Siesta Key Holiday Rentals

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Check prices for these dates

Tonight
11 Aug - 12 Aug
Tomorrow
12 Aug - 13 Aug
This weekend
15 Aug - 17 Aug
Next weekend
22 Aug - 24 Aug

Holiday Rentals in Siesta Key

Tropical Beach Resorts
Relax by the serene pool surrounded by lush tropical vegetation and lounge under the shade of a blue umbrella.

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4858)
"Very Nice Resort!"
The price is HK$1,094
HK$1,414 total
includes taxes & fees
1 Sept - 2 Sept
Tropical Beach Resorts
SeaSpray Resort
Living area

SeaSpray Resort

4.0 star property
9.4 out of 10, Exceptional, (12)
"Nice place to stay in SK! "
The price is HK$1,641
HK$1,854 total
includes taxes & fees
1 Sept - 2 Sept
SeaSpray Resort
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times
Relax by the serene pool surrounded by lush greenery and palm trees, set amidst a tranquil atmosphere.

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

10.0 out of 10, Exceptional, (22)
"The house was in great condition and near everything. "
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times
The Ringling Beach House
Classic hotel with a symmetrical facade, central entrance, and upper-level balcony.

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (317)
"We loved the Villa!! It was spacious and stocked with every kitchen item you can imagine. "
The Ringling Beach House
Captiva Beach Resort
Relax in the Captiva chair, surrounded by lush greenery and a stylish sign.

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1122)
"Everything was perfect with our stay. We will be back soon."
Captiva Beach Resort
The Residences at Siesta Key Beach by Hyatt Vacation Club
Property amenity

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (275)
"Fun place to stay for family vacation "
The price is HK$3,703
HK$4,584 total
includes taxes & fees
27 Aug - 28 Aug
The Residences at Siesta Key Beach by Hyatt Vacation Club
Siesta Key Island Rentals
Enjoy cooking in this kitchen with a refrigerator, oven, and dishwasher, and a convenient green tiled backsplash.

Siesta Key Island Rentals

3.0 star property
9.4 out of 10, Exceptional, (43)
"Quiet neighborhood, clean and well maintained property, responsive management."
Siesta Key Island Rentals
The Inn On Siesta Key
Relax by the serene pool surrounded by lush greenery and palm trees, with lounge chairs and umbrellas for a comfortable stay.

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (181)
"A very accommodating property. Very clean and well maintained. The staff are extremely helpful and friendly. Great location."
The Inn On Siesta Key
Siesta Palms By the Beach
Stunning palm tree stands tall amidst lush greenery.

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (126)
"An outstanding experience — a place that leaves you with a strong desire to return."
Siesta Palms By the Beach
Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!
Guests can enjoy a wide, sandy beach with the ocean at their doorstep.

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

9.4 out of 10, Exceptional, (34)
"Very nice location, clean, nice amenities"
Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
Guests can enjoy access to a wide, sandy beach with clear waters.

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
Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views
Relax by the serene pool surrounded by lush vegetation and natural rock formations.

Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views

10.0 out of 10, Exceptional, (40)
"This was the perfect place to stay for a large family with kids. The location to the beach and restaurants couldn't have been more convenient. Amazing vacation!"
Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views
Siesta Heron Suites & Villas
Enjoy cooking in this well-lit kitchen with a stainless steel range, sink, and coffee maker.

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
5 STAR SIESTA KEY, 80 STEPS to BEACH, RESORT POOL, 6 BEDROOMS, SPACIOUS LIVING
Guests can enjoy a peaceful beach experience with calm seas and plenty of space to relax.

5 STAR SIESTA KEY, 80 STEPS to BEACH, RESORT POOL, 6 BEDROOMS, SPACIOUS LIVING

10.0 out of 10, Exceptional, (140)
"This is a beautifully furnished and managed property. We stayed for a week with 7 adults and 4 small children, and we all had a great time."
5 STAR SIESTA KEY, 80 STEPS to BEACH, RESORT POOL, 6 BEDROOMS, SPACIOUS LIVING
Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course
Relax by the heart-shaped pool surrounded by lush greenery and palm trees, with lounge chairs and a serene atmosphere.

Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course

10.0 out of 10, Exceptional, (45)
"This was an amazing house. It had everything you could want, walkable to everything, restaurant shopping , and the beach. We never needed to rent a car. So many things to do at this house. Every age range of people were completely satisfied. I would definitely stay at this house again it was beautiful top to bottom. "
Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course
Gulfside No Roads to Cross 1-bedroom condo with AC, WiFi On Siesta Key Beach..
Relax by the ocean with a gazebo and comfortable seating for two.

Gulfside No Roads to Cross 1-bedroom condo with AC, WiFi On Siesta Key Beach..

9.6 out of 10, Exceptional, (8)
"The rental was spacious and very clean!!I would definitely stay here again. Place looked exactly like the pictures!! "
Gulfside No Roads to Cross 1-bedroom condo with AC, WiFi On Siesta Key Beach..
Enjoy the Siesta Key Beach Life to the fullest! Beach AND Pool Access
Relax on the beach with comfortable seating and a picnic table, surrounded by tranquil surroundings.

Enjoy the Siesta Key Beach Life to the fullest! Beach AND Pool Access

9.2 out of 10, Wonderful, (40)
"Enjoyable stay"
Enjoy the Siesta Key Beach Life to the fullest! Beach AND Pool Access
Siesta Key Village-Suite #3: A Block to the Beach!
Relax on the beach with comfortable chairs and umbrellas, perfect for a leisurely day.

Siesta Key Village-Suite #3: A Block to the Beach!

9.4 out of 10, Exceptional, (51)
"Great little place in the middle of everything in Siesta Key Village. Within walking distance of beach, restaurant, drinks, ice cream and much more. Definitely recommend and will stay again!!"
The price is HK$1,170
HK$2,813 total
includes taxes & fees
12 Aug - 13 Aug
Siesta Key Village-Suite #3: A Block to the Beach!
SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND
Enjoy a game of beach volleyball on the sandy court with a net.

SIESTA KEY PRIVATE BEACH HOUSE-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 HK$3,124
HK$7,183 total
includes taxes & fees
12 Aug - 13 Aug
SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND
Beachside Retreat with Pool and Beach Access
Enjoy a peaceful retreat on the balcony with a glass-top table and comfortable seating for four.

Beachside Retreat with Pool and Beach Access

8.8 out of 10, Excellent, (40)
"Great location for all our visitors to walk to many various restaurants and shops"
Beachside Retreat with Pool and Beach Access
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

Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"This is a beautiful place! The apartment was spotless, comfortable, and wonderfully quiet — a true relaxing getaway. The only downside (and I truly mean the only one) was the beach experience. While the beach itself is private and lovely, getting a spot with chairs and an umbrella was unnecessarily complicated. The beach attendants (Doing their jobs) wouldn’t allow us to sit in the area that supposedly belongs to the complex unless we rented their chairs and umbrellas. We already pay to stay here, so being told we couldn’t enjoy that part of the beach without additional rental fees felt… strange. Suggestion: At the pool, it would be helpful to post signs reminding guests about noise levels. This weekend, there was a large group playing very loud music. The office staff came twice to ask them to lower it, which unfortunately led to unpleasant cursing. Of course, that’s not the hotel’s fault — it’s simply a shame when some guests don’t know how to behave in shared spaces. Overall, the property is beautiful and well-maintained, and I would gladly return — hopefully with a smoother beach experience next time. Thanks to all the staff for a great experience. "
Maritta 5-night trip
Posted 11 hours ago
Tropical Beach Resorts

Frequently asked questions

Can I find a holiday rental in Siesta Key?

Yes, there are holiday rentals in Siesta Key close to Jim Neville Marine Preserve, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Siesta Key like the popular beaches and live music. You can also check out the entertainment venues while you're visiting.

What are some of the best holiday rentals that Siesta Key has to offer?

Siesta Key Island Rentals: This highly rated holiday home rental in Siesta Key comes with free WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind. Another good choice for your trip to Siesta Key is Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times.

How many holiday rentals are there in Siesta Key?

With 812 Expedia holiday rentals, you're guaranteed to find just the right place for your Siesta Key stay.

What can I see and do in Siesta Key?

Siesta Key Beach and Crescent Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Jim Neville Marine Preserve. While here, Siesta Key Marina and Point of Rocks are other places worth a visit.

What are holiday rentals like in Siesta Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Siesta Key. Holiday rentals offer extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a family trip or a small group gathering.