Vacation Rentals & Beach Rentals in Siesta Key

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176 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: Ceiling Fans Swing set or jungle gym

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Price per night from

$265

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: Ceiling Fans Swing set or jungle gym

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Price per night from

$114

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Ceiling Fans Swing set or jungle gym

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Price per night from

$177

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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: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$445

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Ceiling Fans

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: Swing set or jungle gym, Ceiling Fans

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: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$488

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$130

“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, Ceiling Fans

1 of 2 filters match

Price per night from

$148

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, Ceiling Fans

1 of 2 filters match

Price per night from

$656

120 Steps to the Beach with beach gear included!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Ceiling Fans

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Price per night from

$422

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: Swing set or jungle gym, Ceiling Fans

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Price per night from

$311

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: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$266

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: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$311

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: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$266

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

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$266

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: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$311

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: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$303

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: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$266

Siesta Beach House - 204

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$115

Siesta Beach House - 202

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Ceiling Fans

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, Ceiling Fans

1 of 2 filters match

Price per night from

$181

Siesta Beach House - 203 / Sunny Daze

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$115

Sea Club II

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$166

Beach Road - Capri

Siesta Key studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$91

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, Ceiling Fans

1 of 2 filters match

Price per night from

$299

Lovely Siesta Key 3BR 2.5BA Condo, Island Paradise

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$490

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, Ceiling Fans

1 of 2 filters match

Price per night from

$237

#1 EXCLUSIVE Siesta Key Beach House /3 payments

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$257

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, Ceiling Fans

1 of 2 filters match

Price per night from

$229

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$488

Coconut at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$488

Split Leaf at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$488

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, Ceiling Fans

1 of 2 filters match

Price per night from

$331

Siesta Key Waterfront Estate heated Pool Privacy!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$713

Crescent Arms; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$410

Sea Shell; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$319

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Ceiling Fans

1 of 2 filters match

Price per night from

$239

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