Siesta Key Vacation Rentals

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Our top choices for Siesta Key vacation rentals

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5160)
"Great place, easy beach access and property was beautiful. "
United States
Maria
$147 nightly
The price is $166
Dec 21 - Dec 22
Total with taxes and fees
Tropical Beach Resorts

The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta
2.0 star property
Sarasota
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.
$236 nightly
The price is $263
Dec 21 - Dec 22
Total with taxes and fees
The Mermaid at Tiny House Siesta

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
$299 nightly
The price is $338
Dec 21 - Dec 22
Total with taxes and fees
The Inn On Siesta Key

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
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.

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
$352 nightly
The price is $398
Dec 24 - Dec 25
Total with taxes and fees
Siesta Heron Suites & Villas

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1174)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
$167 nightly
The price is $187
Dec 21 - Dec 22
Total with taxes and fees
Captiva Beach Resort

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (54)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
Siesta Key Island Rentals

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2214)
"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

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (346)
"Enjoyable stay. "
United States
Lori
$200 nightly
The price is $226
Dec 21 - Dec 22
Total with taxes and fees
Tiny House Siesta

Tiny House Calypso with 1st floor sleeping

Tiny House Calypso with 1st floor sleeping
Sarasota
9.0 out of 10, Wonderful, (9)
"Third time here and best visit will book again in future "
United States
Desirae
$230 nightly
The price is $257
Dec 21 - Dec 22
Total with taxes and fees
Tiny House Calypso with 1st floor sleeping

Tiny Coral Oasis- beachy tiny house for your getaway

Tiny Coral Oasis- beachy tiny house for your getaway
Sarasota
9.0 out of 10, Wonderful, (20)
"Clean and Cute! Good communication with Host."
United States
Anonymous traveler
$191 nightly
The price is $213
Dec 22 - Dec 23
Total with taxes and fees
Tiny Coral Oasis- beachy tiny house for your getaway

POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES

POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES
South Village
9.6 out of 10, Exceptional, (41)
"Loved the pool and view!"
United States
Victoria P.
$256 nightly
The price is $286
Dec 21 - Dec 22
Total with taxes and fees
POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
South Village
9.6 out of 10, Exceptional, (300)
"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
Jan 19 - Jan 20, 2026
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club

[lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (25)
"The property was very clean and conveniently located ."
United States
David
$313 nightly
The price is $319
Dec 25 - Dec 26
Total with taxes and fees
[lounge like locals] walk to siesta beach +bikes

Tiny House Green Lifeguard Stand - sleeps 5

Tiny House Green Lifeguard Stand - sleeps 5
Sarasota
9.6 out of 10, Exceptional, (27)
"It was a great fit for our family and we enjoyed the experience. "
United States
Stephanie H.
$266 nightly
The price is $297
Dec 24 - Dec 25
Total with taxes and fees
Tiny House Green Lifeguard Stand - sleeps 5

Siesta Key Village -Suite #2: A Block to the Beach, In the HEART of the Village!

Siesta Key Village -Suite #2: A Block to the Beach, In the HEART of the Village!
Siesta Key Village
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.
$349 nightly
The price is $377
Dec 21 - Dec 22
Total with taxes and fees
Siesta Key Village -Suite #2: A Block to the Beach, In the HEART of the Village!

Spacious 2BR Close to World-Famous Sand Beach Club at Siesta Key #102A by RVA

Spacious 2BR Close to World-Famous Sand Beach Club at Siesta Key #102A by RVA
South 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

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

Siesta Key Village-Suite #3: A Block to the Beach!
Siesta Key Village
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.
$349 nightly
The price is $377
Dec 21 - Dec 22
Total with taxes and fees
Siesta Key Village-Suite #3: A Block to the Beach!

Siesta Key ~New Waterview studio ~ sleeps 4 ~ pool

Siesta Key ~New Waterview studio ~ sleeps 4 ~ pool
Siesta Key
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

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (79)
"Perfect location, helpful staff, awesome place! "
United States
Mark Gregory
$309 nightly
The price is $349
Dec 21 - Dec 22
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
$395
Month
Price
January
$395
February
$555
March
$561
April
$450
May
$394
June
$389
July
$424
August
$359
September
$330
October
$304
November
$336
December
$375
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 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 Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village.

How many vacation rentals are there in Siesta Key?

With 391 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.