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Wireless Internet
Air conditioning
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353 Houses

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Peaceful Home, close to siesta key and DT Sarasota

Fruitville house

3 bedrooms
2 bathrooms

sleeps 13

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Price per night from

$339

Meadows Townhouse With Golf View in Sarasota

Fruitville house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$149

Great rentals within 20 miles that match your search

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

$301

Amazing Beachfront Condo, Siesta Key,

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$344

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN CONDO!

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$272

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

6 bedrooms
5 bathrooms

sleeps 14

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Price per night from

$1,000

Monthly Rental, 2 bed, 2 bath, Ocean view.

Sarasota condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$115

Shorewalk Condo ED near the Beaches Anna Maria Island, Longboat Key, IMG, Shops

Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$402

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!

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Price per night from

$453

Venice Island Bellagio Home w/ 3BR & 3BA

Venice house

3 bedrooms
3 bathrooms

sleeps 6

“Great Vacation” Thanks for allowing us to stay in your beautiful home in Venice Florida. It was very comfortable and had all the convenience of home. Everything we needed was close by (restaurants and grocery store). We really liked the bike trails along the canal since we brought our bikes. We would rent your house again.

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Price per night from

$104

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

Luxurious 2 BR Condo-Short Walk to Siesta Beach/1 Small Dog (25 lbs Max) Allowed

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

“a fine 2 weeks in Siesta” charming property, that was comfortable for four. The unit was very clean and fresh upon arrival. The neighbours were friendly and the overall property well kept. Siesta Key is a quiet community with usual shopping amenities over the causeway. This property was a brief 10 minute walk to the beach. Would we stay again, yes.

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Price per night from

$166

Vacation Home on Alligator Drive . Winter 2025 Special !

Venice house

3 bedrooms
2 bathrooms

sleeps 5

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Price per night from

$149

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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Price per night from

$273

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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Price per night from

$509

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

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

$272

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

Anna Maria Island Beach Paradise 10

Holmes Beach studio

Studio
1 bathroom

sleeps 2

Responds fast! avg. 3 hours 20 minutes

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Price per night from

$227

A Paradise for Golfers and Tennis players

Bradenton apartment

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 27 minutes

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Price per night from

$139

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

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

Three bedroom house directly on beach with gulf vi

Siesta Key house

3 bedrooms
4 bathrooms

sleeps 7

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Price per night from

$402

BAY VIEW. SUNSETS. CLOSE TO ANNA MARIA ISLAND AND IMG ACADEMY

Bradenton house

3 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$367

Pool & Hot Tub-Pine Bay Forest 3-Bedroom Condo, Near AMI Beaches 3 month min

Bradenton condo

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$107

Charming Siesta Key Village Unbeatable Location

Siesta Key condo

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$190

Beautiful Home Near Many Golf Courses in LWR/Sarasota, FL.

Lakewood Ranch apartment

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$100

Casa Calm: King Room, Yoga, Spa

Sarasota private room

1 bedroom
1 bathroom

sleeps 2

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Price per night from

$183

ZILLI VILLA

Longboat Key villa

2 bedrooms
2 bathrooms

sleeps 10

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Price per night from

$488

River Strand Golf and Country Club Resort

Bradenton condo

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$230

Tara Golf & Country Club Condo

Bradenton condo

2 bedrooms
2 bathrooms

sleeps 6

“Wonderful, peaceful location and beautiful condo.” This condo is wonderful and has everything anyone would want or need for a wonderful stay. We loved the property and the owners. It is located in a private championship golf course community and is just across the street from all the amenities. The amenities include tennis, pool, workout room, and of course golf at its best. There is a wonderful grill room and beautiful dining room facing the driving range. Very close to a hugh shopping area and enclosed mall. Very convenient to travel anywhere from here. Very nice rental in a wonderful area.

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Price per night from

$144