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Sarasota Luxury Holiday Rentals

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1842 rentals in Sarasota.
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Sun Deck
Luxury Condominium at Siesta Dunes Beachside Pool Hot Tub Tennis Sun Deck
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Sunset across the street
Great little dining deck.
Cute Efficiency Apartment - nice neighborhood
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The MacGregor House is 1925 Old Florida elegance
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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We're open again! Enjoy this spacious living room!
Full kitchen
Walking distance from the Bay! Charming 2 Bedroom House, Fenced and Private
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tropical Garden
Front of the house
Sunset on Lido beach
Five star Downtown Sarasota tropical garden Cottage
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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
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Sarasota Waterfront Suite
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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A Wonderful Pool House on a lake full of wildlife.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sarasota's best kept secret! Beautiful Rennnovated Villa, 2Br 2 Bath, sleeps 4-6
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Great Location and Best Price in Sarasota
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Save time - get the best Sarasota rentals sent straight to your email!
Living the Dream on Lido I, cute condo one block to the beach
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW LISTING!!! Beautiful Beach Cottage Minutes from Siesta Key - Welcome Home!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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A Bayside Treasure - Exceptional Waterfront Views!!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Renovated, Centrally Located, Sarasota Rental House, Close To Amish Community
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Full Gulf Views Across from Siesta Key Beach
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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ON BEACH! ALL Remodeled!! Nice pool. Free beach chairs,lots of activities area
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Secluded Home with Private, heated, saltwater pool Pet Friendly
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beach Front 3BR 2 BA Villa Near Siesta Key Village
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Immaculate, close to everything Sarasota
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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THANKSGIVING AVAILABLE� 3BED/3BATH, GREAT VIEWS!'WARRIOR' AIR PURIFIER! �
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Immaculate, Newly Remodeled Close to Siesta Beach
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Roomy Beach Cottage: 4 bd/3 ba: 100 ft to beach path; priv pool/BBQ/walk to town
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Full Gulffront Luxury Condo on Crescent Beach - Breathtaking Panoramic Views
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Townhouse with Garage - Across from Siesta Key Beach!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Just a three minute walk from the white sand of the world renowned Siesta Beach
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Firethorn 822 at Midnight Cove Siesta Key, FL.
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Vacation delight! Cozy condo just steps from the beach and St. Armands circle.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Luxury Beach Condo on Crescent Beach - #1 Beach in USA
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Large Private Home On Water With Pool/Spa On #1Beach In Us! - Siesta Key
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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THANKSGIVING AVAIL�/CHRISTMAS AVAIL�DISCOUNT! NEW RENO 2BED/2BTH ON BEACH
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spotless, Close to everything Beaches are Open (Read Our Reviews)
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Midcentury Modern 3 BR - Pool in Sarasota, Close to Beaches!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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ONE MILE from beautiful Siesta Key, #1 beach in the USA!!!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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5 ⭐️, WATERFRONT HOME, SIESTA KEY, BOAT LIFT, DOCK, HEATED POOL, HOT TUB, GRILL
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Romantic.....1 Block To Sarasota Bay, 1 Mile To Downtown, 2 Miles To Lido Beach!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Palm Bay Club #168 (Recently updated) Private beach perfect for a Stay-cation
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Spacious beach house sleeping 13 with private heated pool and hot tub
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Beautiful White Sand Siesta Key
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Oceanfront/Beachfront Condo in Premier Complex - Y Building
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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BRAND NEW HOME! Private Heated Pool-Walking Distance to St. Armand's!
Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 19
Match: Sleeps
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Adorable Beach Cottage Bungalow in Sunny Sarasota
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Private Garden Cottage hide away in the heart of Sarasota
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lido Beach and St. Armand's Circle at your Footsteps. Ask about the guest house!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Siesta Key - Beach Front Condo at Siesta Dunes
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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VILLA DE LUXE SIESTA KEY- 10 PERS. A 2 MN DE LA PLAGE- PISCINE ET SPA CHAUFFE
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Ground Floor - Delightful and Totally Divine - Free Netflix, WI-FI, Chromcast
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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RECENTLY RENOVATED! Only steps to the beach and premium everything!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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At the Beach - Where Tomorrow is Just Another Day in Paradise
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Location, Location, Location-7 Houses to the Beach! Roof Top Deck! Amazing Pool!
Holiday Rental House
7 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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CUTE 2 BED 2 BATH COTTAGE 2 MI FROM THE BEACH- NO SMOKING
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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