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2026-11-07
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Holiday Homes in Sarasota

Siesta Heron 2

8254 Midnight Pass Road, Sarasota, United States Show map

Situated 3.3 km from the shaped Crescent Beach, the 1-bedroom Siesta Heron 2 Sarasota villa offers guests to enjoy an aqua park and a golf course. This accommodation features opportunities for… More

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Kingston Arms 1St Fl Cottage

500 S Washington Dr, Sarasota, United States Show map

Situated about a 5-minute walk from the upscale Saint Armands Circle Outdoor Mall, the 2-bedroom Kingston Arms 1St Fl Cottage Sarasota offers guests to relax by a swimming pool. This holiday home… More

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Pool - Near Beach - Outdoor Games For Family - Close To Dt - Vr24-00067

2105 Hyde Park Circle, Sarasota, United States Show map

Featuring a swimming pool, the 1-bedroom Pool - Near Beach - Outdoor Games For Family - Close To Dt - Vr24-00067 Sarasota villa is located merely 6 minutes' walk from Arlington Park and is suitable… More

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Bay Oaks Bayfront 2-Story Condo

6157 Midnight Pass Rd, C-32, Sarasota, United States Show map

The 2-bedroom Bay Oaks Bayfront 2-Story Condo Sarasota villa hosts up to 6 guests and provides proximity to Crescent Arms, situated merely 0.6 km away. More

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1128 Pl - Premium

1128 Peppertree Lane, Sarasota, United States Show map

Situated just 0.7 km from Crescent Arms, the 2-bedroom 1128 Pl - Premium Villa Sarasota is ideal for up to 4 guests. This Sarasota villa features opportunities for fisheries in the area, around a 10… More

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The Swordfish On Siesta

1146 Crescent St, Sarasota, Fl 34242, Sarasota, United States Show map

Nestled a 10-minute drive from Grand Canal, The Swordfish On Siesta Villa Sarasota entices guests to explore various tourist destinations nearby. More

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The Tropical Retreat

2267 Pine View Cir, Sarasota, United States Show map

With the capacity to host 8 guests, the 4-bedroom The Tropical Retreat Villa Sarasota is located only 1.7 km from such significant cultural landmarks as Gulf Gate Public Library. Providing guests… More

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6018 Wpw - Premium

6018 West Peppertree Way, Sarasota, United States Show map

Located 9 minutes' walk from Crescent Arms, 6018 Wpw - Premium Villa Sarasota is suitable for 4 guests and provides a heated pool to relax in. The 2-bedroom holiday home features opportunities for… More

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Paradise Found

2244 Novus Street, Sarasota, United States Show map

The 3-bedroom Paradise Found Sarasota villa is located nearly a 25-minute walk from the kid-focused Children's Garden and provides snorkelling, snow skiing, and cycling for active guests. Offering… More

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Sunshine Retreat

2472 Temple Street, Sarasota, United States Show map

The 4-bedroom Sunshine Retreat Villa Sarasota offers easy access to such tourist spots as Arlington Park and Aquatic Complex, located nearly a 5-minute walk away. More

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Sapphire Shores Studio King Bed

528 45Th Street, Sarasota, United States Show map

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Waterfront Pool Home - Amazing Sunsets Included

8730 Dunmore Drive, Sarasota, United States Show map

Featuring an outdoor swimming pool, Waterfront Pool Home - Amazing Sunsets Included Sarasota is suitable for up to 6 people and is located 10 minutes' drive from Historic Spanish Point. More

From US$ 201 Book Now

Lakeview 3-Bedroom House

4634 Mcintosh Road, Sarasota, United States Show map

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6042 Wpw Premium Plus

6042 West Peppertree Way, Sarasota, United States Show map

Offering a heated pool, the 3-bedroom 6042 Wpw Premium Plus Sarasota villa is situated just 9 minutes' walk from Crescent Arms and can accommodate up to 6 guests. This Sarasota holiday home features… More

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1 Bedroom Condo Downtown Sarasota - Close To Beaches Enjoy Sarasota!

1703 North Tamiami Trail, Sarasota, United States Show map

Situated only a 5-minute stroll from Marietta Museum of Art and Whimsy, the 1-bedroom 1 Bedroom Condo Downtown Sarasota - Close To Beaches Enjoy Sarasota! villa can host up to 2 guests and offers a… More

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Wish Upon A Starfish Pool Home

7510 Starfish Dr, Sarasota, United States Show map

Offering access to entertainment venues such as Siesta Key Marina, situated about a 25-minute stroll away, the 3-bedroom Wish Upon A Starfish Pool Home Sarasota can host up to 7 guests. Providing… More

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Luxury Sarasota Waterfront Home - Pool, Boat Dock & Near Siesta Key Beach

7767 N Holiday Dr, Sarasota, United States Show map

The 4-bedroom Luxury Sarasota Waterfront Home - Pool, Boat Dock & Near Siesta Key Beach is located 2.5 km from Turtle Beach and provides a Jacuzzi. Suitable for up to 8 guests, this accommodation… More

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Fully Renovated Beach House

5433 Nutmeg Ave, Sarasota, United States Show map

Nestled 15 minutes' drive from Urfer Family Park, Fully Renovated Beach House Sarasota villa entices guests to explore various tourist destinations nearby. The 3-bedroom holiday home hosts up to 8… More

From US$ 228 Book Now

Family Fiesta

2141 Fiesta Dr, Sarasota, United States Show map

Along with access to such natural sites as Bee Ridge Park, approximately a 25-minute walk away, the 3-bedroom Family Fiesta Villa Sarasota offers an outdoor swimming pool. Providing guests with Wi-Fi… More

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Centrally Located Sarasota Home W/ Heated Pool!

546 Magellan Dr, Sarasota, United States Show map

Featuring a heated pool, Centrally Located Sarasota Home W/ Heated Pool! is suitable for up to 6 people and is located 4.6 km from The Ringling Museum. Providing guests with Wi-Fi and private parking… More

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The Beach Club At Siesta #106B

1020 Sun N Sea Drive, Unit 106 B, Sarasota, United States Show map

Located just 0.7 km from Turtle Beach, the 2-bedroom The Beach Club At Siesta #106B Sarasota villa boasts a swimming pool, a Jacuzzi for a relaxing experience. Staying at this Sarasota holiday home… More

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The Britannia Breeze-5 Min To Siesta Key, Sleeps 9

5773 Britannia Dr, Sarasota, United States Show map

Nestled 5 minutes' drive from Bee Ridge Park, The Britannia Breeze-5 Min To Siesta Key, Sleeps 9 Villa Sarasota entices guests to explore various tourist destinations nearby. The 4-bedroom villa… More

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Resort-Style Sarasota Villas Near Beaches, Pool & Tennis - Sarasota Sweets - Roelens

7893 Timberwood Cir #183 / 3776 Spanish Pine Ct #210, Sarasota, United States Show map

Situated 5 km from the shaped Crescent Beach, Resort-Style Sarasota Villas Near Beaches, Pool & Tennis - Sarasota Sweets - Roelens is suitable for 8 guests and provides an outdoor swimming pool for… More

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Waterview Dream

8370 Wingate Drive, Sarasota, United States Show map

Situated 3.3 km from Historic Spanish Point, the 3-bedroom Waterview Dream Villa Sarasota entices guests to explore various tourist attractions in the area. This 2-bathroom villa hosts up to 6 guests… More

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Bluewater Escape

2922 Captiva Way, Sarasota, United States Show map

Featuring a year-round outdoor swimming pool, Bluewater Escape Villa Sarasota is located in a beach part of Sarasota, 3.2 km from Turtle Beach. More

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Artsy Abode At Siesta Key

5923 Richard Place, Sarasota, United States Show map

Staying at the 2-bedroom Artsy Abode At Siesta Key Villa Sarasota, guests can visit Public Beach Access 10, which is approximately 4 km away. This Sarasota holiday home is suitable for up to 3 guests… More

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Resort Pool & Hot Tub: Home 8 Mi To Dtwn Sarasota

7125 Fruitville Rd #Lo36, Sarasota, United States Show map

The 2-bedroom Resort Pool & Hot Tub: Home 8 Mi To Dtwn Sarasota is located within 3 km of Big Cat Habitat Gulf Coast Sanctuary Zoo, giving access to various tourist spots nearby. This Sarasota… More

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Siesta Sun Oasis - 5545

5545 Shadow Lawn Dr, Sarasota, United States Show map

Suitable for 10 guests, Siesta Sun Oasis - 5545 Villa Sarasota offers a location 5 minutes' walk from St. Boniface Episcopal Church Labyrinth and features barbecue and a golf course. The 5-bedroom… More

From US$ 1720 Book Now

6 Mi To Beach! Home W/ Poolside Oasis In Sarasota

2562 25Th Street, Sarasota, United States Show map

Nestled a 25-minute stroll from Siesta Key Rum, the welcoming 6 Mi To Beach! Home W/ Poolside Oasis In Sarasota is boasting spa therapy, a patio, and a firepit area for guests' enjoyment. Located 2.4… More

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Family Friendly Retreat Near Siesta Key Beach Gear

1812 Livingstone Street, Sarasota, United States Show map

Situated 10 minutes' drive from Escape Countdown, Family Friendly Retreat Near Siesta Key Beach Gear Sarasota villa entices guests to explore various tourist attractions in the area. More

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º Tropical Escape Sarasota º Experience Florida Up-Close!

3222 59Th Street, Sarasota, United States Show map

º Tropical Escape Sarasota º Experience Florida Up-Close! villa provides easy access to various city attractions, such as Detwiler's Farm Market, situated 6 minutes' walk away. More

From US$ 204 Book Now

Group Vacation Home- Pool Table, Hot Tub, Fire Pit

4307 Foremere Place, Sarasota, United States Show map

Staying at Group Vacation Home- Pool Table, Hot Tub, Fire Pit Sarasota, guests can visit Jamaica Royale, which is nearly a 10-minute ride away. More

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Siesta Sol Art Bungalow- 2 Miles To Siesta Key!

2822 Post Road, Sarasota, United States Show map

Situated only 450 metres from Gulf Gate Public Library, the 2-bedroom Siesta Sol Art Bungalow- 2 Miles To Siesta Key! Sarasota offers quick access to numerous city landmarks nearby. More

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Downtown Srq 3Br 2Ba, Playground, Unit 1, Sleeps 6

2031 4Th Street, Sarasota, United States Show map

The 3-bedroom Downtown Srq 3Br 2Ba, Playground, Unit 1, Sleeps 6 Villa Sarasota offers quick access to such city attractions as The Artful Giraffe Gift Shop, located just a 5-minute walk away. More

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Pvt Room In Shared Home Near Beach

2108 Jo An Drive Unit A, Sarasota, United States Show map

Located just 1.3 km from the friendly Edson Keith Estate Park, the 1-bedroom Pvt Room In Shared Home Near Beach Sarasota provides access to various tourist attractions in the vicinity. This Sarasota… More

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Coastal Beauty With Sunset Cruise For Bookings Over 10 Nights

3521 Almeria Avenue, Sarasota, United States Show map

Up to 8 guests can stay at Coastal Beauty With Sunset Cruise For Bookings Over 10 Nights Sarasota villa and enjoy Pelican Plaza Shopping Center, located about a 5-minute walk away. Featuring a hot… More

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Luxe Bayfront Sarasota Home Rental: Pool, Lanai!

1730 Caribbean Dr, Sarasota, United States Show map

The 3-bedroom Luxe Bayfront Sarasota Home Rental: Pool, Lanai! is located 3.2 km from Edson Keith Estate Park and provides a Jacuzzi. Suitable for up to 6 guests, this accommodation offers… More

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Welcome To The Bray Escape 4 Miles To Siesta Key

7995 Wright Avenue, Sarasota, United States Show map

Welcome To The Bray Escape 4 Miles To Siesta Key Sarasota villa offers proximity to such city sites as Faith Lutheran Church, located merely a 6-minute walk away. More

From US$ 217 Book Now

Pelican Gardens 7 By Lido Beach

170 Roosevelt Dr, Sarasota, United States Show map

Pelican Gardens 7 By Lido Beach Sarasota villa offers proximity to nearby tourist spots, such as Bayfront Park, situated 3.6 km away. More

From US$ 303 Book Now

4 Mi To Siesta Beach: Condo W/ Community Perks!

3604 Pine Point Ct, Sarasota, United States Show map

The 2-bedroom 4 Mi To Siesta Beach: Condo W/ Community Perks! Sarasota villa is located approximately 7 km from Siesta Key Village and provides hiking for active guests. Featuring a Jacuzzi, this… More

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Sarasota 3-Home Group Stay By Heartfull Homes

1661 9Th Street, Sarasota, United States Show map

Located within 5 minutes' walk of Westcoast Black Theater Troupe, Sarasota 3-Home Group Stay By Heartfull Homes gives easy access to various tourist attractions in the area. More

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Cozy Cottage Near Beaches And Downtown Sarasota Vr-00163

2458 Waldemere Street, Sarasota, United States Show map

The 2-bedroom Cozy Cottage Near Beaches And Downtown Sarasota Vr-00163 offers easy access to such tourist spots as Arlington Park and Aquatic Complex, located just a 5-minute walk away. More

From US$ 139 Book Now

Key West Style-Livin'

628 42Nd St., Sarasota, United States Show map

Key West Style-Livin' Villa Sarasota is located about a 20-minute walk from Sarasota Classic Car Museum and provides cycling and fisheries for active guests. Located in the vicinity of Ca d Zan… More

From US$ 258 Book Now

4 Mi To Siesta Key Beach: Condo W/ Pool Access

3473 Clark Rd Unit 171, Sarasota, United States Show map

Accommodating up to 6 guests, the 2-bedroom 4 Mi To Siesta Key Beach: Condo W/ Pool Access Sarasota villa is situated within 25 minutes' walk of renowned cultural sites such as Gulf Gate Public… More

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Summer Shores Estate

209 Garfield Drive, Sarasota, United States Show map

Located 25 minutes' walk from Bird Key Park, Summer Shores Estate Sarasota villa offers a casino for guests' leisure. The 12-bedroom holiday home features opportunities for horseback riding, cycling,… More

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Lido Dream Combined Duplex Both N & S

438 And 440 S Boulevard Of The Presidents, Sarasota, United States Show map

The 4-bedroom Lido Dream Combined Duplex Both N & S Villa Sarasota offers proximity to nearby tourist spots, such as Save Our Seabirds, situated about a 25-minute walk away. With a maximum capacity… More

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1200-602 - Premium Plus

1200 Peppertree Lane #602, Sarasota, United States Show map

Located only 9 minutes on foot from Jamaica Royale, the 2-bedroom 1200-602 - Premium Plus Sarasota villa provides an outdoor swimming pool as well as fisheries to diversify guests' leisure. Offering… More

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Private Theater Retreat Stylish 2Br 10Min To Siesta Key

5020 Swift Road, Sarasota, United States Show map

The 1-bedroom Private Theater Retreat Stylish 2Br 10Min To Siesta Key Villa Sarasota is located approximately 25 minutes' walk from Nontando, giving access to various tourist spots nearby. The… More

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1255-305 - Premium Plus

1255 Peppertree Drive #305, Sarasota, United States Show map

Along with proximity to the shaped Crescent Beach, just a 10-minute walk away, the 2-bedroom 1255-305 - Premium Plus Sarasota villa offers opportunities for fisheries in the area. Providing guests… More

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1125

1125 Peppertree Drive #605, Sarasota, United States Show map

Offering an outdoor swimming pool, the 2-bedroom 1125 Villa Sarasota is situated only a 9-minute walk from Crescent Arms and can accommodate up to 4 guests. This holiday home features opportunities… More

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