosts up to 4 guests and provides proximity to Sarasota Jungle Gardens, situated nearly a 5-minute walk away. More

From US$ 126 Book Now

Bayside Escape-Condo W Dock Pool And Near Beach

Midnight Pass Road 9022, Sarasota, United States Show map

Featuring an outdoor swimming pool, Bayside Escape-Condo W Dock Pool And Near Beach Sarasota villa is suitable for up to 7 people and is located 5 km from the shaped Crescent Beach. Providing guests… More

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Pet Friendly Downtown 2 Story With Oversized 2 Car Garage Near Lido Beach And St Armands Circle

629 North Osprey Avenue, Sarasota, United States Show map

Overlooking the garden, Pet Friendly Downtown 2 Story With Oversized 2 Car Garage Near Lido Beach And St Armands Circle Sarasota villa enjoys a prime setting 6 minutes' walk from Sarasota Commons… More

From US$ 211 Book Now

4 Mi To Siesta Key Beach: Sunny Home W/ Hot Tub!

2149 Inner Cass Cir, Sarasota, United States Show map

During the stay at 4 Mi To Siesta Key Beach: Sunny Home W/ Hot Tub! Sarasota, guests can indulge in a Jacuzzi or visit Edson Keith Estate Park, located 3.2 km away. This 2-bedroom villa boasts spa… More

From US$ 313 Book Now

Beautiful Home - Oasis Backyard With Heat Pool

7325 Meadowbrook Drive, Sarasota, United States Show map

Located approximately a 25-minute walk from Sarasota International Convention Center, the 3-bedroom Beautiful Home - Oasis Backyard With Heat Pool Sarasota gives access to various tourist sites in… More

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Crescent Beach House

6910 Midnight Pass Road, Unit A, Sarasota, United States Show map

Staying at the 5-bedroom Crescent Beach House Sarasota villa, guests can visit Siesta Key Marina, which is only 1 km away. The Sarasota holiday home is suitable for up to 14 guests and features… More

From US$ 1826 Book Now

Alta Vista Respite

2619 Browning Street, Sarasota, United States Show map

The 2-room Alta Vista Respite Villa Sarasota is located about a 25-minute stroll from Pinecraft Public Park and allows guests to enjoy fisheries. More

From US$ 166 Book Now

Playa De Siesta Sarasota Siesta Key

2910 Valley Forge St, Sarasota, Fl 34231, Usa, Sarasota, United States Show map

Offering access to entertainment venues such as Siesta Key Marina, situated approximately 25 minutes' walk away, the 3-bedroom Playa De Siesta Sarasota Siesta Key Villa can host up to 6 guests. The… More

From US$ 393 Book Now

Beautiful Glam Mid-Century 1 Block From Sarasota Bay With Firepit

2400 Alameda Avenue, Sarasota, United States Show map

The 2-bedroom Beautiful Glam Mid-Century 1 Block From Sarasota Bay With Firepit Villa is nestled only an 8-minute walk from Marietta Museum of Art and Whimsy and can accommodate up to 5 guests. More

From US$ 169 Book Now

Spacious Vacation Rental Condo With Lagoon Views, Beach Access, And Pool

6327 Midnight Pass Road, Sarasota, United States Show map

Featuring an outdoor swimming pool, the 3-bedroom Spacious Vacation Rental Condo With Lagoon Views, Beach Access, And Pool Sarasota villa is located a mere 6 minutes' walk from crescent arms private… More

From US$ 320 Book Now

Kingston Arms 1St Floor

500 S Washington Dr, Sarasota, United States Show map

The welcoming Kingston Arms 1St Floor Villa Sarasota is located merely 5 minutes' walk from the upscale Saint Armands Circle Outdoor Mall and invites guests to enjoy guided snorkelling trips. This 2… More

From US$ 331 Book Now

Siesta Breakers Penthouse On The Beach

6480 Midnight Pass Rd, Sarasota, United States Show map

The 3-bedroom Siesta Breakers Penthouse On The Beach Sarasota villa accommodates up to 8 guests and offers proximity to Crescent Arms, located only a 6-minute walk away. Providing guests with Wi-Fi… More

From US$ 904 Book Now

Mermaid Shores

2822 Tuckerstown Dr, Sarasota, United States Show map

Featuring an outdoor swimming pool for guests' relaxation, the 4-bedroom Mermaid Shores Sarasota villa is located nearly a 25-minute stroll from Escape Countdown. The Sarasota holiday home can host… More

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Charming Sarasota Vacation Home Near Downtown

2675 Bay St, Sarasota, United States Show map

Charming Sarasota Vacation Home Near Downtown, located just steps from Jim Neville Marine Preserve, can host up to 4 guests. Located about a 25-minute walk from Pinecraft Public Park, the 2-bedroom… More

From US$ 183 Book Now

Vintage Downtown Escape, Heated Cocktail Pool, Tiki Bar & Walk To City Of Sarasota

1745 4Th Street, Sarasota, United States Show map

The 3-bedroom Vintage Downtown Escape, Heated Cocktail Pool, Tiki Bar & Walk To City Of Sarasota villa offers quick access to such tourist spots as Catholic Church, situated merely a 6-minute walk… More

From US$ 333 Book Now

Lido Beach Respite

800 South Boulevard Of Presidents #18, Sarasota, United States Show map

The 2-bedroom Lido Beach Respite Sarasota villa accommodates up to 6 guests and offers a convenient location merely 1.1 km from shopping venues such as the upscale Saint Armands Circle Outdoor Mall. More

From US$ 319 Book Now

Anything Is Possible

235 N. Adams Drive, Sarasota, United States Show map

Located only 6 minutes on foot from the upscale Saint Armands Circle Outdoor Mall, the 3-bedroom Anything Is Possible Villa Sarasota provides a swimming pool as well as fisheries to diversify guests'… More

From US$ 824 Book Now

Escape Near To Siesta Key With Hot Tub, Bbq, And Fire Pit

6005 Lords Avenue, Sarasota, United States Show map

With the capacity to host 6 guests, the 2-bedroom Escape Near To Siesta Key With Hot Tub, Bbq, And Fire Pit Villa Sarasota is located nearly 25 minutes' walk from such significant cultural landmarks… More

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Family Friendly With Large Pool

3438 Anglin Drive, Sarasota, United States Show map

Offering a Jacuzzi for a relaxing experience, Family Friendly With Large Pool Villa Sarasota is located a 10-minute drive from the upscale Saint Armands Circle Outdoor Mall. The 4-bedroom villa… More

From US$ 702 Book Now

Siesta Sands Beach Resort 4Th Floor With Elevator

1001 Point Of Rocks Rd, Sarasota, United States Show map

Situated 2.6 km from the friendly Edson Keith Estate Park, the 2-bedroom Siesta Sands Beach Resort 4Th Floor With Elevator Sarasota villa offers guests to enjoy a patio, barbecue, and a golf course. More

From US$ 501 Book Now

Siesta Keys Neighbor 5Min To Beach - Entire Suite Apartment

2205 Jo An Drive, Sarasota, United States Show map

The 1-bedroom Siesta Keys Neighbor 5Min To Beach - Entire Suite Apartment Sarasota villa hosts up to 2 guests and provides proximity to Escape Room Sarasota, situated merely 8 minutes' walk away. More

From US$ 341 Book Now

Sarasota House W/ Private Pool - 4 Mi To Beach!

Sarasota, Fl, 34239, Sarasota, United States Show map

Located nearly a 10-minute drive from Marie Selby Botanical Gardens, the 2-bedroom Sarasota House W/ Private Pool - 4 Mi To Beach! villa has a heated pool and is ideal for up to 4 guests. Guests can… More

From US$ 211 Book Now

Oasis On Siesta Key

5444 Cape Leyte Dr, Sarasota, United States Show map

Located 3 km from Siesta Key Marina, Oasis On Siesta Key Villa Sarasota offers karaoke for guests' leisure. The 4-bedroom holiday home features opportunities for diving, archery, and bowling in the… More

From US$ 485 Book Now

Peaceful Pinecone

3755 Pinecone Ct 173, Sarasota, United States Show map

During the stay at the 2-bedroom Peaceful Pinecone Villa Sarasota, guests can indulge in horseback riding, cycling, and fisheries or visit Red Bug Slough Preserve, located 4.5 km away. Featuring a… More

From US$ 229 Book Now

Family - Heated Pool - Near Siesta Key - Anna Maria - Img

151 Adair Avenue, Sarasota, United States Show map

The 1-bedroom Family - Heated Pool - Near Siesta Key - Anna Maria - Img Villa Sarasota is located 3.2 km from Sarasota International Convention Center and provides a swimming pool, ensuring a… More

From US$ 354 Book Now

Beach Side Babe

410 Garfield Dr, Us, Sarasota, United States Show map

The 1-bedroom Beach Side Babe Sarasota villa offers quick access to such city attractions as Coolidge Park, located just a 7-minute walk away. More

From US$ 318 Book Now

The Salty Seahorse

7117 Queen Palm Cir, Sarasota, United States Show map

Located a 10-minute ride from The Ringling Museum, The Salty Seahorse Villa Sarasota gives access to various tourist sites in the vicinity. More

From US$ 196 Book Now