Siesta Key Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Siesta Key vacation rentals

Property grounds
Tropical Beach Resorts

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5175)
"Great location, value, clean, friendly staff. Will definitely stay there again. "
United States
JoAnna
The price is P8,439
P10,864 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Tropical Beach Resorts
Property amenity
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
South Village
9.6 out of 10, Exceptional, (302)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
The price is P24,718
P30,918 total
includes taxes & fees
Jan 21 - Jan 22, 2026
The Residences at Siesta Key Beach by Hyatt Vacation Club
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2219)
"Very nice place !"
United States
Ivette
Hibiscus Suites - Gateway to Siesta Key
Living area
Tiny House Siesta

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (346)
"Enjoyable stay. "
United States
Lori
The price is P5,476
P13,325 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Tiny House Siesta
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Inn On Siesta Key

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
The price is P22,371
P28,935 total
includes taxes & fees
Dec 28 - Dec 29
The Inn On Siesta Key
Private kitchen
Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is P10,929
P24,166 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Siesta Heron Suites & Villas
Living area
SeaSpray Resort

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (82)
"Very clean very quiet and a great location to the beach."
United States
Dave
The price is P17,924
P20,254 total
includes taxes & fees
Jan 4 - Jan 5, 2026
SeaSpray 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.
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Top Siesta Key Hotel Reviews

The Ringling Beach House

The Ringling Beach House

10/10 Excellent
"Nice beach house center to town and the Main Beach. Beach access across street as well. "
Timothy 4-night trip
Posted 3 days ago
The Ringling Beach House

Find out more about Siesta Key

Search for holiday rentals in Siesta Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Siesta Key using one of the methods below:

  • View our selection of featured holiday rentals in Siesta Key
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  • Enter your travel dates to view the best deals on holiday rentals in Siesta Key while they last

Look no further and take a look at our great range of rental properties in Siesta Key!

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.

How many vacation rentals are there in Siesta Key?

With 390 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.