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, (5066)
"Clean room, great A/C, close to beach, very quiet, easy parking, close to restaurants, clean beach, very nice staff. "
United States
Marta
$181 nightly
The price is $204
Nov 2 - Nov 3
Total with taxes and fees
Tropical Beach Resorts
Captiva Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (1150)
"Very good stay, clean, safe, and steps from the beach"
United States
Brandon
$167 nightly
The price is $187
Nov 2 - Nov 3
Total with taxes and fees
Captiva Beach Resort
SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (56)
"Clean room, incredibly helpful staff. Will be staying here again"
United States
Caleb
$249 nightly
The price is $281
Nov 2 - Nov 3
Total with taxes and fees
SeaSpray Resort
The Ringling Beach House
3.5 star property
9.0 out of 10, Wonderful, (333)
"Just a Great 1st time beach stay. These people and their property are amazing. "
United States
Dana
The Ringling Beach House
The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (293)
"Loved our stay! "
United States
Michelle
$474 nightly
The price is $536
Nov 19 - Nov 20
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times
9.8 out of 10, Exceptional, (24)
"Beatiful property, one block from the beach. Plenty of amenities"
United States
ervin m.
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times
Siesta Key Island Rentals
3.0 star property
9.6 out of 10, Exceptional, (48)
"This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. "
United States
Julianna
$294 nightly
The price is $333
Oct 31 - Nov 1
Total with taxes and fees
Siesta Key Island Rentals
Siesta Palms By the Beach
3.5 star property
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
The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (186)
"Great place to stay! "
United States
Carlos
$246 nightly
The price is $279
Nov 3 - Nov 4
Total with taxes and fees
The Inn On Siesta Key
Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views
10.0 out of 10, Exceptional, (40)
"This was the perfect place to stay for a large family with kids. The location to the beach and restaurants couldn't have been more convenient. Amazing vacation!"
United States
Frances E.
Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views
Private Home Directly on Siesta Key Beach!
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!
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
9.8 out of 10, Exceptional, (26)
"Location was great! Alex was very helpful and quick to respond. Definitely recommend this place to stay in the beautiful Siesta Key!"
United States
Marla H.
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
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
$294 nightly
The price is $333
Nov 3 - Nov 4
Total with taxes and fees
Siesta Heron Suites & Villas
Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!
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!
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
10.0 out of 10, Exceptional, (12)
"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
9.4 out of 10, Exceptional, (67)
"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
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND
9.6 out of 10, Exceptional, (55)
"House was very nice. Was clean when we arrived. Plenty of space and beautiful view "
United States
Rob M.
$759 nightly
The price is $846
Nov 3 - Nov 4
Total with taxes and fees
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND
Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!
9.4 out of 10, Exceptional, (35)
"Great location and experience"
United States
Mayt M.
Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!
Private Pool/Spa in Siesta Key Village, Steps to the Beach! Island Time West
9.6 out of 10, Exceptional, (64)
"Great location!"
United States
Janet M.
Private Pool/Spa in Siesta Key Village, Steps to the Beach! Island Time West
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
9.6 out of 10, Exceptional, (141)
"Perfect location! So easy to walk to the beach!"
United States
Melody W.
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
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
$297
Month
Price
January
$335
February
$470
March
$452
April
$349
May
$288
June
$319
July
$300
August
$291
September
$255
October
$327
November
$297
December
$330
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 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 Coastal Cottage - Direct Beach Access.

How many vacation rentals are there in Siesta Key?

With 805 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.