Vacation Rentals & Beach Rentals in Siesta Key

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Cozy & Bright+++Minutes to Anna Maria Island, IMG Academy and more

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

Match: Swing set or jungle gym Wheelchair accessible

All filters match

Price per night from

$117

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

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swing set or jungle gym Wheelchair accessible

All filters match

Price per night from

$286

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Serene Sarasota Getaway near shopping and golfing.

Fruitville villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$127

TROPICCAL, 4 min from the beaches! Meticulously cleaned and sanitized!

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

“Lovely home in an awesome location!” Literally a minute's drive from the beach, this very clean and welcoming home is also convenient to great restaurants and shopping opportunities. It really is in a perfect location, especially considering the affordable price. Walking to restaurants and a rental shop is easy thanks to the sidewalk on Cortes. We even enjoyed a morning run to the beach - biking to the beach would also be a great option (3.5 mi one way.) The home might appear small at first, but we fit 6 comfortably, including 4 teenagers! The best part is the lovely décor that greets you after a long day at the beach or running around. Two thumbs up!

Responds fast! avg. 2 hours 33 minutes

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$143

2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Happy Customer” We had an amazing time. The owners were so nice & made us feel so welcomed. I couldnt have been happier with our stay & we look forward to staying there again soon when life slows back down. Highly recommend this home♡

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$308

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 25 minutes

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$257

House of Blues - Lovely 2-Bedroom Condo with Pool, W&D and Patio

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$200

Little Palms Villa. A lakeside home with style.

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Excellent” Our stay at 4638 Runabout way was amazing. We loved that the house was very nice, spacious, and clean for my family and I. We loved swimming in the pool everyday. The service was excellent all around. We would definitely stay there again.

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$194

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

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$103

Unit #112 Sand Cay Beach Resort Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$278

Amazing Beachfront Condo, Siesta Key,

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$343

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$270

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$995

2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!

Bradenton Beach cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Best home away from home at the beach.” I spent a lot of time searching for a bungalow at the beach and my expectations were surpassed when I opened the door! The owners were thoughtful in design, layout and furnishings to provide a laid back experience at the beach. I wished I could have stayed forever - it was that nice. I especially enjoyed the fully stocked kitchen which included colorful dishes to match the colorful walls and great blue floor! Best of all - location - you can walk everywhere as you are right in the historic Bridge Street neighborhood.

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$245

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$343

Venice Island on BEACH 8th flr near Siesta Key

Venice apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$240

A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

“Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)and hop in a free taxi . The house is well appointed and beds are very comfortable. We traveled with a 10 yr.old, 11yr. old , and 15 yr. old my 15 yr. old niece slept in the trundle bed and commented on how comfortable the bed was. In the kitchen you will find a drawer full of menus for the many nearby restaurants and information for water activities. I highly recommend parasailing while your there ! Considering how close everything is the street is very quiet and the owners were great to deal with. Thanks Kathi and Grant!

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$499

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.

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$270

“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

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$245

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$283

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$109

Zilli Tower 503

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$341

Arnold Palmer Design 36 Holes - Lakewood National Resort

Lakewood Ranch villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$240

Zilli Ocean Front 201 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$296

180 Panoramic beach View and amazing Sunset.

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$456

Skyline Resort

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$251

Eagles Nest

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$251

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$319

3 bedroom tropical Family home with private pool.

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$284

Zilli Ocean Front 202 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$307

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$456

Excellent Location - Gulf/Beach View - Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 38 minutes

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$343

Riverfront Tropical Paradise W/ Private Island-Newly Updated Listing

Braden River house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$250

Unit #316 Sand Cay Beach Resort Gulf Front

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$342

Unit #305 Sand Cay Beach Resort Gulf View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$305

Unit #309 Sand Cay Beach Resort Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$278

Unit #302 Sand Cay Beach Resort Gulf Front

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$342

Unit #320 Sand Cay Beach Resort Gulf Front

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$342

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