Siesta Key Vacation Rentals

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Our top choices for Siesta Key vacation rentals

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (30 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
$307 nightly
The price is $314
May 11 - May 12
Total with taxes and fees
[escape to paradise] siesta key beach getaway

[Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (29 reviews)
"The space was clean and well-equipped, and the host was easily reachable and responded quickly when I asked a question. The private beach access was nice. I would stay here again. "
United States
Natalie M.
$294 nightly
The price is $301
May 12 - May 13
Total with taxes and fees
[Beach Elements] pool view withprivate beach access

[Sunny in Siesta] king bed + walk to beach

[Sunny in Siesta] king bed + walk to beach
South Village
9.8 out of 10, Exceptional, (13 reviews)
"Great location and accommodation. "
United States
ESTELEN
$274 nightly
The price is $279
May 13 - May 14
Total with taxes and fees
[Sunny in Siesta] king bed + walk to beach

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (66 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
$328 nightly
The price is $370
May 13 - May 14
Total with taxes and fees
Siesta Key Island Rentals

Newly Renovated Beach-Side villa | Pool | Dock

Newly Renovated Beach-Side villa | Pool | Dock
Siesta Key Village
9.4 out of 10, Exceptional, (16 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
$401 nightly
The price is $423
May 11 - May 12
Total with taxes and fees
Newly Renovated Beach-Side villa | Pool | Dock

Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ
Siesta Key Village
9.0 out of 10, Wonderful, (14 reviews)
"We enjoyed our stay at Everglades Villa. The location was the best feature as we were able to walk to Siesta Key Village and the beach. "
United States
Lisa S.
$454 nightly
The price is $478
May 12 - May 13
Total with taxes and fees
Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
$418 nightly
The price is $418
May 26 - May 27
Total with taxes and fees
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key, Sea Horse Villa, Pool. Daily rentals

Siesta Key, Sea Horse Villa, Pool. Daily rentals
South Village
9.4 out of 10, Exceptional, (52 reviews)
"Beautiful place close to the beach’s and love it would stay here again "
United States
Steve D.
$231 nightly
The price is $257
May 10 - May 11
Total with taxes and fees
Siesta Key, Sea Horse Villa, Pool. Daily rentals

Lulu's Key House Kemp Ridley 1/1 Downstairs

Lulu's Key House Kemp Ridley 1/1 Downstairs
3.5 star property
Siesta Key Village
10.0 out of 10, Exceptional, (4 reviews)
"Absolutely beautiful place. Very clean, easy check-in, wonderful location"
United States
Christine
$458 nightly
The price is $515
May 12 - May 13
Total with taxes and fees
Lulu's Key House Kemp Ridley 1/1 Downstairs

Fully renovated Siesta Key Condo | Walk to Beach | Pool | Dog OK | Perfect Location in SK Village

Fully renovated Siesta Key Condo | Walk to Beach | Pool | Dog OK | Perfect Location in SK Village
Siesta Key Village
9.4 out of 10, Exceptional, (81 reviews)
"This condo has been nicely appointed and has everything you need for a beach vacation. It's also in the village near all shops and eateries. "
United States
Abi-Gayil G.
$515 nightly
The price is $574
May 10 - May 11
Total with taxes and fees
Fully renovated Siesta Key Condo | Walk to Beach | Pool | Dog OK | Perfect Location in SK Village

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very Good, (42 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
$295 nightly
The price is $333
May 11 - May 12
Total with taxes and fees
Siesta Heron Suites & Villas

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
South Village
9.6 out of 10, Exceptional, (48 reviews)
"Everything was very clean, great location, perfect for a couple and enjoyed the pool area too"
United States
Dirk T
$240 nightly
The price is $267
May 10 - May 11
Total with taxes and fees
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #1: A block to the Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (47 reviews)
"The apartment is clean and comfortable! Location is amazing! The beach, restaurants, and bars are all very close. The beach is great and easily accessible. 100% would stay here again! "
United States
Alex
$400 nightly
The price is $435
May 10 - May 11
Total with taxes and fees
Siesta Key Village-Suite #1: A block to the Beach!

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (122 reviews)
"Enjoyed our stay great location easy walk to village and the beach"
United States
Gregory
$299 nightly
The price is $338
May 27 - May 28
Total with taxes and fees
SeaSpray Resort

Siesta Shores 2Bed/2Bath Heated Pool!

Siesta Shores 2Bed/2Bath Heated Pool!
Sarasota
10.0 out of 10, Exceptional, (4 reviews)
"Such a great condo! Absolutely loved it. The pool area is so inviting and lovely. Perfect location to shopping and the beach. "
United States
Kristy C.
$425 nightly
The price is $425
May 10 - May 11
Total with taxes and fees
Siesta Shores 2Bed/2Bath Heated Pool!

Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
Siesta Key
9.2 out of 10, Wonderful, (36 reviews)
"Very nice, clean and quiet place."
United States
Monika Z.
$417 nightly
The price is $465
May 10 - May 11
Total with taxes and fees
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

VILLA 3 · Siesta Key, Pool View. Walk to Beach. Daily Rentals

VILLA 3 · Siesta Key, Pool View. Walk to Beach. Daily Rentals
Sarasota
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.
$277 nightly
The price is $309
May 10 - May 11
Total with taxes and fees
VILLA 3 · Siesta Key, Pool View. Walk to Beach. Daily Rentals

Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout

Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout
South Village
9.8 out of 10, Exceptional, (90 reviews)
"Location, amazing!!!"
United States
Krista M.
$590 nightly
The price is $658
May 13 - May 14
Total with taxes and fees
Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (87 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
$269 nightly
The price is $300
May 20 - May 21
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

2 Bedroom 2 Bath home near Siesta Key Beach

2 Bedroom 2 Bath home near Siesta Key Beach
Sarasota
8.6 out of 10, Excellent, (39 reviews)
"House was conveniently located. "
United States
CHRISTINE V.
$213 nightly
The price is $238
May 11 - May 12
Total with taxes and fees
2 Bedroom 2 Bath home near Siesta Key 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
$370
$432
Month
Price
January
$418
February
$526
March
$565
April
$428
May
$370
June
$432
July
$421
August
$396
September
$364
October
$360
November
$397
December
$435
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 $188 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 399 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. While here, Crescent Beach and Siesta Key Marina 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.