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Holiday Homes in Siesta Key

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978 rentals in Siesta Key.
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Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!, holiday rental in Siesta Key

Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Siesta Key -  2bdrm on the beach - amazing views!!, holiday rental in Siesta Key

Siesta Key - 2bdrm on the beach - amazing views!!

2 bedrooms
2 bathrooms
Sleeps 5
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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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Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa, holiday rental in Siesta Key

Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa

5 bedrooms
4 bathrooms
Sleeps 13
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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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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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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# 1 beach in USA  SIESTA KEY Gulf side 2 Bed 2 Bath at Jamaica Royale  #104!, holiday rental in Siesta Key

# 1 beach in USA SIESTA KEY Gulf side 2 Bed 2 Bath at Jamaica Royale #104!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Siesta Key Inn - 1Br/1B Sabal Palm #2A, holiday rental in Siesta Key

Siesta Key Inn - 1Br/1B Sabal Palm #2A

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Siesta Key-#1 Beach,  2017 Renovation w/ private entrance,  Intracoastal/Marina, holiday rental in Siesta Key

Siesta Key-#1 Beach, 2017 Renovation w/ private entrance, Intracoastal/Marina

2 bedrooms
2 bathrooms
Sleeps 4
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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Island House Beach Resort V22, holiday rental in Siesta Key

Island House Beach Resort V22

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Siesta Key Beachfront Condo with Gulf View!, holiday rental in Siesta Key

Siesta Key Beachfront Condo with Gulf View!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Luxury Romantic Oceanfront Siesta Beach Condo #304, holiday rental in Siesta Key

Luxury Romantic Oceanfront Siesta Beach Condo #304

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Siesta Palms by the Beach - Sea Spray #123, holiday rental in Siesta Key

Siesta Palms by the Beach - Sea Spray #123

1 bedroom
1 bathroom
Sleeps 4
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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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Beachfront Getaway in Siesta Key, holiday rental in Siesta Key

Beachfront Getaway in Siesta Key

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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New Listing! Charming Island Getaway - Steps to Sand, Walk to Dining & Shops, holiday rental in Siesta Key

New Listing! Charming Island Getaway - Steps to Sand, Walk to Dining & Shops

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Midnight Cove #714 in Siesta Key, FL- Sun, Sand & *Save 9% to 25% per Week*, holiday rental in Siesta Key

Midnight Cove #714 in Siesta Key, FL- Sun, Sand & *Save 9% to 25% per Week*

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Island House Beach Resort 15N, holiday rental in Siesta Key

Island House Beach Resort 15N

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Newly Listed... NEW Decor by Jan 10th 2021!  Walk to SK Beach, 2 Heated Pools, W, holiday rental in Siesta Key

Newly Listed... NEW Decor by Jan 10th 2021! Walk to SK Beach, 2 Heated Pools, W

3 bedrooms
2 bathrooms
Sleeps 8
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 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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Island House Beach Resort 8N, holiday rental in Siesta Key

Island House Beach Resort 8N

2 bedrooms
2 bathrooms
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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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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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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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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Tropical bungalow steps from the baby powder sand of Siesta Beach and Village, holiday rental in Siesta Key

Tropical bungalow steps from the baby powder sand of Siesta Beach and Village

1 bedroom
1 bathroom
Sleeps 4
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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2 Bed/2 Bath Condo Resort View on Siesta Key Beach, holiday rental in Siesta Key

2 Bed/2 Bath Condo Resort View on Siesta Key Beach

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Very Clean! 2 min. drive to Siesta Key! Stay a few nights or a month!, holiday rental in Siesta Key

Very Clean! 2 min. drive to Siesta Key! Stay a few nights or a month!

2 bedrooms
2 bathrooms
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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Ringling Bungalow - Lagoon View, holiday rental in Siesta Key

Ringling Bungalow - Lagoon View

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Island House Beach Resort V27, holiday rental in Siesta Key

Island House Beach Resort V27

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Siesta Beach Zen Den, holiday rental in Siesta Key

Siesta Beach Zen Den

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Siesta Beach House - 311 / Beach Cove, holiday rental in Siesta Key

Siesta Beach House - 311 / Beach Cove

2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Siesta Beach is only a half a block!  Sleeps 6-8, holiday rental in Siesta Key

Siesta Beach is only a half a block! Sleeps 6-8

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Breathtaking Full Gulf Views Steps From The White Sands Of Siesta Key Beach, holiday rental in Siesta Key

Breathtaking Full Gulf Views Steps From The White Sands Of Siesta Key Beach

2 bedrooms
2 bathrooms
Sleeps 4
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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Siesta Beach House #211 Beautiful Updated Unit, holiday rental in Siesta Key

Siesta Beach House #211 Beautiful Updated Unit

2 bedrooms
2 bathrooms
Sleeps 7
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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Private 2Bed/2Bath Siesta Oasis w/ Direct Water View, Near Beach and Bay, holiday rental in Siesta Key

Private 2Bed/2Bath Siesta Oasis w/ Direct Water View, Near Beach and Bay

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Watch Sunsets From Your Lanai ON THE BEACH plus FREE Boat Docks!, holiday rental in Siesta Key

Watch Sunsets From Your Lanai ON THE BEACH plus FREE Boat Docks!

2 bedrooms
2 bathrooms
Sleeps 6
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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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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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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Crystal Sands Unit 308 Siesta Key, Florida, holiday rental in Siesta Key

Crystal Sands Unit 308 Siesta Key, Florida

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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SHARK UNIT-THE BEST SPOT ON SIESTA KEY BEACH & VILLAGE! !, holiday rental in Siesta Key

SHARK UNIT-THE BEST SPOT ON SIESTA KEY BEACH & VILLAGE! !

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Just Minutes from the White Sandy Siesta Beach, holiday rental in Siesta Key

Just Minutes from the White Sandy Siesta Beach

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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