Siesta Key Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Siesta Key vacation rentals

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.
$353 nightly
The price is $353
Apr 21 - Apr 22
Total with taxes and fees
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

[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.
$354 nightly
The price is $362
Apr 22 - Apr 23
Total with taxes and fees
[escape to paradise] siesta key beach getaway

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.
$297 nightly
The price is $331
Apr 22 - Apr 23
Total with taxes and fees
VILLA 3 · Siesta Key, Pool View. Walk to Beach. Daily Rentals

Siesta Cooler: Only Minutes Walk to Siesta Beach!

Siesta Cooler: Only Minutes Walk to Siesta Beach!
Siesta Key Village
9.6 out of 10, Exceptional, (71 reviews)
"Perfect little place for a long weekend away. Conveniently located by everything "
United States
Emily D.
$397 nightly
The price is $432
Apr 21 - Apr 22
Total with taxes and fees
Siesta Cooler: Only Minutes Walk to Siesta Beach!

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
$463 nightly
The price is $522
May 12 - May 13
Total with taxes and fees
Lulu's Key House Kemp Ridley 1/1 Downstairs

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, (13 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
Apr 21 - Apr 22
Total with taxes and fees
Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

Beachside villa in Siesta Key | Canal Front | pool

Beachside villa in Siesta Key | Canal Front | pool
Siesta Key Village
9.8 out of 10, Exceptional, (19 reviews)
"Nice clean and a short walk to everything!"
United States
Ralph S.
$364 nightly
The price is $384
Apr 26 - Apr 27
Total with taxes and fees
Beachside villa in Siesta Key | Canal Front | pool

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (112 reviews)
"Perfect location, nice amenities for the beach, pet friendly, would stay here again! Super convenient and clean "
United States
Jayline
$329 nightly
The price is $372
May 10 - May 11
Total with taxes and fees
SeaSpray Resort

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (65 reviews)
"We had a wonderful time-perfect location to beach and village. Was nice to come back to a very comfortable and relaxing home. Definitely recommend-5 stars! "
United States
Laura
$363 nightly
The price is $411
Apr 21 - Apr 22
Total with taxes and fees
Siesta Key Island Rentals

Siesta Key Village-Suite #3: A Block to the Beach!

Siesta Key Village-Suite #3: A Block to the Beach!
Siesta Key Village
9.2 out of 10, Wonderful, (72 reviews)
"Great location in Siesta Key Village, can walk to all the shops and restaurants as well as the beach "
United States
Erica S.
$360 nightly
The price is $389
Apr 22 - Apr 23
Total with taxes and fees
Siesta Key Village-Suite #3: A Block to the Beach!

[Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (28 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.
$332 nightly
The price is $341
Apr 27 - Apr 28
Total with taxes and fees
[Beach Elements] pool view withprivate beach access

Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach

Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
Siesta Key
9.8 out of 10, Exceptional, (113 reviews)
"Great location and the private beach was so nice! "
United States
Ashley N.
$330 nightly
The price is $368
Apr 22 - Apr 23
Total with taxes and fees
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach

LUXURY HOUSE BY THE CANAL ☀️

LUXURY HOUSE BY THE CANAL ☀️
Siesta Key
9.6 out of 10, Exceptional, (117 reviews)
"Was very clean, easy to access, quiet and had all we needed for a great beach vacation."
United States
Denelle G.
$507 nightly
The price is $566
Apr 21 - Apr 22
Total with taxes and fees
LUXURY HOUSE BY THE CANAL ☀️

Beachside Studio Located Across from Main Beach and Half Mile to Village

Beachside Studio Located Across from Main Beach and Half Mile to Village
Sarasota
8.8 out of 10, Excellent, (163 reviews)
"Useful place, everything was clean and it has a good location."
United States
Felipe
$249 nightly
The price is $279
Apr 21 - Apr 22
Total with taxes and fees
Beachside Studio Located Across from Main Beach and Half Mile to Village

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.
$259 nightly
The price is $290
Apr 28 - Apr 29
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very Good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
$480 nightly
The price is $538
May 17 - May 18
Total with taxes and fees
Unwind Poolside + Walk to Beach! Sarasota Retreat

[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)
"Amazing stay, very clean & convenient "
United States
Ellen
$289 nightly
The price is $295
Apr 22 - Apr 23
Total with taxes and fees
[Sunny in Siesta] king bed + walk to beach

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (196 reviews)
"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"
United States
Amanda
$316 nightly
The price is $357
Apr 28 - Apr 29
Total with taxes and fees
The Inn On Siesta Key

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very Good, (41 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
$317 nightly
The price is $358
May 12 - May 13
Total with taxes and fees
Siesta Heron Suites & Villas

Studio Retreat Across the Street from Beautiful Siesta Key Beach

Studio Retreat Across the Street from Beautiful Siesta Key Beach
Siesta Key
8.8 out of 10, Excellent, (159 reviews)
"Pristinely clean comfortable and very close to beach with free parking it was a great place to stay! Would recommend!"
United States
Stina
$327 nightly
The price is $365
Apr 22 - Apr 23
Total with taxes and fees
Studio Retreat Across the Street from Beautiful 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Siesta Key Hotel Reviews

Price trends for vacation rentals in Siesta Key

Less expensive
More expensive
Next month
October
February
$370
Month
Price
January
$407
February
$481
March
$474
April
$360
May
$370
June
$393
July
$412
August
$359
September
$354
October
$343
November
$375
December
$393
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 $187 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 Gull Villa – Spacious 2BR, Walk to Siesta Key & Village, 1945 Triplex and Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool.

How many vacation rentals are there in Siesta Key?

With 393 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.