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Swimming pool
Wireless Internet
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Private pool

Heated pool
Private indoor pool
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Cot available
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Safe
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Shared indoor pool
Private outdoor pool (heated)
Private outdoor pool (unheated)
Shared outdoor pool (heated)
Cribs
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Swing set or jungle gym
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Pets
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Beach or lakeside relaxation
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Golf course on site or within 15 min walk
Golf within 30mins drive

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667 beach rentals

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Anna Maria Island/ IMG Academy/ Beach/ HotTub/ Bikes/ Kayaks/ Golf/ Fishing

Bradenton house

3 bedrooms
2 bathrooms

sleeps 8

Match: Trampoline Swimming pool

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Price per night from

$286

Beachplace Building 7 Great View

Longboat Key condo

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Trampoline, Swimming pool

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Price per night from

$180

Frangi Pani at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Trampoline, Swimming pool

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Price per night from

$489

Siesta Key Beach | Private Pool

Fruitville house

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Trampoline, Swimming pool

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Price per night from

$399

Beach Vacation rental

Siesta Key condo

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Trampoline, Swimming pool

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Price per night from

$246

Ten35 Seaside - Direct Gulf View: Residence 601

Siesta Key condo

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Trampoline, Swimming pool

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Price per night from

$925

2 bedroom Condo Bay Oaks Siesta Key

Sarasota condo

2 bedrooms
1 bathroom

sleeps 3

1 of 2 match: Trampoline, Swimming pool

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Price per night from

$573

Come join us for your Winter Migration!!!!!!!!!!

Bradenton Beach condo

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Trampoline, Swimming pool

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Price per night from

$103

Best of both worlds! Fish in bay or go to beach!

Siesta Key condo

1 bedroom
1 bathroom

sleeps 4

“Modern place in an awesome location” My family really enjoyed our time at this place. It was very clean, a convenient end unit, and close to the beautiful beach. Having the Intracoastal and pool was great, too. Being fully stocked and 2 TVs was a welcome surprise. Thanks for a great stay!

1 of 2 match: Trampoline, Swimming pool

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Price per night from

$228

1 bedroom single story condo near pool

Longboat Key condo

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Trampoline, Swimming pool

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Price per night from

$295

2 bedroom poolside condo steps from ocean beach and dock on bay

Longboat Key condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Trampoline, Swimming pool

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Price per night from

$425

1 bedroom single story ocean view

Longboat Key condo

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Trampoline, Swimming pool

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Price per night from

$360

2 bedroom Florida condo unit 13 at family friendly resort

Longboat Key condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Trampoline, Swimming pool

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Price per night from

$425

Guava Getaway - Relax, Renew, and Rejuvenate

Lakewood Ranch condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Trampoline, Swimming pool

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Price per night from

$171

Siesta Key/Derby Bay

Siesta Key villa

3 bedrooms
2 bathrooms

sleeps 6

“Perfect!” Our family really enjoyed staying here! The villa was very well maintained and cleaned. It was stocked with everything you would need. The owner was very responsive to any concerns. We had a super nice neighbor and my boys loved fishing off the dock. I would recommend renting a golf cart to go to the beach if you have children (with toys etc) or elderly people with walking concerns. It is quite a walk to get to the beach (because you also have to walk down to the cross walk then across the street). The beach in front of the Aloha Kai property is very wide (great because it was never crowded like in front of other resorts) but it was an even farther walk to the water. We have always stayed beach front but needed more rooms than were available in my booking time frame this year. This property has changed the way I will book on siesta in the future. My boys LOVED fishing everyday off the dock. They caught lots of cool fish right off the back. The street that this villa is on was very quiet for our stay. Everyone was very kind & the property is very beautiful! We hope to come back very soon! It was a wonderful experience.

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$287

#1 Beach - "Super Clean" - 2 Level Townhouse - 1400sf 2Br/2.5 Bth- 5 Star Rating

Siesta Key condo

2 bedrooms
3 bathrooms

sleeps 6

“Great stay in Sarasota” My husband and our two daughters spent a wonderful four days in Sarasota. The townhome we stayed in was beautiful and had all the amenities we needed. We spent every day at the beach and relaxed at the townhome in the evenings. We would definitely stay here again and have recommended this place to our family and friends. Thanks Louie!

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Trampoline, Swimming pool

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Price per night from

$434

Luxury Lakerfront Condo! 2x Pools~WiFi~Lanai. By IMG~Beaches~Restaurants~AMI~SRQ

Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 11 minutes

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$138

Superb Lakerfront Condo! 2x Pools~WiFi~Lanai. By IMG~Beaches~Restaurants~AMI~SRQ

Bradenton apartment

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 11 minutes

1 of 2 match: Trampoline, Swimming pool

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Price per night from

$138

4 minute flip flop walk to the beach! Starfish 2/2

Siesta Key house

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Trampoline, Swimming pool

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Price per night from

$338

Bright Clean Happy Vacation Condo

Venice condo

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Trampoline, Swimming pool

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Price per night from

$115

Siesta Key Gulf View Condo

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 1 hour 33 minutes

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$447

Paradise Found

Lakewood Ranch apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 36 minutes

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$252

Luxury Waterfront Views/Pool/1400sf/2 min to Beach

Siesta Key condo

2 bedrooms
3 bathrooms

sleeps 6

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$339

Siesta Key vaca rental

Siesta Key condo

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$229

Relaxing and quite apartment in a great location

Sarasota apartment

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$189

Bay Mariner - Gorgeous water front condo!

Tallevast studio

Studio
1 bathroom

sleeps 2

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$99

The Meadows golf course view villa

North Sarasota villa

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$122

Welcome to Paradise-6 miles from Anna Maria Island Beaches

Bradenton villa

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$205

Downtown Hideaway Close to all

Sarasota condo

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$161

Private Retreat on Siesta Dr

Sarasota house

4 bedrooms
4 bathrooms

sleeps 8

Responds fast! avg. 1 hour 49 minutes

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$515

St Armand's Private Home on Jackson Drive

Lido Key house

3 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$381

Captains Quarters

Casey Key apartment

1 bedroom
1 bathroom

sleeps 2

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$155

Just another day in paradise! Sunrise condominiums!

Bee Ridge condo

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$115

CLOSE TO THE BEACHES WITH A POOL

South Venice house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$258

Remodeled 4BR Pool Home / Golf View/Near Beaches

South Bradenton house

4 bedrooms
3 bathrooms

sleeps 14

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$515

Updated 4/2 pool home, 5 Mins to Siesta Key

Siesta Key house

4 bedrooms
2 bathrooms

sleeps 9

Responds fast! avg. 1 hour 26 minutes

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$326

New Coastal Pool + Game Room home - sleeps 10

Sarasota house

3 bedrooms
2 bathrooms

sleeps 10

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$566

Siesta Key Villa

Siesta Key villa

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Trampoline, Swimming pool

1 of 2 filters match

Price per night from

$332

Viewing 38 of 667
rentals in Siesta Key

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Vacation Rentals & Beach Rentals in Siesta Key

Per night

667 beach rentals

Viewing 38 of 667rentals in Siesta Key

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Viewing 38 of 667
rentals in Siesta Key