Siesta Key Vacation Rentals

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Our top choices for Siesta Key vacation rentals

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5143)
"Wonderful trip! Great location! Great staff!"
United States
Kevin
$147 nightly
The price is $166
Dec 14 - Dec 15
Total with taxes and fees
Tropical Beach Resorts

Condo in South Village

Captiva Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (1171)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
$153 nightly
The price is $171
Dec 14 - Dec 15
Total with taxes and fees
Captiva Beach Resort
3.5 star property
9.6 out of 10, Exceptional, (299)
"Great spacious room with updated amenities as well as a great white beach and amazing staff! "
United States
Rebecca
$444 nightly
The price is $502
Dec 17 - Dec 18
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club

Aparthotel in Siesta Key

SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (76)
"Clean room, incredibly helpful staff. Will be staying here again"
United States
Caleb
$199 nightly
The price is $225
Dec 14 - Dec 15
Total with taxes and fees
SeaSpray Resort

Apartment in Siesta Key

The Ringling Beach House
3.5 star property
9.0 out of 10, Wonderful, (344)
"great location, very clean, quiet"
United States
Joaquin
$338 nightly
The price is $383
Dec 24 - Dec 25
Total with taxes and fees
The Ringling Beach House

Vacation Home in Siesta Key

Siesta Key Island Rentals
3.0 star property
9.6 out of 10, Exceptional, (53)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
$247 nightly
The price is $279
Dec 15 - Dec 16
Total with taxes and fees
Siesta Key Island Rentals

Aparthotel in South Village

Siesta Palms By the Beach
3.5 star property
9.4 out of 10, Exceptional, (137)
"Comfy and clean, nice and close to the beach. Pool was very clean. Quiet, safe area. Would highly recommend!"
United States
Lynn
Siesta Palms By the Beach

Cottage in Siesta Key

The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
$517 nightly
The price is $585
Dec 28 - Dec 29
Total with taxes and fees
The Inn On Siesta Key
6.8 out of 10, (5)
$183 nightly
The price is $204
Dec 12 - Dec 13
Total with taxes and fees
3-bedroom 2-bathroom Siesta Key townhome close to beaches, city and airport.

Vacation Home in Siesta Key

Siesta Heron Suites & Villas
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
$287 nightly
The price is $325
Dec 14 - Dec 15
Total with taxes and fees
Siesta Heron Suites & Villas

Vacation Home in Siesta Key Village

Steps to Beach/Siesta Village-Resort Pool w/Slide
10.0 out of 10, Exceptional, (41)
"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!"
United States
Frances E.
Steps to Beach/Siesta Village-Resort Pool w/Slide
9.8 out of 10, Exceptional, (25)
"The check in and kitchen environment was great no complaints "
United States
nicholas c.
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times
9.6 out of 10, Exceptional, (29)
"It was a great stay. Property is close to water, has chairs for patrons. Easy walk on the beach to other areas. Shopping and restaurants near by. Thank you for a wonderful vacation"
United States
Nani
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
9.8 out of 10, Exceptional, (8)
"Beautiful place to stay… direct walk to the beach from your back door. Amazing view! Clean with all the amenities you need. "
United States
Michele B.
Private Home Directly on Siesta Key Beach!
10.0 out of 10, Exceptional, (14)
"Had a great time with great accommodations"
United States
Henry P.
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
9.4 out of 10, Exceptional, (69)
"We loved the property. Was perfect location and very clean. Was a great all around experience."
United States
Dallas S.
Surfside Beachfront 3BR — Gulf Views & Walk-Out Access on Siesta Key
9.2 out of 10, Wonderful, (23)
"We enjoyed the beautiful beach, pools and resort! The condo was a great place for our family to stay! We will definitely be back!"
United States
Lisa W.
#1 Beach @ Siesta condo/best deal out there! Jamaica Royale Siesta Key Condo 109
10.0 out of 10, Exceptional, (9)
Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village
9.6 out of 10, Exceptional, (145)
"Great location and fit all our boxes for beach getaway. "
United States
Lisa M.
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
9.4 out of 10, Exceptional, (20)
"Jayme was super helpful when needed with our stay "
United States
Gabby L.
$232 nightly
The price is $236
Dec 14 - Dec 15
Total with taxes and fees
[Beach Elements] pool view withprivate 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

Price trends for vacation rentals in Siesta Key

Less expensive
More expensive
This month
Next month
September
February
$377
$410
Month
Price
January
$410
February
$543
March
$521
April
$436
May
$381
June
$396
July
$430
August
$411
September
$335
October
$348
November
$365
December
$377
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 $166 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.