Search 105,200+ Vacation Rentals
✕

Siesta Key Beach Rentals & Vacation Rentals - 242 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

242 Vacation rentals

(6)

1 / 37

Siesta Key House

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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 (6 reviews)

Book

from $400 / night

Book
1 / 41

Siesta Key House

  • 3
  • 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

$395

Book

from $395 / night

Book

(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

Inquire
1 / 20

Siesta Key Villa

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$285

Inquire

from $285 / night

Inquire
1 / 24

Siesta Key Condo

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

$243

Inquire

from $243 / night

Inquire

(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

Inquire

(9)

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

Very Good (9 reviews)

Book

from $140 / night

Book
1 / 26

Siesta Key House

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

$266

Inquire

from $266 / night

Inquire
1 / 33

Siesta Key Condo

  • 1
  • 4
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$199

Inquire

from $199 / night

Inquire
1 / 24

Siesta Key Condo

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

$180

Inquire

from $180 / night

Inquire
1 / 29

Siesta Key House

  • 5
  • 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$595

Book

from $595 / night

Book

(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

Inquire

(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

Excellent (6 reviews)

Inquire

from $146 / night

Inquire
1 / 24

Siesta Key Condo

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

$180

Inquire

from $180 / night

Inquire
1 / 24

Siesta Key Condo

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

$243

Inquire

from $243 / night

Inquire
1 / 29

Siesta Key House

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

$310

Inquire

from $310 / night

Inquire

(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

Inquire
1 / 24

Siesta Key Condo

  • 2
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$243

Inquire

from $243 / night

Inquire

(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

Inquire

(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

Inquire

(11)

1 / 24

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Child friendly
  • 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)

Book

from $495 / night

Book
1 / 24

Siesta Key House

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

$214

Inquire

from $214 / night

Inquire
1 / 24

Siesta Key Condo

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

$180

Inquire

from $180 / night

Inquire

(5)

1 / 16

Siesta Key Condo

  • 1
  • 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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 (5 reviews)

Inquire

from $195 / night

Inquire
1 / 24

Siesta Key Condo

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

$243

Inquire

from $243 / night

Inquire

(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

Inquire

(1)

1 / 24

Siesta Key Condo

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

$243

Excellent (1 reviews)

Inquire

from $243 / night

Inquire

(25)

1 / 24

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Nearest beach 0.08 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

$142

Excellent (25 reviews)

Book

from $142 / night

Book
1 / 24

Siesta Key Condo

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$195

Inquire

from $195 / night

Inquire

(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

Inquire
1 / 24

Siesta Key Condo

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

$160

Inquire

from $160 / night

Inquire

(4)

1 / 11

Siesta Key Condo

  • 2
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
“We recently stayed at this condo for a few weeks. The condo is in very good shape and is charming. The management staff is amazing and always easy to reach. Very close to the beach and the pool. Overall, we had a pleasant experience...”
- Review left on 08/30/2013

$100

Excellent (4 reviews)

Inquire

from $100 / night

Inquire
1 / 24

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$150

Inquire

from $150 / night

Inquire

(2)

1 / 18

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$229

Excellent (2 reviews)

Inquire

from $229 / night

Inquire
1 / 35

Siesta Key House

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

$179

Inquire

from $179 / night

Inquire

(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

Inquire
1 / 24

Siesta Key House

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

$200

Inquire

from $200 / night

Inquire
1 / 31

Siesta Key House

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

$300

Inquire

from $300 / night

Inquire
1 / 24

Siesta Key Condo

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

$243

Inquire

from $243 / night

Inquire

(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

Inquire

About Siesta Key

If you're planning a vacation to this island paradise, you may want to consider Siesta Key vacation rentals. This beautiful barrier island spans eight miles just off the coast of Sarasota in the Gulf of Mexico. Resorts can be overcrowded and overpriced, but Siesta Key vacation home rentals are always private and generally quite affordable. This destination is known as a great romantic getaway, and there are plenty of cozy little cottages for two that will set the perfect mood for your honeymoon or other romantic rendezvous. Regardless of your lifestyle and budget, there is something here to meet your needs.

Things to do

If staying on dry land sounds like a bore, you'll find almost 50 miles of waterways and canals inside the island, not to mention the surrounding Gulf of Mexico and Sarasota and Roberts Bays. Many Siesta Key, FL vacation rentals provide boat docks, and boat rentals are available for you to get out and explore the waters. Other water sports are popular here as well, including fishing, snorkeling, parasailing, and sailboarding. If you'd rather not captain your own ship, plenty of local charter companies offer guided tours. Many of the local restaurants also offer temporary docking, so that you can go to dinner straight from your afternoon on the water. What better way to work up an appetite for some fresh seafood than a day spent in the sand, sun, and surf? We couldn't call it an "island paradise" if it didn't offer warm breezes, cool water, swaying palm trees, and some of the world's finest beaches, including Turtle Beach and Palmer Point Beach. Relaxing on the pure quartz beaches with family and friends is certainly a favorite pastime here, and visitors enjoy the charming beach hideaways and ample bird-watching opportunities. You might also spot some friendly dolphins and manatees dotting the surrounding gulf and bay waters.

Climate

As a top Florida vacation destination you can imagine that Siesta Key offers flawless weather all year round. With over 250 sunny days per year, and a July high of 91 degrees, you're pretty much guaranteed a vacation unspoiled by the elements no matter when you visit. Try booking your trip for the "shoulder season" away from peak times or school vacations to keep crowds at bay. Low humidity makes Siesta Key comfortable, as well as warm. 

Events

If you visit the island during the beginning of May, the beach literally comes alive with figures made of sand during the island's unique sand sculpture contest that draws in world-class artists. Of course, anyone can try their hand at a sandcastle or sand sculpture any time of year. Take part in the Siesta Key drum circle on the Siesta Key public beach EVERY Sunday night. Beginning about an hour before sundown, instruments ranging from drums, flutes, guitars, shakers and cowbells create the circle. Be part of the audience, or participate with music and dance. Enjoy a stroll through the galleries of Palm Avenue on the first Friday of every month. In addition to fine galleries, this area along lower Main Street is known for its unique variety of shops and restaurants. The Siesta Fiesta is in mid-April and celebrates local artisans while fostering a feeling of camraderie around the town. 

Food

After a day out on the beach or screaming while parasailing you're likely to work up an appetite. A place like Senor Siesta. rated #1 on TripAdvisor for Siesta Key restaurants, could fit the bill. With delicious and affordable latin cuisine available such as the empanada appetizer, you will be happy you chose to eat there. If you're looking for a more European flavor, why not try out Bonjour French Cafe & Crepes? For dessert, you should grab a scoop or three at Ciao Gelato or Big Olaf Cremery. Lastly, for a more down home feel, eat at The Cottage Restaurant which has all types of classic American dishes made to perfection. You won't go hungry in Siesta Key, trust us.  

​All of this and more can be found within walking distance or a leisurely drive of Siesta Key vacation rentals, so start planning your trip today! 
Read More