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Holiday Rentals in Sarasota

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2603 rentals in Sarasota.
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St.Armands Circle condo ( Kingston Arms ), holiday rental in Sarasota
St.Armands Circle condo ( Kingston Arms ), holiday rental in Sarasota
St.Armands Circle condo ( Kingston Arms ), holiday rental in Sarasota

St.Armands Circle condo ( Kingston Arms )

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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~ Cozy Apartment Close to Siesta Key ~, holiday rental in Sarasota
~ Cozy Apartment Close to Siesta Key ~, holiday rental in Sarasota
~ Cozy Apartment Close to Siesta Key ~, holiday rental in Sarasota

~ Cozy Apartment Close to Siesta Key ~

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 in Sarasota
A Wonderful Pool House on a lake full of wildlife., holiday rental in Sarasota
A Wonderful Pool House on a lake full of wildlife., holiday rental in Sarasota

A Wonderful Pool House on a lake full of wildlife.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Gorgeous, Gut-Renovated Villa in Village Des Pins, Sarasota, 2BR 2 BD sleeps 4-6, holiday rental in Sarasota
Gorgeous, Gut-Renovated Villa in Village Des Pins, Sarasota, 2BR 2 BD sleeps 4-6, holiday rental in Sarasota
Gorgeous, Gut-Renovated Villa in Village Des Pins, Sarasota, 2BR 2 BD sleeps 4-6, holiday 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
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Available a week in Dec Living the Dream on Lido close to beach and st Armand’s, holiday rental in Sarasota
Available a week in Dec Living the Dream on Lido close to beach and st Armand’s, holiday rental in Sarasota
Available a week in Dec Living the Dream on Lido close to beach and st Armand’s, holiday rental in Sarasota

Available a week in Dec Living the Dream on Lido close to beach and st Armand’s

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Siesta Key Gulf Side~1st Floor Villa, 3 Heated Pools,  Updated, Beachy Chic #100, holiday rental in Sarasota
Siesta Key Gulf Side~1st Floor Villa, 3 Heated Pools,  Updated, Beachy Chic #100, holiday rental in Sarasota
Siesta Key Gulf Side~1st Floor Villa, 3 Heated Pools,  Updated, Beachy Chic #100, holiday rental in Sarasota

Siesta Key Gulf Side~1st Floor Villa, 3 Heated Pools, Updated, Beachy Chic #100

Holiday Rental House
2 bedrooms
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
More info
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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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Secluded Home with Private, heated, saltwater pool   Pet Friendly, holiday rental in Sarasota
Secluded Home with Private, heated, saltwater pool   Pet Friendly, holiday rental in Sarasota
Secluded Home with Private, heated, saltwater pool   Pet Friendly, holiday rental in Sarasota

Secluded Home with Private, heated, saltwater pool Pet Friendly

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Immaculate, Newly Remodeled Close to Siesta Beach, holiday rental in Sarasota
Immaculate, Newly Remodeled Close to Siesta Beach, holiday rental in Sarasota
Immaculate, Newly Remodeled Close to Siesta Beach, holiday rental in Sarasota

Immaculate, Newly Remodeled Close to Siesta Beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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ROYS PLACE private, tropical, romantic paradise., holiday rental in Sarasota
ROYS PLACE private, tropical, romantic paradise., holiday rental in Sarasota
ROYS PLACE private, tropical, romantic paradise., holiday rental in Sarasota

ROYS PLACE private, tropical, romantic paradise.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Perfectly located in Sarasota for Beaching, Biking, Dining, Boating, Golf & Arts, holiday rental in Sarasota
Perfectly located in Sarasota for Beaching, Biking, Dining, Boating, Golf & Arts, holiday rental in Sarasota
Perfectly located in Sarasota for Beaching, Biking, Dining, Boating, Golf & Arts, holiday rental in Sarasota

Perfectly located in Sarasota for Beaching, Biking, Dining, Boating, Golf & Arts

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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OPEN Post H-Ian: Roomy Beach Cottage: 4 bd/3 ba: 100 ft to beach path; priv poo, holiday rental in Sarasota
OPEN Post H-Ian: Roomy Beach Cottage: 4 bd/3 ba: 100 ft to beach path; priv poo, holiday rental in Sarasota
OPEN Post H-Ian: Roomy Beach Cottage: 4 bd/3 ba: 100 ft to beach path; priv poo, holiday rental in Sarasota

OPEN Post H-Ian: Roomy Beach Cottage: 4 bd/3 ba: 100 ft to beach path; priv poo

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Vacation delight! Cozy condo just steps from the beach and St. Armands circle., holiday rental in Sarasota
Vacation delight! Cozy condo just steps from the beach and St. Armands circle., holiday rental in Sarasota
Vacation delight! Cozy condo just steps from the beach and St. Armands circle., holiday rental in Sarasota

Vacation delight! Cozy condo just steps from the beach and St. Armands circle.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Walk to waterfront, Downtown and Southside Village, holiday rental in Sarasota
Walk to waterfront, Downtown and Southside Village, holiday rental in Sarasota
Walk to waterfront, Downtown and Southside Village, holiday rental in Sarasota

Walk to waterfront, Downtown and Southside Village

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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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 4
Match: Sleeps
More info
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ROYS PLACE Romantic Near Downtown with Private Heated Pool!, holiday rental in Sarasota
ROYS PLACE Romantic Near Downtown with Private Heated Pool!, holiday rental in Sarasota
ROYS PLACE Romantic Near Downtown with Private Heated Pool!, holiday rental in Sarasota

ROYS PLACE Romantic Near Downtown with Private Heated Pool!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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CUTE 2 BED 2 BATH COTTAGE 2 MI FROM THE BEACH- NO SMOKING, holiday rental in Sarasota
CUTE 2 BED 2 BATH COTTAGE 2 MI FROM THE BEACH- NO SMOKING, holiday rental in Sarasota
CUTE 2 BED 2 BATH COTTAGE 2 MI FROM THE BEACH- NO SMOKING, holiday rental in Sarasota

CUTE 2 BED 2 BATH COTTAGE 2 MI FROM THE BEACH- NO SMOKING

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Siesta Key Jamaica Royale 71 Beachside, holiday rental in Sarasota
Siesta Key Jamaica Royale 71 Beachside, holiday rental in Sarasota
Siesta Key Jamaica Royale 71 Beachside, holiday rental in Sarasota

Siesta Key Jamaica Royale 71 Beachside

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Central Sarasota home>Downtown/Beaches/Boating/Legacy Bike Trail. Pets welcome, holiday rental in Sarasota
Central Sarasota home>Downtown/Beaches/Boating/Legacy Bike Trail. Pets welcome, holiday rental in Sarasota
Central Sarasota home>Downtown/Beaches/Boating/Legacy Bike Trail. Pets welcome, holiday rental in Sarasota

Central Sarasota home>Downtown/Beaches/Boating/Legacy Bike Trail. Pets welcome

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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1/10 mile to Lido Beach, holiday rental in Sarasota
1/10 mile to Lido Beach, holiday rental in Sarasota
1/10 mile to Lido Beach, holiday rental in Sarasota

1/10 mile to Lido Beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Heated Pool! Close 2 Siesta & Lido Beaches, Downtown & Pinecraft, holiday rental in Sarasota
Heated Pool! Close 2 Siesta & Lido Beaches, Downtown & Pinecraft, holiday rental in Sarasota
Heated Pool! Close 2 Siesta & Lido Beaches, Downtown & Pinecraft, holiday rental in Sarasota

Heated Pool! Close 2 Siesta & Lido Beaches, Downtown & Pinecraft

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Beautiful White Sand Siesta Key, holiday rental in Sarasota
Beautiful White Sand Siesta Key, holiday rental in Sarasota
Beautiful White Sand Siesta Key, holiday rental in Sarasota

Beautiful White Sand Siesta Key

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Lido Beach Walk! One block to beach, easy 10 min stroll to St Armand's Circle., holiday rental in Sarasota
Lido Beach Walk! One block to beach, easy 10 min stroll to St Armand's Circle., holiday rental in Sarasota
Lido Beach Walk! One block to beach, easy 10 min stroll to St Armand's Circle., holiday rental in Sarasota

Lido Beach Walk! One block to beach, easy 10 min stroll to St Armand's Circle.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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An intercoastal delight with deeded beach access, holiday rental in Sarasota
An intercoastal delight with deeded beach access, holiday rental in Sarasota
An intercoastal delight with deeded beach access, holiday rental in Sarasota

An intercoastal delight with deeded beach access

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Midcentury Modern 3 BR - Pool in Sarasota, Close to Beaches!, holiday rental in Sarasota
Midcentury Modern 3 BR - Pool in Sarasota, Close to Beaches!, holiday rental in Sarasota
Midcentury Modern 3 BR - Pool in Sarasota, Close to Beaches!, holiday rental in Sarasota

Midcentury Modern 3 BR - Pool in Sarasota, Close to Beaches!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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ONE MILE from beautiful Siesta Key, #1 beach in the USA!!!, holiday rental in Sarasota
ONE MILE from beautiful Siesta Key, #1 beach in the USA!!!, holiday rental in Sarasota
ONE MILE from beautiful Siesta Key, #1 beach in the USA!!!, holiday rental in Sarasota

ONE MILE from beautiful Siesta Key, #1 beach in the USA!!!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Lido/Sarasota, walk to Beach &St. Armands, HEATED POOL home w/grill, holiday rental in Sarasota
Lido/Sarasota, walk to Beach &St. Armands, HEATED POOL home w/grill, holiday rental in Sarasota
Lido/Sarasota, walk to Beach &St. Armands, HEATED POOL home w/grill, holiday rental in Sarasota

Lido/Sarasota, walk to Beach &St. Armands, HEATED POOL home w/grill

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Lido Beach and St. Armand's Circle at your Footsteps. Ask about the guest house!, holiday rental in Sarasota
Lido Beach and St. Armand's Circle at your Footsteps. Ask about the guest house!, holiday rental in Sarasota
Lido Beach and St. Armand's Circle at your Footsteps. Ask about the guest house!, holiday rental in Sarasota

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
More info
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Family friendly with large pool, holiday rental in Sarasota
Family friendly with large pool, holiday rental in Sarasota
Family friendly with large pool, holiday rental in Sarasota

Family friendly with large pool

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
More info
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Luxurious Mediterranean Estate with Private Beach!, holiday rental in Sarasota
Luxurious Mediterranean Estate with Private Beach!, holiday rental in Sarasota
Luxurious Mediterranean Estate with Private Beach!, holiday rental in Sarasota

Luxurious Mediterranean Estate with Private Beach!

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 6
Match: Sleeps
More info
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5⭐️ SIESTA KEY WATERFRONT RANCH, POOL, DOCK, LIFT, DESK AREA, MASSAGE ROOM, holiday rental in Sarasota
5⭐️ SIESTA KEY WATERFRONT RANCH, POOL, DOCK, LIFT, DESK AREA, MASSAGE ROOM, holiday rental in Sarasota
5⭐️ SIESTA KEY WATERFRONT RANCH, POOL, DOCK, LIFT, DESK AREA, MASSAGE ROOM, holiday rental in Sarasota

5⭐️ SIESTA KEY WATERFRONT RANCH, POOL, DOCK, LIFT, DESK AREA, MASSAGE ROOM

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Adorable Beach Cottage Bungalow in Sunny Sarasota, holiday rental in Sarasota
Adorable Beach Cottage Bungalow in Sunny Sarasota, holiday rental in Sarasota
Adorable Beach Cottage Bungalow in Sunny Sarasota, holiday rental in Sarasota

Adorable Beach Cottage Bungalow in Sunny Sarasota

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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ST. ARMANDS CIRCLE, 3 Bedroom 3 Bath, Heated Pool, holiday rental in Sarasota
ST. ARMANDS CIRCLE, 3 Bedroom 3 Bath, Heated Pool, holiday rental in Sarasota
ST. ARMANDS CIRCLE, 3 Bedroom 3 Bath, Heated Pool, holiday rental in Sarasota

ST. ARMANDS CIRCLE, 3 Bedroom 3 Bath, Heated Pool

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Heated Pool/Spa, Putting Green, Game Room. Walk/Bike to Everything, holiday rental in Sarasota
Heated Pool/Spa, Putting Green, Game Room. Walk/Bike to Everything, holiday rental in Sarasota
Heated Pool/Spa, Putting Green, Game Room. Walk/Bike to Everything, holiday rental in Sarasota

Heated Pool/Spa, Putting Green, Game Room. Walk/Bike to Everything

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 19
Match: Sleeps
More info
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Beautiful tranquil pool home near America's No 1 Beach, holiday rental in Sarasota
Beautiful tranquil pool home near America's No 1 Beach, holiday rental in Sarasota
Beautiful tranquil pool home near America's No 1 Beach, holiday rental in Sarasota

Beautiful tranquil pool home near America's No 1 Beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Newly Renovated 4th Floor Condo Directly Across For The Siesta Key Beach, holiday rental in Sarasota
Newly Renovated 4th Floor Condo Directly Across For The Siesta Key Beach, holiday rental in Sarasota
Newly Renovated 4th Floor Condo Directly Across For The Siesta Key Beach, holiday rental in Sarasota

Newly Renovated 4th Floor Condo Directly Across For The Siesta Key Beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Another Day in Paradise!, holiday rental in Sarasota
Another Day in Paradise!, holiday rental in Sarasota
Another Day in Paradise!, holiday rental in Sarasota

Another Day in Paradise!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Secluded luxury with heated Saltwater Pool with Spa, holiday rental in Sarasota
Secluded luxury with heated Saltwater Pool with Spa, holiday rental in Sarasota
Secluded luxury with heated Saltwater Pool with Spa, holiday rental in Sarasota

Secluded luxury with heated Saltwater Pool with Spa

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Waterfront Home near Siesta Key with a pool, holiday rental in Sarasota
Waterfront Home near Siesta Key with a pool, holiday rental in Sarasota
Waterfront Home near Siesta Key with a pool, holiday rental in Sarasota

Waterfront Home near Siesta Key with a pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Rooftop Deck w/ Gulf Views, Steps to Beach, Private Heated Pool/Spa, holiday rental in Sarasota
Rooftop Deck w/ Gulf Views, Steps to Beach, Private Heated Pool/Spa, holiday rental in Sarasota
Rooftop Deck w/ Gulf Views, Steps to Beach, Private Heated Pool/Spa, holiday rental in Sarasota

Rooftop Deck w/ Gulf Views, Steps to Beach, Private Heated Pool/Spa

Holiday Rental House
7 bedrooms
8 bathrooms
Sleeps 19
Match: Sleeps
More info
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Stunning Siesta Key,, Shell Beach .02 miles Shell Beach, holiday rental in Sarasota
Stunning Siesta Key,, Shell Beach .02 miles Shell Beach, holiday rental in Sarasota
Stunning Siesta Key,, Shell Beach .02 miles Shell Beach, holiday rental in Sarasota

Stunning Siesta Key,, Shell Beach .02 miles Shell Beach

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
More info
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Sunny Walk-out Patio, Spacious Master Suite, Wi-Fi, holiday rental in Sarasota
Sunny Walk-out Patio, Spacious Master Suite, Wi-Fi, holiday rental in Sarasota
Sunny Walk-out Patio, Spacious Master Suite, Wi-Fi, holiday rental in Sarasota

Sunny Walk-out Patio, Spacious Master Suite, Wi-Fi

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Ultimate getaway. Great Location. Lido Beach and St Armands Circle, holiday rental in Sarasota
Ultimate getaway. Great Location. Lido Beach and St Armands Circle, holiday rental in Sarasota
Ultimate getaway. Great Location. Lido Beach and St Armands Circle, holiday rental in Sarasota

Ultimate getaway. Great Location. Lido Beach and St Armands Circle

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Affordable 2ba/1ba Waterfront Cottage in Sarasota close to downtown and beaches, holiday rental in Sarasota
Affordable 2ba/1ba Waterfront Cottage in Sarasota close to downtown and beaches, holiday rental in Sarasota
Affordable 2ba/1ba Waterfront Cottage in Sarasota close to downtown and beaches, holiday rental in Sarasota

Affordable 2ba/1ba Waterfront Cottage in Sarasota close to downtown and beaches

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Mid-Century Modern W/Private Lap Pool In secluded Garden and art studio, holiday rental in Sarasota
Mid-Century Modern W/Private Lap Pool In secluded Garden and art studio, holiday rental in Sarasota
Mid-Century Modern W/Private Lap Pool In secluded Garden and art studio, holiday rental in Sarasota

Mid-Century Modern W/Private Lap Pool In secluded Garden and art studio

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Lovely updated Pool Home on famous St. Armand's Circle, Sarasota, Florida, holiday rental in Sarasota
Lovely updated Pool Home on famous St. Armand's Circle, Sarasota, Florida, holiday rental in Sarasota
Lovely updated Pool Home on famous St. Armand's Circle, Sarasota, Florida, holiday rental in Sarasota

Lovely updated Pool Home on famous St. Armand's Circle, Sarasota, Florida

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Beautiful, Updated, Ground Floor Condo.  Convenient to Beach, Pool & Village, holiday rental in Sarasota
Beautiful, Updated, Ground Floor Condo.  Convenient to Beach, Pool & Village, holiday rental in Sarasota
Beautiful, Updated, Ground Floor Condo.  Convenient to Beach, Pool & Village, holiday rental in Sarasota

Beautiful, Updated, Ground Floor Condo. Convenient to Beach, Pool & Village

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Casa Calm: King Room, Yoga, Spa, holiday rental in Sarasota
Casa Calm: King Room, Yoga, Spa, holiday rental in Sarasota
Casa Calm: King Room, Yoga, Spa, holiday rental in Sarasota

Casa Calm: King Room, Yoga, Spa

Private Room
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Payment Protection

Private Heated Pool Home Short Walk to St Armands & Lido Beach, holiday rental in Sarasota
Private Heated Pool Home Short Walk to St Armands & Lido Beach, holiday rental in Sarasota
Private Heated Pool Home Short Walk to St Armands & Lido Beach, holiday rental in Sarasota

Private Heated Pool Home Short Walk to St Armands & Lido Beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Frequently Asked Questions about Sarasota