Search 105,200+ Vacation Rentals

Siesta Key Beach Rentals & Vacation Rentals with Swimming Pool - 257 Rentals Available.

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

257 Vacation rentals

Filters applied: Swimming pool

(33)

1 / 24

Siesta Key Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.25 mi
  • Swimming pool
  • Child friendly
“Excellent property with lot of parking, laundy on site and warm water in the pool, which was really appreciated on the cooler dates, speacially by the kids. Close walk to a white sandy beach was on asset. Condo was very spacious and full equipped. We...”
- Review left on 01/02/2013

$101.00

Excellent (33 reviews)

Book

from $101.00 / night

1 / 66

Siesta Key House

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

$712.00

Book

from $712.00 / night

(3)

1 / 34

Siesta Key House

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

$200.00

Excellent (3 reviews)

Book

from $200.00 / night

(1)

1 / 25

Siesta Key House

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

$326.00

Excellent (1 reviews)

Book

from $326.00 / night

(5)

1 / 24

Siesta Key Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.25 mi
  • Swimming pool
  • Child friendly
“Had an excellent time! Unit was clean and precisely as described. Great location on Siesta Key with a short walk for Groceries, Food and Libations. Beach was a 5min walk across the street (using the signaled crosswalk) through the beachside section...”
- Review left on 03/13/2017

$101.00

Excellent (5 reviews)

Book

from $101.00 / night

(25)

1 / 24

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
“This was our first trip to Siesta Key, but not our last! We are already booking another stay at Siesta Breakers for next year. It is a great location on the Beach and great access to the mainland...”
- Review left on 07/14/2014

$173.00

Excellent (25 reviews)

Book

from $173.00 / night

(1)

1 / 24

Siesta Key Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$180.00

Excellent (1 reviews)

Inquire

from $180.00 / night

1 / 24

Siesta Key Condo

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

$229.00

Inquire

from $229.00 / night

(1)

1 / 24

Siesta Key Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$272.00

Excellent (1 reviews)

Inquire

from $272.00 / 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

$179.00

Excellent (1 reviews)

Book

from $179.00 / 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

$266.00

Very Good (5 reviews)

Book

from $266.00 / night

1 / 31

Siesta Key House

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

$310.00

Book

from $310.00 / night

(1)

1 / 24

Siesta Key Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$272.00

Excellent (1 reviews)

Inquire

from $272.00 / night

(5)

1 / 22

Siesta Key Condo

  • 1
  • 4
  • 3 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
“We stayed for a week and had the best time ever. The accommodations are top notch, locals are very friendly, food delicious and breathtaking beaches. Definitely looking forward to coming back”
- Review left on 12/15/2015

$150.00

Excellent (5 reviews)

Inquire

from $150.00 / night

(1)

1 / 24

Siesta Key Condo

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

$229.00

Excellent (1 reviews)

Inquire

from $229.00 / night

1 / 26

Siesta Key House

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

$310.00

Book

from $310.00 / night

1 / 24

Siesta Key Condo

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

$158.00

Inquire

from $158.00 / night

(1)

1 / 47

Siesta Key House

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$235.00

Excellent (1 reviews)

Book

from $235.00 / night

1 / 24

Siesta Key Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$272.00

Inquire

from $272.00 / night

1 / 24

Siesta Key Condo

  • 2
  • 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$180.00

Inquire

from $180.00 / night

1 / 14

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$99.00

Book

from $99.00 / night

1 / 24

Siesta Key Condo

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$140.00

Inquire

from $140.00 / night

1 / 36

Siesta Key Condo

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$500.00

Inquire

from $500.00 / night

(12)

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

$89.00

Excellent (12 reviews)

Inquire

from $89.00 / night

1 / 24

Siesta Key Condo

  • 2
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$243.00

Inquire

from $243.00 / night

1 / 32

Siesta Key House

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

$250.00

Book

from $250.00 / night

(6)

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

$125.00

Excellent (6 reviews)

Inquire

from $125.00 / night

(6)

1 / 20

Siesta Key House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“The villa was very nice , well equipped, immaculate and very comfortable. We enjoyed the courtyard and pool very much and are stay was very relaxing. The area has everything you would want on vacation along with one of the best beaches. Dave from...”
- Review left on 04/28/2015

$146.00

Excellent (6 reviews)

Book

from $146.00 / night

(1)

1 / 24

Siesta Key Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$200.00

Excellent (1 reviews)

Inquire

from $200.00 / night

(5)

1 / 18

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$307.00

Excellent (5 reviews)

Inquire

from $307.00 / night

1 / 24

Siesta Key House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$250.00

Inquire

from $250.00 / night

(2)

1 / 41

Siesta Key Condo

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Our stay at Siesta Palms was great. The condo was very clean and up to date. We enjoyed the beautiful pool and proximity to the beach. The owners couldn't have been kinder or more accommodating. I highly recommend this condo...”
- Review left on 04/15/2016

$257.00

Excellent (2 reviews)

Book

from $257.00 / night

(2)

1 / 41

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly

$143.00

Excellent (2 reviews)

Inquire

from $143.00 / night

(1)

1 / 24

Siesta Key Condo

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$329.00

Excellent (1 reviews)

Inquire

from $329.00 / night

(4)

1 / 24

Siesta Key Condo

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Thank you for a wonderful week! The room was beautiful and Mary Ann and staff were all so accommodating to anything that you may need! We would highly recommend Siesta Palms to everyone! We are looking forward to coming back as soon as possible,...”
- Review left on 07/13/2016

$199.00

Excellent (4 reviews)

Book

from $199.00 / night

(2)

1 / 24

Siesta Key Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$180.00

Very Good (2 reviews)

Inquire

from $180.00 / night

(3)

1 / 15

Siesta Key Villa

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“This property was beautiful. Clean, spacious, close to the gulf and the pool. The beach was amazing! I definitely see why it was voted #1 beach in USA. We rented bikes - what a great deal ... the rental was located just before entrance to Siesta key...”
- Review left on 01/05/2013

$154.00

Excellent (3 reviews)

Inquire

from $154.00 / night

1 / 29

Siesta Key House

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

$270.00

Book

from $270.00 / night

(2)

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

$286.00

Very Good (2 reviews)

Book

from $286.00 / night

(3)

1 / 38

Siesta Key House

  • 5
  • 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.75 mi
  • Swimming pool
“Beautiful home with so many added features! We are definitely coming back and staying at The Grand Canal...”
- Review left on 10/20/2015

$450.00

Average (3 reviews)

Book

from $450.00 / night