Siesta Key Vacation Rentals

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Vacation Rentals in Siesta Key

Tropical Beach Resorts

3.5 star property
South Village
9.4 out of 10, Exceptional, (5098)
"The room was clean and the staff was very nice."
United States
Jill
$164 nightly
The price is $185
Nov 17 - Nov 18
Total with taxes and fees
Tropical Beach Resorts

Captiva Beach Resort

3.0 star property
South Village
9.0 out of 10, Wonderful, (1156)
"Very good stay, clean, safe, and steps from the beach"
United States
Brandon
$167 nightly
The price is $187
Nov 17 - Nov 18
Total with taxes and fees
Captiva Beach Resort

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
South Village
9.6 out of 10, Exceptional, (294)
"Fun place to stay for family vacation "
United States
Todd
$364 nightly
The price is $412
Dec 17 - Dec 18
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club

SeaSpray Resort

4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (68)
"Pleasant stay, walk to beach and the Village. Good size mini apartment "
United States
Lisa L
$239 nightly
The price is $270
Nov 17 - Nov 18
Total with taxes and fees
SeaSpray Resort

The Ringling Beach House

3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (335)
"Clean, friendly and beach!"
United States
Mary
The Ringling Beach House

Siesta Key Island Rentals

3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (50)
"Very nice place, we loved it. Great location. "
United States
Derrick
Siesta Key Island Rentals

The Inn On Siesta Key

3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (189)
"This property was great and it is a quick walk to the beach and village. The Cabana suited our family of four. We had enough space to spread out and relax. If we return to Siesta Key, we would stay here again."
United States
Brooke
$221 nightly
The price is $250
Nov 18 - Nov 19
Total with taxes and fees
The Inn On Siesta Key

Siesta Palms By the Beach

3.5 star property
South Village
9.4 out of 10, Exceptional, (136)
"Comfy and clean, nice and close to the beach. Pool was very clean. Quiet, safe area. Would highly recommend!"
United States
Lynn
Siesta Palms By the Beach

Siesta Heron Suites & Villas

3.5 star property
Siesta Key
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
Nov 18 - Nov 19
Total with taxes and fees
Siesta Heron Suites & Villas

Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views

Siesta Key Village
10.0 out of 10, Exceptional, (40)
"Very clean, new, close to downtown and the beach as well. Pool was the nicest we’ve seen, and the entire downstairs became a hangout all week for both kids and adults. Service from property manager Sarah was top notch!"
United States
Pete D.
Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Siesta Key
9.6 out of 10, Exceptional, (28)
"Everything is super clean and super good. The beach is super nice. The atmosphere is incredible."
United States
Yasiel G.
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6

Siesta Key
10.0 out of 10, Exceptional, (13)
"Had a great time with great accommodations"
United States
Henry P.
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6

Beachfront 3-Bedroom Condo on Siesta Key – Steps to the Sand & Gulf Views

Siesta Key
9.4 out of 10, Exceptional, (68)
"This is our second time staying here. Absolutely love this rental. Very clean and walking distance to the village "
United States
Curtis R.
Beachfront 3-Bedroom Condo on Siesta Key – Steps to the Sand & Gulf Views

Private Home Directly on Siesta Key Beach!

Siesta Key
9.8 out of 10, Exceptional, (8)
"The home was beautiful and well equipped and management was quick to respond to any questions that we had. Direct access to a gorgeous beach was definitely the highlight!! "
United States
Brandi C.
Private Home Directly on Siesta Key Beach!

Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Siesta Key
9.6 out of 10, Exceptional, (55)
"We had a wonderful stay. This is truly a very short walk to the beach as well as to the Siesta Key restaurants and shops. We truly enjoyed our stay!"
United States
Anne W.
$926 nightly
The price is $1,033
Nov 17 - Nov 18
Total with taxes and fees
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

5 STAR SIESTA KEY, 80 STEPS to BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING

Siesta Key
10.0 out of 10, Exceptional, (142)
"Very close to the beach, a short walk to the village, and plenty of common space for family gathering. "
United States
Andrea G.
5 STAR SIESTA KEY, 80 STEPS to BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING

Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course

Siesta Key
10.0 out of 10, Exceptional, (48)
"We booked a few days to vacation with our family and best friend's family. The pictures don't do the home justice. Not to mention its close proximity to everything and the beach access directly across the street. We even got to watch storms a few hours off the coast from the balcony and roof top deck, and it was absolutely beautiful. We've already started looking at dates for next year, as we'd happily choose the home and its owners again. "
United States
Gynyne M.
Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course

Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

Siesta Key Village
9.6 out of 10, Exceptional, (142)
"Great location and fit all our boxes for beach getaway. "
United States
Lisa M.
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!

Siesta Key
9.6 out of 10, Exceptional, (8)
"We loved this house. We celebrated a cousins 50th birthday and had so much fun. The location is close to all restaurants and beach. The golf cart was so fun to use. The house is nicely stocked with necessary items, pool noodles and toys. There was everything needed for the beach.The most important part was the owners were very responsive to all questions. We look forward to coming and staying here again."
United States
Nina D.
Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!

#1 Beach @ Siesta condo/best deal out there! Jamaica Royale Siesta Key Condo 109

Siesta Key
9.2 out of 10, Wonderful, (23)
"8 minute walk to in my favorite beach. Easy to communicate with Michelle, she responded immediately to a question I had. Everything as posted on VRBO. Pool perfect temperature!"
United States
Larry B.
#1 Beach @ Siesta condo/best deal out there! Jamaica Royale Siesta Key Condo 109
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
September
February
$313
Month
Price
January
$332
February
$501
March
$470
April
$388
May
$283
June
$291
July
$283
August
$275
September
$257
October
$265
November
$326
December
$313
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 $185 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 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 Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times and Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village.

How many vacation rentals are there in Siesta Key?

With 815 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.