Crawl Key Winter Rental
2217 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
AU $1,029/Night
For 7 Nights AU $7,204
3003.13 ft²
12 Guests
5 Bedrooms
6 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
AU $1,706/Night
For 7 Nights AU $11,945
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Pool
- Balcony/Terrace
- View
AU $413/Night
For 7 Nights AU $2,890
880 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
AU $501/Night
For 7 Nights AU $3,505
1367.02 ft²
10 Guests
1 Bedroom
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $937/Night
For 7 Nights AU $6,562
880 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
AU $397/Night
For 7 Nights AU $2,778
AU $314/Night
For 7 Nights AU $2,195
5 Guests
3 Bedrooms
1 Bathroom
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
AU $588/Night
For 7 Nights AU $4,117
525.28 ft²
46 Guests
16 Bathrooms
Free Cancellation
Resort
- Private Beach
- Oceanfront
- Hot Tub
AU $282/Night
For 7 Nights AU $1,972
634 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
AU $500/Night
For 7 Nights AU $3,500
2045.14 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Air Conditioner
- Internet
AU $1,347/Night
For 7 Nights AU $9,432
1280 ft²
4 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Private Pool
- Fireplace/Heating
- Pool
AU $481/Night
For 7 Nights AU $3,369
Why Choose Rent By Owner for your Crawl 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 Crawl Key
How to Book Your Crawl 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 Crawl 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
Frequently Asked Questions About Crawl Key Winter Rentals
1. What are the top Winter Rentals in Crawl Key?
There are a lot of options in Crawl Key. If you plan on staying in the Crawl 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 Crawl Key:
- Key Lime Kottage- Waterfront Home on Gulf of Mexico w/Private Pool, Dock & More
- Sunset Catch- Gulf Front, Open Water Views, Private Pool and Dock, Kayaks.
- Waterfront! Why rent on a canal when you can be on Bonefish Bay.Newly Remodeled
- Waterfront, 100ft Dock, Kayaks, Bikes, Pool, Hot Tub, Basketball & Pickleball
- Private, Gated, Oceanfront, Beachfront 5-Star Estate with dock, putting green.
- Grouper House: 4 Masters/6 BA, Pool/Dock, BoatRamp
- Perfect 7-Night Keys Getaway: Pool, Tiki & Dock
- Outstanding pool and outdoor area 5 minute walk to beach!
- Pirate Point, Luxe 5BR Escape w/Pool, Tiki, & Dock Minutes from the Beach
- Waterfront - 5 BR, 4 BA, Pool w Tub, 80' Dock, Tiki Hut, Beach Nearby, Parking
2. How many Winter Rentals are available in Crawl Key?
Currently, the total number of properties listed by RBO in 2026 is over 408 in the Crawl Key area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Crawl Key.
More Rentals You May Like Near Crawl Key
1485.42 ft²
6 Guests
1 Bedroom
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
AU $762/Night
For 7 Nights AU $5,335
900 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
AU $480/Night
For 7 Nights AU $3,359
900 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
AU $382/Night
For 7 Nights AU $2,673
1280 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Private Pool
- Oceanfront
- Fireplace/Heating
AU $506/Night
For 7 Nights AU $3,543
990 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Pool
AU $543/Night
For 7 Nights AU $3,801
1100 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Pool
- Ocean View
- Balcony/Terrace
AU $353/Night
For 7 Nights AU $2,473
925 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
AU $363/Night
For 7 Nights AU $2,544
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
AU $650/Night
For 7 Nights AU $4,552
1450 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
AU $634/Night
For 7 Nights AU $4,441
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
AU $385/Night
For 7 Nights AU $2,695
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
AU $388/Night
For 7 Nights AU $2,714
924 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
AU $608/Night
For 7 Nights AU $4,259
