A yellow lifeguard tower with an American flag on a beach with people and umbrellas.

Siesta Key Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

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

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (377 reviews)
"The house was clean and simple. Perfect for a couple to stay for a few nights. Not too far from the beach. Very quiet and safe area."
United States
bruno
The price is CA $93
CA $276 total
includes taxes & fees
Jul 19 - Jul 20
Tiny House Siesta

Tiny Coral Oasis- beachy tiny house for your getaway

Tiny Coral Oasis- beachy tiny house for your getaway
Sarasota
9.0 out of 10, Wonderful, (20 reviews)
"Cute tiny house Clean and comfortable Had a great time"
United States
DeAnna T.
The price is CA $146
CA $275 total
includes taxes & fees
Jul 22 - Jul 23
Tiny Coral Oasis- beachy tiny house for your getaway

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (44 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is CA $149
CA $451 total
includes taxes & fees
Jul 19 - Jul 20
Siesta Heron Suites & Villas

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (31 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
The price is CA $143
CA $447 total
includes taxes & fees
Jul 19 - Jul 20
[escape to paradise] siesta key beach getaway

Siesta Key - Poolside Suite - Studio - Heated Pool

Siesta Key - Poolside Suite - Studio - Heated Pool
Siesta Key
8.4 out of 10, Very good, (15 reviews)
"My wife and I stayed to explore Siesta Key for our anniversary and her birthday. Both the property and our room were very clean, with a nice pool area. Lisa was fantastic to work with and was very accommodating to our travel needs as we had our jetski with us. Check in/out was very easy, a plus was not having to check in at an off sight location as we’ve had to do at other properties. The location was very close to everything we wanted and there’s a free trolley stop right outside the...
United States
keith
The price is CA $251
CA $571 total
includes taxes & fees
Jul 25 - Jul 26
Siesta Key - Poolside Suite - Studio - Heated Pool

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,371 reviews)
"Excellent location, great place to stay! "
United States
Lynn
The price is CA $179
CA $202 total
includes taxes & fees
Aug 2 - Aug 3
Hibiscus Suites - Gateway to Siesta Key

Canalfront Siesta key entire King suite

Canalfront Siesta key entire King suite
Bay Isle
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful stay nice secluded.but still close to all sites to see very relaxing you couldnt find more wonderful host Sue & Nandy beautiful experience "
United States
Brian B.
The price is CA $153
CA $408 total
includes taxes & fees
Aug 3 - Aug 4
Canalfront Siesta key entire King suite

Beachside Bliss- 1 mi to the beach w/ heated pool

Beachside Bliss- 1 mi to the beach w/ heated pool
Sarasota
9.0 out of 10, Wonderful, (7 reviews)
"The apartment is far from the Hotel, We have to walk a long way, I paid a certain amount price to be right near the Beach"
United States
Yalile
Beachside Bliss- 1 mi to the beach w/ heated pool

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (151 reviews)
"Very nice room and easy access to an amazing beach."
United States
Michael
The price is CA $378
CA $427 total
includes taxes & fees
Aug 9 - Aug 10
SeaSpray Resort

2 Bedroom 2 Bath home near Siesta Key Beach

2 Bedroom 2 Bath home near Siesta Key Beach
Sarasota
8.6 out of 10, Excellent, (40 reviews)
"Great little place -perfect for a few days in siesta "
United States
Linda K.
The price is CA $167
CA $436 total
includes taxes & fees
Jul 22 - Jul 23
2 Bedroom 2 Bath home near Siesta Key Beach

Tiny House Green Lifeguard Stand - sleeps 5

Tiny House Green Lifeguard Stand - sleeps 5
Sarasota
9.4 out of 10, Exceptional, (32 reviews)
"Very clean & tidy! The house stayed cool & comfortable the whole night! My husband & I enjoyed this unique place & would definitely book again!"
United States
Jennifer S.
The price is CA $150
CA $277 total
includes taxes & fees
Jul 19 - Jul 20
Tiny House Green Lifeguard Stand - sleeps 5

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,666 reviews)
"perfect stay and location for a family!"
United States
Jessica
The price is CA $214
CA $278 total
includes taxes & fees
Aug 9 - Aug 10
Tropical Beach Resorts

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (72 reviews)
"Great location, very clean and spacious."
United States
Jason
Siesta Key Island Rentals

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 reviews)
"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"
United States
Amanda
The Inn On Siesta Key

Beach Club at Siesta Key Poolside D

Beach Club at Siesta Key Poolside D
4.0 star property
South Village
9.4 out of 10, Exceptional, (3 reviews)
"Nice getaway. "
United States
Jeff
Beach Club at Siesta Key Poolside D

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, (89 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
The price is CA $139
CA $424 total
includes taxes & fees
Aug 2 - Aug 3
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Palm Haven at Cape Leyte

Palm Haven at Cape Leyte
2.0 star property
Siesta Key
The price is CA $488
CA $1,012 total
includes taxes & fees
Jul 21 - Jul 22
Palm Haven at Cape Leyte

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,286 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
The price is CA $232
CA $285 total
includes taxes & fees
Aug 16 - Aug 17
Captiva Beach Resort

Siesta Key Studio close to beaches, city, and airport.

Siesta Key Studio close to beaches, city, and airport.
Siesta Key
8.4 out of 10, Very good, (13 reviews)
"Great location, great parking, quiet, great shower."
United States
Andy L.
The price is CA $188
CA $343 total
includes taxes & fees
Jul 20 - Jul 21
Siesta Key Studio close to beaches, city, and airport.

Coastal Home w Hot Tub Firepit and Music Lounge

Coastal Home w Hot Tub Firepit and Music Lounge
2.0 star property
Siesta Key
The price is CA $565
CA $1,036 total
includes taxes & fees
Jul 20 - Jul 21
Coastal Home w Hot Tub Firepit and Music Lounge
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

Find out more about Siesta Key

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Siesta Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

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 3 bed 2 Bath, heated pool, walk to beach and village.

How many vacation rentals are there in Siesta Key?

With 414 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. You’ll find favorite places to visit like Lido Beach and St. Armands Circle in the larger area.

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.