Wine Country Villas - Vacation Rentals in Sarasota Square

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From US $381

         

9.6 (49 Reviews)

Villa

WINTER SPECIAL! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Sarasota

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From US $220

         

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10.0 (3 Reviews)

Villa

Lanai and Community Pool Access Sarasota Oasis!

• Parking
• Accessibility
• Security/Safety

• Florida
• Sarasota

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From US $260

         

9.4 (51 Reviews)

Villa

Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk

• Security/Safety
• Barbecue/Outdoor Cooking
• Child Friendly

• Sarasota
• Siesta Key

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From US $314

         

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10.0 (1 Review)

Villa

Sarasota Resort-Like Living Near Siesta Key For 10

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Sarasota

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From US $394

         

10.0 (2 Reviews)

Villa

Crystal Sands Villa 12 - Private Beach

• Air Conditioner
• Parking
• Pool

• Sarasota
• Siesta Key

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From US $125

         

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10.0 (1 Review)

House

Villa Pine Tree Pool close to the beaches Siesta Key

• Air Conditioner
• Parking
• Pool

• Florida
• Sarasota

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From US $382

         

10.0 (5 Reviews)

Villa

Beachy villa on Siesta Key with heated pool, screened in lanai, and ground level

• Air Conditioner
• Parking
• Pool

• Sarasota
• Siesta Key

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From US $250

         

10.0 (42 Reviews)

Villa

Sandy Shores Villa near Sieta Key and other beaches

• Air Conditioner
• Parking
• Pool

• Sarasota
• Gulf Gate Estates

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From US $373

         

10.0 (37 Reviews)

Villa

Newly Remodeled-150 Yards to Beach and Restaurants!

• Air Conditioner
• Parking
• Pool

• Sarasota
• Siesta Key

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From US $350

         

10.0 (37 Reviews)

Villa

Completely Remodeled- 150 Yards to Beach and Restaurants!

• Air Conditioner
• Parking
• Pool

• Sarasota
• Siesta Key

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From US $413

         

10.0 (17 Reviews)

Villa

Crystal Sands Villa 15 - Private Beach

• Air Conditioner
• Parking
• Pool

• Sarasota
• Siesta Key

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From US $368

         

10.0 (13 Reviews)

Villa

2025 completely remodeled private villa, 7 min walk to beach, entertainment

• Air Conditioner
• Parking
• Pool

• Sarasota
• Siesta Key

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From US $313

         

10.0 (13 Reviews)

Villa

Modern, Spacious Villa close to #1 Siesta Key Beach! FreeWiFi, Updated

• Air Conditioner
• Parking
• Pool

• Florida
• Sarasota

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From US $222

         

10.0 (11 Reviews)

Villa

Beautiful Villa in Sarasota Resort-style Community

• Air Conditioner
• Parking
• Pool

• Florida
• Sarasota

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From US $295

         

10.0 (7 Reviews)

Villa

Sparkling Clean Villa at Vista Hermosa. Walk to Beach, Dining, Shopping & More 167

• Air Conditioner
• Parking
• Pool

• Sarasota
• Siesta Key

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From US $416

         

10.0 (4 Reviews)

Villa

Beachy 3-bedroom Villa on Siesta Key with WiFi, AC

• Air Conditioner
• Parking
• Pool

• Sarasota
• Siesta Key

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From US $477

         

10.0 (1 Review)

Villa

Perfect Getaway Villa with 2 bedrooms/2 baths, quick walk to the beach!

• Air Conditioner
• Parking
• Pool

• Sarasota
• Siesta Key

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From US $473

         

10.0 (1 Review)

Villa

Crystal Sands Villa 20 - Private Beach

• Air Conditioner
• Parking
• Pool

• Sarasota
• Siesta Key

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From US $472

         

10.0 (1 Review)

Villa

Beautiful Two Bedroom/Two Bath Bianco Sands, Quick Walk to Beach!

• Air Conditioner
• Parking
• Pool

• Sarasota
• Siesta Key

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From US $461

         

10.0 (1 Review)

Villa

Beautiful Two Bedroom/Two Bath Bianco Sands, Quick Walk to Beach!

• Air Conditioner
• Parking
• Pool

• Sarasota
• Siesta Key

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From US $429

         

10.0 (1 Review)

Villa

Luxurious 4-Bedroom Retreat near Siesta Key

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Sarasota

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From US $421

         

10.0 (1 Review)

Villa

Stunning Pool-side 2 bed/2 Bath With A Quick Walk to Beach!

• Air Conditioner
• Parking
• Pool

• Sarasota
• Siesta Key

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From US $245

         

10.0 (1 Review)

Villa

Our American Dream - Charming villa close to Siesta Key Beach

• Air Conditioner
• Pool
• TV

• Florida
• Sarasota

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From US $214

         

10.0 (1 Review)

Villa

Spacious 2 BD and 2BA Villa 13 minutes from Siesta Key!

• Air Conditioner
• Parking
• Pool

• Florida
• Sarasota

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★ Pro Tip: Winecountryvillas makes it easy to compare the best listings on Winecountryvillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Winecountryvillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Sarasota Square.