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Wireless Internet
Air conditioning
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Private pool

Heated pool
Private indoor pool
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Internet access
DVD player
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Private tennis court
Cot available
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Children's pool
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Pool or snooker table
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Shared outdoor pool (heated)
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Linen provided
Staffed property
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Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
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Non-Smoking property
Smoking - Ask
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Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
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Golf course on site or within 15 min walk
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Beach or lakeside relaxation
Golf within 30mins drive
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143 Houses

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Paradise 4 Bedroom Pool Home Close to Siesta Key Beach and IMG Academy

North Sarasota house

4 bedrooms
3 bathrooms

sleeps 10

Responds fast! avg. 9 minutes

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Price per night from

$432

Great rentals within 20 miles that match your search

2 bedroom Condo Bay Oaks Siesta Key

Sarasota condo

2 bedrooms
1 bathroom

sleeps 3

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Price per night from

$575

Beautiful Crescent Beach on Siesta Key One of the

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$302

SPECIAL! $650 8/24 - 8/31. PRIME LOCATION AMI DIRECTLY ON BEACH HEATED POOL

Bradenton Beach house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$288

3BR/4BA TOWNHOUSE - POOL VIEW PARADISE - PRIVATE BEACH ACCESS

Siesta Key townhouse

2 bedrooms
4 bathrooms

sleeps 6

Responds fast! avg. 2 hours 38 minutes

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Price per night from

$432

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

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$286

Ideal Retreat next to USA's #1 Beach—Siesta Key

Sarasota condo

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$161

All Inclusive Executive Rental

Sarasota apartment

2 bedrooms
1 bathroom

sleeps 6

Responds fast! avg. 1 hour 46 minutes

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Price per night from

$167

****Walk to Beach-5min! Waterfront Canal! Private Pool~spa~Kayaks, Bikes!

Siesta Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$456

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

$338

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

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 5

“Escape from reality” We had an amazing vacation. Accommodations were great and very comfortable. Breakfast on the lanai and sunset fishing on the beach were 2 of our families favorite things to do. You also have the bay right behind you where you can kayak or paddle board. The community was quiet which was prefect for our getaway. We will definitely be staying here again.

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Price per night from

$604

Heritage Oaks

Heritage Oaks Golf and Country Club condo

2 bedrooms
2 bathrooms

sleeps 5

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Price per night from

$97

Stunning 2,550 Sq.ft House, FL

Bradenton house

4 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$287

Spectacular Beach House With GulfView Only Steps to a Pristine Beach

Holmes Beach house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$690

Luxury Beach Cotttage

Sarasota cottage

1 bedroom
1 bathroom

sleeps 2

“Beautiful little cottage” We stayed at this lovely little cottage on Siesta Key mid-April. The cottage is very nice, with all the amenities, even a washer/dryer for extended stays. It's cozy, with high ceilings, a nice bathroom and kitchen/living room. The bed seemed a little small (only a double), but it was very comfortable. The wireless internet was not working when we were there, which was a little frustrating. There is a beautiful pool and nice garden areas. The private beach was also very nice. All of the staff and the owner were extremely pleasant and welcoming. We enjoyed our time there.

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$534

Luxury Romantic Oceanfront Siesta Beach Condo #304

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

“What a View!” This is a very nicely decorated 1 bedroom and bath on Siesta Key Beach. You have an unobstructed view of the beach the minute you look into the condo. There's a great view from the bedroom as well! Very easy walk fo the beach..chairs and umbrella provided as well as all the amenities of home. We'd stay here again!

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$184

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.

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Price per night from

$478

Lifestyle on the island

Holmes Beach apartment

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$173

River Strand Country Club Resort Vacation Home

Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$153

Sunset Point Siesta Key FL AWESOME RENTAL !!

Siesta Key villa

2 bedrooms
2 bathrooms

sleeps 4

“Beautiful inside and out. Perfect location” My family and I stayed in this beautiful rental during February 2015. We could not have asked for a more perfect spot. The rental is just steps away from the beach and has a wonderful view of the beautiful sunsets. Siesta Key Village is an easy walk away and has great restaurants and shops. We are hoping to go back as soon as we can!

Responds fast! avg. 3 hours 50 minutes

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Price per night from

$805

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 5

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Price per night from

$206

Amazing views, 11th flr, On the beach

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$411

Sandy Toes Town Home

Siesta Key townhouse

3 bedrooms
3 bathrooms

sleeps 6

“Time in Paradise” We recently had the luck to spend two months in paradise. This condo was comfortably appointed, well stock to meet all our needs, and most importantly in the perfect location. The beach was a short walk to the left and stores and restaurants were just a short walk to the right. We had a great time and enjoyed everything Sarasota, Siesta Key, and this Sandy Toes Condo had to offer. Thanks Mark!

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$274

Siesta Key private beach access

Siesta Key villa

3 bedrooms
3 bathrooms

sleeps 8

“Siesta Key Townhouse” This was a wonderful place to stay! The house was very clean and spacious and had everything we needed for a week at the beach.

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$511

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

$516

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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$246

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

$122

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

$190