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781 houses

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Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

3 bedrooms
2 bathrooms

sleeps 12

Match: Rental types Cot available Kettle Staffed property

All filters match

Price per night from

$149

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.

3 of 4 match: Rental types, Cot available, Kettle, Staffed property

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Price per night from

$189

Private Beach Access - Home away from Home - 2 BR 2 BA - Furnished Condo

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

2 of 4 match: Rental types, Kettle, Cot available, Staffed property

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Price per night from

$178

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

1 bedroom
1 bathroom

sleeps 2

3 of 4 match: Cot available, Rental types, Kettle, Staffed property

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Price per night from

$344

Beautiful house for rent at siesta key beach with pool, theater and game room

Siesta Key house

7 bedrooms
3 bathrooms

sleeps 15

Responds fast! avg. 1 hour 59 minutes

2 of 4 match: Kettle, Staffed property, Rental types, Cot available

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Price per night from

$2,850

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

2 bedrooms
1 bathroom

sleeps 7

Responds fast! avg. 1 hour 57 minutes

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

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Price per night from

$194

A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub

Holmes Beach house

3 bedrooms
3 bathrooms

sleeps 6

“Perfect Luxury” Our 5-week stay at this vacation rental was absolutely perfect. The house was everything you could ask for and more. We have stayed in many vacation rentals in the last 20 or so years that we have been coming to anna Maria Island and I have to say this one was right at the top of the list. The kitchen was outfitted with everything you could want. The beds were very comfortable. The neighborhood was nice and quiet. Short walk to the beach. The owners were very nice to deal with and always responded quickly and were very warm and helpful. Definitely can recommend this vacation rental.

3 of 4 match: Staffed property, Rental types, Cot available, Kettle

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Price per night from

$476

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

2 bedrooms
1 bathroom

sleeps 6

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

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Price per night from

$229

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

1 bedroom
1 bathroom

sleeps 3

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

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Price per night from

$234

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

Sarasota apartment

1 bedroom
1 bathroom

sleeps 4

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

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Price per night from

$482

Manatee River Cottage in Historic Old Town

Palmetto cottage

3 bedrooms
1 bathroom

sleeps 7

2 of 4 match: Rental types, Staffed property, Cot available, Kettle

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Price per night from

$148

+++ Clean & Bright +++ Minutes to Anna Maria Island

Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 9 minutes

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

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Price per night from

$178

Beach front condo in Longboat Key

Longboat Key condo

1 bedroom
1 bathroom

sleeps 4

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

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Price per night from

$430

Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & Save 10% to 25% per Week

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

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Price per night from

$284

Midnight Cove #532 in Siesta Key, FL- Sun, Sand & Save 7.5% to 22.5% per Week

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 4

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

2 of 4 filters match

Price per night from

$144

Midnight Cove #714 in Siesta Key, FL- Sun, Sand & Save 7.5% to 22.5% per Week

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 4

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

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Price per night from

$144

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

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

2 of 4 filters match

Price per night from

$337

Zilli Tower 503

Longboat Key condo

1 bedroom
1 bathroom

sleeps 6

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

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Price per night from

$343

Stunning & Serene +++ Minutes from Anna Maria Island, IMG Academy and more!

Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 9 minutes

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

2 of 4 filters match

Price per night from

$114

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

Lido Key villa

2 bedrooms
1 bathroom

sleeps 6

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

2 of 4 filters match

Price per night from

$184

Gulf and Bay Club 3bdrm “E” Luxury END CORNER Unit - RIGHT ON BEACH

Siesta Key condo

3 bedrooms
4 bathrooms

sleeps 8

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

2 of 4 filters match

Price per night from

$903

Zilli Ocean Front 201 & Suite

Longboat Key condo

1 bedroom
1 bathroom

sleeps 6

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

2 of 4 filters match

Price per night from

$297

Zilli Ocean Front 202 & Suite

Longboat Key condo

1 bedroom
1 bathroom

sleeps 6

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

2 of 4 filters match

Price per night from

$308

2 Bedroom, 2 Bathroom condo / Heated pool / 7 minute walk to beach

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

2 of 4 filters match

Price per night from

$178

Beachfront Condo Siesta Key

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

2 of 4 filters match

Price per night from

$453

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.

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

2 of 4 filters match

Price per night from

$515

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.

2 of 4 match: Rental types, Cot available, Kettle, Staffed property

2 of 4 filters match

Price per night from

$115