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Holiday Rentals in Siesta Key

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998 rentals in Siesta Key.
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WE LIKE BLUE, SIESTA BLUE! 2 BED BAYSIDE CONDO ON SIESTA KEY, holiday rental in Siesta Key

WE LIKE BLUE, SIESTA BLUE! 2 BED BAYSIDE CONDO ON SIESTA KEY

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Newly Renovated Beach House on canal * 5 minute walk to village and beach, holiday rental in Siesta Key

Newly Renovated Beach House on canal * 5 minute walk to village and beach

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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WHAT A VIEW !! 2 BED BAYSIDE CONDO ON SIESTA KEY, holiday rental in Siesta Key

WHAT A VIEW !! 2 BED BAYSIDE CONDO ON SIESTA KEY

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Top Floor Oceanfront View Of The #1 Beach In The USA! - Beautiful Decor!, holiday rental in Siesta Key

Top Floor Oceanfront View Of The #1 Beach In The USA! - Beautiful Decor!

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Newly renovated condo with premium features on Siesta Key, holiday rental in Siesta Key

Newly renovated condo with premium features on Siesta Key

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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BEST HOUSE ON SIESTA - Sleeps 24+ - Heated Private Pool w/ Slide, Spa, Gratto,, holiday rental in Siesta Key

BEST HOUSE ON SIESTA - Sleeps 24+ - Heated Private Pool w/ Slide, Spa, Gratto,

8 bedrooms
8 bathrooms
Sleeps 24
Match: Sleeps
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Best Location - luxury villa with pool, very close to beach and restaurants!, holiday rental in Siesta Key

Best Location - luxury villa with pool, very close to beach and restaurants!

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Fantastic Beachfront Condo, at Surf & Racquet Resort on Siesta Key Beach, holiday rental in Siesta Key

Fantastic Beachfront Condo, at Surf & Racquet Resort on Siesta Key Beach

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Palm Oasis - Relax in Comfort - 1 rental per calendar month, holiday rental in Siesta Key

Palm Oasis - Relax in Comfort - 1 rental per calendar month

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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2 MINUTE WALK TO SIESTA BEACH!! (really)  1 MINUTE TO POOL.  GREAT VALUE!!!, holiday rental in Siesta Key

2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Siesta Key/Derby Bay, holiday rental in Siesta Key

Siesta Key/Derby Bay

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Perfect Local In Village,1 1/2 Block From #1 Beach In USA, Pool, Wifi, Sun & Fun, holiday rental in Siesta Key

Perfect Local In Village,1 1/2 Block From #1 Beach In USA, Pool, Wifi, Sun & Fun

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Siesta Key Villa A - Only 150 yards to Crescent Beach and heated pool!, holiday rental in Siesta Key

Siesta Key Villa A - Only 150 yards to Crescent Beach and heated pool!

2 bedrooms
1 bathroom
Sleeps 4
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Siesta Key Villa B - Only 150 yds. to Crescent Beach and heated pool!, holiday rental in Siesta Key

Siesta Key Villa B - Only 150 yds. to Crescent Beach and heated pool!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cathy's Crescent Condos-Siesta Key,  FL GULF FRONT, holiday rental in Siesta Key

Cathy's Crescent Condos-Siesta Key, FL GULF FRONT

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Midnight Cove #532 in Siesta Key, FL- Sun, Sand & *Save 9% to 25% per Week*, holiday rental in Siesta Key

Midnight Cove #532 in Siesta Key, FL- Sun, Sand & *Save 9% to 25% per Week*

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Siesta Key Inn 1Br/1B Sabal Palm #1A, holiday rental in Siesta Key

Siesta Key Inn 1Br/1B Sabal Palm #1A

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Super Cute, Super Clean Large One Bedroom - Fully Remodeled!, holiday rental in Siesta Key

Super Cute, Super Clean Large One Bedroom - Fully Remodeled!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Steps From Siesta Key Beach! 1BR w/ Heated Pool, holiday rental in Siesta Key

Steps From Siesta Key Beach! 1BR w/ Heated Pool

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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1 Bedroom/ 1 Bath Condo Steps From Siesta Key Sand with Pool Access-Gulf Holiday, holiday rental in Siesta Key

1 Bedroom/ 1 Bath Condo Steps From Siesta Key Sand with Pool Access-Gulf Holiday

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Siesta Key Old Florida Cottage, Great Location at a Great Price, holiday rental in Siesta Key

Siesta Key Old Florida Cottage, Great Location at a Great Price

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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GULF FRONT ON #1 Beach! Siesta Dunes (by owner), holiday rental in Siesta Key

GULF FRONT ON #1 Beach! Siesta Dunes (by owner)

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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4 Bedroom with Gulf View Siesta Key FL Beach Fun, holiday rental in Siesta Key

4 Bedroom with Gulf View Siesta Key FL Beach Fun

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Quiet and Comfortable Condo Near Turtle Beach, holiday rental in Siesta Key

Quiet and Comfortable Condo Near Turtle Beach

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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A Siesta Tropical Retreat - Island Pool Oasis -super close to Village & #1 beach, holiday rental in Siesta Key

A Siesta Tropical Retreat - Island Pool Oasis -super close to Village & #1 beach

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Charming Siesta Key Village  Unbeatable Location, holiday rental in Siesta Key

Charming Siesta Key Village Unbeatable Location

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Siesta Key Vacation Townhouse directly across the street from #1 Beach in the US, holiday rental in Siesta Key

Siesta Key Vacation Townhouse directly across the street from #1 Beach in the US

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Siesta Key - Sarasota, Super Cute One Bedroom, Steps to the Beach!, holiday rental in Siesta Key

Siesta Key - Sarasota, Super Cute One Bedroom, Steps to the Beach!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Rent Siesta Now: A Shore Thing!, holiday rental in Siesta Key

Rent Siesta Now: A Shore Thing!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Aloha Kai - 2 beautful unit and close to pool!, holiday rental in Siesta Key

Aloha Kai - 2 beautful unit and close to pool!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Direct Gulf-Front / End Unit Fisherman's Cove A201, holiday rental in Siesta Key

Direct Gulf-Front / End Unit Fisherman's Cove A201

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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CONTACT US FOR GREAT APRIL AND  MAY DISCOUNTS!, holiday rental in Siesta Key

CONTACT US FOR GREAT APRIL AND MAY DISCOUNTS!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Romantic Siesta Key Beachfront Condo-full beach view. 50 steps to the beach, holiday rental in Siesta Key

Cozy Romantic Siesta Key Beachfront Condo-full beach view. 50 steps to the beach

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Best Deals on Siesta Key, holiday rental in Siesta Key

Best Deals on Siesta Key

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Sandy Toes Town Home, holiday rental in Siesta Key

Sandy Toes Town Home

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Deluxe 3-BR Siesta Key Townhouse - Heated Pool - Siesta Key Village, holiday rental in Siesta Key

Deluxe 3-BR Siesta Key Townhouse - Heated Pool - Siesta Key Village

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Dolphin Bungalow - Courtyard View, holiday rental in Siesta Key

Dolphin Bungalow - Courtyard View

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Siesta Key, Heated pool, Gulf and Bay, Cute Siesta Key Condo, Gated, holiday rental in Siesta Key

Siesta Key, Heated pool, Gulf and Bay, Cute Siesta Key Condo, Gated

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key, holiday rental in Siesta Key

Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Ground Floor, holiday rental in Siesta Key

Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Ground Floor

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2 BR, 2 Bath, Siesta Key Village Condo with Pool, holiday rental in Siesta Key

2 BR, 2 Bath, Siesta Key Village Condo with Pool

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Seaside Villas Unit 3BR 5241, holiday rental in Siesta Key

Seaside Villas Unit 3BR 5241

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Private Studio Apartment - Separate, Private Entrance - Walk to Siesta Village, holiday rental in Siesta Key

Private Studio Apartment - Separate, Private Entrance - Walk to Siesta Village

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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1BR - Garden Apartment of Siesta Key Townhouse - Heated Pool -Siesta Key Village, holiday rental in Siesta Key

1BR - Garden Apartment of Siesta Key Townhouse - Heated Pool -Siesta Key Village

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Crescent Beach - 2 Bedroom - Beachfront Condo Complex - Heated Pool, holiday rental in Siesta Key

Crescent Beach - 2 Bedroom - Beachfront Condo Complex - Heated Pool

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Siesta Key Luxurious Beachfront Condo, holiday rental in Siesta Key

Siesta Key Luxurious Beachfront Condo

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beachwalk - Siesta Key Beach - 3BR Townhouse - Heated Pool - upscale, holiday rental in Siesta Key

Beachwalk - Siesta Key Beach - 3BR Townhouse - Heated Pool - upscale

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sunset Royale - 214- Spectacular views of Siesta Key Beach walking distance to v, holiday rental in Siesta Key

Sunset Royale - 214- Spectacular views of Siesta Key Beach walking distance to v

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Crescent Beach on Siesta Key One of the, holiday rental in Siesta Key

Beautiful Crescent Beach on Siesta Key One of the

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Peaceful Haven on Siesta Key with Beach Access, holiday rental in Siesta Key

Peaceful Haven on Siesta Key with Beach Access

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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