Cottage
10.0(47 Reviews)
1 Bedroom
1 Bath
4 Guests
Parking
Pool
Balcony/Terrace
Kitchen
AU $405/Night
7 Nights - AU $2,837
Upper Harbor Key Cottage Rentals
10.0
Villa
9.2(16 Reviews)
2 Bedrooms
2 Baths
6 Guests
850.35 ft²
Private Beach
Oceanfront
Hot Tub- Parking
AU $827/Night
7 Nights - AU $5,790
Cottage
8.6(373 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Parking
- Pool
Ocean View
AU $364/Night
7 Nights - AU $2,551
Cottage
10.0(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $692/Night
7 Nights - AU $4,847
House
9.1(550 Reviews)
33 Bedrooms
4 Baths
18 Guests
398.26 ft²
- Parking
- Pool
Air Conditioner
Internet
AU $241/Night
7 Nights - AU $1,684
Cottage
9.8(220 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $659/Night
7 Nights - AU $4,614
Resort
8.7(6 Reviews)
1 Bath
4 Guests
721.18 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Parking
AU $319/Night
7 Nights - AU $2,233
Cottage
9.8(64 Reviews)
1 Bedroom
1 Bath
4 Guests
550 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
AU $438/Night
7 Nights - AU $3,065
Villa
7.8(19 Reviews)
2 Bedrooms
2 Baths
6 Guests
753.47 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $703/Night
7 Nights - AU $4,925
Cottage
9.8(57 Reviews)
1 Bedroom
1 Bath
4 Guests
480 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
AU $512/Night
7 Nights - AU $3,587
New
House
2 Bedrooms
2 Baths
4 Guests
796.53 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
AU $604/Night
7 Nights - AU $4,228
Cottage
9.8(49 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
AU $468/Night
7 Nights - AU $3,275
Why Choose Rent By Owner for your Upper Harbor Key Cottage Rentals?
What makes our Cottage Rentals 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 Upper Harbor Key
How to Book Your Upper Harbor Key Cottage Rentals
What's our booking process?
Our platform allows you to browse a curated selection of cottage rentals. 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.
Common Cottage Rentals Amenities
What amenities can you expect?
Our Cottage Rentals 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 Upper Harbor Key Rental Cottages
1. What are the top Cottages in Upper Harbor Key?
There are a lot of options in Upper Harbor Key. If you plan on staying in the Upper Harbor Key area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Cottages in Upper Harbor Key:
- Peaceful ocean front cottage.
- Cozy, Perfect Conch Cottage! - VO315
- Cottage with swimming pool and dockage, just minutes to Key West!
- Quaint cottage, pool, dockage just minutes to Key West!
- Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
- Private Oceanfront Cottage with dockage, pool just minutes to Key West!
- Canal front, dockage, 2 bedroom, 2 bath
- water at your back door
- NAUTILUS.ocean front cottage retreat ~
- Canal Front home with easy Ocean access
2. How many Cottages are available in Upper Harbor Key?
Currently, the total number of properties listed by RBO in 2026 is over 71 in the Upper Harbor Key area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Upper Harbor Key.
More Rentals You May Like Near Upper Harbor Key
House
2 Bedrooms
1 Bath
6 Guests
645.83 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
AU $575/Night
7 Nights - AU $4,026
Cottage
9.8(32 Reviews)
2 Bedrooms
2 Baths
6 Guests
875 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $681/Night
7 Nights - AU $4,771
Cottage
9.8(25 Reviews)
2 Bedrooms
2 Baths
4 Guests
1082 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $289/Night
7 Nights - AU $2,024
Cottage
9.8(17 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
AU $443/Night
7 Nights - AU $3,098
Cottage
9.8(6 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
AU $1,064/Night
7 Nights - AU $7,445
Cottage
9.6(55 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $479/Night
7 Nights - AU $3,357
Cottage
9.6(53 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $658/Night
7 Nights - AU $4,608
Cottage
9.6(47 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
AU $357/Night
7 Nights - AU $2,498
Cottage
9.6(35 Reviews)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $487/Night
7 Nights - AU $3,409
Cottage
9.6(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
800 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $537/Night
7 Nights - AU $3,757
Cottage
9.4(35 Reviews)
2 Bedrooms
2 Baths
8 Guests
1500 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
AU $851/Night
7 Nights - AU $5,958
Cottage
9.4(29 Reviews)
2 Bedrooms
1 Bath
6 Guests
926 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $653/Night
7 Nights - AU $4,568
