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, (5,224 reviews)
"Great place to stay. Very nice getaway. "
United States
Joyeeta
$164 nightly
The price is $185
Jan 15 - Jan 16
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 reviews)
"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.
$187 nightly
The price is $209
Jan 15 - Jan 16
Total with taxes and fees
The Mermaid at Tiny House Siesta
3.5 star property
9.6 out of 10, Exceptional, (306 reviews)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
$384 nightly
The price is $434
Jan 19 - Jan 20
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Great little place to stay and enjoy the nearby beaches and restaurants! The communication was on point. We will be back "
United States
Jacob
$364 nightly
The price is $410
Jan 18 - Jan 19
Total with taxes and fees
Coastal Breeze Siesta - Turtle

Vacation Home in Sarasota

Beachy Sarasota Duplex
10.0 out of 10, Exceptional, (3 reviews)
"Great experience. House was in a great location and having a Dunkin walking distance was a plus. Definitely would recommend. Thank you A"
United States
pete t.
$399 nightly
The price is $414
Jan 13 - Jan 14
Total with taxes and fees
Beachy Sarasota Duplex

Mobile Home in Sarasota

Tiny House Siesta
2.0 star property
8.4 out of 10, Very Good, (347 reviews)
"Enjoyable stay. "
United States
Lori
$207 nightly
The price is $233
Jan 15 - Jan 16
Total with taxes and fees
Tiny House Siesta
2.5 star property
8.6 out of 10, Excellent, (2,231 reviews)
"Very nice place !"
United States
Ivette
$144 nightly
The price is $163
Jan 13 - Jan 14
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

Vacation Home in Siesta Key

Siesta Heron Suites & Villas
3.5 star property
8.6 out of 10, Excellent, (38 reviews)
"Clean pool great apartment could use more seating in living room. Beach chairs was cool patio was awesome parking good water pressure great bed clean and comfy "
United States
jason
$301 nightly
The price is $340
Jan 13 - Jan 14
Total with taxes and fees
Siesta Heron Suites & Villas
9.6 out of 10, Exceptional, (81 reviews)
"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.
$264 nightly
The price is $295
Jan 13 - Jan 14
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
9.8 out of 10, Exceptional, (27 reviews)
"The property was very clean and conveniently located ."
United States
David
$260 nightly
The price is $263
Jan 14 - Jan 15
Total with taxes and fees
[lounge like locals] walk to siesta beach +bikes
9.6 out of 10, Exceptional, (42 reviews)
"Everything was very clean, great location, perfect for a couple and enjoyed the pool area too"
United States
Dirk T
$230 nightly
The price is $257
Jan 13 - Jan 14
Total with taxes and fees
POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES

Aparthotel in Siesta Key

SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (84 reviews)
"Very clean very quiet and a great location to the beach."
United States
Dave
$339 nightly
The price is $383
Jan 13 - Jan 14
Total with taxes and fees
SeaSpray Resort
9.2 out of 10, Wonderful, (5 reviews)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
United States
Rolly N.
$297 nightly
The price is $297
Jan 13 - Jan 14
Total with taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
9.0 out of 10, Wonderful, (9 reviews)
"Third time here and best visit will book again in future "
United States
Desirae
$186 nightly
The price is $208
Jan 15 - Jan 16
Total with taxes and fees
Tiny House Calypso with 1st floor sleeping
9.4 out of 10, Exceptional, (51 reviews)
"Stayed at the property prior to our cruise out of port canaveral. Was perfect for our needs - steps to the beach and close to many stores/cafes/etc. would definitely stay again. "
United States
John K.
$266 nightly
The price is $297
Feb 3 - Feb 4
Total with taxes and fees
Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk
9.0 out of 10, Wonderful, (37 reviews)
"Very nice "
United States
Dan M.
$341 nightly
The price is $369
Jan 13 - Jan 14
Total with taxes and fees
Siesta Key Village -Suite #2: A Block to the Beach, In the HEART of the Village!

Vacation Home in Siesta Key Village

Lulu's Key House Leatherback 2/2 Downstairs
4.0 star property
$561 nightly
The price is $631
Jan 25 - Jan 26
Total with taxes and fees
Lulu's Key House Leatherback 2/2 Downstairs
9.6 out of 10, Exceptional, (22 reviews)
"Jayme was super helpful when needed with our stay "
United States
Gabby L.
$340 nightly
The price is $350
Jan 17 - Jan 18
Total with taxes and fees
[Beach Elements] pool view withprivate beach access
9.6 out of 10, Exceptional, (44 reviews)
"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.
$298 nightly
The price is $333
Jan 20 - Jan 21
Total with taxes and fees
POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIALS villa 3
9.0 out of 10, Wonderful, (34 reviews)
"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.
$180 nightly
The price is $201
Jan 14 - Jan 15
Total with taxes and fees
Aqua Oasis- Tiny House sleeps 4 & Pet friendly
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
March
$423
$560
Month
Price
January
$423
February
$560
March
$573
April
$443
May
$391
June
$408
July
$431
August
$359
September
$351
October
$351
November
$371
December
$408
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 free 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 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. 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.