Siesta Key Vacation Rentals

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Our top choices for Siesta Key vacation rentals

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.
$499 nightly
The price is $524
Mar 26 - Mar 27
Total with taxes and fees
Beachy Sarasota Duplex
9.6 out of 10, Exceptional, (85 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
$260 nightly
The price is $291
Mar 26 - Mar 27
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
9.6 out of 10, Exceptional, (65 reviews)
"Host was great, clean room, balcony was nice. It’s on the Main Street so not quite until the bars closed. Overall a great place to visit. "
United States
Brandon N.
$440 nightly
The price is $481
Mar 31 - Apr 1
Total with taxes and fees
Siesta Cooler: Only Minutes Walk to Siesta Beach!
9.8 out of 10, Exceptional, (30 reviews)
"Fantastic place! Host was excellent no issues. Would stay here again."
United States
David B.
$488 nightly
The price is $501
Mar 17 - Mar 18
Total with taxes and fees
[lounge like locals] walk to siesta beach +bikes
9.0 out of 10, Wonderful, (10 reviews)
"Third time here and best visit will book again in future "
United States
Desirae
$217 nightly
The price is $243
Apr 6 - Apr 7
Total with taxes and fees
Tiny House Calypso with 1st floor sleeping
9.6 out of 10, Exceptional, (122 reviews)
"You are in your own piece of paradise when you stay here. Many amenities available. Ven, our host was always available when needed."
United States
Elizabeth D.
$486 nightly
The price is $543
Mar 12 - Mar 13
Total with taxes and fees
1 mile to Siesta Key! Early Bird Special & Low Wkly Rates! Heated Pool! BBQ

Vacation Home in Siesta Key Village

Newly Renovated Beach-Side villa | Pool | Dock
9.4 out of 10, Exceptional, (14 reviews)
"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
$426 nightly
The price is $453
Mar 13 - Mar 14
Total with taxes and fees
Newly Renovated Beach-Side villa | Pool | Dock
9.0 out of 10, Wonderful, (113 reviews)
"Enjoyable stay "
United States
Brian
$321 nightly
The price is $359
Mar 29 - Mar 30
Total with taxes and fees
Bright & Beachy–Beach Club Siesta Key 100A by RVA
9.0 out of 10, Wonderful, (81 reviews)
"Awesome stay!"
United States
Bri C.
$354 nightly
The price is $394
Mar 28 - Mar 29
Total with taxes and fees
Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
9.6 out of 10, Exceptional, (27 reviews)
"It had everything we needed. Comfortable bed. Great location. Easy wall to the beach "
United States
Noreen W.
$423 nightly
The price is $436
Mar 18 - Mar 19
Total with taxes and fees
[Beach Elements] pool view withprivate beach access

Vacation Home in Sarasota

The Mermaid at Tiny House Siesta
10.0 out of 10, Exceptional, (3 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.
$188 nightly
The price is $210
Mar 16 - Mar 17
Total with taxes and fees
The Mermaid at Tiny House Siesta

Vacation Home in Siesta Key Village

Gulf Villa | Beachfront Vibes & Dock | Pool | BBQ
8.8 out of 10, Excellent, (11 reviews)
"My absolute favorite place to stay! Clean, friendly and perfect location to the beach and village."
United States
Tisha P.
$511 nightly
The price is $543
Mar 15 - Mar 16
Total with taxes and fees
Gulf Villa | Beachfront Vibes & Dock | Pool | BBQ
9.4 out of 10, Exceptional, (102 reviews)
"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.
$346 nightly
The price is $385
Mar 24 - Mar 25
Total with taxes and fees
Couple’s Escape-Beach Club at Siesta Key 106C by RVA
9.2 out of 10, Wonderful, (92 reviews)
"Really nice place to stay "
United States
Claudia
$425 nightly
The price is $475
Mar 12 - Mar 13
Total with taxes and fees
Spacious 2BR Close to World-Famous Sand Beach Club at Siesta Key #102A by RVA
9.6 out of 10, Exceptional, (45 reviews)
"Everything was very clean, great location, perfect for a couple and enjoyed the pool area too"
United States
Dirk T
$538 nightly
The price is $587
Mar 17 - Mar 18
Total with taxes and fees
Near beach. Pool view. King bed. Daily rentals
9.0 out of 10, Wonderful, (13 reviews)
"Great location, clean, good communication. "
United States
Alexandra P.
$534 nightly
The price is $569
Mar 12 - Mar 13
Total with taxes and fees
Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ
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
$547 nightly
The price is $616
Mar 17 - Mar 18
Total with taxes and fees
Coastal Breeze Siesta - Turtle

Apartment in South Village

King bed. Pool. Daily rentals
9.4 out of 10, Exceptional, (44 reviews)
"Beautiful place close to the beach’s and love it would stay here again "
United States
Steve D.
$574 nightly
The price is $626
Mar 21 - Mar 22
Total with taxes and fees
King bed. Pool. Daily rentals
9.2 out of 10, Wonderful, (71 reviews)
"Second time staying here. Great location. "
United States
Nathan H.
$416 nightly
The price is $455
Mar 15 - Mar 16
Total with taxes and fees
Siesta Key Village-Suite #3: A Block to the Beach!
9.2 out of 10, Wonderful, (38 reviews)
"A great location with easy walk to the beach!"
United States
Alan M.
$416 nightly
The price is $455
Mar 15 - Mar 16
Total with taxes and fees
Siesta Key Village-Suite #4: A block to the Beach!
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
October
March
$517
$427
Month
Price
January
$431
February
$465
March
$517
April
$427
May
$381
June
$387
July
$422
August
$386
September
$383
October
$377
November
$389
December
$396
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 $332 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 give good reviews to this Siesta Key vacation home rental, which 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. Another good choice for your trip to Siesta Key is Siesta Heron Suites & Villas.

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 Shell 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.