Upper Harbor Key Winter Rental
New
House
8.0(1 Review)
4 Bedrooms
3 Baths
8 Guests
2952 ft²
Private Pool
Oceanfront
Hot Tub
Fireplace/Heating
US $879/Night
7 Nights - US $6,154
House
10.0(1 Review)
1 Bedroom
2 Baths
4 Guests
861.11 ft²
- Oceanfront
- Hot Tub
Spa
Pool
US $474/Night
7 Nights - US $3,316
Villa
7.4(3 Reviews)
1 Bedroom
1 Bath
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $1,209/Night
7 Nights - US $8,466
House
10.0(213 Reviews)
2 Bedrooms
3 Baths
6 Guests
1200 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $490/Night
7 Nights - US $3,429
House
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
850.35 ft²
- Hot Tub
- Spa
- Pool
Pet Friendly
US $424/Night
7 Nights - US $2,970
House
10.0(47 Reviews)
2 Bedrooms
2 Baths
6 Guests
864 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $444/Night
7 Nights - US $3,108
House
9.4(6 Reviews)
2 Bedrooms
2 Baths
7 Guests
- Pet Friendly
Parking
Internet
Child Friendly
US $310/Night
7 Nights - US $2,170
Cottage
10.0(45 Reviews)
1 Bedroom
1 Bath
4 Guests
- Pool
Balcony/Terrace
Kitchen- Parking
US $284/Night
7 Nights - US $1,989
House
9.2(21 Reviews)
2 Bedrooms
2 Baths
5 Guests
861.11 ft²
Private Beach- Oceanfront
- Hot Tub
- Fireplace/Heating
US $336/Night
7 Nights - US $2,349
House
10.0(40 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $706/Night
7 Nights - US $4,942
Villa
9.2(16 Reviews)
2 Bedrooms
2 Baths
6 Guests
850.35 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Pool
US $908/Night
7 Nights - US $6,356
House
10.0(37 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
- Oceanfront
- Hot Tub
- Pool
Ocean View
US $370/Night
7 Nights - US $2,587
Why Choose Rent By Owner for your Upper Harbor 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 Upper Harbor Key
How to Book Your Upper Harbor 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 Upper Harbor 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 Upper Harbor Key Winter Rentals
1. What are the top Winter Rentals 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 Winter Rentals in Upper Harbor Key:
- Waterfront Beach Houses with Dock & Heated Pool!
- Beautiful Oceanfront Home on Ramrod Key - Three Lots, Dock & Poolside Tiki Bar
- Island Sunrise Resort- 3 acre estate with open water sunrises.
- Awesome Open Water View at Blue Heron Estate
- Oceanfront Home-Pool, Dock-Available Daily, Weekly or Monthly.
- Looking for a place to stay?
- A Tropical Luxury Getaway, Your own private resort!
- Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!
- ISLAND PARADISE
- Oceanfront Sunsets in the Florida Keys
2. How many Winter Rentals are available in Upper Harbor Key?
Currently, the total number of properties listed by RBO in 2026 is over 672 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 Winter Rentals in Upper Harbor Key.
More Rentals You May Like Near Upper Harbor Key
Resort
9.0(5 Reviews)
1 Bath
4 Guests
721.18 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Spa
US $207/Night
7 Nights - US $1,451
Villa
10.0(23 Reviews)
2 Bedrooms
2 Baths
4 Guests
850 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $600/Night
7 Nights - US $4,201
House
10.0(15 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $578/Night
7 Nights - US $4,043
House
10.0(13 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Parking
US $635/Night
7 Nights - US $4,447
House
10.0(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
864 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $430/Night
7 Nights - US $3,009
House
10.0(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
1150 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $349/Night
7 Nights - US $2,444
House
10.0(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
864 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $335/Night
7 Nights - US $2,343
House
10.0(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $306/Night
7 Nights - US $2,145
House
10.0(8 Reviews)
2 Bedrooms
2 Baths
4 Guests
864 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $1,083/Night
7 Nights - US $7,579
House
10.0(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
864 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $402/Night
7 Nights - US $2,811
House
10.0(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1353 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $346/Night
7 Nights - US $2,422
House
10.0(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
865 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $586/Night
7 Nights - US $4,099
