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2026-11-07
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Holiday Homes in Sarasota

Chic Sarasota Gem Beach Bbq Workspace Patio

5723 Nutmeg Avenue, Sarasota, United States Show map

The 2-bedroom Chic Sarasota Gem Beach Bbq Workspace Patio villa can host up to 6 guests and is situated around a 10-minute ride from family venues such as Livingston's Amusements. Providing guests… More

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Blue Ranch Retreat

4658 Maceachen Boulevard, Sarasota, United States Show map

Offering an aqua park and a golf course for guests' leisure, Blue Ranch Retreat Villa Sarasota is situated 3.9 km from Pinecraft Public Park. This 3-bedroom villa features opportunities for cycling… More

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Lulu'S Crescent Cottages - Entire Two Unit Complex

1119 And 1121 Crescent St, Sarasota, United States Show map

Located nearly a 10-minute drive from Grand Canal, the 4-bedroom Lulu'S Crescent Cottages - Entire Two Unit Complex Sarasota has a heated pool and is ideal for up to 12 guests. Guests can enjoy… More

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Sarasota Wellness Retreat Sleeps 14 Patio Group Space

3014 Baldwin Avenue, Sarasota, United States Show map

Sarasota Wellness Retreat Sleeps 14 Patio Group Space villa hosts up to 14 guests and is nestled around 25 minutes' walk from natural sites such as Colonial Oaks Park. Located 2.6 km from Urfer… More

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2400 Novus Sarasota

2400 Novus Street, Sarasota, United States Show map

Located approximately 25 minutes' walk from Eloise Werlin Park, the 3-bedroom 2400 Novus Sarasota Villa provides access to various tourist attractions in the vicinity. This Sarasota holiday home is… More

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Casamigos - 1805

1805 Orchid St, Sarasota, United States Show map

The 5-bedroom Casamigos - 1805 Villa Sarasota offers quick access to such tourist spots as Sarasota Square, situated only a 5-minute walk away. This Sarasota holiday home boasts an aqua park and a… More

From US$ 718 Book Now

Pickleball Retreat With Private Pool & Spa

5505 Ruby Lane, Sarasota, United States Show map

The 3-bedroom Pickleball Retreat With Private Pool & Spa Sarasota villa is situated around 5 minutes on foot from Sarasota Christian Church and offers guests to relax with a Jacuzzi. Offering a… More

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Lakefront, Sun All Day! - Villa Youppie - Sarasota- Roelens Vacations

4940 Flagstone Drive, Sarasota, United States Show map

Offering an aqua park and a sundeck for guests' leisure, Lakefront, Sun All Day! - Villa Youppie - Sarasota- Roelens Vacations is situated 4.6 km from Red Bug Slough Preserve. Suitable for up to 8… More

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Caribbean Dream - 313

313 Beach Rd #S1, Sarasota, United States Show map

Suitable for 7 guests, Caribbean Dream - 313 Villa Sarasota offers a location a 5-minute walk from Sarasota Beach and features an aqua park and a golf course. The 2-bedroom villa features… More

From US$ 799 Book Now

Private Home 2 Miles From Siesta Key

2256 Constitution Blvd, Sarasota, United States Show map

Offering a location about 25 minutes' walk from the friendly Edson Keith Estate Park, the 2-bedroom Private Home 2 Miles From Siesta Key Sarasota gives access to various tourist spots in the area. More

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Casa Cocoanut

1314 12Th Street, Sarasota, United States Show map

Casa Cocoanut Villa Sarasota, located a 5-minute walk from Eternal Reefs, can host up to 4 guests. The 1-bedroom villa is 1.3 km from Florida Studio Theatre and 2.5 km from Stardust Events Center… More

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Gulf Front 202 - Meet Me Where The Waves Are | Free Cancellation

6154 Midnight Pass Rd, Sarasota, United States Show map

Offering a heated pool, the 2-bedroom Gulf Front 202 - Meet Me Where The Waves Are | Free Cancellation Sarasota villa is situated approximately a 10-minute walk from the shaped Crescent Beach and can… More

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Bay Tree Beach Side

8630 Midnight Pass Rd, Sarasota, United States Show map

Located a mere 9 minutes' stroll from Turtle Beach, the 2-bedroom Bay Tree Beach Side Sarasota villa provides a swimming pool as well as snorkelling, cycling, and fisheries to diversify guests'… More

From US$ 629 Book Now

Cypress Lake Pool Home

4813 Cypress Lake Court, Sarasota, United States Show map

Cypress Lake Pool Home Sarasota is located around 6 km from Sarasota Classic Car Museum and provides cycling and fisheries for active guests. Featuring a Jacuzzi, this 3-bathroom villa is within a 10… More

From US$ 456 Book Now

The Shaded Sanctuary

3331 Old Oak Dr, Sarasota, United States Show map

Located around a 15-minute walk from The Landing Shopping Center, the 3-bedroom The Shaded Sanctuary Villa Sarasota entices guests to relax in a hot tub. Guests can enjoy fisheries at this 1-bathroom… More

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Lido Shores Sanctuary

336 Morningside Drive, Sarasota, United States Show map

Featuring a swimming pool, the 4-bedroom Lido Shores Sanctuary Sarasota villa is suitable for up to 10 people and is located 3.8 km from Big Sarasota Pass. Providing guests with Wi-Fi and a private… More

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King Bed, Near Siesta Beach, Lido, And Downtown!

2815 Rosewood Place, Sarasota, United States Show map

Staying at the 3-bedroom King Bed, Near Siesta Beach, Lido, And Downtown! Sarasota villa, guests can easily reach Sarasota Square, located 2.8 km away. With a maximum capacity of 8 guests, this… More

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Siesta Key Estate

6628 Peacock Road, Sarasota, United States Show map

Located just 400 metres from Siesta Key Marina, the 12-bedroom Siesta Key Estate Villa Sarasota provides an outdoor swimming pool as well as mini golf, cycling, and billiard to diversify guests'… More

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Seabreeze Pool Retreat.

3978 Berlin Drive, Sarasota, United States Show map

Located approximately 10 minutes' drive from Escape Countdown, the 3-bedroom Seabreeze Pool Retreat. Villa Sarasota has an outdoor swimming pool and is ideal for up to 6 guests. More

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3 Bedroom Florida Beach Getaway House

6056 Carlton Avenue, Sarasota, United States Show map

Located around a 10-minute ride from Livingston's Amusements, the 3-bedroom 3 Bedroom Florida Beach Getaway House Sarasota villa boasts a heated pool with a hot tub. Featuring a terrace, the Sarasota… More

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Siesta Coastal Retreat Vr24-00082

1555 Siesta Drive, Sarasota, United States Show map

Located 10 minutes' drive from the Diverse South Lido County Waterfront Park, Siesta Coastal Retreat Vr24-00082 Villa Sarasota offers a games room for guests' leisure. The 2-bedroom holiday home… More

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Shore Is Something - 129

129 Mckinley Drive, Sarasota, United States Show map

Located merely an 8-minute walk from the Diverse South Lido County Waterfront Park, Shore Is Something - 129 Sarasota villa is suitable for 12 guests and provides a swimming pool to relax in. This 10… More

From US$ 3438 Book Now

Coconut Cove Walk To Beach

6713 Midnight Pass Rd 4, Sarasota, United States Show map

The 1-bedroom Coconut Cove Walk To Beach Sarasota villa is located nearly a 25-minute walk from Jamaica Royale and welcomes its guests to enjoy snorkelling, cycling, and fisheries. With a maximum… More

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Kingston Arms 11-B

500 S. Washington Drive, Sarasota, United States Show map

Featuring a heated pool, the 2-bedroom Kingston Arms 11-B Villa Sarasota is located approximately a 5-minute walk from St. Armand's Key Island and is suitable for up to 4 guests. Providing guests… More

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Off Tropic

1746 Hillview St, Sarasota, United States Show map

Positioned within 25 minutes' walk of bustling shopping destinations such as Sarasota Farmers Market, the 3-bedroom Off Tropic Villa Sarasota offers guests to use parking. This Sarasota holiday home… More

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Siesta Key Room Cozy Convenient

2108 Jo An Drive, Sarasota, United States Show map

Accommodating up to 2 guests, Siesta Key Room Cozy Convenient Sarasota villa is situated 2.5 km from renowned cultural sites such as Gulf Gate Public Library. More

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Stylish Pool Home 4Br Near Siesta Key Palm Noir

2441 Webber St, Sarasota, United States Show map

Along with access to such natural sites as Pinecraft Public Park, about a 25-minute walk away, the 2-bedroom Stylish Pool Home 4Br Near Siesta Key Palm Noir Sarasota offers a swimming pool. Situated… More

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Vitamin Sea

330 Caruso Place, Sarasota, United States Show map

Offering access to entertainment venues such as Florida Studio Theatre, situated approximately 4 km away, the 4-bedroom Vitamin Sea Sarasota villa can host up to 8 guests. This Sarasota holiday home… More

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Oceanview 100 Percent Private, Tiki, 100Ft To Beach Path!

603 Beach Rd, Siesta Key, Fl 34242, Usa, Sarasota, United States Show map

Situated within 5 minutes' walk of Sarasota Beach, the 7-bedroom Oceanview 100 Percent Private, Tiki, 100Ft To Beach Path! Sarasota villa offers quick access to numerous city landmarks nearby. More

From US$ 7895 Book Now

Private Heated Pool & Fenced Yard - Pets Welcome - Private Gate To St Armands

55 N Washington Dr, Sarasota, Fl 34236, Usa, Sarasota, United States Show map

Located nearly 5 minutes' walk from St. Armands Key Lutheran Church, the 6-bedroom Private Heated Pool & Fenced Yard - Pets Welcome - Private Gate To St Armands Sarasota villa gives easy access to… More

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Cozy Home In Gulf Gate

2206 Hively Street, Sarasota, United States Show map

Nestled a 25-minute walk from Nontando, Cozy Home In Gulf Gate Sarasota entices guests to explore various tourist destinations nearby. More

From US$ 123 Book Now

Poseidons Palace

5613 Cape Leyte Dr, Sarasota, United States Show map

Located merely 6 minutes' walk from Siesta Key Beach, the 3-bedroom Poseidons Palace Sarasota villa features a heated pool and can accommodate up to 8 guests. The property boasts a picnic area and a… More

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Excelsior: The Sky Loft

6263 Midnight Pass Rd 3-403, Sarasota, United States Show map

Situated just a 5-minute walk from Crescent Arms, Excelsior: The Sky Loft Villa Sarasota offers guests to relax by a swimming pool. Featuring a Jacuzzi, the 2-bedroom holiday home is in the vicinity… More

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Private Pool Home Siesta Key Siesta Sol

5021 Midnight Pass Road, Sarasota, United States Show map

Located approximately 25 minutes' walk from Siesta Key Beach, the 3-bedroom Private Pool Home Siesta Key Siesta Sol Sarasota has an outdoor swimming pool and is ideal for up to 8 guests. Guests can… More

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1077 Pd

1077 Peppertree Drive #1077, Sarasota, United States Show map

Located about 25 minutes' walk from Sarasota Beach, the 2-bedroom 1077 Pd Villa Sarasota has a heated pool and is ideal for up to 4 guests. Guests can enjoy fisheries at this property, located 4.5 km… More

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Pinecraft Blue Heron Tiny Home

3100 Hawthorne Street, Sarasota, United States Show map

Situated 4.4 km from Florida Studio Theatre, Pinecraft Blue Heron Tiny Home Sarasota entices guests to explore various tourist attractions in the area. More

From US$ 177 Book Now

Siesta Heron 7

8254 Midnight Pass Road, Sarasota, United States Show map

Positioned within a 7-km distance of bustling shopping destinations such as Tervis Tumbler Gift Shop, the 3-bedroom Siesta Heron 7 Sarasota villa offers guests to use a car park. This Sarasota… More

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New Upscale & Modern Heated Pool Home In Walkable Downtown!

275 Lime Circle, Sarasota, United States Show map

New Upscale & Modern Heated Pool Home In Walkable Downtown! Sarasota enjoys a convenient location, a 25-minute walk from Pinecraft Public Park, and offers guests to unwind in a hot tub. More

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Escape By The Sea

3951 Roberts Point Road, Sarasota, United States Show map

During the stay at Escape By The Sea Villa Sarasota, guests can indulge in hiking, horseback riding, and squash or visit Lido Key Sandy Beach, located a 10-minute drive away. Offering horse riding… More

From US$ 485 Book Now

Avanti Villa On Grand Canal - 534

534 Canal Road, Sarasota, United States Show map

Nestled approximately 5 minutes' walk from Public Beach Access 10, the 3-bedroom Avanti Villa On Grand Canal - 534 Sarasota comes with an aqua park and a golf course for added enjoyment. Located 2.5… More

From US$ 583 Book Now

Gulf Front 305 - The Barefoot Siesta Getaway | Free Cancellation

6154 Midnight Pass Rd, Sarasota, United States Show map

Located just 1.4 km from Siesta Key Marina, the 2-bedroom Gulf Front 305 - The Barefoot Siesta Getaway | Free Cancellation Sarasota villa has a swimming pool and is ideal for up to 4 guests. More

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Yellow Pine Duplex Close To Pool & Tennis

3610 Yellow Pine Ct, Sarasota, United States Show map

Yellow Pine Duplex Close To Pool & Tennis Sarasota villa is located 4.4 km from Crescent Arms and provides snorkelling, cycling, and fisheries for active guests. Offering guided snorkelling trips… More

From US$ 278 Book Now

Siesta Sands Paradise 4Br 3Ba Sleep 16

2424 Whippoorwill Circle, Sarasota, United States Show map

Located nearly a 10-minute ride from Lukewood Park, Siesta Sands Paradise 4Br 3Ba Sleep 16 Sarasota villa offers a games room for guests' entertainment. Featuring garden views, the Sarasota holiday… More

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Charming Vacation Rental Close To Downtown!

Sarasota, United States Show map

Offering a location 3.1 km from Catholic Church, Charming Vacation Rental Close To Downtown! Sarasota villa gives access to various tourist spots in the area. More

From US$ 278 Book Now

Boho Villa 10 Mins From Siesta

3818 Villa Franca Avenue, Sarasota, United States Show map

Staying at Boho Villa 10 Mins From Siesta Sarasota, guests can easily reach Bayfront Park, located approximately a 10-minute ride away. More

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Salty Sun Sets Estate

6536 Peacock Road, Sarasota, United States Show map

Offering guests to work out with bicycles, the 13-bedroom Salty Sun Sets Estate Villa Sarasota is situated around 5 minutes' walk from Siesta Key Marina. This property boasts an aqua park and a golf… More

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Liza'S Florida House

2239 Clematis Street, Sarasota, United States Show map

The 1-bedroom Liza'S Florida House Villa Sarasota can host up to 6 guests, boasting a convenient location around a 25-minute stroll from iconic cultural attractions such as Towles Court Artist Colony. More

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Your Crew'S Perfect Gulf Coast Base

2225 Alice Road, Sarasota, United States Show map

Nestled 3.6 km from Bay Island, Your Crew'S Perfect Gulf Coast Base Sarasota villa entices guests to explore various tourist destinations nearby. More

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Florida Oasis Fully Equipped • 12 Min To Beaches

3772 Pinecone Court, Sarasota, United States Show map

The 2-bedroom Florida Oasis Fully Equipped • 12 Min To Beaches Sarasota villa is located around 5 km from the shaped Crescent Beach and provides a Jacuzzi. This property hosts up to 4 guests and… More

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Poolside Paradise

4212 Des Plaines Drive, Sarasota, United States Show map

Featuring a heated pool, the 3-bedroom Poolside Paradise Sarasota villa is suitable for up to 8 people and is located within 15 minutes' drive of Unconditional Surrender Sculpture Museum. Providing… More

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