Photo by Susie West

Casey Key Holiday 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

Our top choices for Casey Key holiday rentals

1. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (701 reviews)
"Enjoyed our stay"
United States
Robin
The price is HK$1,446
HK$1,634 total
includes taxes & fees
6 Dec - 7 Dec
A Beach Retreat

2. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (288 reviews)
"My boyfriend and I had a wonderful time. Easy late check in. Nice clean room. Property beautiful. Private beach beautiful. We definitely plan to come back and have family join."
United States
Jamie
The price is HK$1,351
HK$1,662 total
includes taxes & fees
10 Dec - 11 Dec
Casey Key Resort

3. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (6,065 reviews)
"Great resort and location!"
United States
Christine
The price is HK$1,080
HK$1,425 total
includes taxes & fees
16 Nov - 17 Nov
Tropical Beach Resorts

4. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,337 reviews)
"Great location that's very close to the beach, large and clean room with a kitchenette, and very helpful and friendly staff. Loved our stay here!"
United States
Bob
The price is HK$1,208
HK$1,498 total
includes taxes & fees
17 Nov - 18 Nov
Captiva Beach Resort

5. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,486 reviews)
"This place was perfect!"
United States
Kat
The price is HK$1,075
HK$1,215 total
includes taxes & fees
16 Nov - 17 Nov
Hibiscus Suites - Gateway to Siesta Key

6. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (209 reviews)
"The room was clean and had all of the necessities. The place was adorable and the location is great!"
United States
Dolores
The price is HK$2,464
HK$2,785 total
includes taxes & fees
16 Nov - 17 Nov
SeaSpray Resort

7. Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (320 reviews)
"Debbie and Sean are excellent hosts. Very clean, very comfortable, very quiet. Pet friendly, which is awesome also. Great location also just a couple miles from downtown or the beach.."
United States
Joseph
The price is HK$1,275
HK$1,441 total
includes taxes & fees
16 Nov - 17 Nov
Kon Tiki Inn

8. Beach Tree Cottage,Walk To Beach& Siesta

Beach Tree Cottage,Walk To Beach& Siesta
2.0 star property
Siesta Key Village
The price is HK$1,087
HK$3,002 total
includes taxes & fees
16 Nov - 17 Nov
Beach Tree Cottage,Walk To Beach& Siesta

9. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (392 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 HK$463
HK$1,581 total
includes taxes & fees
3 Dec - 4 Dec
Tiny House Siesta

10. 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 HK$683
HK$2,350 total
includes taxes & fees
18 Nov - 19 Nov
Siesta Heron Suites & Villas

11. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,384
HK$3,337 total
includes taxes & fees
16 Nov - 17 Nov
Beach View 100ft To Beach and SPA

12. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
The price is HK$1,765
HK$4,078 total
includes taxes & fees
16 Nov - 17 Nov
Yellow Palm Cottage, Heart of Siesta Key

13. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
8.8 out of 10, Excellent, (31 reviews)
"Without a doubt, the best place—very spacious and in an excellent location. You have the beach right out front, and Gasparilla Beach—which is very beautiful—is just 25 minutes away. Communication with the owner was excellent, the sunsets were fantastic, and the terrace overlooking the bay—with the breeze blowing—was a delight. We will definitely be back!"
United States
Niovys
The price is HK$1,135
HK$4,802 total
includes taxes & fees
17 Nov - 18 Nov
Chadwick Cove Resort & Marina

14. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
The price is HK$1,553
HK$3,750 total
includes taxes & fees
16 Nov - 17 Nov
BlueDolphin Cottage Walk To Siesta Beach

15. PinkMango Cottage Steps to Beach&Village

PinkMango Cottage Steps to Beach&Village
2.0 star property
Siesta Key Village
The price is HK$1,723
HK$4,030 total
includes taxes & fees
16 Nov - 17 Nov
PinkMango Cottage Steps to Beach&Village

16. Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
The price is HK$2,134
HK$4,797 total
includes taxes & fees
23 Nov - 24 Nov
Unwind Poolside + Walk to Beach! Sarasota Retreat

17. Beach Road

Beach Road
2.0 star property
Siesta Key
The price is HK$4,864
HK$6,811 total
includes taxes & fees
8 Dec - 9 Dec
Beach Road

18. Sun Outdoors Sarasota

Sun Outdoors Sarasota
2.5 star property
Fordville
The price is HK$3,531
HK$3,989 total
includes taxes & fees
16 Nov - 17 Nov
Sun Outdoors Sarasota

19. Pineapple Paradise 2 13 min to Beach Fire Pit

Pineapple Paradise 2 13 min to Beach Fire Pit
2.0 star property
Central Sarasota
The price is HK$1,193
HK$3,136 total
includes taxes & fees
16 Nov - 17 Nov
Pineapple Paradise 2 13 min to Beach Fire Pit

20. Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
The price is HK$3,336
HK$8,052 total
includes taxes & fees
17 Nov - 18 Nov
Gulf View Condominiums
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.

Find holiday rentals that suit your style

Explore a world of travel with Expedia