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, (5162)
"Great place, easy beach access and property was beautiful. "
United States
Maria
$147 nightly
The price is $166
Dec 22 - Dec 23
Total with taxes and fees
Tropical Beach Resorts

Vacation Home in Sarasota

The Mermaid at Tiny House Siesta
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.
$232 nightly
The price is $259
Dec 22 - Dec 23
Total with taxes and fees
The Mermaid at Tiny House Siesta

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
$309 nightly
The price is $350
Dec 22 - Dec 23
Total with taxes and fees
The Inn On Siesta Key
9.6 out of 10, Exceptional, (81)
"We loved our stay at the Drift Inn. Very clean, just the right amount of room for 4, easy access to the beach and pool. The beds were very comfortable. The owner was very quick to respond to questions from beginning to end. We would stay here again."
United States
Kimberly P.
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

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
$351 nightly
The price is $397
Dec 22 - Dec 23
Total with taxes and fees
Siesta Heron Suites & Villas

Condo in South Village

Captiva Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (1176)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
$167 nightly
The price is $187
Dec 22 - Dec 23
Total with taxes and fees
Captiva Beach Resort

Vacation Home in Siesta Key

Siesta Key Island Rentals
3.0 star property
9.6 out of 10, Exceptional, (54)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
Siesta Key Island Rentals
2.5 star property
8.6 out of 10, Excellent, (2215)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
$145 nightly
The price is $163
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

Mobile Home in Sarasota

Tiny House Siesta
2.0 star property
8.4 out of 10, Very Good, (346)
"Enjoyable stay. "
United States
Lori
$222 nightly
The price is $250
Dec 22 - Dec 23
Total with taxes and fees
Tiny House Siesta
9.0 out of 10, Wonderful, (9)
"Third time here and best visit will book again in future "
United States
Desirae
$232 nightly
The price is $259
Dec 22 - Dec 23
Total with taxes and fees
Tiny House Calypso with 1st floor sleeping
9.0 out of 10, Wonderful, (20)
"Clean and Cute! Good communication with Host."
United States
Anonymous traveler
$194 nightly
The price is $216
Dec 30 - Dec 31
Total with taxes and fees
Tiny Coral Oasis- beachy tiny house for your getaway
9.6 out of 10, Exceptional, (41)
"Loved the pool and view!"
United States
Victoria P.
$257 nightly
The price is $287
Dec 22 - Dec 23
Total with taxes and fees
POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES
3.5 star property
9.6 out of 10, Exceptional, (301)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
$441 nightly
The price is $498
Jan 21 - Jan 22, 2026
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club
9.8 out of 10, Exceptional, (25)
"The property was very clean and conveniently located ."
United States
David
$282 nightly
The price is $286
Dec 25 - Dec 26
Total with taxes and fees
[lounge like locals] walk to siesta beach +bikes
9.6 out of 10, Exceptional, (27)
"It was a great fit for our family and we enjoyed the experience. "
United States
Stephanie H.
$250 nightly
The price is $280
Jan 4 - Jan 5, 2026
Total with taxes and fees
Tiny House Green Lifeguard Stand - sleeps 5
9.0 out of 10, Wonderful, (36)
"Place was perfect for a quick 3 day getaway! Hosts replied promptly to any questions I had, location was great, comfortable bed. Parking is a little tight but they say that from the start so I just kept it parked and walked everywhere. Would stay here again and would recommend!"
United States
angie s.
Siesta Key Village -Suite #2: A Block to the Beach, In the HEART of the Village!
9.2 out of 10, Wonderful, (92)
"Really nice place to stay "
United States
Claudia
Spacious 2BR Close to World-Famous Sand Beach Club at Siesta Key #102A by RVA
9.2 out of 10, Wonderful, (64)
"Well maintained, great location. We really enjoyed tge time there. Definitely looking forward to more trips."
United States
Barry L.
$298 nightly
The price is $318
Dec 22 - Dec 23
Total with taxes and fees
Siesta Key Village-Suite #3: A Block to the Beach!
8.4 out of 10, Very Good, (20)
"The place was perfect for our 3 day getaway!"
United States
Amy
$301 nightly
The price is $301
Dec 23 - Dec 24
Total with taxes and fees
Siesta Key ~New Waterview studio ~ sleeps 4 ~ pool

Aparthotel in Siesta Key

SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (79)
"Perfect location, helpful staff, awesome place! "
United States
Mark Gregory
$297 nightly
The price is $336
Dec 24 - Dec 25
Total with taxes and fees
SeaSpray Resort
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
Next month
October
March
$398
Month
Price
January
$398
February
$565
March
$570
April
$467
May
$396
June
$392
July
$420
August
$351
September
$327
October
$299
November
$317
December
$354
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 Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village and 3-bedroom 2-bathroom Siesta Key townhome close to beaches, city and airport..

How many vacation rentals are there in Siesta Key?

With 390 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.