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

Casey Key Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Casey Key holiday rentals

A wooden structure with a thatched roof overlooking a beach.

1. 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 HK$1,464
HK$1,801 total
includes taxes & fees
30 Sept - 1 Oct
Casey Key Resort
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

2. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (684 reviews)
"Great stay!!"
United States
Genghis
The price is HK$1,483
HK$1,675 total
includes taxes & fees
29 Sept - 30 Sept
A Beach Retreat
An outdoor patio with a grill, white chairs, and a red umbrella.

3. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,453 reviews)
"This place was perfect!"
United States
Kat
The price is HK$961
HK$1,086 total
includes taxes & fees
29 Sept - 30 Sept
Hibiscus Suites - Gateway to Siesta Key
A pool area with a waterfall feature, lounge chairs, and palm trees.

4. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,923 reviews)
"Amazing resort,"
United States
kurt
The price is HK$1,060
HK$1,402 total
includes taxes & fees
29 Sept - 30 Sept
Tropical Beach Resorts
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

5. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,310 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is HK$1,293
HK$1,594 total
includes taxes & fees
29 Sept - 30 Sept
Captiva Beach Resort
A modern kitchen with stainless steel appliances, granite countertops, and wooden cabinets.

6. Explore Sarasota: Condo w/ Pool Access, Near Dtwn

Explore Sarasota: Condo w/ Pool Access, Near Dtwn
3.5 star property
Sarasota
The price is HK$596
HK$2,083 total
includes taxes & fees
29 Sept - 30 Sept
Explore Sarasota: Condo w/ Pool Access, Near Dtwn
A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

7. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (185 reviews)
"Property and room were beautiful!! Right across the street from the beach ⛱️"
United States
Michelle Suzanne
The price is HK$1,758
HK$1,986 total
includes taxes & fees
29 Sept - 30 Sept
SeaSpray Resort
A beach with tall grasses and a sunset sky.

8. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is HK$2,965
HK$5,420 total
includes taxes & fees
30 Sept - 1 Oct
Siesta Heron 6 / Sunset
A compact living space with a kitchen, a dining area, and a sofa with cushions.

9. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (386 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$503
HK$1,628 total
includes taxes & fees
13 Oct - 14 Oct
Tiny House Siesta
A spacious living room with a leather sofa, a glass coffee table, and a wooden dining table. Large windows provide ample natural light and a view of the outdoors.

10. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (45 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is HK$770
HK$2,447 total
includes taxes & fees
30 Sept - 1 Oct
Siesta Heron Suites & Villas
An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.

11. Minorga Sand Dollar on the Key

Minorga Sand Dollar on the Key
3.5 star property
Siesta Key Village
The price is HK$2,157
HK$5,096 total
includes taxes & fees
10 Oct - 11 Oct
Minorga Sand Dollar on the Key
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

12. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.4 out of 10, Exceptional, (81 reviews)
"The property was clean and had great decor! They provide everything you need for the beach and the pool is a great added bonus. Perfect location with being so close the restaurants and the beach. We are already planning our next stay!"
United States
Meghan
The price is HK$809
HK$2,556 total
includes taxes & fees
30 Sept - 1 Oct
Siesta Key Island Rentals
A wooden-paneled room with a round table and four chairs, a flat-screen TV mounted on the wall, and a refrigerator in the background.

13. Sun Outdoors Sarasota

Sun Outdoors Sarasota
2.5 star property
Fordville
The price is HK$3,530
HK$3,989 total
includes taxes & fees
29 Sept - 30 Sept
Sun Outdoors Sarasota
An aerial view of a coastal town with beachfront properties, a marina, and clear blue waters.

14. 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 HK$1,261
HK$4,942 total
includes taxes & fees
29 Sept - 30 Sept
Chadwick Cove Resort & Marina
A covered outdoor area with white furniture, including chairs and a table, overlooking a beach.

15. Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
The price is HK$3,336
HK$8,050 total
includes taxes & fees
29 Sept - 30 Sept
Gulf View Condominiums
A residential backyard with a lawn, a wooden deck, and a white house with a grey roof.

16. 4 Mi to Dtwn! Studio w/ Screened Porch in Sarasota

4 Mi to Dtwn! Studio w/ Screened Porch in Sarasota
3.0 star property
Ridge Wood Heights
The price is HK$941
HK$1,985 total
includes taxes & fees
1 Oct - 2 Oct
4 Mi to Dtwn! Studio w/ Screened Porch in Sarasota
A water slide in a pool area with a rocky backdrop and a small waterfall.

17. Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.4 out of 10, Exceptional, (8 reviews)
"I would stay again, very accommodating"
United States
Deliondra
The price is HK$1,177
HK$3,572 total
includes taxes & fees
29 Sept - 30 Sept
Cedar Run Resort - Roam Hospitality
A clear view of a beach with a wooden picnic table and palm trees.

18. Beach Road

Beach Road
2.0 star property
Siesta Key
The price is HK$5,397
HK$7,412 total
includes taxes & fees
2 Oct - 3 Oct
Beach Road
A modern living room with a sofa, coffee table, and artwork on the walls.

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 HK$934
HK$3,105 total
includes taxes & fees
29 Sept - 30 Sept
Pineapple Paradise 1 13 min to Beach Fire Pit
A living room with a sofa, armchair, coffee table, and a potted plant.

20. Siesta Vibe Pool Walk To Crescent Beach

Siesta Vibe Pool Walk To Crescent Beach
2.0 star property
South Village
The price is HK$937
HK$3,059 total
includes taxes & fees
29 Sept - 30 Sept
Siesta Vibe Pool Walk To 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

The Westin Sarasota

The Westin Sarasota

10/10 Excellent
"Great stay. Highly recommend."
Melanie 1-night trip
Posted 7 hours ago
The Westin Sarasota

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