Upper Harbor Key Cottage Rentals
Cottage
10.0(66 Reviews)
2 Bedrooms
1 Bath
6 Guests
700 ft²
Oceanfront
Ocean View
Balcony/Terrace
View
R8,665/Night
7 Nights - R60,657
Villa
9.2(16 Reviews)
2 Bedrooms
2 Baths
6 Guests
850.35 ft²
Private Beach- Oceanfront
Hot Tub
Pool
R14,679/Night
7 Nights - R102,755
Cottage
8.6(344 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
Fireplace/Heating- Pool
- Ocean View
R4,441/Night
7 Nights - R31,088
Cottage
10.0(44 Reviews)
1 Bedroom
1 Bath
4 Guests
- Pool
- Balcony/Terrace
Kitchen
Parking
R4,142/Night
7 Nights - R28,987
House
9.1(550 Reviews)
33 Bedrooms
4 Baths
18 Guests
398.26 ft²
- Fireplace/Heating
- Pool
Pet Friendly- Parking
R7,404/Night
7 Nights - R51,830
Cottage
10.0(2 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
R9,789/Night
7 Nights - R68,514
Resort
9.0(3 Reviews)
1 Bath
4 Guests
721.18 ft²
- Private Beach
- Oceanfront
- Hot Tub
Spa
R4,350/Night
7 Nights - R30,458
Cottage
10.0(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
R6,484/Night
7 Nights - R45,396
Villa
7.8(19 Reviews)
2 Bedrooms
2 Baths
6 Guests
753.47 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
R7,338/Night
7 Nights - R51,361
Cottage
9.8(218 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
R5,678/Night
7 Nights - R39,737
Cottage
9.8(132 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
R6,130/Night
7 Nights - R42,906
Cottage
9.8(62 Reviews)
1 Bedroom
1 Bath
4 Guests
550 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R3,998/Night
7 Nights - R27,984
Why Choose Rent By Owner for your Upper Harbor Key Cottage Rentals?
What makes our Cottage Rentals special?
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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
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Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Upper Harbor Key
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.
- waterfront cottage near key west, sleeps 6
- Cottage with Pool and Dockage, just minutes to Key West
- Fishermen’s Paradise
- 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!
- A slice of paradise
- Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
- Waterfront Home
2. How many Cottages are available in Upper Harbor Key?
Currently, the total number of properties listed by RBO in 2026 is over 77 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
Cottage
9.8(55 Reviews)
1 Bedroom
1 Bath
4 Guests
480 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R4,377/Night
7 Nights - R30,636
Cottage
9.8(48 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
R7,090/Night
7 Nights - R49,631
Cottage
9.8(46 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R3,918/Night
7 Nights - R27,435
Cottage
9.8(41 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
R3,289/Night
7 Nights - R23,021
Cottage
9.8(30 Reviews)
3 Bedrooms
2 Baths
6 Guests
872 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
R10,464/Night
7 Nights - R73,251
Cottage
9.8(25 Reviews)
2 Bedrooms
2 Baths
4 Guests
1082 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R3,220/Night
7 Nights - R22,536
Cottage
9.8(6 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R10,136/Night
7 Nights - R70,955
Cottage
9.6(55 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
R5,413/Night
7 Nights - R37,894
Cottage
9.6(35 Reviews)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
R4,067/Night
7 Nights - R28,469
Cottage
9.6(14 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
R5,022/Night
7 Nights - R35,162
Cottage
9.6(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
800 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
R4,953/Night
7 Nights - R34,661
Cottage
9.4(32 Reviews)
2 Bedrooms
2 Baths
8 Guests
1500 ft²
- Pool
- Pet Friendly
- Kitchen
- Parking
R7,060/Night
7 Nights - R49,421
