Upper Harbor Key Holiday Homes
864 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $958/Night
For 7 Nights US $6,708
2798.62 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Villa
- Private Beach
- Oceanfront
- Hot Tub
US $811/Night
For 7 Nights US $5,676
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
US $1,097/Night
For 7 Nights US $7,678
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Kitchen
- Air Conditioner
- Internet
US $670/Night
For 7 Nights US $4,693
2228.13 ft²
10 Guests
5 Bedrooms
4 Bathrooms
House
- Pet Friendly
- Parking
- Air Conditioner
US $304/Night
For 7 Nights US $2,128
888 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $412/Night
For 7 Nights US $2,887
753.47 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Pool
US $454/Night
For 7 Nights US $3,177
1288 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Group Friendly
House
US $399/Night
For 7 Nights US $2,795
861.11 ft²
5 Guests
2 Bedrooms
2 Bathrooms
House
- Private Beach
- Oceanfront
- Hot Tub
US $304/Night
For 7 Nights US $2,125
6 Guests
2 Bedrooms
3 Bathrooms
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $387/Night
For 7 Nights US $2,709
850.35 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Villa
- Private Beach
- Oceanfront
- Hot Tub
US $908/Night
For 7 Nights US $6,356
1200 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Pool
- Ocean View
US $481/Night
For 7 Nights US $3,368
Why Choose Rent By Owner for your Upper Harbor Key Holiday Homes?
What makes our Holiday Homes 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 Holiday Homes
What's our booking process?
Our platform allows you to browse a curated selection of holiday homes. 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 Holiday Homes Amenities
What amenities can you expect?
Our Holiday Homes 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
Upper Harbor Key Holiday Homes Frequently Asked Questions
1. What are the top Holiday Homes 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 Holiday Homes in Upper Harbor Key:
- White Home - Receive 400 dollars ntowards a BOAT RENTAL!
- Blue Home - Receive 400 dollars ntowards a BOAT RENTAL!
- Yellow Home - Receive 400 dollars ntowards a BOAT RENTAL!
- Beautiful Oceanfront Home on Ramrod Key - Three Lots, Dock & Poolside Tiki Bar
- Waterfront Beach Houses with Dock & Heated Pool!
- Island Sunrise Resort- 3 acre estate with open water sunrises.
- Awesome Open Water View at Blue Heron Estate
- Starfish - Ocean front with dock and pool
- Looking for a place to stay?
- A Tropical Luxury Getaway, Your own private resort!
2. How many Holiday Homes are available in Upper Harbor Key?
Currently, the total number of properties listed by RBO in 2026 is over 1204 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 Holiday Homes in Upper Harbor Key.
More Rentals You May Like Near Upper Harbor Key
398.26 ft²
18 Guests
33 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Pet Friendly
US $458/Night
For 7 Nights US $3,206
1200 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $553/Night
For 7 Nights US $3,868
1200 ft²
6 Guests
1 Bedroom
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $525/Night
For 7 Nights US $3,678
1200 ft²
6 Guests
2 Bedrooms
4 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $605/Night
For 7 Nights US $4,237
960 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $159/Night
For 7 Nights US $1,116
700 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Ocean View
- Balcony/Terrace
US $536/Night
For 7 Nights US $3,752
864 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $578/Night
For 7 Nights US $4,048
1296 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $495/Night
For 7 Nights US $3,468
864 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $436/Night
For 7 Nights US $3,053
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $733/Night
For 7 Nights US $5,132
US $297/Night
For 7 Nights US $2,080
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Pool
- Balcony/Terrace
- Kitchen
US $255/Night
For 7 Nights US $1,788
