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, (5190)
"Great place to stay. Very nice getaway. "
United States
Joyeeta
$164 nightly
The price is $185
Jan 4 - Jan 5
Total with taxes and fees
Tropical Beach Resorts
2.5 star property
8.6 out of 10, Excellent, (2222)
"Very nice place !"
United States
Ivette
$145 nightly
The price is $163
Jan 4 - Jan 5
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

Cottage in Siesta Key

The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (192)
"Great place to stay! "
United States
Carlos
$261 nightly
The price is $295
Jan 4 - Jan 5
Total with taxes and fees
The Inn On 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
$208 nightly
The price is $235
Jan 5 - Jan 6
Total with taxes and fees
Tiny House Siesta

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.
$188 nightly
The price is $210
Jan 4 - Jan 5
Total with taxes and fees
The Mermaid at Tiny House Siesta
3.5 star property
9.6 out of 10, Exceptional, (304)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
$466 nightly
The price is $526
Jan 21 - Jan 22
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club

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
$308 nightly
The price is $349
Jan 13 - Jan 14
Total with taxes and fees
Siesta Heron Suites & Villas
2.0 star property
10.0 out of 10, Exceptional, (1)
"Great little place to stay and enjoy the nearby beaches and restaurants! The communication was on point. We will be back "
United States
Jacob
$393 nightly
The price is $442
Jan 18 - Jan 19
Total with taxes and fees
Coastal Breeze Siesta - Turtle

Aparthotel in Siesta Key

SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (83)
"Very clean very quiet and a great location to the beach."
United States
Dave
$275 nightly
The price is $311
Jan 7 - Jan 8
Total with taxes and fees
SeaSpray Resort
9.8 out of 10, Exceptional, (10)
"Amazing stay, very clean & convenient "
United States
Ellen
$236 nightly
The price is $241
Jan 2 - Jan 3
Total with taxes and fees
[Sunny in Siesta] king bed + walk to beach

Vacation Home in Siesta Key

Siesta Key Island Rentals
3.0 star property
9.6 out of 10, Exceptional, (55)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
$299 nightly
The price is $338
Jan 6 - Jan 7
Total with taxes and fees
Siesta Key Island Rentals
9.6 out of 10, Exceptional, (81)
"Wonderful experience! It was perfect for a girls’ weekend which included me, my mother & my 12 yr old daughters. There was enough restaurants in walking distance, the beach was in walking distance and we appreciated the trolley and frog hopper to get to Turtle Beach for kayaking. "
United States
Michelle A.
$265 nightly
The price is $296
Jan 12 - Jan 13
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
9.8 out of 10, Exceptional, (26)
"The property was very clean and conveniently located ."
United States
David
$292 nightly
The price is $298
Jan 8 - Jan 9
Total with taxes and fees
[lounge like locals] walk to siesta beach +bikes
9.6 out of 10, Exceptional, (42)
"Everything was very clean, great location, perfect for a couple and enjoyed the pool area too"
United States
Dirk T
$220 nightly
The price is $246
Jan 4 - Jan 5
Total with taxes and fees
POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES
9.6 out of 10, Exceptional, (21)
"Jayme was super helpful when needed with our stay "
United States
Gabby L.
$303 nightly
The price is $312
Jan 3 - Jan 4
Total with taxes and fees
[Beach Elements] pool view withprivate beach access
9.6 out of 10, Exceptional, (44)
"The location of the property could not have been better. A very short walk to the quietest beach on Siesta Key. The manager was very attentive when we called with a minor issue and had it resolved quickly. The property could use a pretty thorough cleaning of the baseboards and other nooks and crannies but overall it was pretty clean. We would stay again."
United States
Mel S.
$220 nightly
The price is $246
Jan 4 - Jan 5
Total with taxes and fees
POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIALS villa 3
9.8 out of 10, Exceptional, (102)
"Such a great location! It was clean, spacious for the 2 of us, and ease of communication. Thank you for making our Christmas special. "
United States
Laura
$355 nightly
The price is $397
Jan 4 - Jan 5
Total with taxes and fees
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
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.
$333 nightly
The price is $333
Jan 4 - Jan 5
Total with taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
9.0 out of 10, Wonderful, (34)
"We enjoyed our stay at this property. Highly recommend giving this place a shot. we'll be back for sure if we visit the area."
United States
Jason V.
$181 nightly
The price is $202
Jan 4 - Jan 5
Total with taxes and fees
Aqua Oasis- Tiny House sleeps 4 & Pet friendly
9.0 out of 10, Wonderful, (9)
"Third time here and best visit will book again in future "
United States
Desirae
$190 nightly
The price is $212
Jan 5 - Jan 6
Total with taxes and fees
Tiny House Calypso with 1st floor sleeping
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
March
$399
$560
Month
Price
January
$399
February
$560
March
$566
April
$446
May
$376
June
$384
July
$427
August
$344
September
$338
October
$333
November
$319
December
$389
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 $180 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 394 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. You’ll find favorite places to visit like Lido Beach and St. Armands Circle in the larger area.

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.