Vacation Rentals in Sarasota, Florida

50 Properties Available

Private vacation home

The Big Kahuna | Two Luxe Villas + Double the Fun Steps from Siesta Key Beach

$3706 / night

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Private vacation home

Sport Court Feat. Pickleball - Theatre Room - Pool

$2262 / night

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Private vacation home

Steps to Beach/Pool w/Slide and Chipping Green

$2259 / night

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Private vacation home

Aloft on Canal ~ Near Beach ~ Pool & Slide

$2163 / night

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Private vacation home

Tropical Breeze: Renovation Sleeps 16 Hot tub Pool

$1981 / night

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Private vacation home

Sarasota Renovated Waterfront Home with Dock on Wide Open Bay

$1663 / night

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Villa

A fantasy island Beachfront biohacking estate w Renowned yogi in Palace

$1656 / night

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Private vacation home

Walk to St. Armands and Lido Key Beach/Gulf Views

$1548 / night

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Private vacation home

Resort Pool w/Slide - Walk to Beach & Village

$1439 / night

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Private vacation home

Resort Pool w/Slide - Walk to Beach & Village

$1439 / night

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Private vacation home

Sarasota Bayfront Estate - Sunset Views, Near Crescent Beach & Siesta Key Beach

$1424 / night

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Private vacation home

Casa Coquina | Pet Friendly, Ping Pong Table, Private Pool, Steps to Beach

$1379 / night

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Private vacation home

Coastal Retreat Near Siesta Key- 5 Bedrooms, Pool & Spa- 1 month minimum

$1369 / night

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Private vacation home

Gulf Views. Walk to St Armands+Beach. Pool+Slide

$1292 / night

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$AWESOME!!! SEISTA KEY SARASOTA FL BEACH\/WATER FRONT! BEST LOCATION IN FLORIDA!!$ Private vacation home

AWESOME!!! SEISTA KEY SARASOTA FL BEACH\/WATER FRONT! BEST LOCATION IN FLORIDA!!

$1273 / night

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Private vacation home

Tamiami Vice | Private Heated Pool, & a Short Drive to Siesta Key Beach

$1250 / night

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Private vacation home

Luna Nueva: Private Pool, New Renovation, Sleeps 8

$1227 / night

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Private vacation home

A Private Waterfront Sanctuary on Bay Island, Moments from Siesta Key.

$1209 / night

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Private vacation home

Siesta Key Pool Palace - Walk to Beach

$1165 / night

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Private vacation home

Siesta Key FL Spacious 4-bedroom House with Private Beach Access and Heated Pool

$1143 / night

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Private vacation home

Luxury Coastal Retreat - Designer Home Near Siesta Key Beach with Pool

$1128 / night

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Private vacation home

Luxury Lido Retreat with Pool, Spa, Firepit & Rooftop Views

$1105 / night

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Private vacation home

Holiday house Sarasota for 1 - 12 persons with 6 bedrooms - Holiday home

$1090 / night

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Private vacation home

Luxurious home with amazing rooftop deck views

$1051 / night

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Condo

Hyatt Siesta Key one of the most sought after property on the Key!

$1050 / night

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Private vacation home

Coastal Cottage: Renovation Sleep 6 Hot tub, Pool

$991 / night

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Private vacation home

Pearl on the Bay - A breathtaking Pool & Bayfront property - an unparalleled vacation experience

$981 / night

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Private vacation home

Large Private Home, 5 Min Walk to Beach, Pool

$968 / night

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Private vacation home

Luxury Estate with Dual Pools on 2.5 Acres Near Downtown Sarasota & Beaches

$961 / night

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Private vacation home

LUXURY VILLA SIESTA KEY- 10 PERS. 2 MIN FROM THE BEACH - POOL AND HEATED SPA

$954 / night

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Condo

Stunning 2 Bedroom Condo with Beach & Pool Access on Siesta Key!

$936 / night

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$Hemingway House | Beautiful Traditional Home w\/ Spacious Outdoor Dining Area & Private Pool!$ Private vacation home

Hemingway House | Beautiful Traditional Home w\/ Spacious Outdoor Dining Area & Private Pool!

$925 / night

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Private vacation home

Private Resort. Heated Pool. Game Room. Sleeps 16

$924 / night

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Private vacation home

Siesta Key Home, Heated Pool, Spa, near the beach! - Talk To The Sand

$907 / night

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Apart-hotel

2 Connecting Suites at a Hotel

$864 / night

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Condo

Unit #304 Sand Cay Beach Resort Gulf Front

$829 / night

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Private vacation home

St Armand's Home with pool

$829 / night

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Private vacation home

Newly remodeled beach house with private, gated beach access and private pool

$821 / night

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Private vacation home

Marvelous 3bd 2bt Home Heated Pool Close to Siesta

$820 / night

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Private vacation home

Awesome rustic Siesta Key private pool home!

$815 / night

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Private vacation home

Beautiful Siesta Key Sunsets and Private Dock - 800 a night 6-7 day min

$800 / night

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$Amazing 4\/4.5 Siesta Key House on Canal w\/ Pool WALK TO THE BEACH$ Private vacation home

Amazing 4\/4.5 Siesta Key House on Canal w\/ Pool WALK TO THE BEACH

$780 / night

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Private vacation home

Casamigos | West of the Trail - Private Home with Tiki Bar, Heated Pool, and Spa, Near Siesta Key!

$768 / night

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Private vacation home

Oasis Right On Siesta Key

$762 / night

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Private vacation home

Lido Palms | Walk to Lido Key Beach, Heated Pool & Spa, Rooftop Balcony with Views

$755 / night

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Private vacation home

The Seagrape Villa - Luxury Accommodation in Paradise

$754 / night

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$\nYour Perfect Westcoast Vacation Getaway\n12 guests, Pool, A beautiful deck!!!$ Private vacation home

\nYour Perfect Westcoast Vacation Getaway\n12 guests, Pool, A beautiful deck!!!

$753 / night

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Private vacation home

Mermaids Oasis | Private Pool, Hot Tub, & 5 Minute Walk to St. Armands Circle & Lido Key Beach!

$753 / night

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Private vacation home

Eagles Nest - Luxury Waterfront Pool Home close Siesta Key by The Bay & Key Collection

$747 / night

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Private vacation home

3-bedroom house in awesome Sarasota with WiFi, AC. Enjoy your stay

$746 / night

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