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54 Houses

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Oceanfront home w/sunset views of Sarasota Bay

Sarasota house

3 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$629

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

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 1 hour 1 minutes

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Price per night from

$266

Crescent Beach Villas - La Estrella: By Beachside Management

Siesta Key villa

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$274

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

1 bedroom
1 bathroom

sleeps 3

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Price per night from

$234

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 3 hours 25 minutes

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Price per night from

$258

Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.

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Price per night from

$189

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

1 bedroom
1 bathroom

sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

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$115

Jamaica Royale #104! Completely renovated, Gulf side, beautiful 2b/2b Condo!

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$337

Amazing views, 11th flr, On the beach

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$409

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

1 bedroom
1 bathroom

sleeps 6

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Price per night from

$109

GUEST HOUSE

Fruitville guest house

1 bedroom
1 bathroom

sleeps 2

Responds fast! avg. 29 minutes

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Price per night from

$107

☆ King in Master • 1st Floor • Heated Pool • ¼ mile walk to Siesta Key ☆

Sarasota condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$193

Newly discounted rates! Gorgeous one bedroom across from beach, near village!

Siesta Key condo

1 bedroom
1 bathroom

sleeps 3

“Anniversary Trip” Had a wonderful time at LA Siesta Condominiums for our anniversary vacation. Beautifully furnished and do close to the best beach in the USA

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Price per night from

$245

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$161

A Wonderful Pool House on a lake full of wildlife.

Sarasota house

3 bedrooms
2 bathrooms

sleeps 6

“Location location” Great house convincent , clean , close to everything

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Price per night from

$121

Spacious Apt. #1 Historic Walkable Downtown, between Siesta & Lido Beach

Sarasota apartment

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$482

Siesta Key beach & sunsets - 2018 Spring & Summer openings!

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$131

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

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 4

“Perfect, Perfect, Perfect” Nice condo with everything close by! Owners were great to deal with and as stated it would be . We plan on visiting again and would recommend this place to anyone.

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Price per night from

$271

Beach, Village, Dock, Private Heated Pool... Fantastic Location, No Car Needed!

Siesta Key house

2 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$457

Pet Friendly Guest House - Enjoy some peace at Indian Beach - Saphire Shores!

Sarasota cottage

1 bathroom

sleeps 2

“Charming studio in lovely quiet neighborhood with fenced in private outside area.” This studio has everything you'll need. It's located in a beautiful neighborhood, great for walking. There's a small park just down the road a couple of blocks where you can sit and watch the amazing sun sets or just enjoy watching the boats ride by. The owners are very nice and have a few fur babies of their own, so they may allow you to bring your doggie,too! Sue/Dawn......thank you!!!! I hope to return & stay again.

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Price per night from

$229

BEAUTY ON THE BEACH! Crescent Arms 601S FULL FRONT VIEW

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$314

#7 Loft Apartment in Historic District Downtown Sarasota

Sarasota apartment

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$305

#1 EXCLUSIVE Siesta Key Beach House /3 payments

Siesta Key house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$258

Renovated Beach Front 2BR/2BA Condo, Steps to beach, Gulf of Mexico Views

Siesta Key house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$277

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

Lido Key villa

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$184

4 Bedroom with Gulf View Siesta Key FL Beach Fun

Siesta Key apartment

4 bedrooms
4 bathrooms

sleeps 10

“Fantastic Location and Beautiful Accomodations” Our daughters and their families stayed here in February. The condo was everything we expected and more. It has a breathtaking view of the Gulf from the screened in lani which runs the width of the unit. The four bedrooms were perfect for our group of nine and the kitchen / dining area was well stocked with appliances , pots & pans , dishes , glassware , etc. Condo has easy access to heated pool and ample parking. Owner made the rental process smooth as silk , and we all felt right at home as soon as we had checked in. Right across street from world famous Siesta Beach. Would highly recommend.

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Price per night from

$515