Casey Key Winter Rental
Condo
10.0(57 Reviews)
1 Bedroom
1 Bath
4 Guests
650 ft²
Parking
Ocean View
Balcony/Terrace
View
US $374/Night
7 Nights - US $2,616
House
10.0(2 Reviews)
1 Bedroom
2 Baths
6 Guests
1603.82 ft²
Oceanfront- Parking
Pool- Ocean View
US $298/Night
7 Nights - US $2,089
Hotel
9.4(550 Reviews)
1 Bath
Breakfast- Pool
- Balcony/Terrace
Kitchen
US $114/Night
7 Nights - US $799
House
10.0(48 Reviews)
1 Bedroom
1 Bath
4 Guests
664 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $189/Night
7 Nights - US $1,322
House
10.0(1 Review)
2 Bedrooms
1 Bath
6 Guests
850.35 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $180/Night
7 Nights - US $1,260
Villa
10.0(45 Reviews)
2 Bedrooms
1 Bath
4 Guests
850 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $175/Night
7 Nights - US $1,224
Villa
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
2572.57 ft²
Private Beach- Oceanfront
- Parking
- Pool
US $329/Night
7 Nights - US $2,303
House
10.0(37 Reviews)
1 Bedroom
1 Bath
3 Guests
700 ft²
Private Pool- Oceanfront
- Parking
- Pool
US $224/Night
7 Nights - US $1,568
Resort
9.4(215 Reviews)
34 Baths
76 Guests
936.46 ft²
- Private Beach
- Oceanfront
- Parking
- Pool
US $269/Night
7 Nights - US $1,882
House
10.0(16 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $282/Night
7 Nights - US $1,975
House
9.2(23 Reviews)
3 Bedrooms
2 Baths
8 Guests
1851.39 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $282/Night
7 Nights - US $1,973
House
10.0(6 Reviews)
2 Bedrooms
2 Baths
6 Guests
950 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $218/Night
7 Nights - US $1,524
Why Choose Rent By Owner for your Casey Key Winter Rental?
What makes our Winter Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Casey Key
How to Book Your Casey Key Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Casey Key
Common Winter Rental Amenities
What amenities can you expect?
Our Winter Rental are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Casey Key, FL
North Jetty Beach
Nokomis Beach
Casey Key Winter Rental Frequently Asked Questions
1. What are the top Winter Rentals in Casey Key?
There are a lot of options in Casey Key. If you plan on staying in the Casey Key area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Casey Key:
- Bayshore Beach House - Walk to Nokomis Beach! Close to Siesta Key, Venice Beach
- Tropical Oasis Estate on Casey Key - Large Pool, Private Dock, Steps to Beach
- Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
- Welcome to your santuary! New 25 rates for oversized pool and quiet corner lot.
- Rare private beachfront estate on the Gulf.
- Beach time! Walk to the beach!
- LAKEFRONT-FREE KAYAKS, BICYCLES, PADDLEBOARDS-WALK, BICYCLE, OR PADDLE TO BEACH
- Family Friendly Beach Condo
- 3-bedroom house, beautiful pool and landscape, short walk to Casey Key Beach
- Canal-Front Luxury | Heated Saltwater Pool/Spa | Fishing Dock | Near the Beach!
2. How many Winter Rentals are available in Casey Key?
Currently, the total number of properties listed by RBO in 2026 is over 249 in the Casey Key area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Casey Key.
More Rentals You May Like Near Casey Key
House
3 Bedrooms
2 Baths
6 Guests
2787.85 ft²
Hot Tub- Parking
- View
Air Conditioner
US $317/Night
7 Nights - US $2,219
House
10.0(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Kitchen
- Air Conditioner
Internet
US $246/Night
7 Nights - US $1,721
Apartment
10.0(4 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $296/Night
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Condo
10.0(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $211/Night
7 Nights - US $1,480
House
10.0(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
1250 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $386/Night
7 Nights - US $2,703
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
7 Guests
800 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $286/Night
7 Nights - US $2,004
Condo
10.0(2 Reviews)
1 Bedroom
1 Bath
3 Guests
530 ft²
- Oceanfront
- Parking
- Pool
Spa
US $132/Night
7 Nights - US $927
House
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
1400 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $291/Night
7 Nights - US $2,036
House
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
1920 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $272/Night
7 Nights - US $1,904
House
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $270/Night
7 Nights - US $1,889
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
936 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $205/Night
7 Nights - US $1,434
House
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $205/Night
7 Nights - US $1,433
