Siesta Key Vacation Rentals

Save 10% or more on select stays with Expedia Rewards

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide.

Vacation Rentals in Siesta Key

Tropical Beach Resorts
3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL, 34242
Fully refundableReserve now, pay when you stay
The price is $134 per night from Aug 1 to Aug 2
Stay at this 3.5-star beach aparthotel in Siesta Key. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the WiFi and the helpful staff in ...
4.6/5 Wonderful! (3,355 reviews)
"Staff were incredible friendly and helpful. Property was beautiful. It was a great stay."

Reviewed on Jul 5, 2022

Tropical Beach Resorts
Captiva Beach Resort
2 out of 5
6772 Sara Sea Circle, Siesta Key, FL, 34242
The price is $224 per night from Jul 10 to Jul 11
Stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. ...
4.4/5 Excellent! (861 reviews)
"staff were friendly and other guests were fun and friendly!"

Reviewed on Jun 26, 2022

Captiva Beach Resort
The Ringling Beach House
3.5 out of 5
523 Beach Road, Siesta Key, FL, 34242
Fully refundableReserve now, pay when you stay
The price is $443 per night from Jul 15 to Jul 16
Stay at this 3.5-star apartment in Siesta Key. Enjoy free WiFi, free parking, and a terrace. Our guests praise the WiFi and the helpful staff in our reviews. ...
4.4/5 Wonderful! (163 reviews)
"The place was clean and walking distance to the beach!"

Reviewed on Jun 13, 2022

The Ringling Beach House
You could be seeing lower prices

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
Hyatt Residence Club Sarasota, Siesta Key Beach
3.5 out of 5
915 Seaside Drive, Siesta Key, FL, 34242
The price is $709 per night from Jul 10 to Jul 11
Stay at this 3.5-star beach aparthotel in Siesta Key. Enjoy free breakfast, free WiFi, and free valet parking. Our guests praise the helpful staff and the property ...
4.7/5 Exceptional! (93 reviews)
"Super nice and luxury property"

Reviewed on May 23, 2022

Hyatt Residence Club Sarasota, Siesta Key Beach
Siesta Palms By the Beach
3.5 out of 5
1017 Point of Rocks Rd, Siesta Key, FL, 34242
Stay at this 3.5-star condo in Siesta Key. Enjoy free WiFi, free parking, and a terrace. Our guests praise the pool and the helpful staff in our reviews. Popular ...
4.8/5 Exceptional! (27 reviews)
"The stay was amazing at Siesta Palms! My family and I ended up extending one more night. The place is incredibly clean, warm and very well furnished! I love the fact that they provided us with beach amenities like umbrellas and beach chairs and that is just a few steps away from the beautiful Siesta ..."

Reviewed on May 26, 2022

Siesta Palms By the Beach
Gulf Holiday by Beachside Management
4 out of 5
73 Avenida Messina, Siesta Key, FL, 34242
Stay at this 4-star condo in Siesta Key. Enjoy free WiFi, free parking, and a terrace. Our guests praise the pool and the helpful staff in our reviews. Popular ...
3.9/5 Good! (50 reviews)
"The property was clean and the location to the beach was great. I also liked that beach towels and chairs were available for the beach."

Reviewed on Jun 13, 2022

Gulf Holiday by Beachside Management
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
The price is $189 per night from Jul 11 to Jul 12
Stay at this condo in Siesta Key. Enjoy WiFi, onsite parking, and a TV. Our guests praise the WiFi and the bathrooms in our reviews. Popular attractions Siesta ...
4.6/5 Wonderful! (28 reviews)
"We would absolutely stay here again. Location is perfect, right across the street to the beach and within a 10-15 min walk to the village with restaurants and shopping. The trolly stop is also right near the property if you don’t want to walk. The beach is gorgeous and clean. The condo was impeccable ..."

Reviewed on Jun 29, 2022

Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
Palm Bay Club by Beachside Management
3.5 out of 5
5960 Midnight Pass Road, Siesta Key, FL, 34242
Stay at this 3.5-star beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the pool and the convenient parking in ...
3.7/5 Good! (27 reviews)
"Loved that the property has both ocean and bay sides !… Beautiful grounds and friendly staff"

Reviewed on May 15, 2022

Palm Bay Club by Beachside Management
Clean and Beautiful Condo with Private Beach in Beautiful Siesta Key #1 Beaches
The price is $179 per night from Aug 1 to Aug 2
Stay at this beach condo in Siesta Key. Enjoy a beach locale, WiFi, and onsite parking. Our guests praise the comfy beds and the family amenities in our reviews. ...
4.8/5 Exceptional! (107 reviews)
June 2022
"Description of property is very honest and clear. Communication was easy with property manager. Even allowed us to check in early. Loved having a fully stocked condo with cooking and beach things. We were able to find some shade at the pool each day, which was important for us because we have an ..."

Reviewed on Jun 18, 2022

Clean and Beautiful Condo with Private Beach in Beautiful Siesta Key #1 Beaches
Beachside Studio Located Across from Main Beach and Half Mile to Village
The price is $154 per night from Jul 20 to Jul 21
Stay at this apartment in Siesta Key. Enjoy WiFi, onsite parking, and an LED TV. Popular attractions Siesta Key Beach and Lido Beach are located nearby. Discover ...
4.3/5 Excellent! (23 reviews)
great place
"We had a great stay at this property. Great location, super clean. The laundry area was very convenient. The only negative thing I would say is we wished there was a spot for outdoor seating/eating. Would definitely stay here again!"

Reviewed on Apr 24, 2022

Beachside Studio Located Across from Main Beach and Half Mile to Village
Don't see what you're looking for?
See all available properties in Siesta Key
View all properties
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.

Price trends for vacation rentals in Siesta Key

Less expensive
More expensive
This month
Next month
October
March
$224
$211
Month
Price
January
$239
February
$355
March
$375
April
$308
May
$220
June
$227
July
$224
August
$211
September
$194
October
$186
November
$214
December
$264
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.

Other types of properties in Siesta Key you may be interested in

Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL, 34242
Fully refundableReserve now, pay when you stay
The price is $134 per night from Aug 1 to Aug 2
Tropical Beach Resorts
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
140 Columbus Blvd., Siesta Key, FL, 34242
The price is $188 per night from Jul 6 to Jul 7
Tropical Breeze Resort
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.

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 accommodation rentals, 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. Explore our selection of Florida vacation homes

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 months, such as October or November. For more hustle and bustle, you may prefer to visit in July or August. 

Prices vary throughout the year. Winter is the cheapest time to visit, with Summer the most expensive. 

Your chosen location, property type, and amenities will impact the cost of your trip, too. Right now, the selection of Siesta Key vacation rentals we have selected for you on this page range between $134 per night and $709 per night. Entering your desired dates in the search wizard 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. Or explore even further and have a look at our Florida Keys vacation rentals, rentals in Panama City or vacation homes in Orlando. 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

Recent reviews of Siesta Key properties
expedia verified reviews