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

Siesta Key Vacation Rentals

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Our top choices for Siesta Key vacation rentals

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,973 reviews)
"Amazing resort,"
United States
kurt
The price is CA $181
CA $241 total
includes taxes & fees
Oct 19 - Oct 20
Tropical Beach Resorts

2. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (197 reviews)
"Best short vacation"
United States
Rommel
The price is CA $280
CA $317 total
includes taxes & fees
Nov 2 - Nov 3
SeaSpray Resort

3. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,468 reviews)
"This place was perfect!"
United States
Kat
The price is CA $177
CA $199 total
includes taxes & fees
Oct 21 - Oct 22
Hibiscus Suites - Gateway to Siesta Key

4. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,321 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is CA $243
CA $299 total
includes taxes & fees
Oct 18 - Oct 19
Captiva Beach Resort

5. The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
8.8 out of 10, Excellent, (398 reviews)
"Nice kitchen and clean place"
United States
Ricardo
The Ringling Beach House

6. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (387 reviews)
"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."
United States
Staci
The price is CA $78
CA $280 total
includes taxes & fees
Oct 17 - Oct 18
Tiny House Siesta

7. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
The price is CA $210
CA $522 total
includes taxes & fees
Oct 18 - Oct 19
Yellow Palm Cottage, Heart of Siesta Key

8. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
The price is CA $241
CA $556 total
includes taxes & fees
Oct 19 - Oct 20
BlueDolphin Cottage Walk To Siesta Beach

9. Siesta Vibe Pool Walk To Crescent Beach

Siesta Vibe Pool Walk To Crescent Beach
2.0 star property
South Village
The price is CA $170
CA $555 total
includes taxes & fees
Oct 17 - Oct 18
Siesta Vibe Pool Walk To Crescent Beach

10. Beach Tree Cottage,Walk To Beach& Siesta

Beach Tree Cottage,Walk To Beach& Siesta
2.0 star property
Siesta Key Village
The price is CA $189
CA $498 total
includes taxes & fees
Oct 19 - Oct 20
Beach Tree Cottage,Walk To Beach& Siesta

11. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (46 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is CA $136
CA $440 total
includes taxes & fees
Oct 19 - Oct 20
Siesta Heron Suites & Villas

12. Siesta Sands Beach Resort 4th Floor With Elevator

Siesta Sands Beach Resort 4th Floor With Elevator
3.5 star property
South Village
The price is CA $418
CA $1,072 total
includes taxes & fees
Oct 26 - Oct 27
Siesta Sands Beach Resort 4th Floor With Elevator

13. Beach Road - Capri

Beach Road - Capri
2.5 star property
Siesta Key
The price is CA $740
CA $965 total
includes taxes & fees
Oct 25 - Oct 26
Beach Road - Capri

14. Siesta Sands Beach Resort Gulf View

Siesta Sands Beach Resort Gulf View
2.5 star property
South Village
10.0 out of 10, Exceptional, (1 review)
"Loved to property! Clean and accommodating. Had a beautiful ocean view and could walk right out to the beach. Pool area was clean."
United States
Jessica
The price is CA $459
CA $1,067 total
includes taxes & fees
Nov 8 - Nov 9
Siesta Sands Beach Resort Gulf View

15. House of The Sun Siesta Key Crescent Beach

House of The Sun Siesta Key Crescent Beach
4.0 star property
South Village
8.0 out of 10, Very good, (2 reviews)
"The area is beautiful. The condo was very nice. Has everything in it. You can cook if you prefer. The Gulf of Mexico was right behind the condo walk out on to the beach. It also has a pool. I have no complains I would def go back again . "
United States
Margaret Theresa
The price is CA $372
CA $1,041 total
includes taxes & fees
Oct 22 - Oct 23
House of The Sun Siesta Key Crescent Beach

16. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is CA $552
CA $999 total
includes taxes & fees
Oct 26 - Oct 27
Siesta Heron 6 / Sunset

17. 4 Mi to Siesta Key Beach: Condo w/ Pool Access

4 Mi to Siesta Key Beach: Condo w/ Pool Access
4.0 star property
Sarasota
10.0 out of 10, Exceptional, (1 review)
"The property was clean and decorated so cute. It was easy to find and simple check in. We had a problem with the ac and they fixed it right away. The host was great and communicated very well. Highly recommended!"
United States
Lori
The price is CA $117
CA $407 total
includes taxes & fees
Oct 19 - Oct 20
4 Mi to Siesta Key Beach: Condo w/ Pool Access

18. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (692 reviews)
"Enjoyed our stay"
United States
Robin
The price is CA $262
CA $296 total
includes taxes & fees
Nov 4 - Nov 5
A Beach Retreat

19. Pineapple Paradise 1 13 min to Beach Fire Pit

Pineapple Paradise 1 13 min to Beach Fire Pit
2.0 star property
Central Sarasota
The price is CA $159
CA $503 total
includes taxes & fees
Oct 26 - Oct 27
Pineapple Paradise 1 13 min to Beach Fire Pit

20. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (839 reviews)
"I loved this hotel"
United States
Raisare
The price is CA $411
CA $505 total
includes taxes & fees
Oct 18 - Oct 19
Bridgewalk 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

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.

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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 St. Boniface Episcopal Church Labyrinth, 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 Siesta Heron Suites & Villas.

How many vacation rentals are there in Siesta Key?

With 401 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, Safe Harbor Siesta Key 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.