Search 105,200+ Vacation Rentals
✕

Siesta Key Beach Rentals & Vacation Rentals - 325 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

325 Vacation rentals

(35)

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

$85.00

Excellent (35 reviews)

Inquire

from $85.00 / night

Inquire

(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

$85.00

Excellent (5 reviews)

Inquire

from $85.00 / night

Inquire

(13)

1 / 17

Siesta Key Condo

  • 1
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“We stayed in Crescent Royale #409. Condo was extremely clean and well supplied. We had flown in and was thrillled to see beach chairs, umbrellas, towels and etc. that we couldn't bring along. The property was peaceful and quiet. Only problem was RED...”
- Review left on 10/04/2016

$120.00

Very Good (13 reviews)

Book

from $120.00 / night

Book

(26)

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

$147.00

Excellent (26 reviews)

Inquire

from $147.00 / night

Inquire
1 / 43

Siesta Key House

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

Responds fast! Avg. 2 hours 14 minutes

$310.00

Book

from $310.00 / night

Book
1 / 33

Siesta Key House

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

Responds fast! Avg. 2 hours 14 minutes

$380.00

Book

from $380.00 / night

Book
1 / 39

Siesta Key House

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

Responds fast! Avg. 2 hours 14 minutes

$380.00

Book

from $380.00 / night

Book

(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

Inquire

(7)

1 / 38

Siesta Key House

  • 5
  • 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$450.00

Excellent (7 reviews)

Book

from $450.00 / night

Book

(1)

1 / 25

Siesta Key House

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

Responds fast! Avg. 2 hours 14 minutes

$380.00

Excellent (1 reviews)

Book

from $380.00 / night

Book
1 / 51

Siesta Key House

  • 8
  • 24
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 14 minutes

$713.00

Book

from $713.00 / night

Book
1 / 24

Siesta Key House

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

Responds fast! Avg. 2 hours 14 minutes

$170.00

Book

from $170.00 / night

Book
1 / 31

Siesta Key House

  • 4
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 14 minutes

$380.00

Book

from $380.00 / night

Book
1 / 17

Siesta Key House

  • 3
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 14 minutes

$240.00

Book

from $240.00 / night

Book
1 / 16

Siesta Key House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 14 minutes

$240.00

Book

from $240.00 / night

Book
1 / 35

Siesta Key House

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

Responds fast! Avg. 2 hours 14 minutes

$380.00

Book

from $380.00 / night

Book
1 / 45

Siesta Key House

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 14 minutes

$175.00

Book

from $175.00 / night

Book
1 / 31

Siesta Key House

  • 4
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 14 minutes

$310.00

Book

from $310.00 / night

Book
1 / 40

Siesta Key House

  • 4
  • 8
  • min stay varies
  • Child friendly
  • Pet friendly

Responds fast! Avg. 2 hours 14 minutes

$235.00

Book

from $235.00 / night

Book

(6)

1 / 22

Siesta Key Condo

  • 1
  • 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 59 minutes

“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

$127.00

Excellent (6 reviews)

Book

from $127.00 / night

Book
1 / 40

Siesta Key House

  • 8
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 14 minutes

$713.00

Book

from $713.00 / night

Book
1 / 38

Siesta Key House

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

Responds fast! Avg. 2 hours 10 minutes

$235.00

Book

from $235.00 / night

Book
1 / 40

Siesta Key House

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

Responds fast! Avg. 2 hours 14 minutes

$380.00

Book

from $380.00 / night

Book
1 / 43

Siesta Key House

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

Responds fast! Avg. 2 hours 14 minutes

$380.00

Book

from $380.00 / night

Book

(6)

1 / 18

Siesta Key Condo

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

$236.00

Excellent (6 reviews)

Inquire

from $236.00 / night

Inquire
1 / 38

Siesta Key House

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

Responds fast! Avg. 2 hours 14 minutes

$380.00

Book

from $380.00 / night

Book

(3)

1 / 33

Siesta Key House

  • 3
  • 9
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

$395.00

Excellent (3 reviews)

Book

from $395.00 / night

Book

(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

Inquire

(1)

1 / 25

Siesta Key Cottage

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

Responds fast! Avg. 3 hours 11 minutes

$153.00

Excellent (1 reviews)

Book

from $153.00 / night

Book
1 / 36

Siesta Key House

  • 8
  • 24
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 14 minutes

$713.00

Book

from $713.00 / night

Book
1 / 24

Siesta Key House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 14 minutes

$205.00

Book

from $205.00 / night

Book
1 / 27

Siesta Key House

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

Responds fast! Avg. 2 hours 14 minutes

$170.00

Book

from $170.00 / night

Book

(6)

1 / 21

Siesta Key Condo

  • 1
  • 3
  • 7 nights min
  • 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

$200.00

Excellent (6 reviews)

Inquire

from $200.00 / night

Inquire
1 / 66

Siesta Key House

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

Responds fast! Avg. 2 hours 14 minutes

$713.00

Book

from $713.00 / night

Book
1 / 14

Siesta Key Condo

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

Responds fast! Avg. 3 hours 56 minutes

$99.00

Book

from $99.00 / night

Book
1 / 26

Siesta Key House

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

Responds fast! Avg. 2 hours 14 minutes

$170.00

Book

from $170.00 / night

Book
1 / 29

Siesta Key House

  • 4
  • 13
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 14 minutes

$270.00

Book

from $270.00 / night

Book

(2)

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

$186.00

Excellent (2 reviews)

Inquire

from $186.00 / night

Inquire

(1)

1 / 24

Siesta Key Apartment

  • 3
  • 8
  • min stay varies
  • Child friendly

$350.00

Excellent (1 reviews)

Book

from $350.00 / night

Book
1 / 29

Siesta Key House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 14 minutes

$205.00

Book

from $205.00 / night

Book

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