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Sarasota Holiday Vacation with Pools

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Bedrooms

Bathrooms

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Distinctive Features

Distance from

5 km
120 rentals in Sarasota.
Siesta Beach House - 105, vacation rental in Sarasota
Siesta Beach House - 105, vacation rental in Sarasota
Siesta Beach House - 105, vacation rental in Sarasota

Siesta Beach House - 105

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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*Paradise Steps from World Famous Siesta Beach* Modern Light-filled 2/2 Condo, vacation rental in Sarasota
*Paradise Steps from World Famous Siesta Beach* Modern Light-filled 2/2 Condo, vacation rental in Sarasota
*Paradise Steps from World Famous Siesta Beach* Modern Light-filled 2/2 Condo, vacation rental in Sarasota

*Paradise Steps from World Famous Siesta Beach* Modern Light-filled 2/2 Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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Relaxing and quite apartment in a great location, vacation rental in Sarasota
Relaxing and quite apartment in a great location, vacation rental in Sarasota
Relaxing and quite apartment in a great location, vacation rental in Sarasota

Relaxing and quite apartment in a great location

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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Gorgeous, Gut-Renovated Villa in Village Des Pins, Sarasota, 2BR 2 BD sleeps 4-6, vacation rental in Sarasota
Gorgeous, Gut-Renovated Villa in Village Des Pins, Sarasota, 2BR 2 BD sleeps 4-6, vacation rental in Sarasota
Gorgeous, Gut-Renovated Villa in Village Des Pins, Sarasota, 2BR 2 BD sleeps 4-6, vacation rental in Sarasota

Gorgeous, Gut-Renovated Villa in Village Des Pins, Sarasota, 2BR 2 BD sleeps 4-6

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Sarasota Villa, vacation rental in Sarasota
Sarasota Villa, vacation rental in Sarasota
Sarasota Villa, vacation rental in Sarasota

Sarasota Villa

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Renovated Studio, Walk to Lido Beach, Heated Pool, vacation rental in Sarasota
Renovated Studio, Walk to Lido Beach, Heated Pool, vacation rental in Sarasota
Renovated Studio, Walk to Lido Beach, Heated Pool, vacation rental in Sarasota

Renovated Studio, Walk to Lido Beach, Heated Pool

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
More info
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Piece of Paradise, vacation rental in Sarasota
Piece of Paradise, vacation rental in Sarasota
Piece of Paradise, vacation rental in Sarasota

Piece of Paradise

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps, All pools
More info
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Renovated Studio, Walk to Beach, Pool, Upscale, vacation rental in Sarasota
Renovated Studio, Walk to Beach, Pool, Upscale, vacation rental in Sarasota
Renovated Studio, Walk to Beach, Pool, Upscale, vacation rental in Sarasota

Renovated Studio, Walk to Beach, Pool, Upscale

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
More info
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Payment Protection
THE LIDO RESIDENCE, vacation rental in Sarasota
THE LIDO RESIDENCE, vacation rental in Sarasota
THE LIDO RESIDENCE, vacation rental in Sarasota

THE LIDO RESIDENCE

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, All pools
More info
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Firethorn 612 at Midnight Cove Siesta Key, FL., vacation rental in Sarasota
Firethorn 612 at Midnight Cove Siesta Key, FL., vacation rental in Sarasota
Firethorn 612 at Midnight Cove Siesta Key, FL., vacation rental in Sarasota

Firethorn 612 at Midnight Cove Siesta Key, FL.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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Monthly Rental, 2 bed, 2 bath, Ocean view.  , vacation rental in Sarasota
Monthly Rental, 2 bed, 2 bath, Ocean view.  , vacation rental in Sarasota
Monthly Rental, 2 bed, 2 bath, Ocean view.  , vacation rental in Sarasota

Monthly Rental, 2 bed, 2 bath, Ocean view.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Newly Renovated! Private Beach Front Complex, vacation rental in Sarasota
Newly Renovated! Private Beach Front Complex, vacation rental in Sarasota
Newly Renovated! Private Beach Front Complex, vacation rental in Sarasota

Newly Renovated! Private Beach Front Complex

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Chinaberry 922 at Midnight Cove Siesta Key, FL., vacation rental in Sarasota
Chinaberry 922 at Midnight Cove Siesta Key, FL., vacation rental in Sarasota
Chinaberry 922 at Midnight Cove Siesta Key, FL., vacation rental in Sarasota

Chinaberry 922 at Midnight Cove Siesta Key, FL.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Sarasota 2BR 2BTH Condo Close to Siesta Key Beach, vacation rental in Sarasota
Sarasota 2BR 2BTH Condo Close to Siesta Key Beach, vacation rental in Sarasota
Sarasota 2BR 2BTH Condo Close to Siesta Key Beach, vacation rental in Sarasota

Sarasota 2BR 2BTH Condo Close to Siesta Key Beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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Firethorn 322 at Midnight Cove Siesta Key, FL., vacation rental in Sarasota
Firethorn 322 at Midnight Cove Siesta Key, FL., vacation rental in Sarasota
Firethorn 322 at Midnight Cove Siesta Key, FL., vacation rental in Sarasota

Firethorn 322 at Midnight Cove Siesta Key, FL.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Firethorn 830 at Midnight Cove Siesta Key, vacation rental in Sarasota
Firethorn 830 at Midnight Cove Siesta Key, vacation rental in Sarasota
Firethorn 830 at Midnight Cove Siesta Key, vacation rental in Sarasota

Firethorn 830 at Midnight Cove Siesta Key

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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3BR 2BTH 1180sqft Condo 15 Minutes From Beaches, vacation rental in Sarasota
3BR 2BTH 1180sqft Condo 15 Minutes From Beaches, vacation rental in Sarasota
3BR 2BTH 1180sqft Condo 15 Minutes From Beaches, vacation rental in Sarasota

3BR 2BTH 1180sqft Condo 15 Minutes From Beaches

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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7 Minute Walk to Lido beach, Walk to Ritz Carlton, vacation rental in Sarasota
7 Minute Walk to Lido beach, Walk to Ritz Carlton, vacation rental in Sarasota
7 Minute Walk to Lido beach, Walk to Ritz Carlton, vacation rental in Sarasota

7 Minute Walk to Lido beach, Walk to Ritz Carlton

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Coastal Cottage, vacation rental in Sarasota
Coastal Cottage, vacation rental in Sarasota
Coastal Cottage, vacation rental in Sarasota

Coastal Cottage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Modern & Beautiful Siesta Key Village Condo, Pool, vacation rental in Sarasota
Modern & Beautiful Siesta Key Village Condo, Pool, vacation rental in Sarasota
Modern & Beautiful Siesta Key Village Condo, Pool, vacation rental in Sarasota

Modern & Beautiful Siesta Key Village Condo, Pool

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Walk to Lido Beach & Armand Cir Restaurants, Cable, vacation rental in Sarasota
Walk to Lido Beach & Armand Cir Restaurants, Cable, vacation rental in Sarasota
Walk to Lido Beach & Armand Cir Restaurants, Cable, vacation rental in Sarasota

Walk to Lido Beach & Armand Cir Restaurants, Cable

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
More info
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Sea Shell Cottage, vacation rental in Sarasota
Sea Shell Cottage, vacation rental in Sarasota
Sea Shell Cottage, vacation rental in Sarasota

Sea Shell Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Stunning & Bright Sarasota Home , vacation rental in Sarasota
Stunning & Bright Sarasota Home , vacation rental in Sarasota
Stunning & Bright Sarasota Home , vacation rental in Sarasota

Stunning & Bright Sarasota Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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New Coastal Pool + Game Room home - sleeps 10, vacation rental in Sarasota
New Coastal Pool + Game Room home - sleeps 10, vacation rental in Sarasota
New Coastal Pool + Game Room home - sleeps 10, vacation rental in Sarasota

New Coastal Pool + Game Room home - sleeps 10

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
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Payment Protection
Beautiful Location On Bay Side, Water View, Pool, vacation rental in Sarasota
Beautiful Location On Bay Side, Water View, Pool, vacation rental in Sarasota
Beautiful Location On Bay Side, Water View, Pool, vacation rental in Sarasota

Beautiful Location On Bay Side, Water View, Pool

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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Payment Protection
Private Retreat on Siesta Dr, vacation rental in Sarasota
Private Retreat on Siesta Dr, vacation rental in Sarasota
Private Retreat on Siesta Dr, vacation rental in Sarasota

Private Retreat on Siesta Dr

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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Payment Protection
Heart of St. Armands!  Walk to Lido Beach, Cable, vacation rental in Sarasota
Heart of St. Armands!  Walk to Lido Beach, Cable, vacation rental in Sarasota
Heart of St. Armands!  Walk to Lido Beach, Cable, vacation rental in Sarasota

Heart of St. Armands! Walk to Lido Beach, Cable

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
More info
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Payment Protection
Coastal Reflections, vacation rental in Sarasota
Coastal Reflections, vacation rental in Sarasota
Coastal Reflections, vacation rental in Sarasota

Coastal Reflections

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
New Listing, on the 1st Floor, Walk to Lido Beach & Armand’s Cir,  Heated Pool,, vacation rental in Sarasota
New Listing, on the 1st Floor, Walk to Lido Beach & Armand’s Cir,  Heated Pool,, vacation rental in Sarasota
New Listing, on the 1st Floor, Walk to Lido Beach & Armand’s Cir,  Heated Pool,, vacation rental in Sarasota

New Listing, on the 1st Floor, Walk to Lido Beach & Armand’s Cir, Heated Pool,

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
More info
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Payment Protection
Doveplum 724 at Midnight Cove Siesta Key, FL., vacation rental in Sarasota
Doveplum 724 at Midnight Cove Siesta Key, FL., vacation rental in Sarasota
Doveplum 724 at Midnight Cove Siesta Key, FL., vacation rental in Sarasota

Doveplum 724 at Midnight Cove Siesta Key, FL.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Walk to Siesta Key, 2-Levels, Htd Pool, WiFi/YTube, vacation rental in Sarasota
Walk to Siesta Key, 2-Levels, Htd Pool, WiFi/YTube, vacation rental in Sarasota
Walk to Siesta Key, 2-Levels, Htd Pool, WiFi/YTube, vacation rental in Sarasota

Walk to Siesta Key, 2-Levels, Htd Pool, WiFi/YTube

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Zen Bungalow, vacation rental in Sarasota
Zen Bungalow, vacation rental in Sarasota
Zen Bungalow, vacation rental in Sarasota

Zen Bungalow

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Walk to Beach with Gated Access, Pool/Hot Tub, vacation rental in Sarasota
Walk to Beach with Gated Access, Pool/Hot Tub, vacation rental in Sarasota
Walk to Beach with Gated Access, Pool/Hot Tub, vacation rental in Sarasota

Walk to Beach with Gated Access, Pool/Hot Tub

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Walk to Lido Beach/Armand Cir, Wifi/Smart TV, Heated Pool/spa, Updated Corner Un, vacation rental in Sarasota
Walk to Lido Beach/Armand Cir, Wifi/Smart TV, Heated Pool/spa, Updated Corner Un, vacation rental in Sarasota
Walk to Lido Beach/Armand Cir, Wifi/Smart TV, Heated Pool/spa, Updated Corner Un, vacation rental in Sarasota

Walk to Lido Beach/Armand Cir, Wifi/Smart TV, Heated Pool/spa, Updated Corner Un

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
More info
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Check-out
Payment Protection
Flamingo Cottage, vacation rental in Sarasota
Flamingo Cottage, vacation rental in Sarasota
Flamingo Cottage, vacation rental in Sarasota

Flamingo Cottage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Chinaberry 924 at Midnight Cove Siesta Key, FL., vacation rental in Sarasota
Chinaberry 924 at Midnight Cove Siesta Key, FL., vacation rental in Sarasota
Chinaberry 924 at Midnight Cove Siesta Key, FL., vacation rental in Sarasota

Chinaberry 924 at Midnight Cove Siesta Key, FL.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Doveplum 221 at Midnight Cove Siesta Key, FL., vacation rental in Sarasota
Doveplum 221 at Midnight Cove Siesta Key, FL., vacation rental in Sarasota
Doveplum 221 at Midnight Cove Siesta Key, FL., vacation rental in Sarasota

Doveplum 221 at Midnight Cove Siesta Key, FL.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Home with Private Pool, Fenced Yard, Smart TV, Single Car Garage, BBQ, vacation rental in Sarasota
Home with Private Pool, Fenced Yard, Smart TV, Single Car Garage, BBQ, vacation rental in Sarasota
Home with Private Pool, Fenced Yard, Smart TV, Single Car Garage, BBQ, vacation rental in Sarasota

Home with Private Pool, Fenced Yard, Smart TV, Single Car Garage, BBQ

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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Payment Protection
Heated pool home near Siesta Key, vacation rental in Sarasota
Heated pool home near Siesta Key, vacation rental in Sarasota
Heated pool home near Siesta Key, vacation rental in Sarasota

Heated pool home near Siesta Key

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Gorgeous Condo, 2nd F., WiFi/Cable/Smart TV, Pool, vacation rental in Sarasota
Gorgeous Condo, 2nd F., WiFi/Cable/Smart TV, Pool, vacation rental in Sarasota
Gorgeous Condo, 2nd F., WiFi/Cable/Smart TV, Pool, vacation rental in Sarasota

Gorgeous Condo, 2nd F., WiFi/Cable/Smart TV, Pool

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Ohana, vacation rental in Sarasota
Ohana, vacation rental in Sarasota
Ohana, vacation rental in Sarasota

Ohana

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Clean comfort in Sarasota-book now for comfort, vacation rental in Sarasota
Clean comfort in Sarasota-book now for comfort, vacation rental in Sarasota
Clean comfort in Sarasota-book now for comfort, vacation rental in Sarasota

Clean comfort in Sarasota-book now for comfort

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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Payment Protection
☆ King in Master • 1st Floor • Heated Pool • ¼ mile walk to Siesta Key ☆, vacation rental in Sarasota
☆ King in Master • 1st Floor • Heated Pool • ¼ mile walk to Siesta Key ☆, vacation rental in Sarasota
☆ King in Master • 1st Floor • Heated Pool • ¼ mile walk to Siesta Key ☆, vacation rental in Sarasota

☆ King in Master • 1st Floor • Heated Pool • ¼ mile walk to Siesta Key ☆

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
St Armand's Private Home on Jackson Drive, vacation rental in Sarasota
St Armand's Private Home on Jackson Drive, vacation rental in Sarasota
St Armand's Private Home on Jackson Drive, vacation rental in Sarasota

St Armand's Private Home on Jackson Drive

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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Payment Protection
Artsy Sarasota,FL. Palm-Aire CC 2bd/2 bath  Condo, vacation rental in Sarasota
Artsy Sarasota,FL. Palm-Aire CC 2bd/2 bath  Condo, vacation rental in Sarasota
Artsy Sarasota,FL. Palm-Aire CC 2bd/2 bath  Condo, vacation rental in Sarasota

Artsy Sarasota,FL. Palm-Aire CC 2bd/2 bath Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Full Gulf Views, Private Beach, Walk to Village Shops, vacation rental in Sarasota
Full Gulf Views, Private Beach, Walk to Village Shops, vacation rental in Sarasota
Full Gulf Views, Private Beach, Walk to Village Shops, vacation rental in Sarasota

Full Gulf Views, Private Beach, Walk to Village Shops

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
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Payment Protection
Oceanfront home w/sunset views of Sarasota Bay, vacation rental in Sarasota
Oceanfront home w/sunset views of Sarasota Bay, vacation rental in Sarasota
Oceanfront home w/sunset views of Sarasota Bay, vacation rental in Sarasota

Oceanfront home w/sunset views of Sarasota Bay

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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Payment Protection
Heated Pool Near Arlington Park Outdoor Kitchen, vacation rental in Sarasota
Heated Pool Near Arlington Park Outdoor Kitchen, vacation rental in Sarasota
Heated Pool Near Arlington Park Outdoor Kitchen, vacation rental in Sarasota

Heated Pool Near Arlington Park Outdoor Kitchen

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Check-out
Payment Protection
NEW! The Oasis - Heated Private Pool, Hot Tub - 5mi to beach, vacation rental in Sarasota
NEW! The Oasis - Heated Private Pool, Hot Tub - 5mi to beach, vacation rental in Sarasota
NEW! The Oasis - Heated Private Pool, Hot Tub - 5mi to beach, vacation rental in Sarasota

NEW! The Oasis - Heated Private Pool, Hot Tub - 5mi to beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Walk to Waters Edge, Wi-Fi, Dogs Allowed, 50's Retro Furnishings, Saltwater Pool, vacation rental in Sarasota
Walk to Waters Edge, Wi-Fi, Dogs Allowed, 50's Retro Furnishings, Saltwater Pool, vacation rental in Sarasota
Walk to Waters Edge, Wi-Fi, Dogs Allowed, 50's Retro Furnishings, Saltwater Pool, vacation rental in Sarasota

Walk to Waters Edge, Wi-Fi, Dogs Allowed, 50's Retro Furnishings, Saltwater Pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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Payment Protection
Showing results 1-50 of 3,731

About Sarasota
Florida's Gulf Coast is packed with gems, and Sarasota is one that shines particularly brightly. Settle into this lively and welcoming community, and feel like a local by staying at your choice of Sarasota vacation homes.
Sarasota Climate
Like most of Florida, Sarasota boasts humid summers and mild winters. During the peak of summer in July and August, temperatures often exceed 90 degrees, and the area receives frequent thunderstorms. In the winter, Sarasota experiences temperatures in the 70s, and the skies remain relatively dry.
How to Get Around Sarasota
Flying into the Sarasota area is easy, thanks to several convenient airport options. Whether you fly to the Sarasota-Bradenton International Airport, the Tampa International Airport, or the St. Pete-Clearwater International Airport, you'll be just a short drive from most Sarasota vacation homes. Since Sarasota spans both the mainland and islands, you'll cover the most ground by car.
Top Things to Do in Sarasota
With art, architecture, and flora, The Ringling has something for everyone. You could easily spend an entire day touring the Venetian Gothic Ca' d'Zan, delighting in the details of the 44,000-piece Howard Bros. Circus Model, smelling the flowers in Mable Ringling's Rose Garden, or looking for treasures in John Ringling's Renaissance-style Museum of Art Courtyard.
Can't Miss Sarasota Events
No matter the season, you'll find a festival or special event to pique your interest in Sarasota. Dance, music, and theater lovers should mark their calendars for the Ringling International Arts Festival, which celebrates the best of contemporary performing arts. In January, the Forks and Corks Food and Wine Festival treats attendees to wine and food tastings, celebrity chef events, and food demonstrations. In April, the Sarasota Film Festival spans 10 days, highlights over 200 films, and welcomes more than 250 filmmakers. With panels, symposia, and talks with filmmakers, this is one of the city's most popular events each year.