Search 105,200+ Vacation Rentals

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

262 Vacation rentals

(6)

1 / 18

Siesta Key Condo

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“just got back from a great vacation in siesta key . The condo was clean and the beds were extremely comfortable. The owner also provided all the necessary items needed to go and enjoy the beautiful beach !!!! The condo is located close to the beach...”
- Review left on 05/09/2016

$154

Very Good (6 reviews)

Inquire

from $154 / night

1 / 33

Siesta Key House

  • 5
  • 13
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $250 / night

1 / 35

Siesta Key House

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $179 / night

(1)

1 / 34

Siesta Key House

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$179

Excellent (1 reviews)

Inquire

from $179 / night

1 / 24

Siesta Key House

  • 4
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $214 / night

(1)

1 / 28

Siesta Key House

  • 2
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“My family and I had the best time! We enjoyed the house and the pool so much we didn't even go out. Spent 3 days of bliss. This was a last minute reservation and the management company and the owner were fantastic in dealing with my request. My...”
- Review left on 06/23/2016

$179

Excellent (1 reviews)

Inquire

from $179 / night

1 / 33

Siesta Key Condo

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $199 / night

1 / 35

Siesta Key House

  • 3
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $206 / night

(7)

1 / 23

Siesta Key Condo

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Unfortunately my wife and I could only stay a few days. The condo is well kept, well equipped. Short 300 yard walk to the beach was awesome. We have stayed many times in Siesta Key and were impressed with our first visit to this condo. Would...”
- Review left on 03/04/2016

$135

Very Good (7 reviews)

Inquire

from $135 / night

1 / 31

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $300 / night

(1)

1 / 34

Siesta Key House

  • 3
  • 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$229

Excellent (1 reviews)

Inquire

from $229 / night

(7)

1 / 15

Siesta Key House

  • 4
  • 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“We used this house as a work retreat and a celebration! Overall, the house was perfect. Plenty of space, the views were awesome, the living room was great for a work meeting (5 people). The balconies were great. A good location...away from the town...”
- Review left on 01/23/2017

$714

Excellent (7 reviews)

Inquire

from $714 / night

1 / 25

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $266 / night

1 / 32

Siesta Key House

  • 5
  • 14
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $250 / night

(1)

1 / 10

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning
“My husband and I enjoyed our two week respite from winter at this lovely well equipped condo. The unit was very clean, with great beach access and a pool on the property. A very well stocked grocery store is within walking distance of the complex,...”
- Review left on 01/09/2017

$146

Excellent (1 reviews)

Inquire

from $146 / night

(2)

1 / 19

Siesta Key House

  • 5
  • 12
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Beautiful home with so many added features! We are definitely coming back and staying at The Grand Canal...”
- Review left on 10/20/2015

$250

Excellent (2 reviews)

Inquire

from $250 / night

1 / 23

Siesta Key Condo

  • 3
  • 6
  • 30 nights min
  • Child friendly
  • Air conditioning

from $220 / night

(1)

1 / 16

Siesta Key Condo

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“Siesta Key is the best beach I ever been so far and this place that Jack and Darlene provide is a dream. Everything is clean and in perfect working condition. The beach is very nice (and I have visited many being a South Floridian), crystal clear and...”
- Review left on 09/19/2016

$172

Excellent (1 reviews)

Inquire

from $172 / night

(1)

1 / 25

Siesta Key House

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$326

Excellent (1 reviews)

Inquire

from $326 / night

(5)

1 / 21

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“We really enjoyed our stay and would come back . The only reason I gave four stars is we had six people and the sleeper sofa was so bad that they slept on the floor. The rental was well equipped for cooking in and beach stuff( cart to haul chairs,...”
- Review left on 08/07/2016

$266

Very Good (5 reviews)

Inquire

from $266 / night

(8)

1 / 30

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Child friendly
  • Air conditioning
“My husband & I chose this condo on-line. It was immaculate, very nicely renovated, had a wonderful view of the boat docks and pool, and an owner who could not have been nicer. Midnight Cove II community is a gem. People & staff are friendly, the...”
- Review left on 01/30/2017

$118

Excellent (8 reviews)

Inquire

from $118 / night

(11)

1 / 24

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
“We stayed for a long weekend with 4 other couples. The house is clean and well decorated and beautiful. The kitchen is well equipped. The pool and property are great and tons of beach chairs are available. We had a great time...”
- Review left on 12/16/2016

$495

Excellent (11 reviews)

Inquire

from $495 / night

1 / 41

Siesta Key House

  • 3
  • 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Ask about children

from $395 / night

1 / 34

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $214 / night

(11)

1 / 40

Siesta Key Condo

  • 2
  • 6
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great place! Everything was wonderful,beach was a short walk away. Love all the new addition to public beach. Pool was heated,we went swimming every day. Unit was very clean and comfortable,couldn't ask for a better place. Took the free taxi to...”
- Review left on 01/06/2017

$89

Excellent (11 reviews)

Inquire

from $89 / night

(8)

1 / 17

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great property, beautiful pool, super close to the beach and the village - will totally be back! Awesome property management as well...”
- Review left on 06/13/2016

$143

Excellent (8 reviews)

Inquire

from $143 / night

(4)

1 / 11

Siesta Key Condo

  • 2
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
“Lovely location, spectacular beach. Condo well equipped with everything you may need. Comfortable, clean, and very close to all amenities. Thoroughly enjoyed our stay...”
- Review left on 04/02/2011

$107

Excellent (4 reviews)

Inquire

from $107 / night

(3)

1 / 11

Siesta Key Villa

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great complex. Villa was very nice. Beds were comfortable. Had everything we needed. The beach is beautiful. Beach chairs provided. Didn't need to ever leave...”
- Review left on 07/05/2012

$144

Excellent (3 reviews)

Inquire

from $144 / night

(2)

1 / 10

Siesta Key Condo

  • 1
  • 4
  • 14 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“FIVE STARS!!!!! Terry the owner is a great guy that insured our stay in his condo went well. The condo has a great location just a couple of blocks from the Siesta Key Beach. The condo has everything you need for a great beach experience. The...”
- Review left on 01/24/2017

$80

Excellent (2 reviews)

Inquire

from $80 / night

1 / 10

Siesta Key Apartment

  • 1
  • 3
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
“The place was in the perfect spot and couldn't have been better. Very clean, great location. Would definitely stay again...”
- Review left on 04/22/2016

$140

Book

from $140 / night

1 / 29

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $310 / night

(1)

1 / 18

Siesta Key Cottage

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“We loved the home. We had our whole family, parents, children, grandchildren, and it was spacious enough for everyone to have their own space. The tropical back yard was gorgeous. The kitchen was very well equipped. The only negative is the...”
- Review left on 10/24/2016

$286

Very Good (1 reviews)

Inquire

from $286 / night

(14)

1 / 13

Siesta Key Apartment

  • 1
  • 4
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
“The rental was very clean. The location was a block from the beach and not far from the town, so walking to dinner was easy.The towels were new, furnishings were updated and pleasant. Everything, but the following was perfect. The bed pillows could...”
- Review left on 12/12/2016

$175

Excellent (14 reviews)

Inquire

from $175 / night

(4)

1 / 21

Siesta Key Condo

  • 1
  • 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We actually stayed in unit #113 and it was simple but clean with updated kitchen. The grounds, pool, and amenities were well maintained and clean. The Gulf view was amazing! We have visited many beaches but this was the most beautiful with a quiet...”
- Review left on 07/07/2016

$195

Excellent (4 reviews)

Inquire

from $195 / night

(5)

1 / 24

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.01 mi
  • Swimming pool
“We recently spent a week in Siesta Key, our fourth year in a row making this our Fall vacation spot. This year, we we fortunate to find an available week at Sandy' Siesta that matched out travel plans. What a great spot! A short walk to the...”
- Review left on 12/16/2016

$122

Excellent (5 reviews)

Inquire

from $122 / night

(5)

1 / 37

Siesta Key House

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“House was newly renovated, nicely funnies and clean. Short walk to Siesta Key Beach and 1 mile to town. Very sweet neighborhood...”
- Review left on 03/05/2017

$400

Excellent (5 reviews)

Inquire

from $400 / night

1 / 24

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $129 / night

1 / 26

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $266 / night

(5)

1 / 33

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“My family of 3 stumbled across Fish Cove while searching for a vacation destination in Florida. It really looked too good to be true, but I can assure you that it did delivered and surpassed every expectation we had set! I worked to plan our visit...”
- Review left on 12/26/2016

$165

Excellent (5 reviews)

Inquire

from $165 / night

(2)

1 / 20

Siesta Key Townhouse

  • 3
  • 10
  • 7 nights min
  • Ask about children
  • Air conditioning
“The home was beautiful and thank God for the functional elevator. It's proximity to the beach and Siesta Key Village was perfect...”
- Review left on 07/18/2016

$200

Very Good (2 reviews)

Inquire

from $200 / night