Sarasota, Florida

Vacation Rentals in Sarasota, Florida

Discover 1,719 vacation rental properties in Sarasota. From 1 to 11 bedrooms. Average $252/night. 100% have pools.

1,719 verified listings Book securely on VRBO Prices updated March 2026

1,719 properties available

Beach Retreat on Lido Key across from the beach! Save now with off-season rates!

Beach Retreat on Lido Key across from the beach! Save now with off-season rates!

1 bath
PoolA/CWiFiBalcony
$131/night
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Michelles Cottage1: Less than 2 miles from siesta key beach

Michelles Cottage1: Less than 2 miles from siesta key beach

1 bed 1 bath
PoolA/CWiFiBalcony
$119/night
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Beautiful Villa in Private Resort-Style Community

Beautiful Villa in Private Resort-Style Community

2 beds 2 baths
PoolA/CWiFiBalcony
$250/night
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Full Gulf Views Across from Siesta Key Beach

Full Gulf Views Across from Siesta Key Beach

2 beds 2 baths
PoolA/CWiFiBalcony
$201/night
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Studio Retreat Across the Street from Beautiful Siesta Key Beach

Studio Retreat Across the Street from Beautiful Siesta Key Beach

1 bed 1 bath
PoolA/CWiFiBalcony
$142/night
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Penthouse Condo with Water Views

Penthouse Condo with Water Views

2 beds 2 baths
PoolA/CWiFiBalcony
$157/night
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Barb's Three Wishes; Sun, Sand, Siesta

Barb's Three Wishes; Sun, Sand, Siesta

2 beds 1 bath
PoolA/CWiFiBalcony
$132/night
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Spectacular Siesta Key Beachfront Condo, Sarasota Surf & Racquet Club

Spectacular Siesta Key Beachfront Condo, Sarasota Surf & Racquet Club

2 beds 2 baths
PoolA/CWiFiBalcony
$372/night
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Sea Club 2 Condo Siesta Key

Sea Club 2 Condo Siesta Key

1 bed 1 bath
PoolA/CWiFiBalcony
$142/night
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Siesta Key Voted #1 Beach Siesta Dunes 2 Bedroom Condo Beautiful Beach Book Now

Siesta Key Voted #1 Beach Siesta Dunes 2 Bedroom Condo Beautiful Beach Book Now

2 beds 2 baths
PoolA/CWiFiBalcony
$224/night
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Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #1: A block to the Beach!

1 bed 1 bath
PoolA/CWiFiBalcony
$152/night
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Steps away from the #1 beach! Spectacular views on the GIANT balcony!

Steps away from the #1 beach! Spectacular views on the GIANT balcony!

2 beds 2 baths
PoolA/CWiFiBalcony
$292/night
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A few steps from the beach with community pool

A few steps from the beach with community pool

2 beds 2 baths
PoolA/CWiFiBalcony
$194/night
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Pet Friendly Condo a Block to Siesta Key Village, Newly Updated Interior & Pool

Pet Friendly Condo a Block to Siesta Key Village, Newly Updated Interior & Pool

2 beds 2 baths
PoolA/CWiFiBalcony
$264/night
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Buy 12 nights get 14 July 2024. Amazing Beachfront unit w/pool

Buy 12 nights get 14 July 2024. Amazing Beachfront unit w/pool

2 beds 2 baths
PoolA/CWiFiBalcony
$338/night
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Hear the Waves Feel the Sand Great View sleeps 6

Hear the Waves Feel the Sand Great View sleeps 6

2 beds 2 baths
PoolA/CWiFiBalcony
$241/night
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Renovated! Private Beachfront Complex, 3 Pools, WiFi, Cable, Complex BBQ

Renovated! Private Beachfront Complex, 3 Pools, WiFi, Cable, Complex BBQ

1 bed 1 bath
PoolA/CWiFiBalcony
$185/night
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Unit 52 -1 Bedroom 1 Bathroom Condominium With Gulf Views

Unit 52 -1 Bedroom 1 Bathroom Condominium With Gulf Views

1 bed 1 bath
PoolA/CWiFiBalcony
$377/night
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Great Siesta Beach View! End unit, See the sunset here for your vacation.

Great Siesta Beach View! End unit, See the sunset here for your vacation.

2 beds 2 baths
PoolA/CWiFiBalcony
$152/night
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Gorgeous Cottage Steps From Beach Access - Heated Pool

Gorgeous Cottage Steps From Beach Access - Heated Pool

1 bed 1 bath
PoolA/CWiFiBalcony
$277/night
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Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building

Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building

2 beds 2 baths
PoolA/CWiFiBalcony
$295/night
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Lovely Pet Friendly Condo a Block from Siesta Key Village, Two Pools & Tiki Bar

Lovely Pet Friendly Condo a Block from Siesta Key Village, Two Pools & Tiki Bar

2 beds 2 baths
PoolA/CWiFiBalcony
$264/night
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Beachside Studio Located Across from Main Beach and Half Mile to Village

Beachside Studio Located Across from Main Beach and Half Mile to Village

1 bed 1 bath
PoolA/CWiFiBalcony
$121/night
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Palm Bay Club #168 (Recently updated) Private beach perfect for a Stay-cation

Palm Bay Club #168 (Recently updated) Private beach perfect for a Stay-cation

2 beds 2 baths
PoolA/CWiFiBalcony
$216/night
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Discounted rates for gorgeous one bdrm directly across from beach, near village!

Discounted rates for gorgeous one bdrm directly across from beach, near village!

1 bed 1 bath
PoolA/CWiFiBalcony
$236/night
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New to Rental market Luxury remodeled condo located directly on Siesta Key Beach

New to Rental market Luxury remodeled condo located directly on Siesta Key Beach

2 beds 2 baths
PoolA/CWiFiBalcony
$330/night
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Siesta Key 2BR /1Bath Villa Barefoot Bungalows -“Cozy” 1000 ft from beach.

Siesta Key 2BR /1Bath Villa Barefoot Bungalows -“Cozy” 1000 ft from beach.

2 beds 1 bath
PoolA/CWiFiBalcony
$230/night
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Siesta Key Village Studio on Canal Near Beach

Siesta Key Village Studio on Canal Near Beach

1 bath
PoolA/CWiFiBalcony
$137/night
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Unit 98- 1 Bedroom and 1 Bathroom Condominium with Partial South Views

Unit 98- 1 Bedroom and 1 Bathroom Condominium with Partial South Views

1 bed 1 bath
PoolA/CWiFiBalcony
$352/night
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“MOONMIST” Siesta Key villa with private hot tub in a 'jungle' setting

“MOONMIST” Siesta Key villa with private hot tub in a 'jungle' setting

2 beds 2 baths
PoolA/CWiFiBalcony
$159/night
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Gorgeous Cottages - Steps From Beach Access - Heated Pool

Gorgeous Cottages - Steps From Beach Access - Heated Pool

1 bed 1 bath
PoolA/CWiFiBalcony
$282/night
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"Safe & Clean" Key West Suite , only 60 steps to the Siesta Key Public Beach -

"Safe & Clean" Key West Suite , only 60 steps to the Siesta Key Public Beach -

3 beds 2 baths
PoolA/CWiFiBalcony
$307/night
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Beach Front 3BR 2 BA Villa Near Siesta Key Village

Beach Front 3BR 2 BA Villa Near Siesta Key Village

3 beds 2 baths
PoolA/CWiFiBalcony
$507/night
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Sunny Walk-out Patio, Spacious Master Suite, Wi-Fi

Sunny Walk-out Patio, Spacious Master Suite, Wi-Fi

2 beds 2 baths
PoolA/CWiFiBalcony
$236/night
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Doveplum 724- 2 Story, 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided,...

Doveplum 724- 2 Story, 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided,...

2 beds 2 baths
PoolA/CWiFiBalcony
$207/night
View Details → Book on VRBO
Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key

Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key

2 beds 2 baths
PoolA/CWiFiBalcony
$215/night
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Million Dollar Location Budget Friendly Price

Million Dollar Location Budget Friendly Price

1 bed 1 bath
PoolA/CWiFiBalcony
$177/night
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Crystal Sands Villa #7 -

Crystal Sands Villa #7 -

2 beds 2 baths
PoolA/CWiFiBalcony
$277/night
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Clean Family Friendly 2 Bed, Private Beach Access, Renovated, GREAT LOCATION!

Clean Family Friendly 2 Bed, Private Beach Access, Renovated, GREAT LOCATION!

2 beds 1 bath
PoolA/CWiFiBalcony
$180/night
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Unit 42- 1 Bedroom 1 Bathroom Condominium With Gulf Views

Unit 42- 1 Bedroom 1 Bathroom Condominium With Gulf Views

1 bed 1 bath
PoolA/CWiFiBalcony
$377/night
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Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

2 beds 2 baths
PoolA/CWiFiBalcony
$199/night
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Bayside condo on the water with a pool

Bayside condo on the water with a pool

1 bed 1 bath
PoolA/CWiFiBalcony
$208/night
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Siesta Key - Siesta Dunes - Deluxe Beachfront Condo with Gulf of Mexico Views

Siesta Key - Siesta Dunes - Deluxe Beachfront Condo with Gulf of Mexico Views

2 beds 2 baths
PoolA/CWiFiBalcony
$323/night
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Perfect for Families, Steps to Siesta Key Beach and Village!

Perfect for Families, Steps to Siesta Key Beach and Village!

3 beds 2 baths
PoolA/CWiFiBalcony
$338/night
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Unit 28- 1 Bedroom and 1 Bathroom Condominium with Partial South Views

Unit 28- 1 Bedroom and 1 Bathroom Condominium with Partial South Views

1 bed 1 bath
PoolA/CWiFiBalcony
$352/night
View Details → Book on VRBO
Beautiful Ground Floor 1bed/1.5 Bath Condo with Pool and Beach Access!

Beautiful Ground Floor 1bed/1.5 Bath Condo with Pool and Beach Access!

1 bed 1 bath
PoolA/CWiFiBalcony
$249/night
View Details → Book on VRBO
Spacious vacation rental condo with lagoon views, beach access, and pool

Spacious vacation rental condo with lagoon views, beach access, and pool

3 beds 2 baths
PoolA/CWiFiBalcony
$184/night
View Details → Book on VRBO
Gulf-Side Beautiful Condo with Pool Overlooking the Gulf!

Gulf-Side Beautiful Condo with Pool Overlooking the Gulf!

1 bed 1 bath
PoolA/CWiFiBalcony
$160/night
View Details → Book on VRBO

Showing 48 of 1,719 properties

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