Siesta Key Vacation Rentals

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Vacation Rentals in Siesta Key

Aparthotel in South Village

3.5 star property
9.4 out of 10, Exceptional, (5139)
"Wonderful trip! Great location! Great staff!"
United States
Kevin
$155 nightly
The price is $175
Dec 8 - Dec 9
Total with taxes and fees
Tropical Beach Resorts

Condo in South Village

3.0 star property
9.0 out of 10, Wonderful, (1171)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
$167 nightly
The price is $187
Dec 8 - Dec 9
Total with taxes and fees
Captiva Beach Resort

Aparthotel in Sarasota

2.5 star property
8.6 out of 10, Excellent, (2205)
"This place is a gem!! I only stayed one night but wish it was more. The room was very clean and the staff was fantastic. The area is beautiful and at an excellent price. I highly recommend you stay here if you are in Siesta Keys!!"
United States
Ryan
$150 nightly
The price is $170
Dec 14 - Dec 15
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

Apartment in Siesta Key

3.5 star property
9.0 out of 10, Wonderful, (342)
"great location, very clean, quiet"
United States
Joaquin
$163 nightly
The price is $185
Dec 9 - Dec 10
Total with taxes and fees
The Ringling Beach House

Mobile Home in Sarasota

2.0 star property
8.4 out of 10, Very Good, (344)
"Enjoyable stay. "
United States
Lori
$215 nightly
The price is $242
Dec 8 - Dec 9
Total with taxes and fees
Tiny House Siesta

Vacation Home in Sarasota

2.0 star property
10.0 out of 10, Exceptional, (2)
"It was exactly as listed on here. No problems with the check in it was very smooth as well as the check out process. Location was AMAZING, we were able to walk just 10 minutes to a longhorn to eat dinner and right next to it there was a bar near the beach and we were able to go back to the property just by walking. Really calm the area and the tiny house is very comfortable."
United States
Jackeline R.
$185 nightly
The price is $206
Dec 8 - Dec 9
Total with taxes and fees
The Mermaid at Tiny House Siesta

Aparthotel in Siesta Key

4.0 star property
9.4 out of 10, Exceptional, (73)
"Clean room, incredibly helpful staff. Will be staying here again"
United States
Caleb
$249 nightly
The price is $281
Dec 8 - Dec 9
Total with taxes and fees
SeaSpray Resort

Apartment in Siesta Key

9.4 out of 10, Exceptional, (19)
"Jayme was super helpful when needed with our stay "
United States
Gabby L.
$227 nightly
The price is $231
Dec 8 - Dec 9
Total with taxes and fees
[Beach Elements] pool view withprivate beach access

Vacation Home in Siesta Key

9.8 out of 10, Exceptional, (24)
"Clean and comfortable. "
United States
Laney
$258 nightly
The price is $262
Dec 8 - Dec 9
Total with taxes and fees
[escape to paradise] siesta key beach getaway

Aparthotel in South Village

3.5 star property
9.6 out of 10, Exceptional, (298)
"Loved our stay! "
United States
Michelle
$454 nightly
The price is $513
Dec 16 - Dec 17
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club

Vacation Home in Siesta Key

3.0 star property
9.6 out of 10, Exceptional, (52)
"Very nice place, we loved it. Great location. "
United States
Derrick
$264 nightly
The price is $298
Dec 18 - Dec 19
Total with taxes and fees
Siesta Key Island Rentals

Cottage in Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (190)
"Great place to stay! "
United States
Carlos
$259 nightly
The price is $293
Dec 8 - Dec 9
Total with taxes and fees
The Inn On Siesta Key

Villa in South Village

10.0 out of 10, Exceptional, (37)
"We arrived early and the owner was very communicative about when we could get in the space. He sent us a code beforehand, so we were able to go straight in, drop our bags, eat lunch across the street, and head to the beach. Everything is as shown. Super clean, stocked kitchen, plenty of beach gear, etc. We would definitely consider staying again."
United States
TATE J.
$352 nightly
The price is $393
Dec 19 - Dec 20
Total with taxes and fees
Completely Remodeled- 150 Yards to Beach and Restaurants!

Cottage in Siesta Key

9.2 out of 10, Wonderful, (5)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
United States
Rolly N.
$330 nightly
The price is $330
Dec 16 - Dec 17
Total with taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Vacation Home in Sarasota

9.6 out of 10, Exceptional, (189)
"We had a wonderful time.the host was wonderful .we had a leak in the bathroom and he came right over and fixed in in a matter of minutes .we were very impressed.we would stay there again."
United States
Martha C.
$396 nightly
The price is $442
Dec 8 - Dec 9
Total with taxes and fees
Siesta beach....one and only

Condo in South Village

9.6 out of 10, Exceptional, (41)
"Loved the pool and view!"
United States
Victoria P.
$257 nightly
The price is $287
Dec 14 - Dec 15
Total with taxes and fees
POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES

Apartment in Sarasota

9.0 out of 10, Wonderful, (20)
"Clean and Cute! Good communication with Host."
United States
Anonymous traveler
$190 nightly
The price is $212
Dec 16 - Dec 17
Total with taxes and fees
Tiny Coral Oasis- beachy tiny house for your getaway

Vacation Home in Siesta Key Village

8.8 out of 10, Excellent, (11)
"My absolute favorite place to stay! Clean, friendly and perfect location to the beach and village."
United States
Tisha P.
$384 nightly
The price is $400
Dec 8 - Dec 9
Total with taxes and fees
Gulf Villa in Siesta Key | Beachfront Vibes & Dock

Apartment in South Village

9.8 out of 10, Exceptional, (10)
"Amazing stay, very clean & convenient "
United States
Ellen
$231 nightly
The price is $235
Dec 8 - Dec 9
Total with taxes and fees
[Sunny in Siesta] king bed + walk to beach

Vacation Home in Siesta Key

3.5 star property
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
$281 nightly
The price is $318
Dec 8 - Dec 9
Total with taxes and fees
Siesta Heron Suites & Villas
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

Price trends for vacation rentals in Siesta Key

Less expensive
More expensive
This month
Next month
November
February
$366
$399
Month
Price
January
$399
February
$541
March
$525
April
$438
May
$370
June
$408
July
$424
August
$355
September
$332
October
$297
November
$281
December
$366
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Siesta Key. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Siesta Key

Everything you need to know about Siesta Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Siesta Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Siesta Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Siesta Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Siesta Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Siesta Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $175 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Siesta Key rentals

At Expedia, we put the best Siesta Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Siesta Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Siesta Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Siesta Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Siesta Key?

Yes, we give you a choice of vacation rentals in Siesta Key close to Jim Neville Marine Preserve, or you can go with a more secluded option if you'd like a relaxing place to 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 vacation rentals in Siesta Key?

Siesta Key Island Rentals: Visitors like this Siesta Key vacation home rental. It comes with WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind. Some other top choices in Siesta Key are 3-bedroom 2-bathroom Siesta Key townhome close to beaches, city and airport. and Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times.

How many vacation rentals are there in Siesta Key?

With 387 Expedia vacation rentals, you're sure 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 vacation rentals like in Siesta Key?

Vacation rentals are private accommodations you can stay in for several days or longer in Siesta Key. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family trip or a small group gathering.