Holiday Homes in Siesta Key

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Featured Holiday Homes in Siesta Key

Our top choices for Siesta Key holiday homes

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (46)
"This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. "
Siesta Key Island Rentals

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very good, (35)
"It was perfect for my family of 4 for our beach vacation!!"
Siesta Heron Suites & Villas

Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!

10.0 out of 10, Exceptional, (1)
"We loved this house. We celebrated a cousins 50th birthday and had so much fun. The location is close to all restaurants and beach. The golf cart was so fun to use. The house is nicely stocked with necessary items, pool noodles and toys. There was everything needed for the beach.The most important part was the owners were very responsive to all questions. We look forward to coming and staying here again."
Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!

Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows

9.6 out of 10, Exceptional, (109)
"Awesome location, perfect beach supplies provided, and VERY clean! "
Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows

Siesta Beachfront Paradise: Luxurious Home Steps from Beach with Infinity Pool!

10.0 out of 10, Exceptional, (3)
"We loved the house! Great location, beautiful spaces, plenty of room for all of us. Couldn’t have picked a better place for our family to stay for our niece’s wedding! We’d definitely love to stay here again!"
Siesta Beachfront Paradise: Luxurious Home Steps from Beach with Infinity Pool!

Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

9.6 out of 10, Exceptional, (134)
"we had a good stay"
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

Private Home Directly on Siesta Key Beach!

10.0 out of 10, Exceptional, (3)
"Beautiful place to stay… direct walk to the beach from your back door. Amazing view! Clean with all the amenities you need. "
Private Home Directly on Siesta Key Beach!

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

9.6 out of 10, Exceptional, (17)
"We had a great stay at this property! We had five adults and one infant with plenty of room to be comfortable. We enjoyed the short walk to the beach and that beach chairs were provided by the HOA (umbrellas are not but there was one at the property). The owners were wonderful, fast responses to any messages and made sure we had everything we needed to have a great time! Definitely recommend this property if you’re in Siesta Key and looking to be very close to the beach!"
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Siesta Key 2BR 1Bath unit COZY Barefoot Bungalows 1500 ft from beach access#3

9.8 out of 10, Exceptional, (100)
"Perfect location for beach access and a short walk to the village. "
Siesta Key 2BR 1Bath unit COZY Barefoot Bungalows 1500 ft from beach access#3

Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!

10.0 out of 10, Exceptional, (41)
"We had the best family vacation! This location is perfectly situated between the beach and restaurants/bars. We had a great stay!"
Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!

Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

9.8 out of 10, Exceptional, (24)
"The house was in great condition and near everything. "
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

GORGEOUS 3 Bedroom/2 Bath Home NEAR SIESTA KEY!

9.8 out of 10, Exceptional, (14)
"Great house and amazing pool. We go to Sarasota every year and this is the best house yet. Comfortable beds, quiet neighborhood and great location "
GORGEOUS 3 Bedroom/2 Bath Home NEAR SIESTA KEY!

LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

9.6 out of 10, Exceptional, (102)
"Beautiful home and perfect location! Our family had a wonderful time in Siesta Key. Highly recommend this property for your next vacay."
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village

9.6 out of 10, Exceptional, (13)
"Unit was a bit dated, but you couldn't beat the location. Seconds from the beach and minutes from the village via walk. "
The price is AU$1,704
includes taxes & fees
2 Sept - 3 Sept
Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village

Suite w/ Shared Pool, Free WiFi, Central AC - Steps to the White Sand Beach

9.0 out of 10, Wonderful, (55)
"So close to the beach!"
Suite w/ Shared Pool, Free WiFi, Central AC - Steps to the White Sand Beach

Private Pool/Spa in Siesta Key Village, Steps to the Beach! Island Time West

9.6 out of 10, Exceptional, (61)
"Great location!"
The price is AU$974
includes taxes & fees
25 Aug - 26 Aug
Private Pool/Spa in Siesta Key Village, Steps to the Beach! Island Time West

Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!

9.4 out of 10, Exceptional, (34)
"Great location and experience"
Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!

Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

9.6 out of 10, Exceptional, (49)
"This place has a great layout, it was so easy to walk to and from the beach and enjoy the porches and views. Thanks for all the beach equipment too!"
The price is AU$1,304
includes taxes & fees
25 Aug - 26 Aug
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Beachside Retreat with Pool and Beach Access

8.8 out of 10, Excellent, (40)
"Great house. no complaints. Thank you. "
The price is AU$1,757
includes taxes & fees
7 Sept - 8 Sept
Beachside Retreat with Pool and Beach Access

Siesta beach....one and only

9.4 out of 10, Exceptional, (184)
"My family and I had a great stay during our time at the home. "
The price is AU$710
includes taxes & fees
5 Sept - 6 Sept
Siesta beach....one and only
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Siesta Key Hotel Reviews