Vacation Rentals in Sarasota Square, FL: Compare 10+ Sites & Save

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3295 Best Vacation Rentals in Sarasota Square (Starting from $125)

Peaceful Pinecone
Peaceful Pinecone
Apartment
Sarasota, FL, USA
0.3k from Sarasota Square center

Apartments, Accommodations, Pools, Lodgings, Jacuzzis, Places to stay

2 Bedrooms4 Guests
7.0

Good

1 reviews

$268
Average price / night
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Charming Villa in peaceful community minutes to Siesta Key
Charming Villa in peaceful community minutes to Siesta Key
Villa
Sarasota, FL, 34238, United States
0.2k from Sarasota Square center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
9.0

Fabulous

2 reviews

$278
Average price / night
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Villa Pine Tree Pool close to the beaches Siesta Key
Villa Pine Tree Pool close to the beaches Siesta Key
House
Sarasota, FL, USA
0.3k from Sarasota Square center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$125
Average price / night
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BEAUTIFUL VILLA NEAR SIEATA KEY!! This coveted Community includes Pool/Hot tub/Tennis/Pickleball/ Putting Green, and Shuffleboard
BEAUTIFUL VILLA NEAR SIEATA KEY!! This coveted Community includes Pool/Hot tub/Tennis/Pickleball/ Putting Green, and Shuffleboard
House
Sarasota, FL, 34238, United States
0.3k from Sarasota Square center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
8.6

Fabulous

7 reviews

$231
Average price / night
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Sarasota Villa with Pool Access about 4 Mi to Beach!
Sarasota Villa with Pool Access about 4 Mi to Beach!
Villa
Sarasota, FL, USA
0.4k from Sarasota Square center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Hot tubs

2 Bedrooms6 Guests
9.5

Superb

4 reviews

$480
Average price / night
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Pool, Jacuzzi, Pickleball, Tennis, close to Siesta Key Beaches/3772SP
Pool, Jacuzzi, Pickleball, Tennis, close to Siesta Key Beaches/3772SP
Villa
Sarasota, FL, 34238, United States
0.3k from Sarasota Square center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
New to Booking
$202
Average price / night
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Sunny Sarasota Villa with Lanai Less Than 5 Mi to Beach
Sunny Sarasota Villa with Lanai Less Than 5 Mi to Beach
Villa
Sarasota, FL, USA
0.4k from Sarasota Square center

Accessibility, Wellness Facilities, Sports/Activities, Balcony/Terrace, Pool, Security/Safety, Parking

2 Bedrooms4 Guests
8.8

Fabulous

4 reviews

$358
Average price / night
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Beautiful Sarasota Villa with Pool Access and Tennis – 4 Miles to the Beach
Beautiful Sarasota Villa with Pool Access and Tennis – 4 Miles to the Beach
Villa
Sarasota, FL, 34238, United States
0.3k from Sarasota Square center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$239
Average price / night
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LUX VILLAs on beautiful Palmer Ranch
LUX VILLAs on beautiful Palmer Ranch
Villa
Vamo, FL, USA
0.5k from Sarasota Square center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

4 Bedrooms8 Guests
7.8

Good

46 reviews

$454
Average price / night
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Lux Villa/Heated Pool/Hot Tub/Tennis/Pickleball/Close to Beaches!
Lux Villa/Heated Pool/Hot Tub/Tennis/Pickleball/Close to Beaches!
Villa
Sarasota, FL, 34238, United States
0.3k from Sarasota Square center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Microwave

2 Bedrooms6 Guests
8.0

Good

1 reviews

$265
Average price / night
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Lanai and Community Pool Access Sarasota Oasis!
Lanai and Community Pool Access Sarasota Oasis!
Villa
Sarasota, FL, USA
0.5k from Sarasota Square center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Hot tubs

2 Bedrooms5 Guests
10.0

Exceptional

3 reviews

$220
Average price / night
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Escape to Paradise: Updated Sarasota Retreat near Siesta Key Beach and Pool!
Escape to Paradise: Updated Sarasota Retreat near Siesta Key Beach and Pool!
House
Sarasota, FL, 34238, United States
0.3k from Sarasota Square center

AC, Arcade, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms3 Guests
9.6

Exceptional

50 reviews

$190
Average price / night
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Relaxing 2 bed Siesta Key bungalow minutes from the beach
Relaxing 2 bed Siesta Key bungalow minutes from the beach
House
Sarasota, FL, USA
0.6k from Sarasota Square center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Bungalows

2 Bedrooms5 Guests
New to Booking
$201
Average price / night
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Village Des Pins in Sunny Sarasota
Village Des Pins in Sunny Sarasota
Villa
Sarasota, FL, 34238, United States
0.3k from Sarasota Square center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

7 reviews

$171
Average price / night
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Sarasota Costal Vibe 15 min from Siesta Key
Sarasota Costal Vibe 15 min from Siesta Key
House
Sarasota, FL, USA
1.0k from Sarasota Square center

Guest Services, Security/Safety, Balcony/Terrace, Pet Friendly, Internet, Barbecue/Outdoor Cooking, Parking

3 Bedrooms7 Guests
New to Booking
$262
Average price / night
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Family Friendly Villa15 min to Siesta Key Wagon, Chairs, Umbrella, Toys Provided
Family Friendly Villa15 min to Siesta Key Wagon, Chairs, Umbrella, Toys Provided
Villa
Sarasota, FL, 34238, United States
0.3k from Sarasota Square center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.8

Exceptional

122 reviews

$196
Average price / night
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Sarasota 15 min from Siesta
Sarasota 15 min from Siesta
House
Sarasota, FL, USA
1.0k from Sarasota Square center

Air Conditioner, View, Balcony/Terrace, Fireplace/Heating, Security/Safety, Parking, Internet

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$262
Average price / night
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Long term discounts / Resort Style Vacation Villa
Long term discounts / Resort Style Vacation Villa
Villa
Sarasota, FL, 34238, United States
0.3k from Sarasota Square center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.8

Exceptional

15 reviews

$189
Average price / night
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Welcome to The Bray Escape 4 miles to Siesta Key
Welcome to The Bray Escape 4 miles to Siesta Key
House
Sarasota Square, Sarasota, Florida, USA
1.0k from Sarasota Square center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

2 Bedrooms6 Guests
10.0

Exceptional

20 reviews

$288
Average price / night
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Resort Style Villa With Heated Pool, 2 Tennis Courts And Jacuzzi !
Resort Style Villa With Heated Pool, 2 Tennis Courts And Jacuzzi !
Villa
Sarasota, FL, 34238, United States
0.3k from Sarasota Square center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms4 Guests
9.4

Superb

26 reviews

$182
Average price / night
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Pinestone Condo On Palmer Ranch
Pinestone Condo On Palmer Ranch
House
Sarasota, FL, USA
1.1k from Sarasota Square center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay, Condos

2 Bedrooms4 Guests
New to Booking
$292
Average price / night
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Sandy Shores Villa near Sieta Key and other beaches
Sandy Shores Villa near Sieta Key and other beaches
Villa
Sarasota, FL, 34238, United States
0.3k from Sarasota Square center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms8 Guests
10.0

Exceptional

42 reviews

$193
Average price / night
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Charming 2/2 Villa in Village des Pins - 15 min from SIESTA KEY
Charming 2/2 Villa in Village des Pins - 15 min from SIESTA KEY
House
Sarasota, FL, 34238, United States
0.3k from Sarasota Square center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
9.2

Superb

16 reviews

$206
Average price / night
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Serene retreat awaits at prime location in charming Timberwoods/Village des Pins
Serene retreat awaits at prime location in charming Timberwoods/Village des Pins
House
Sarasota, FL, 34238, United States
0.4k from Sarasota Square center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

5 reviews

$285
Average price / night
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Spacious 2 BD and 2BA Villa 13 minutes from Siesta Key!
Spacious 2 BD and 2BA Villa 13 minutes from Siesta Key!
Villa
Sarasota, FL, 34238, United States
0.4k from Sarasota Square center

AC, Arcade, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$200
Average price / night
Check Availability
End Villa/Private View/Heated Pool/Pickleball/7883
End Villa/Private View/Heated Pool/Pickleball/7883
Villa
Sarasota, FL, 34238, United States
0.4k from Sarasota Square center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
10.0

Exceptional

2 reviews

$209
Average price / night
Check Availability
NEAR SIESTA KEY!!! Resort Style Villa with Community Pool/Tennis/Shuffle Board and More
NEAR SIESTA KEY!!! Resort Style Villa with Community Pool/Tennis/Shuffle Board and More
House
Sarasota, FL, 34238, United States
0.4k from Sarasota Square center

AC, Arcade, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms4 Guests
9.8

Exceptional

7 reviews

$243
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Sarasota Square.

Where to stay in Sarasota Square? Best neighborhoods & areas

Sarasota Square Vacation Rentals on the Map

Frequently Asked Questions

You can explore 3295 verified vacation rentals in Sarasota Square. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Sarasota Square vary depending on the season, property size, and location. Rates typically start from around $125 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Sarasota Square include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Sarasota Square welcome pets. Currently, 18 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Sarasota Square often include amenities such as Balcony/Terrace, Sports/Activities, and Wellness Facilities. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.