Vacation Rentals & Beach Rentals in Siesta Key

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296 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

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$267

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Tiny House Siesta - Eleanor- our bright & beautiful Tiny House near the beach

Siesta Key hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$448

Tiny House Siesta - Tiny House Amy

Siesta Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$378

Tiny House Siesta - Tiny Blue Oasis – a tiny house with 3 Queen beds

Siesta Key hotel apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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$460

Tiny House Siesta - Tiny Aqua Oasis- Tiny House that sleeps 6 comfortably

Siesta Key hotel apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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$444

“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

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$435

Tiny House Siesta - Red Lifeguard Stand

Siesta Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$443

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

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$340

Siesta Key vaca rental

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$230

Frangi Pani at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$490

Siesta Key Gulf View Condo

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 39 minutes

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$447

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!

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$228

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.

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$287

Condo wOcean view on Siesta

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 39 minutes

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$402

Siesta Key Villa

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$332

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

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$327

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.

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$163

Tiny House Siesta - Sand Dollar – A private master loft and open living space

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$448

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$224

Beachfront Getaway in Siesta Key

Siesta Key townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Very comfortable, nice amenities and well run.” Loved the beach and the nearby restaurants. The free trolly ride was easy to use and a great way to go into the village.

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$224

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 23 minutes

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$390

Siesta Key beach & sunsets - 2018 Spring & Summer openings!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$131

120 Steps to the Beach with beach gear included!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$424

“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.

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$148

Vista Hermosa - 302C

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$172

Siesta Beach House - 203 / Sunny Daze

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$115

Sea Club II

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$91

Siesta Surf Cottage #3

Siesta Key log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$153

Siesta Beach House - 204

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$115

Siesta Beach House - 310 / Come n' Beach It

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$115

Siesta Surf Cottage #1

Siesta Key log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$140

Siesta Beach House - 202

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$115

Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Turtle Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Romantic place. Perfect for young families with small kids” Firshermans Cove is on a shore side. The views are amazing as well as beach which is clean and not crowded at all. Easy check in/out and very quiet place, was ideal in our case, young family with 1,5 old boy. It was nice stay and we hopefully come back again.

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$266

Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Upscale

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Excellent location for a great vacation!” This is the fifth time we have had the pleasure of vacationing at El Galeon. We love the location with the beautiful beach access and walking to restaurants. We love the Manasota Key and have been vacationing there for the last seventeen years. El Galeon Gulf Unit 2 is our favorite place to stay with plenty of space and everything we need for a wonderful stay. We have already reserved "our place" for 2015.

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$266

Siesta Key - 2BR - Beachfront Condo on Crescent Beach - Heated Pool - Tennis Ct

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$303

Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$311

Turtle Beach - Gulf-Front Condo - 2BR - Free Boat Docks - Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$266

BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Trip to paradise” Renting unit was very easy. Unit was the best layout was great. Amenities within we're well thought, out and for us anything we wanted was there including beach chairs. View of ocean was breath taking along with sunsets. I will come back again.

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Price per night from

$311

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