Siesta Key Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

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, (5149)
"Great place, easy beach access and property was beautiful. "
United States
Maria
$147 nightly
The price is $166
Dec 15 - Dec 16
Total with taxes and fees
Tropical Beach Resorts

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (346)
"Enjoyable stay. "
United States
Lori
$212 nightly
The price is $239
Dec 15 - Dec 16
Total with taxes and fees
Tiny House Siesta

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.
$170 nightly
The price is $190
Dec 15 - Dec 16
Total with taxes and fees
The Mermaid at Tiny House Siesta

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1172)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
$153 nightly
The price is $171
Dec 15 - Dec 16
Total with taxes and fees
Captiva Beach Resort

[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
$282 nightly
The price is $286
Dec 15 - Dec 16
Total with taxes and fees
[lounge like locals] walk to siesta beach +bikes

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
$227 nightly
The price is $257
Dec 15 - Dec 16
Total with taxes and fees
The Inn On Siesta Key

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (53)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
$275 nightly
The price is $310
Dec 18 - Dec 19
Total with taxes and fees
Siesta Key Island Rentals

[Sunny in Siesta] king bed + walk to beach

[Sunny in Siesta] king bed + walk to beach
South Village
9.8 out of 10, Exceptional, (10)
"Amazing stay, very clean & convenient "
United States
Ellen
$249 nightly
The price is $254
Dec 16 - Dec 17
Total with taxes and fees
[Sunny in Siesta] king bed + walk to beach

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
$276 nightly
The price is $312
Dec 15 - Dec 16
Total with taxes and fees
Siesta Heron Suites & Villas

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2212)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
$150 nightly
The price is $170
Dec 15 - Dec 16
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

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
$441 nightly
The price is $498
Jan 14 - Jan 15, 2026
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club

Gulf Villa in Siesta Key | Beachfront Vibes & Dock

Gulf Villa in Siesta Key | Beachfront Vibes & Dock
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.
$389 nightly
The price is $406
Dec 15 - Dec 16
Total with taxes and fees
Gulf Villa in Siesta Key | Beachfront Vibes & Dock

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.
$257 nightly
The price is $287
Dec 15 - Dec 16
Total with taxes and fees
POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
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.
$299 nightly
The price is $299
Dec 16 - Dec 17
Total with taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

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
$170 nightly
The price is $190
Dec 15 - Dec 16
Total with taxes and fees
Tiny House Calypso with 1st floor sleeping

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (77)
"Perfect location, helpful staff, awesome place! "
United States
Mark Gregory
$309 nightly
The price is $349
Dec 15 - Dec 16
Total with taxes and fees
SeaSpray Resort

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.
$334 nightly
The price is $360
Dec 15 - Dec 16
Total with taxes and fees
Siesta Key Village -Suite #2: A Block to the Beach, In the HEART of the Village!

[Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (21)
"Jayme was super helpful when needed with our stay "
United States
Gabby L.
$257 nightly
The price is $262
Dec 17 - Dec 18
Total with taxes and fees
[Beach Elements] pool view withprivate beach access

Couple’s Escape-Beach Club at Siesta Key 106C by RVA

Couple’s Escape-Beach Club at Siesta Key 106C by RVA
South Village
9.4 out of 10, Exceptional, (101)
"Property is amazing spot, did stay a year before and was amazing this time furniture had damage and ac was not cooling perfect."
United States
Ubaldo M.
$305 nightly
The price is $340
Dec 15 - Dec 16
Total with taxes and fees
Couple’s Escape-Beach Club at Siesta Key 106C by RVA

Walk to Siesta key beach | Private Dock | Patio | Pool

Walk to Siesta key beach | Private Dock | Patio | Pool
Siesta Key Village
9.4 out of 10, Exceptional, (14)
"The place was clean and location was perfect! 2 blocks to the beach and 2 blocks to the village. It’s really great and helpful that they provided beach wagon, chairs and umbrella. "
United States
Amy
$337 nightly
The price is $351
Dec 15 - Dec 16
Total with taxes and fees
Walk to Siesta key beach | Private Dock | Patio | Pool
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Siesta Key Hotel Reviews

Price trends for vacation rentals in Siesta Key

Less expensive
More expensive
This month
Next month
October
February
$372
$403
Month
Price
January
$403
February
$539
March
$525
April
$462
May
$391
June
$400
July
$431
August
$408
September
$346
October
$344
November
$347
December
$372
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 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.