A coastal town with a beach, marina, and clear blue waters.

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

In two weeks
In two months
In three months
In four months

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, (687 reviews)
"Great stay!!"
United States
Genghis
The price is NZ$371
includes taxes & fees
4 Nov - 5 Nov
A Beach Retreat

2. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (284 reviews)
"Nice little property,very well kept.Host was very nice and helpful.Will be back again."
United States
Greg
The price is NZ$410
includes taxes & fees
28 Oct - 29 Oct
Casey Key Resort

3. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,947 reviews)
"Amazing resort,"
United States
kurt
The price is NZ$318
includes taxes & fees
7 Oct - 8 Oct
Tropical Beach Resorts

4. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (188 reviews)
"Great place with a bunch of little touches that put it above and beyond"
United States
Rafe
The price is NZ$425
includes taxes & fees
2 Nov - 3 Nov
SeaSpray Resort

5. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,317 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is NZ$344
includes taxes & fees
13 Oct - 14 Oct
Captiva Beach Resort

6. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,459 reviews)
"This place was perfect!"
United States
Kat
The price is NZ$272
includes taxes & fees
18 Oct - 19 Oct
Hibiscus Suites - Gateway to Siesta Key

7. 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 NZ$1,381
includes taxes & fees
22 Oct - 23 Oct
House of The Sun Siesta Key Crescent Beach

8. 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 NZ$365
includes taxes & fees
8 Oct - 9 Oct
Tiny House Siesta

9. 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 NZ$533
includes taxes & fees
8 Oct - 9 Oct
Siesta Heron Suites & Villas

10. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
8.8 out of 10, Excellent, (30 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 NZ$1,102
includes taxes & fees
7 Oct - 8 Oct
Chadwick Cove Resort & Marina

11. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is NZ$1,276
includes taxes & fees
12 Oct - 13 Oct
Siesta Heron 6 / Sunset

12. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
The price is NZ$631
includes taxes & fees
8 Oct - 9 Oct
Beach View 100ft To Beach and SPA

13. 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 NZ$510
includes taxes & fees
14 Oct - 15 Oct
4 Mi to Siesta Key Beach: Condo w/ Pool Access

14. Sun Outdoors Sarasota

Sun Outdoors Sarasota
2.5 star property
Fordville
The price is NZ$858
includes taxes & fees
6 Nov - 7 Nov
Sun Outdoors Sarasota

15. Pineapple Paradise 1 13 min to Beach Fire Pit

Pineapple Paradise 1 13 min to Beach Fire Pit
2.0 star property
Central Sarasota
Pineapple Paradise 1 13 min to Beach Fire Pit

16. Beach Club at Siesta Key Poolside D

Beach Club at Siesta Key Poolside D
4.0 star property
South Village
9.6 out of 10, Exceptional, (4 reviews)
"Nice getaway. "
United States
Jeff
The price is NZ$923
includes taxes & fees
8 Oct - 9 Oct
Beach Club at Siesta Key Poolside D

17. Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
The price is NZ$1,828
includes taxes & fees
11 Oct - 12 Oct
Gulf View Condominiums

18. Siesta Vibe Pool Walk To Crescent Beach

Siesta Vibe Pool Walk To Crescent Beach
2.0 star property
South Village
The price is NZ$695
includes taxes & fees
19 Oct - 20 Oct
Siesta Vibe Pool Walk To Crescent Beach

19. Sarasota Family Home Private Heated Pool Relax

Sarasota Family Home Private Heated Pool Relax
2.0 star property
Whitfield Estates
2.0 out of 10, (1 review)
"Very disappointing stay Unfortunately, our experience at this property was very disappointing. The biggest issue was the air conditioning, which was not working properly during our entire stay. The first night was already very uncomfortable, but during the day it seemed to cool a little better, so we decided not to request a technician at that point. However, the second night was even worse, and the heat made it extremely difficult to sleep and enjoy our stay. We did report the problem to the...
United States
German
The price is NZ$952
includes taxes & fees
7 Oct - 8 Oct
Sarasota Family Home Private Heated Pool Relax

20. Beach Road - Capri

Beach Road - Capri
2.5 star property
Siesta Key
Beach Road - Capri
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 Casey Key Hotel Reviews

Find out more about Casey Key

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Casey Key holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Casey Key. 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 Casey Key. Seeing all the best attractions is bound to make you fall in love with Casey Key. Who knows, you may even be tempted to extend your 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 holiday 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 Casey Key short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia