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

Casey Key Vacation Rentals

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Our top choices for Casey Key vacation 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 CA $263
CA $297 total
includes taxes & fees
Nov 4 - Nov 5
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 CA $265
CA $327 total
includes taxes & fees
Oct 29 - Oct 30
Casey Key Resort

3. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,961 reviews)
"Amazing resort,"
United States
kurt
The price is CA $181
CA $241 total
includes taxes & fees
Oct 11 - Oct 12
Tropical Beach Resorts

4. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (191 reviews)
"Great place with a bunch of little touches that put it above and beyond"
United States
Rafe
The price is CA $293
CA $331 total
includes taxes & fees
Nov 4 - Nov 5
SeaSpray Resort

5. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,318 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is CA $222
CA $275 total
includes taxes & fees
Oct 11 - Oct 12
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, (2,464 reviews)
"This place was perfect!"
United States
Kat
The price is CA $177
CA $200 total
includes taxes & fees
Oct 21 - Oct 22
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 CA $380
CA $1,050 total
includes taxes & fees
Oct 22 - Oct 23
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 CA $78
CA $280 total
includes taxes & fees
Oct 17 - Oct 18
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 CA $143
CA $447 total
includes taxes & fees
Oct 13 - Oct 14
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 CA $201
CA $865 total
includes taxes & fees
Oct 11 - Oct 12
Chadwick Cove Resort & Marina

11. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is CA $568
CA $1,017 total
includes taxes & fees
Oct 12 - Oct 13
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 CA $239
CA $555 total
includes taxes & fees
Oct 16 - Oct 17
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 CA $117
CA $407 total
includes taxes & fees
Oct 13 - Oct 14
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 CA $590
CA $667 total
includes taxes & fees
Oct 11 - Oct 12
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
The price is CA $167
CA $531 total
includes taxes & fees
Oct 19 - Oct 20
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
Beach Club at Siesta Key Poolside D

17. Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
The price is CA $605
CA $1,460 total
includes taxes & fees
Oct 11 - Oct 12
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 CA $170
CA $555 total
includes taxes & fees
Oct 10 - Oct 11
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 CA $354
CA $827 total
includes taxes & fees
Oct 11 - Oct 12
Sarasota Family Home Private Heated Pool Relax

20. Beach Road - Capri

Beach Road - Capri
2.5 star property
Siesta Key
The price is CA $761
CA $989 total
includes taxes & fees
Oct 25 - Oct 26
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.
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Top Casey Key Hotel Reviews

Find out more about Casey 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 Casey 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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