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Our top choices for Casey Key holiday rentals

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (580)
"Great location, recent updates"
United States
Michael
A Beach Retreat

Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very good, (265)
"Amazing place"
United States
Ricardo
Casey Key Resort - Gulf Shores

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (346)
"Enjoyable stay. "
United States
Lori
The price is ฿3,249
฿7,443 total
includes taxes & fees
10 Jan - 11 Jan 2026
Tiny House Siesta

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5175)
"Great location, value, clean, friendly staff. Will definitely stay there again. "
United States
JoAnna
The price is ฿4,458
฿5,739 total
includes taxes & fees
6 Jan - 7 Jan 2026
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2219)
"Very nice place !"
United States
Ivette
Hibiscus Suites - Gateway to Siesta Key

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (247)
"Lovely decor, very clean"
United States
Frederick
The price is ฿8,167
฿9,229 total
includes taxes & fees
20 Jan - 21 Jan 2026
Kon Tiki Inn

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is ฿5,773
฿12,766 total
includes taxes & fees
6 Jan - 7 Jan 2026
Siesta Heron Suites & Villas

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
South Village
9.6 out of 10, Exceptional, (302)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
The price is ฿13,058
฿16,334 total
includes taxes & fees
21 Jan - 22 Jan 2026
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
The price is ฿11,392
฿14,804 total
includes taxes & fees
28 Dec - 29 Dec
The Inn On Siesta Key

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (14)
"Great place and location "
United States
Cathy
The price is ฿3,287
฿17,665 total
includes taxes & fees
4 Jan - 5 Jan 2026
Chadwick Cove Resort & Marina

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (82)
"Very clean very quiet and a great location to the beach."
United States
Dave
The price is ฿9,480
฿10,713 total
includes taxes & fees
4 Jan - 5 Jan 2026
SeaSpray Resort

Lulu's Key House Leatherback 2/2 Downstairs

Lulu's Key House Leatherback 2/2 Downstairs
4.0 star property
Siesta Key Village
Lulu's Key House Leatherback 2/2 Downstairs

Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
The price is ฿12,585
฿31,185 total
includes taxes & fees
9 Jan - 10 Jan 2026
Gulf View Condominiums

4BR Spacious Paradise

4BR Spacious Paradise
2.0 star property
Siesta Key Village
The price is ฿14,968
฿26,225 total
includes taxes & fees
30 Dec - 31 Dec
4BR Spacious Paradise

Coastal Breeze Siesta - Dolphin

Coastal Breeze Siesta - Dolphin
2.0 star property
Siesta Key
The price is ฿5,635
฿13,750 total
includes taxes & fees
18 Jan - 19 Jan 2026
Coastal Breeze Siesta - Dolphin

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)
"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 ฿10,321
฿24,288 total
includes taxes & fees
28 Dec - 29 Dec
House of The Sun Siesta Key Crescent Beach
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

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