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Sarasota Luxury Holiday Homes

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5 km
3,652 rentals in Sarasota.
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village, holiday rental in Sarasota
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village, holiday rental in Sarasota
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village, holiday rental in Sarasota

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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STEPS TO LIDO BEACH, holiday rental in Sarasota
STEPS TO LIDO BEACH, holiday rental in Sarasota
STEPS TO LIDO BEACH, holiday rental in Sarasota

STEPS TO LIDO BEACH

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach, holiday rental in Sarasota
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach, holiday rental in Sarasota
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach, holiday rental in Sarasota

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Siesta Key Vacation Property W/Heated Pool and Beach Access, holiday rental in Sarasota
Siesta Key Vacation Property W/Heated Pool and Beach Access, holiday rental in Sarasota
Siesta Key Vacation Property W/Heated Pool and Beach Access, holiday rental in Sarasota

Siesta Key Vacation Property W/Heated Pool and Beach Access

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Across The Street From #1 Beach, holiday rental in Sarasota
Across The Street From #1 Beach, holiday rental in Sarasota
Across The Street From #1 Beach, holiday rental in Sarasota

Across The Street From #1 Beach

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Prem 2Bed/2Bath Gate House Cottage with private beach access!, holiday rental in Sarasota
Prem 2Bed/2Bath Gate House Cottage with private beach access!, holiday rental in Sarasota
Prem 2Bed/2Bath Gate House Cottage with private beach access!, holiday rental in Sarasota

Prem 2Bed/2Bath Gate House Cottage with private beach access!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price, holiday rental in Sarasota
Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price, holiday rental in Sarasota
Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price, holiday rental in Sarasota

Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ingram House 2, holiday rental in Sarasota
Ingram House 2, holiday rental in Sarasota
Ingram House 2, holiday rental in Sarasota

Ingram House 2

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bright Coastal Condo: Walk to Lido Key Beach!, holiday rental in Sarasota
Bright Coastal Condo: Walk to Lido Key Beach!, holiday rental in Sarasota
Bright Coastal Condo: Walk to Lido Key Beach!, holiday rental in Sarasota

Bright Coastal Condo: Walk to Lido Key Beach!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Centrally located!  6 miles to Siesta and St. Armands. 2 miles to downtown., holiday rental in Sarasota
Centrally located!  6 miles to Siesta and St. Armands. 2 miles to downtown., holiday rental in Sarasota
Centrally located!  6 miles to Siesta and St. Armands. 2 miles to downtown., holiday rental in Sarasota

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Charming Downtown Sarasota Cottage- near Legacy Trail and 10 min to beach!, holiday rental in Sarasota
Charming Downtown Sarasota Cottage- near Legacy Trail and 10 min to beach!, holiday rental in Sarasota
Charming Downtown Sarasota Cottage- near Legacy Trail and 10 min to beach!, holiday rental in Sarasota

Charming Downtown Sarasota Cottage- near Legacy Trail and 10 min to beach!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Steps away from the #1 beach! Spectacular views on the GIANT balcony!, holiday rental in Sarasota
Steps away from the #1 beach! Spectacular views on the GIANT balcony!, holiday rental in Sarasota
Steps away from the #1 beach! Spectacular views on the GIANT balcony!, holiday rental in Sarasota

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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lido/St. Armands, Sarasota-Walk to Beach & St. Armands, Private cottage, holiday rental in Sarasota
Lido/St. Armands, Sarasota-Walk to Beach & St. Armands, Private cottage, holiday rental in Sarasota
Lido/St. Armands, Sarasota-Walk to Beach & St. Armands, Private cottage, holiday rental in Sarasota

Lido/St. Armands, Sarasota-Walk to Beach & St. Armands, Private cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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2 Cottages Rented Together | Amazing Heated Pool | Near Beaches, holiday rental in Sarasota
2 Cottages Rented Together | Amazing Heated Pool | Near Beaches, holiday rental in Sarasota
2 Cottages Rented Together | Amazing Heated Pool | Near Beaches, holiday rental in Sarasota

2 Cottages Rented Together | Amazing Heated Pool | Near Beaches

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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*** Downtown Bungalow ***Beaches / Restaurants / Cafes***Just Minutes away!, holiday rental in Sarasota
*** Downtown Bungalow ***Beaches / Restaurants / Cafes***Just Minutes away!, holiday rental in Sarasota
*** Downtown Bungalow ***Beaches / Restaurants / Cafes***Just Minutes away!, holiday rental in Sarasota

*** Downtown Bungalow ***Beaches / Restaurants / Cafes***Just Minutes away!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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LIDO BEACH/ST. ARMAND'S CIRCLE  #101, holiday rental in Sarasota
LIDO BEACH/ST. ARMAND'S CIRCLE  #101, holiday rental in Sarasota
LIDO BEACH/ST. ARMAND'S CIRCLE  #101, holiday rental in Sarasota

LIDO BEACH/ST. ARMAND'S CIRCLE #101

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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LuLu's Loggerhead Renovated | Walk to Siesta Key Beach | Heated Pool | Ready to, holiday rental in Sarasota
LuLu's Loggerhead Renovated | Walk to Siesta Key Beach | Heated Pool | Ready to, holiday rental in Sarasota
LuLu's Loggerhead Renovated | Walk to Siesta Key Beach | Heated Pool | Ready to, holiday rental in Sarasota

LuLu's Loggerhead Renovated | Walk to Siesta Key Beach | Heated Pool | Ready to

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Immaculate, close to everything Sarasota, holiday rental in Sarasota
Immaculate, close to everything Sarasota, holiday rental in Sarasota
Immaculate, close to everything Sarasota, holiday rental in Sarasota

Immaculate, close to everything Sarasota

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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4 Bed pool House by Bay!  Lido & Siesta Key Beaches very close, holiday rental in Sarasota
4 Bed pool House by Bay!  Lido & Siesta Key Beaches very close, holiday rental in Sarasota
4 Bed pool House by Bay!  Lido & Siesta Key Beaches very close, holiday rental in Sarasota

4 Bed pool House by Bay! Lido & Siesta Key Beaches very close

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Palm Bay Club Bayside Well-Priced Rental Condo on Siesta Key, holiday rental in Sarasota
Palm Bay Club Bayside Well-Priced Rental Condo on Siesta Key, holiday rental in Sarasota
Palm Bay Club Bayside Well-Priced Rental Condo on Siesta Key, holiday rental in Sarasota

Palm Bay Club Bayside Well-Priced Rental Condo on Siesta Key

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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$500 OFF- Private Pool w/ Swim Up Bar and Rock Slide -  Dock w/ Gulf Access - P, holiday rental in Sarasota
$500 OFF- Private Pool w/ Swim Up Bar and Rock Slide -  Dock w/ Gulf Access - P, holiday rental in Sarasota
$500 OFF- Private Pool w/ Swim Up Bar and Rock Slide -  Dock w/ Gulf Access - P, holiday rental in Sarasota

$500 OFF- Private Pool w/ Swim Up Bar and Rock Slide - Dock w/ Gulf Access - P

Holiday Rental House
8 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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Sunsets in Paradise. Walk to beach. Shop & Dine * St. Armands, holiday rental in Sarasota
Sunsets in Paradise. Walk to beach. Shop & Dine * St. Armands, holiday rental in Sarasota
Sunsets in Paradise. Walk to beach. Shop & Dine * St. Armands, holiday rental in Sarasota

Sunsets in Paradise. Walk to beach. Shop & Dine * St. Armands

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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University Pines Studio in Sarasota, holiday rental in Sarasota
University Pines Studio in Sarasota, holiday rental in Sarasota
University Pines Studio in Sarasota, holiday rental in Sarasota

University Pines Studio in Sarasota

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Condo with Private Beach Access, Great Shared Amenities - Private Beach House, holiday rental in Sarasota
Condo with Private Beach Access, Great Shared Amenities - Private Beach House, holiday rental in Sarasota
Condo with Private Beach Access, Great Shared Amenities - Private Beach House, holiday rental in Sarasota

Condo with Private Beach Access, Great Shared Amenities - Private Beach House

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Siesta Key Village-Suite #3: A Block to the Beach!, holiday rental in Sarasota
Siesta Key Village-Suite #3: A Block to the Beach!, holiday rental in Sarasota
Siesta Key Village-Suite #3: A Block to the Beach!, holiday rental in Sarasota

Siesta Key Village-Suite #3: A Block to the Beach!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Siesta Key 2B 2 bath with Heated Pool! Sleeps 6 ! Relaxation & Sunshine!, holiday rental in Sarasota
Siesta Key 2B 2 bath with Heated Pool! Sleeps 6 ! Relaxation & Sunshine!, holiday rental in Sarasota
Siesta Key 2B 2 bath with Heated Pool! Sleeps 6 ! Relaxation & Sunshine!, holiday rental in Sarasota

Siesta Key 2B 2 bath with Heated Pool! Sleeps 6 ! Relaxation & Sunshine!

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Centrally Located, Sarasota Home Close To Amish Community, holiday rental in Sarasota
Centrally Located, Sarasota Home Close To Amish Community, holiday rental in Sarasota
Centrally Located, Sarasota Home Close To Amish Community, holiday rental in Sarasota

Centrally Located, Sarasota Home Close To Amish Community

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Putting green, Rooftop Deck AND Beach/Gulf Views with Private Heated Pool/Spa., holiday rental in Sarasota
Putting green, Rooftop Deck AND Beach/Gulf Views with Private Heated Pool/Spa., holiday rental in Sarasota
Putting green, Rooftop Deck AND Beach/Gulf Views with Private Heated Pool/Spa., holiday rental in Sarasota

Putting green, Rooftop Deck AND Beach/Gulf Views with Private Heated Pool/Spa.

Holiday Rental House
7 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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Sea Club II: Paradise in your own Condo w/ Heated Pool and Private Beach, holiday rental in Sarasota
Sea Club II: Paradise in your own Condo w/ Heated Pool and Private Beach, holiday rental in Sarasota
Sea Club II: Paradise in your own Condo w/ Heated Pool and Private Beach, holiday rental in Sarasota

Sea Club II: Paradise in your own Condo w/ Heated Pool and Private Beach

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Siesta Key Gulf View. Steps from beach, Ground Floor, Pool, Walk to Village!, holiday rental in Sarasota
Siesta Key Gulf View. Steps from beach, Ground Floor, Pool, Walk to Village!, holiday rental in Sarasota
Siesta Key Gulf View. Steps from beach, Ground Floor, Pool, Walk to Village!, holiday rental in Sarasota

Siesta Key Gulf View. Steps from beach, Ground Floor, Pool, Walk to Village!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Modern near Siesta Beach, holiday rental in Sarasota
Modern near Siesta Beach, holiday rental in Sarasota
Modern near Siesta Beach, holiday rental in Sarasota

Modern near Siesta Beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bayside condo on the water with a pool, holiday rental in Sarasota
Bayside condo on the water with a pool, holiday rental in Sarasota
Bayside condo on the water with a pool, holiday rental in Sarasota

Bayside condo on the water with a pool

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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7 Minute Walk to Lido beach, beautiful condo, holiday rental in Sarasota
7 Minute Walk to Lido beach, beautiful condo, holiday rental in Sarasota
7 Minute Walk to Lido beach, beautiful condo, holiday rental in Sarasota

7 Minute Walk to Lido beach, beautiful condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Siesta Key Village-Suite #1: A block to the Beach!, holiday rental in Sarasota
Siesta Key Village-Suite #1: A block to the Beach!, holiday rental in Sarasota
Siesta Key Village-Suite #1: A block to the Beach!, holiday rental in Sarasota

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

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Spacious Home with Pool Close to Beaches and Downtown, holiday rental in Sarasota
Spacious Home with Pool Close to Beaches and Downtown, holiday rental in Sarasota
Spacious Home with Pool Close to Beaches and Downtown, holiday rental in Sarasota

Spacious Home with Pool Close to Beaches and Downtown

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Close to Siesta Beach # 1 in Usa, holiday rental in Sarasota
Close to Siesta Beach # 1 in Usa, holiday rental in Sarasota
Close to Siesta Beach # 1 in Usa, holiday rental in Sarasota

Close to Siesta Beach # 1 in Usa

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Private Beach Steps Away, 2 Levels, 3 Pools, Non-Tower, Waterfront Building, holiday rental in Sarasota
Private Beach Steps Away, 2 Levels, 3 Pools, Non-Tower, Waterfront Building, holiday rental in Sarasota
Private Beach Steps Away, 2 Levels, 3 Pools, Non-Tower, Waterfront Building, holiday rental in Sarasota

Private Beach Steps Away, 2 Levels, 3 Pools, Non-Tower, Waterfront Building

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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STEPS TO LIDO BEACH & ST. ARMAND’S CIRCLE, holiday rental in Sarasota
STEPS TO LIDO BEACH & ST. ARMAND’S CIRCLE, holiday rental in Sarasota
STEPS TO LIDO BEACH & ST. ARMAND’S CIRCLE, holiday rental in Sarasota

STEPS TO LIDO BEACH & ST. ARMAND’S CIRCLE

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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NEW LISTING!!!  Beautiful Beach Cottage Minutes from Siesta Key - Welcome Home!, holiday rental in Sarasota
NEW LISTING!!!  Beautiful Beach Cottage Minutes from Siesta Key - Welcome Home!, holiday rental in Sarasota
NEW LISTING!!!  Beautiful Beach Cottage Minutes from Siesta Key - Welcome Home!, holiday rental in Sarasota

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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Siesta Key GULF SIDE #95 - Serene Private Condo, 3 Pools, Jamaica Royale, holiday rental in Sarasota
Siesta Key GULF SIDE #95 - Serene Private Condo, 3 Pools, Jamaica Royale, holiday rental in Sarasota
Siesta Key GULF SIDE #95 - Serene Private Condo, 3 Pools, Jamaica Royale, holiday rental in Sarasota

Siesta Key GULF SIDE #95 - Serene Private Condo, 3 Pools, Jamaica Royale

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Steps to Beach - Amazing Gulf Views - Resort Pool/Spa/Slide & Mini Golf, holiday rental in Sarasota
Steps to Beach - Amazing Gulf Views - Resort Pool/Spa/Slide & Mini Golf, holiday rental in Sarasota
Steps to Beach - Amazing Gulf Views - Resort Pool/Spa/Slide & Mini Golf, holiday rental in Sarasota

Steps to Beach - Amazing Gulf Views - Resort Pool/Spa/Slide & Mini Golf

Holiday Rental House
8 bedrooms
7 bathrooms
Sleeps 19
Match: Sleeps
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Beachside Studio Located Across from Main Beach and Half Mile to Village, holiday rental in Sarasota
Beachside Studio Located Across from Main Beach and Half Mile to Village, holiday rental in Sarasota
Beachside Studio Located Across from Main Beach and Half Mile to Village, holiday rental in Sarasota

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

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Very tropical, private and peaceful, short walk to everything happening downtown, holiday rental in Sarasota
Very tropical, private and peaceful, short walk to everything happening downtown, holiday rental in Sarasota
Very tropical, private and peaceful, short walk to everything happening downtown, holiday rental in Sarasota

Very tropical, private and peaceful, short walk to everything happening downtown

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Salty Breeze Home w/ Guest Suite, Heated Enclosed Salt Pool/Spa, holiday rental in Sarasota
Salty Breeze Home w/ Guest Suite, Heated Enclosed Salt Pool/Spa, holiday rental in Sarasota
Salty Breeze Home w/ Guest Suite, Heated Enclosed Salt Pool/Spa, holiday rental in Sarasota

Salty Breeze Home w/ Guest Suite, Heated Enclosed Salt Pool/Spa

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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WE ARE OPEN FOR BUSINESS, 2 BD ROOM 
walk to the beach and st Armand’s, holiday rental in Sarasota
WE ARE OPEN FOR BUSINESS, 2 BD ROOM 
walk to the beach and st Armand’s, holiday rental in Sarasota
WE ARE OPEN FOR BUSINESS, 2 BD ROOM 
walk to the beach and st Armand’s, holiday rental in Sarasota

WE ARE OPEN FOR BUSINESS, 2 BD ROOM walk to the beach and st Armand’s

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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#104 Jamaica Royale beautifully renovated!, holiday rental in Sarasota
#104 Jamaica Royale beautifully renovated!, holiday rental in Sarasota
#104 Jamaica Royale beautifully renovated!, holiday rental in Sarasota

#104 Jamaica Royale beautifully renovated!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sarasota Sanctuary Tropical Holiday, holiday rental in Sarasota
Sarasota Sanctuary Tropical Holiday, holiday rental in Sarasota
Sarasota Sanctuary Tropical Holiday, holiday rental in Sarasota

Sarasota Sanctuary Tropical Holiday

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Amazing Waterfront Home with Private Dock & Large Pool w 4 Ensuites, holiday rental in Sarasota
Amazing Waterfront Home with Private Dock & Large Pool w 4 Ensuites, holiday rental in Sarasota
Amazing Waterfront Home with Private Dock & Large Pool w 4 Ensuites, holiday rental in Sarasota

Amazing Waterfront Home with Private Dock & Large Pool w 4 Ensuites

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Ground Floor 1bed/1.5 Bath Condo with Pool and Beach Access!, holiday rental in Sarasota
Beautiful Ground Floor 1bed/1.5 Bath Condo with Pool and Beach Access!, holiday rental in Sarasota
Beautiful Ground Floor 1bed/1.5 Bath Condo with Pool and Beach Access!, holiday rental in Sarasota

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

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Newly Remodeled 3bd/3bh | 10 mins to the Beach, holiday rental in Sarasota
Newly Remodeled 3bd/3bh | 10 mins to the Beach, holiday rental in Sarasota
Newly Remodeled 3bd/3bh | 10 mins to the Beach, holiday rental in Sarasota

Newly Remodeled 3bd/3bh | 10 mins to the Beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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