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Sarasota Luxury Holiday Rentals

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135 rentals in Sarasota.
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Luxury waterfront 5bed/5.5bath nestled in Harbor Acres, holiday rental in Sarasota

Luxury waterfront 5bed/5.5bath nestled in Harbor Acres

5 bedrooms
6 bathrooms
Sleeps 10
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Beautiful 4Bed/3Bath Home with Pool on Canal 5 Min Walk to Lido Beach, holiday rental in Sarasota

Beautiful 4Bed/3Bath Home with Pool on Canal 5 Min Walk to Lido Beach

4 bedrooms
3 bathrooms
Sleeps 7
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2 bedroom Condo Bay Oaks Siesta Key, holiday rental in Sarasota

2 bedroom Condo Bay Oaks Siesta Key

2 bedrooms
1 bathroom
Sleeps 3
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Amazing Hacienda Style Villa - Very Close To Siesta, holiday rental in Sarasota

Amazing Hacienda Style Villa - Very Close To Siesta

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Elegant 5 Bedroom 3 bath Executive Home - HEATED POOL near Siesta Key Beaches!!!, holiday rental in Sarasota

Elegant 5 Bedroom 3 bath Executive Home - HEATED POOL near Siesta Key Beaches!!!

4 bedrooms
3 bathrooms
Sleeps 10
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26 other travellers have booked this property
3br - 5100ft2 - Country Estaste Adventure, holiday rental in Sarasota

3br - 5100ft2 - Country Estaste Adventure

3 bedrooms
5 bathrooms
Sleeps 6
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3 other travellers have booked this property
St. Armands Oasis w/ Private Heated Saltwater Pool, Walk to Beach & Shops, holiday rental in Sarasota

St. Armands Oasis w/ Private Heated Saltwater Pool, Walk to Beach & Shops

3 bedrooms
3 bathrooms
Sleeps 8
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Luxury Beach Cotttage, holiday rental in Sarasota

Luxury Beach Cotttage

1 bedroom
1 bathroom
Sleeps 2
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4 other travellers have booked this property
4 Bed 3bath Water front home, holiday rental in Sarasota

4 Bed 3bath Water front home

4 bedrooms
3 bathrooms
Sleeps 8
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Charming Lido Key Beach House 5 min Walk to Beach!, holiday rental in Sarasota

Charming Lido Key Beach House 5 min Walk to Beach!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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4 other travellers have booked this property
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3 Bedroom 3 Bath, Heated Pool, St. Armands Circle, holiday rental in Sarasota

3 Bedroom 3 Bath, Heated Pool, St. Armands Circle

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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High-End New, Gourmet Kitchen, Heat Option Pool, Downstair Master, Modern, Garag, holiday rental in Sarasota

High-End New, Gourmet Kitchen, Heat Option Pool, Downstair Master, Modern, Garag

3 bedrooms
4 bathrooms
Sleeps 6
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Tranquility at the Preserve, holiday rental in Sarasota

Tranquility at the Preserve

4 bedrooms
5 bathrooms
Sleeps 10
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3 other travellers have booked this property
Sarasota River House Paradise. 4BR. Free kayaks, bikes, fishing, hot tub + more., holiday rental in Sarasota

Sarasota River House Paradise. 4BR. Free kayaks, bikes, fishing, hot tub + more.

4 bedrooms
3 bathrooms
Sleeps 9
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4 other travellers have booked this property
Luxury Sarasota Golf Home, holiday rental in Sarasota

Luxury Sarasota Golf Home

4 bedrooms
4 bathrooms
Sleeps 8
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Oceanfront home w/sunset views of Sarasota Bay, holiday rental in Sarasota

Oceanfront home w/sunset views of Sarasota Bay

3 bedrooms
2 bathrooms
Sleeps 8
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Huge Home w/ Screened Pool, BBQ, Ping-Pong, & Sunroom - Walk to Lido Beach, holiday rental in Sarasota

Huge Home w/ Screened Pool, BBQ, Ping-Pong, & Sunroom - Walk to Lido Beach

4 bedrooms
4 bathrooms
Sleeps 8
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7 other travellers have booked this property
Renovated 3 bedms/2.5 bathms with pool close to Downtown, holiday rental in Sarasota

Renovated 3 bedms/2.5 bathms with pool close to Downtown

3 bedrooms
3 bathrooms
Sleeps 10
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Sarasota House w/Backyard Oasis - 10 mins to Beach, holiday rental in Sarasota

Sarasota House w/Backyard Oasis - 10 mins to Beach

2 bedrooms
2 bathrooms
Sleeps 4
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Just 100 Steps Away from the White Sand of the World Renowned Siesta Beach, holiday rental in Sarasota

Just 100 Steps Away from the White Sand of the World Renowned Siesta Beach

2 bedrooms
2 bathrooms
Sleeps 6
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Casa Freedom - ALL-NEW, Clean & Modern, Less than 3 miles to Beach!, holiday rental in Sarasota

Casa Freedom - ALL-NEW, Clean & Modern, Less than 3 miles to Beach!

4 bedrooms
4 bathrooms
Sleeps 10
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Family Home, Heated Pool. 10 mins to #1 US Beach, holiday rental in Sarasota

Family Home, Heated Pool. 10 mins to #1 US Beach

5 bedrooms
2 bathrooms
Sleeps 10
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2 other travellers have booked this property
The MacGregor House is 1925 Old Florida elegance, holiday rental in Sarasota

The MacGregor House is 1925 Old Florida elegance

4 bedrooms
3 bathrooms
Sleeps 7
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2 other travellers have booked this property
Short Walk to World Famous Siesta Key Beach, holiday rental in Sarasota

Short Walk to World Famous Siesta Key Beach

3 bedrooms
2 bathrooms
Sleeps 6
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Timberwoods Vacation Villas Best Value in Sarasota, holiday rental in Sarasota

Timberwoods Vacation Villas Best Value in Sarasota

2 bedrooms
2 bathrooms
Sleeps 6
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4 other travellers have booked this property
Timberwoods Vacation Villas Best Value in Sarasota - Villa 5, holiday rental in Sarasota

Timberwoods Vacation Villas Best Value in Sarasota - Villa 5

2 bedrooms
2 bathrooms
Sleeps 6
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Timberwoods Vacation Villas Best Value in Sarasota - Villa 2, holiday rental in Sarasota

Timberwoods Vacation Villas Best Value in Sarasota - Villa 2

2 bedrooms
2 bathrooms
Sleeps 6
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Timberwoods Vacation Villas Best Value in Sarasota - Villa 1, holiday rental in Sarasota

Timberwoods Vacation Villas Best Value in Sarasota - Villa 1

2 bedrooms
2 bathrooms
Sleeps 6
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Timberwoods Vacation Villas Best Value in Sarasota - Villa 3, holiday rental in Sarasota

Timberwoods Vacation Villas Best Value in Sarasota - Villa 3

2 bedrooms
2 bathrooms
Sleeps 6
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Timberwoods Vacation Villas Best Value in Sarasota - Villa 4, holiday rental in Sarasota

Timberwoods Vacation Villas Best Value in Sarasota - Villa 4

2 bedrooms
2 bathrooms
Sleeps 5
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Timberwoods Vacation Villa Best Value in Sarasota, holiday rental in Sarasota

Timberwoods Vacation Villa Best Value in Sarasota

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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2 other travellers have booked this property
Downtown Sarasota Historic Burns Court Adorable Bungalow, holiday rental in Sarasota

Downtown Sarasota Historic Burns Court Adorable Bungalow

2 bedrooms
1 bathroom
Sleeps 4
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Incredible Canal Home w/ Private Pool & Spa - Near Beach!, holiday rental in Sarasota

Incredible Canal Home w/ Private Pool & Spa - Near Beach!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Villa Youppie - Roelens Vacations, holiday rental in Sarasota

Villa Youppie - Roelens Vacations

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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1 other traveller has booked this property
Private Beach Access, Heated Saltwater Pool, Sunset Viewing Deck, Gated Complex,, holiday rental in Sarasota

Private Beach Access, Heated Saltwater Pool, Sunset Viewing Deck, Gated Complex,

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Newly Remodeled Spacious Loft  in Sarasota!, holiday rental in Sarasota

Newly Remodeled Spacious Loft in Sarasota!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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'Safe & Clean' Tulip House Enchanting Family Pool Home- 1 mile to Siesta Key, holiday rental in Sarasota

'Safe & Clean' Tulip House Enchanting Family Pool Home- 1 mile to Siesta Key

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2 other travellers have booked this property
2br - Lido Beach, holiday rental in Sarasota

2br - Lido Beach

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pool Home, Under 10 Minutes Drive To World Renowned Siesta Key Beach, holiday rental in Sarasota

Pool Home, Under 10 Minutes Drive To World Renowned Siesta Key Beach

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Available for 2021 Season! 5 Minute Walk to Crescent Beach, WiFi, Siesta Key Dup, holiday rental in Sarasota

Available for 2021 Season! 5 Minute Walk to Crescent Beach, WiFi, Siesta Key Dup

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Spacious Tropical Retreat with Private Pool, holiday rental in Sarasota

Spacious Tropical Retreat with Private Pool

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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1 other traveller has booked this property
Luxury Condominium at Siesta Dunes Beachside Pool Hot Tub Tennis Sun Deck, holiday rental in Sarasota

Luxury Condominium at Siesta Dunes Beachside Pool Hot Tub Tennis Sun Deck

2 bedrooms
2 bathrooms
Sleeps 4
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13 other travellers have booked this property
New Resort Style Villa, Bring Fido, Wifi Included w/ Water View and Amazing Amen, holiday rental in Sarasota

New Resort Style Villa, Bring Fido, Wifi Included w/ Water View and Amazing Amen

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Relax near Siesta Key Beach, holiday rental in Sarasota

Relax near Siesta Key Beach

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beach Front Property, Private Beach, Heated Pool, Tennis Ct, Updated, 2nd Fl,  E, holiday rental in Sarasota

Beach Front Property, Private Beach, Heated Pool, Tennis Ct, Updated, 2nd Fl, E

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Casa Liberty - Very Walkable, Less than 3 miles to the Beach, Shops & Food!, holiday rental in Sarasota

Casa Liberty - Very Walkable, Less than 3 miles to the Beach, Shops & Food!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Downtown Zen Retreat, holiday rental in Sarasota

Downtown Zen Retreat

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Oceanfront dog-friendly home w/ sunset views of Sarasota Bay - snowbirds welcome, holiday rental in Sarasota

Oceanfront dog-friendly home w/ sunset views of Sarasota Bay - snowbirds welcome

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Private Beach, Private Access, Incredible Ocean/Beach Views Throughout, WiFi/Cab, holiday rental in Sarasota

Private Beach, Private Access, Incredible Ocean/Beach Views Throughout, WiFi/Cab

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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SARASOTA : Paradise for golfers and beach lovers, holiday rental in Sarasota

SARASOTA : Paradise for golfers and beach lovers

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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3 other travellers have booked this property
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