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Pet Friendly Holiday Rentals in Siesta Key

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979 rentals in Siesta Key.
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Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!
17 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Siesta Key - 2bdrm on the beach - amazing views!!
37 reviews
2 bedrooms
2 bathrooms
Sleeps 5
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Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa
15 reviews
5 bedrooms
4 bathrooms
Sleeps 13
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Siesta Key-#1 Beach, 2017 Renovation w/ private entrance, Intracoastal/Marina
18 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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Cathy's Crescent Condos-Siesta Key, FL GULF FRONT
20 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Siesta Key Old Florida Cottage, Great Location at a Great Price
61 reviews
1 bedroom
1 bathroom
Sleeps 2
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Palm Oasis - Relax in Comfort - 1 rental per calendar month
4 reviews
4 bedrooms
3 bathrooms
Sleeps 10
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Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key
12 reviews
3 bedrooms
2 bathrooms
Sleeps 8
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# 1 beach in USA SIESTA KEY Gulf side 2 Bed 2 Bath at Jamaica Royale #104!
5 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Siesta Key Inn - 1Br/1B Sabal Palm #2A
5 reviews
1 bedroom
1 bathroom
Sleeps 4
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Newly renovated condo with premium features on Siesta Key
69 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Island House Beach Resort V22
10 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Siesta Key Beachfront Condo with Gulf View!
13 reviews
1 bedroom
1 bathroom
Sleeps 4
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Luxury Romantic Oceanfront Siesta Beach Condo #304
26 reviews
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*
39 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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Beachfront Getaway in Siesta Key
23 reviews
1 bedroom
1 bathroom
Sleeps 4
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Siesta Palms by the Beach - Sea Spray #123
1 bedroom
1 bathroom
Sleeps 4
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Midnight Cove #714 in Siesta Key, FL- Sun, Sand & *Save 9% to 25% per Week*
7 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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New Listing! Charming Island Getaway - Steps to Sand, Walk to Dining & Shops
1 bedroom
1 bathroom
Sleeps 4
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Island House Beach Resort 15N
10 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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WE LIKE BLUE, SIESTA BLUE! 2 BED BAYSIDE CONDO ON SIESTA KEY
34 reviews
2 bedrooms
1 bathroom
Sleeps 4
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Peaceful Haven on Siesta Key with Beach Access
5 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Newly Listed... NEW Decor by Jan 10th 2021! Walk to SK Beach, 2 Heated Pools, W
3 bedrooms
2 bathrooms
Sleeps 8
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Fantastic Beachfront Condo, at Surf & Racquet Resort on Siesta Key Beach
11 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Super Cute, Super Clean Large One Bedroom - Fully Remodeled!
39 reviews
1 bedroom
1 bathroom
Sleeps 4
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Island House Beach Resort 8N
2 bedrooms
2 bathrooms
Sleeps 4
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A Siesta Tropical Retreat - Island Pool Oasis -super close to Village & #1 beach
53 reviews
3 bedrooms
2 bathrooms
Sleeps 9
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2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!
15 reviews
2 bedrooms
1 bathroom
Sleeps 5
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Siesta Key Vacation Townhouse directly across the street from #1 Beach in the US
2 bedrooms
2 bathrooms
Sleeps 6
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Tropical bungalow steps from the baby powder sand of Siesta Beach and Village
47 reviews
1 bedroom
1 bathroom
Sleeps 4
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Steps From Siesta Key Beach! 1BR w/ Heated Pool
4 reviews
1 bedroom
1 bathroom
Sleeps 4
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Charming Siesta Key Village Unbeatable Location
8 reviews
1 bedroom
1 bathroom
Sleeps 4
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GULF FRONT ON #1 Beach! Siesta Dunes (by owner)
56 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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Very Clean! 2 min. drive to Siesta Key! Stay a few nights or a month!
16 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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Island House Beach Resort V27
2 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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2 Bed/2 Bath Condo Resort View on Siesta Key Beach
11 reviews
2 bedrooms
2 bathrooms
Sleeps 5
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Ringling Bungalow - Lagoon View
1 bedroom
1 bathroom
Sleeps 2
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Siesta Beach Zen Den
1 review
1 bedroom
1 bathroom
Sleeps 4
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Siesta Beach House - 311 / Beach Cove
2 bedrooms
3 bathrooms
Sleeps 7
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Siesta Beach is only a half a block! Sleeps 6-8
38 reviews
2 bedrooms
2 bathrooms
Sleeps 8
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Breathtaking Full Gulf Views Steps From The White Sands Of Siesta Key Beach
90 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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Quiet and Comfortable Condo Near Turtle Beach
5 reviews
2 bedrooms
2 bathrooms
Sleeps 5
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Siesta Beach House #211 Beautiful Updated Unit
4 reviews
2 bedrooms
2 bathrooms
Sleeps 7
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Rent Siesta Now: A Shore Thing!
10 reviews
3 bedrooms
2 bathrooms
Sleeps 8
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Private 2Bed/2Bath Siesta Oasis w/ Direct Water View, Near Beach and Bay
12 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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4 Bedroom with Gulf View Siesta Key FL Beach Fun
22 reviews
4 bedrooms
4 bathrooms
Sleeps 10
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Direct Gulf-Front / End Unit Fisherman's Cove A201
2 bedrooms
2 bathrooms
Sleeps 4
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Watch Sunsets From Your Lanai ON THE BEACH plus FREE Boat Docks!
14 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Sandy Toes Town Home
6 reviews
3 bedrooms
3 bathrooms
Sleeps 6
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Crystal Sands Unit 308 Siesta Key, Florida
12 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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