Siesta Key Vacation Rentals

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Vacation Rentals in Siesta Key

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5048)
"Great place and loved the closeness to the beach!"
United States
Nadine
$147 nightly
The price is $166
Oct 21 - Oct 22
Total with taxes and fees
Tropical Beach Resorts
SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (52)
"Pleasant stay, walk to beach and the Village. Good size mini apartment "
United States
Lisa L
$229 nightly
The price is $259
Oct 21 - Oct 22
Total with taxes and fees
SeaSpray Resort
Tiny House Siesta
2.0 star property
8.4 out of 10, Very Good, (333)
"We had a great time at Tiny House, location can not be better and everything was as described."
United States
Elvia
$154 nightly
The price is $173
Oct 21 - Oct 22
Total with taxes and fees
Tiny House Siesta
[escape to paradise] siesta key beach getaway
10.0 out of 10, Exceptional, (22)
"Great place and location"
United States
Karen A.
$261 nightly
The price is $266
Oct 21 - Oct 22
Total with taxes and fees
[escape to paradise] siesta key beach getaway
Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2182)
"very nice helpful people at the desk, nice new clean room good parking, walkable to Crescent beach, beautiful beach"
United States
Emanuela
$129 nightly
The price is $146
Oct 21 - Oct 22
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
Couple’s Beach Escape - The Beach Club at Siesta Key #106C by RVA
9.4 out of 10, Exceptional, (101)
"Rental was clean and well taken care of. Love how close we were to the beach! Would stay here again!"
United States
Mandi R.
$273 nightly
The price is $305
Oct 21 - Oct 22
Total with taxes and fees
Couple’s Beach Escape - The Beach Club at Siesta Key #106C by RVA
Captiva Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (1144)
"Great place close to the beach"
United States
Yuditza
$167 nightly
The price is $187
Oct 26 - Oct 27
Total with taxes and fees
Captiva Beach Resort
[Sunny in Siesta] king bed + walk to beach
9.8 out of 10, Exceptional, (9)
" a very comfortable and pleasant place, highly recommended "
United States
Jose
$236 nightly
The price is $240
Oct 21 - Oct 22
Total with taxes and fees
[Sunny in Siesta] king bed + walk to beach
Beachside Studio Located Across from Main Beach and Half Mile to Village
8.8 out of 10, Excellent, (154)
"Small and cozy - good supply of beach equipment and great location!"
United States
Jamie B.
$226 nightly
The price is $252
Oct 21 - Oct 22
Total with taxes and fees
Beachside Studio Located Across from Main Beach and Half Mile to Village
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
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.
$280 nightly
The price is $280
Oct 21 - Oct 22
Total with taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Heron Suites & Villas
3.5 star property
8.4 out of 10, Very Good, (37)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
$279 nightly
The price is $316
Oct 21 - Oct 22
Total with taxes and fees
Siesta Heron Suites & Villas
Walk to Siesta key beach | Private Dock | Patio | Pool
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
$332 nightly
The price is $348
Oct 21 - Oct 22
Total with taxes and fees
Walk to Siesta key beach | Private Dock | Patio | Pool
Tiny House Green Lifeguard Stand - sleeps 5
9.6 out of 10, Exceptional, (27)
"This tiny house was the cleanest VRBO I have stayed in. Very comfortable and great area, with two restaurants within walking distance. I would absolutely stay here again!"
United States
John B.
$174 nightly
The price is $194
Oct 23 - Oct 24
Total with taxes and fees
Tiny House Green Lifeguard Stand - sleeps 5
2 Bedroom 2 Bath home near Siesta Key Beach
8.4 out of 10, Very Good, (29)
"Perfectly described and wonderful location. "
United States
Bill K.
$208 nightly
The price is $232
Oct 21 - Oct 22
Total with taxes and fees
2 Bedroom 2 Bath home near Siesta Key Beach
Siesta Key Village -Suite #2: A Block to the Beach, In the HEART of the Village!
8.8 out of 10, Excellent, (34)
"We had a great experience staying here. We were in town for a wedding and the location was perfect right downtown with easy access to fun restaurants and bars! Highly recommend. "
United States
Lauren L.
$330 nightly
The price is $354
Oct 21 - Oct 22
Total with taxes and fees
Siesta Key Village -Suite #2: A Block to the Beach, In the HEART of the Village!
The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (292)
"Loved our stay! "
United States
Michelle
$474 nightly
The price is $536
Nov 11 - Nov 12
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club
Tiny House Sand Dollar near Siesta Key
9.0 out of 10, Wonderful, (12)
"The house was very clean and pretty. Loved how convinient it was and it had everything needed for the stay. The location was also perfect with stores and places to eat at walking distance and the beack a 5 minute drive. "
United States
maria D.
$175 nightly
The price is $195
Oct 21 - Oct 22
Total with taxes and fees
Tiny House Sand Dollar near Siesta Key
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
9.6 out of 10, Exceptional, (79)
"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.
$269 nightly
The price is $300
Oct 23 - Oct 24
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Turquoise Water & Soft White Sand - The Beach Club at Siesta Key #104A by RVA
9.0 out of 10, Wonderful, (73)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great, little resort steps from the beach with everything you need for an enjoyable stay."
United States
Stephanie M.
$352 nightly
The price is $392
Oct 21 - Oct 22
Total with taxes and fees
Turquoise Water & Soft White Sand - The Beach Club at Siesta Key #104A by RVA
Resort-Style 2BR w Pool & Private Beach-Beach Club at Siesta Key #204C by RVA
8.8 out of 10, Excellent, (75)
"A nice property with room to relax and enjoy the company of family. We got there and it was clean and ready to go. The property manager was very friendly and eager to assist with what ever needs we may have had. Close to the beach which is why we came."
United States
James B.
$360 nightly
The price is $401
Oct 21 - Oct 22
Total with taxes and fees
Resort-Style 2BR w Pool & Private Beach-Beach Club at Siesta Key #204C by RVA
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
February
$286
Month
Price
January
$330
February
$461
March
$454
April
$354
May
$297
June
$316
July
$290
August
$291
September
$319
October
$262
November
$286
December
$321
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 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 Coastal Cottage - Direct Beach Access and Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times.

How many vacation rentals are there in Siesta Key?

With 818 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.