Vacation Rentals & Beach Rentals in Siesta Key

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379 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: Boat available Linen provided

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Price per night from

$266

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Boat available Linen provided

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Price per night from

$205

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Boat available Linen provided

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Price per night from

$344

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.

Match: Boat available Linen provided

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Price per night from

$509

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!

Match: Boat available Linen provided

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Price per night from

$272

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Boat available Linen provided

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Price per night from

$488

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Boat available Linen provided

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Price per night from

$488

Split Leaf at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Boat available Linen provided

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Price per night from

$488

Coconut at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Boat available Linen provided

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Price per night from

$488

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Tiny House Siesta - Yellow Lifeguard Stand Tiny House

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$422

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$488

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$488

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$488

120 Steps to the Beach with beach gear included!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Linen provided

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Price per night from

$424

Family Tides - High Tides: By Beachside Management

Siesta Key apartment

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

1 of 2 match: Boat available, Linen provided

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Price per night from

$549

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: Boat available, Linen provided

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Price per night from

$659

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.

1 of 2 match: Boat available, Linen provided

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Price per night from

$224

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: Boat available, Linen provided

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Price per night from

$163

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 23 minutes

1 of 2 match: Boat available, Linen provided

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Price per night from

$390

“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: Boat available, Linen provided

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Price per night from

$148

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$131

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

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Linen provided

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Price per night from

$447

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

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Great location!” The unit was just as described and pictures matched. The view of the ocean and bay were gorgeous. The kitchen was well equipped and there were lots of toys and chairs for the beach.

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$311

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

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$266

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

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$303

Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Renovated!

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Experience” This condo is well kept, clean and looks directly onto the Gulf of Mexico. We liked it because the furniture is up to date and replaced when it becomes worn. We also love the fact it is within walking distance of a good restaurant. In fact there is nothing about this rental that we don't like and that is why we return there year after year. A great choice for you to start a great experience!

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$266

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.

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$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.

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$311

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

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$311

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.

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$266

Siesta Key Waterfront Estate heated Pool Privacy!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$717

Two bedroom, two bath condo by Siesta Key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$459

Super Cute Cottage--Private--Walk/Bike to Beach

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$258

Costal Surfside Swank 302: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$515

Casa Mar - Unit 56: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$263

Hidden Paradise - Bungalow 1; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$286

Costal Surfside 298: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$458

Crescent Condos; by Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Boat available, Linen provided

1 of 2 filters match

Price per night from

$515

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