Vacation Rentals & Beach Rentals in Siesta Key

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269 beach rentals

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

Match: Iron Swing set or jungle gym

All filters match

Price per night from

$267

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.

Match: Iron Swing set or jungle gym

All filters match

Price per night from

$115

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Iron Swing set or jungle gym

All filters match

Price per night from

$178

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White Sands Village - Unit 618

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$164

White Sands Village - Unit 112

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$125

Harbor Towers

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$138

Beautiful, Affordable Close to famous Siesta Beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“It was wonderful!” Everything about the trip and condo was great! Mike met us to give us the keys and we called him for suggestions about restaurants, etc. and he was very helpful. The condo was very clean and had everything we needed. It was also great that we were able to use the beach chairs and umbrella. I am already trying to figure out when we can go again.

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$163

Siesta Beach House - 202

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$115

Siesta Surf Cottage #3

Siesta Key log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$153

Siesta Surf Cottage #1

Siesta Key log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$140

Beach Road - Capri

Siesta Key studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$91

Siesta Beach House - 310 / Come n' Beach It

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$115

Siesta Beach House - 204

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$115

Beach Road - Bari

Siesta Key studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$79

Sea Club II

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$91

Siesta Beach House - 203 / Sunny Daze

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$115

Vista Hermosa - 302C

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$172

Luxury Village Townhouse w/ Gulf and Beach Views

Siesta Key townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“A wonderful home in an equally wonderful location.” The home provides a truly enjoyable family situation. The quality of the furnishings is very nice, the living space is very well maintained and clean and my interaction with the owner was always timely and courteous. My wife and I shared the home with our 14 year old granddaughter during our stay and the quiet enjoyment of the pool and the easy 1-2 minute walk to the Gulf of Mexico and the 5 minute walk to the heart of Siesta Key Village made the location hard to beat. Except for our day trips no car was needed. This is our second stay in the home and we will look to reserving it for our next visit. There were absolutely no disappointments only wonderful experiences.

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$659

“gracious and spacious” Lovely home and great location to walk throughout Siesta Key Village and the beautiful sands of the beach!! We were able to have everyone together for a great vacation.

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$148

Beautiful Crescent Beach on Siesta Key One of the

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$301

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$410

Beautiful Townhouse in Prime Location with Private Beach Access!

Siesta Key townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$238

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$230

Quiet and Comfortable Condo Near Turtle Beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Siesta sweet spot” Great value for location. Nice pool, visits with the manitees. Close to everything. This time of year ocean water was amazing

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$201

Relaxing Condo on Siesta Key - Close to beach - Mermaids Rest

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$332

White Sands Village - Unit 909

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$164

Bay Oaks - E82

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$115

Bayside Gulf and Bay Club

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$172

Cape Aqua

Siesta Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Great place, super location” We thoroughly enjoyed our stay at your home. It was very spacious, clean and inviting. We had everything we needed and the location is wonderful. Thanks and we would definitly recommend your home to others

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$192

Siesta Escape - B

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$348

Sand Castle Suites - The Starfish

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$205

Beach Road

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$115

Happy Blue Coconuts - South

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$400

A Shell House Casa

Siesta Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$188

Beach Road - Tropea

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$102

Crystal Sands Villa #2

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$242

Siesta Escape - Combined

Siesta Key house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 18

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$802

Plymouth Harbor

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Iron

1 of 2 filters match

Price per night from

$269

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