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Vacation rentals near Sarasota Square
We found 5,835 vacation rentals — enter your dates for availability
If you want to to stay within easy reach of Sarasota Square, take a look at vacation rentals to find the perfect one for your trip. Whether you're staying in a vacation rental with your kids or with friends, you'll have the best amenities for spending time at your home away from home, such as WiFi and cable TV. What you'll find is a rental for everyone's needs, including options that are accessible or non-smoking.
Vacation rentals with weekly discounts - Sarasota Square
Showing deals for:Nov 7 - Nov 14
Image gallery for Private Oasis in Sarasota Florida
1010 out of 10 rating
Exceptional
(37 reviews)
Private Oasis in Sarasota Florida
Sarasota, FL
5% off
Price is CA $547
CA $547
CA $5,332 total
CA $5,332 total
includes taxes & fees
Image gallery for Tranquil Pool Home Minutes to Siesta Key
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Tranquil Pool Home Minutes to Siesta Key
Sarasota, Florida
5% off
Price is CA $233
CA $233
CA $2,665 total
CA $2,665 total
includes taxes & fees
Image gallery for Family beach home! Fully renovated on water w/pool, boat dock & nearby beach
9.69.6 out of 10 rating
Exceptional
(75 reviews)
Family beach home! Fully renovated on water w/pool, boat dock & nearby beach
Nokomis, FL
10% off
Price is CA $651
CA $651
CA $5,952 total
CA $5,952 total
includes taxes & fees
Image gallery for Beautifully Decorated Pool Home 2 Bed/2 Bath minutes away from Siesta Key Beach!
1010 out of 10 rating
Exceptional
(39 reviews)
Beautifully Decorated Pool Home 2 Bed/2 Bath minutes away from Siesta Key Beach!
Sarasota, FL
10% off
Price is CA $496
CA $496
CA $4,532 total
CA $4,532 total
includes taxes & fees
Image gallery for Spacious salt water pool home minutes from Siesta Key & downtown
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Spacious salt water pool home minutes from Siesta Key & downtown
Sarasota, FL
10% off
Price is CA $182
CA $182
CA $2,317 total
CA $2,317 total
includes taxes & fees
Image gallery for Stylish Retreat on Private Crescent Beach
1010 out of 10 rating
Exceptional
(96 reviews)
Stylish Retreat on Private Crescent Beach
Siesta Key, FL
10% off
Price is CA $437
CA $437
CA $4,033 total
CA $4,033 total
includes taxes & fees
Image gallery for Your Beachside Retreat – Siesta Key’s White Sands Just Steps Away!
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Your Beachside Retreat – Siesta Key’s White Sands Just Steps Away!
Siesta Key, FL
9% off
Price is CA $395
CA $395
CA $3,593 total
CA $3,593 total
includes taxes & fees
Image gallery for SARASOTA Heated Pool - Pet Friendly - Garage w/ EV Charger - Close to Beaches!
1010 out of 10 rating
Exceptional
(44 reviews)
SARASOTA Heated Pool - Pet Friendly - Garage w/ EV Charger - Close to Beaches!
Sarasota, FL
5% off
Price is CA $266
CA $266
CA $2,600 total
CA $2,600 total
includes taxes & fees
Image gallery for Impressive, New 3BD/2BA Townhome in Skye Ranch, Sarasota, 11 Miles to Beaches
1010 out of 10 rating
Exceptional
(12 reviews)
Impressive, New 3BD/2BA Townhome in Skye Ranch, Sarasota, 11 Miles to Beaches
Sarasota, FL
5% off
Price is CA $236
CA $236
CA $2,358 total
CA $2,358 total
includes taxes & fees
Image gallery for Tiki Tide Villa | Private POOL + Tiki Hut!
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Tiki Tide Villa | Private POOL + Tiki Hut!
Sarasota, FL
9% off
Price is CA $534
CA $534
CA $5,111 total
CA $5,111 total
includes taxes & fees
Image gallery for Stunning Siesta Key,, . , Walk to Shell Beach, HEATED POOL - Discounts
9.89.8 out of 10 rating
Exceptional
(119 reviews)
Stunning Siesta Key,, . , Walk to Shell Beach, HEATED POOL - Discounts
Siesta Key, FL
10% off
Price is CA $971
CA $971
CA $8,983 total
CA $8,983 total
includes taxes & fees
Image gallery for Siesta Key FamilyGetaway!!
1010 out of 10 rating
Exceptional
(83 reviews)
Siesta Key FamilyGetaway!!
Siesta Key, FL
10% off
Price is CA $589
CA $589
CA $5,441 total
CA $5,441 total
includes taxes & fees
Image gallery for New home 3/2 renovation 3 miles to Siesta Key
9.29.2 out of 10 rating
Wonderful
(19 reviews)
New home 3/2 renovation 3 miles to Siesta Key
Sarasota, FL
10% off
Price is CA $180
CA $180
CA $1,752 total
CA $1,752 total
includes taxes & fees
Image gallery for Sandy Feet Retreat | Private Pool, Pergola + Ping Pong!
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Sandy Feet Retreat | Private Pool, Pergola + Ping Pong!
Sarasota, FL
9% off
Price is CA $409
CA $409
CA $3,829 total
CA $3,829 total
includes taxes & fees
Image gallery for Welcome To Shoreline: 4BR, Heated Pool, 7miles to Gulf Beaches, Sleeps10
1010 out of 10 rating
Exceptional
(12 reviews)
Welcome To Shoreline: 4BR, Heated Pool, 7miles to Gulf Beaches, Sleeps10
Sarasota, FL
10% off
Price is CA $461
CA $461
CA $4,464 total
CA $4,464 total
includes taxes & fees
Image gallery for Outdoor shower and wonderful private fenced yard
9.89.8 out of 10 rating
Exceptional
(78 reviews)
Outdoor shower and wonderful private fenced yard
Sarasota, FL
5% off
Price is CA $131
CA $131
CA $1,132 total
CA $1,132 total
includes taxes & fees
Image gallery for Book now, and make memories that will last a lifetime in the heart of Sarasota!
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Book now, and make memories that will last a lifetime in the heart of Sarasota!
Sarasota, FL
10% off
Price is CA $248
CA $248
CA $2,296 total
CA $2,296 total
includes taxes & fees
Image gallery for Charming Beach Cottage
9.69.6 out of 10 rating
Exceptional
(27 reviews)
Charming Beach Cottage
Sarasota, FL
19% off
Price is CA $167
CA $167
CA $1,664 total
CA $1,664 total
includes taxes & fees
Image gallery for Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
1010 out of 10 rating
Exceptional
(31 reviews)
Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
Sarasota, FL
10% off
Price is CA $279
CA $279
CA $2,927 total
CA $2,927 total
includes taxes & fees
Image gallery for Siesta Key Beachside Condo-direct beach access
1010 out of 10 rating
Exceptional
(13 reviews)
Siesta Key Beachside Condo-direct beach access
Siesta Key, FL
10% off
Price is CA $408
CA $408
CA $3,755 total
CA $3,755 total
includes taxes & fees
Image gallery for Bay Bliss Bungalow | 65" Smart TV, Lanai + Electric Bikes!
1010 out of 10 rating
Exceptional
(17 reviews)
Bay Bliss Bungalow | 65" Smart TV, Lanai + Electric Bikes!
Sarasota, FL
9% off
Price is CA $277
CA $277
CA $2,696 total
CA $2,696 total
includes taxes & fees
Image gallery for Renovated Jamaica Royale Condo: Private Beach Access, Modern Comforts, and Steps to the Pool!
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Renovated Jamaica Royale Condo: Private Beach Access, Modern Comforts, and Steps to the Pool!
Siesta Key, FL
7% off
Price is CA $312
CA $312
CA $3,532 total
CA $3,532 total
includes taxes & fees
Image gallery for Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
9.69.6 out of 10 rating
Exceptional
(17 reviews)
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
Siesta Key, FL
10% off
Price is CA $366
CA $366
CA $3,563 total
CA $3,563 total
includes taxes & fees
Image gallery for Lock in Sunshine and Savings Before It’s Too Late
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Lock in Sunshine and Savings Before It’s Too Late
Siesta Key, FL
12% off
Price is CA $442
CA $442
CA $4,619 total
CA $4,619 total
includes taxes & fees
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Find the best place to stay - Sarasota Square
GORGEOUS 3 Bedroom/2 Bath Home NEAR SIESTA KEY!
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
NEW - Cheerful 2 bedroom villa - 13 min. to Siesta Key
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
4 Bed pool House by Bay! Lido & Siesta Key Beaches very close
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
112 reviews(112 reviews)
Beautiful, comfortable pool home 15 minutes from Famous Siesta Key Beach.
Sleeps 10 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
8 Minutes to SIESTA BEACH! 3-bedrm Oasis in Sarasota - Kng, Queen, 2 full beds
Sleeps 10 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
LJ's Cottages 3 - BALCONY VIEWS BEACH POOL SAND SUNSETS
Sleeps 8 · 2 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Top rated rentals - Sarasota Square
Great Find
1010 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
As advertised
1010 out of 10
Exceptionalexceptional
147 reviews(147 reviews)
Lovely family getaway
1010 out of 10
Exceptionalexceptional
110 reviews(110 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value