Upper Harbor Key Oceanfront Vacation Rentals
House
10.0(181 Reviews)
2 Bedrooms
3 Baths
6 Guests
1195 ft²
Oceanfront
Parking
Pool
Ocean View
£361/Night
7 Nights - £2,529
House
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
861.11 ft²
- Oceanfront
Hot Tub- Parking
- Pool
£351/Night
7 Nights - £2,460
Cottage
8.6(351 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
£204/Night
7 Nights - £1,426
Cottage
10.0(67 Reviews)
2 Bedrooms
1 Bath
6 Guests
700 ft²
- Oceanfront
- Parking
- Ocean View
Balcony/Terrace
£459/Night
7 Nights - £3,213
House
9.2(21 Reviews)
2 Bedrooms
2 Baths
5 Guests
861.11 ft²
Private Beach- Oceanfront
- Hot Tub
- Parking
£249/Night
7 Nights - £1,742
House
10.0(56 Reviews)
2 Bedrooms
2 Baths
4 Guests
864 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
£693/Night
7 Nights - £4,850
Villa
9.2(16 Reviews)
2 Bedrooms
2 Baths
6 Guests
850.35 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Parking
£674/Night
7 Nights - £4,715
House
10.0(53 Reviews)
2 Bedrooms
2 Baths
6 Guests
1296 ft²
- Parking
- Ocean View
- Balcony/Terrace
View
£625/Night
7 Nights - £4,377
Resort
9.0(5 Reviews)
1 Bath
4 Guests
721.18 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Parking
£164/Night
7 Nights - £1,151
House
10.0(51 Reviews)
2 Bedrooms
2 Baths
6 Guests
864 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
£197/Night
7 Nights - £1,377
Resort
8.6(412 Reviews)
11 Baths
38 Guests
379.97 ft²
- Private Beach
- Oceanfront
Breakfast- Parking
£226/Night
7 Nights - £1,579
House
10.0(47 Reviews)
2 Bedrooms
2 Baths
6 Guests
864 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
£228/Night
7 Nights - £1,598
Why Choose Rent By Owner for your Upper Harbor Key Oceanfront Vacation Rentals?
What makes our Oceanfront Vacation 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 Oceanfront Vacation Rentals
What's our booking process?
Our platform allows you to browse a curated selection of oceanfront vacation 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 Oceanfront Vacation Rentals Amenities
What amenities can you expect?
Our Oceanfront Vacation 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 Oceanfront Rentals
1. What are the top Oceanfront 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 Oceanfront Rentals in Upper Harbor Key:
- Beautiful Oceanfront Home on Ramrod Key - Three Lots, Dock & Poolside Tiki Bar
- Waterfront Beach Houses with Dock & Heated Pool!
- Awesome Open Water View at Blue Heron Estate
- Island Sunrise Resort- 3 acre estate with open water sunrises.
- Starfish - Ocean front with dock and pool
- A Tropical Luxury Getaway, Your own private resort!
- Looking for a place to stay?
- Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!
- ISLAND PARADISE
- Night jasmine oceanfront vacation house
2. How many Oceanfront Rentals are available in Upper Harbor Key?
Currently, the total number of properties listed by RBO in 2026 is over 586 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 Oceanfront Rentals in Upper Harbor Key.
More Rentals You May Like Near Upper Harbor Key
House
8.5(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
850.35 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
£318/Night
7 Nights - £2,223
House
10.0(37 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
£272/Night
7 Nights - £1,905
Villa
10.0(25 Reviews)
2 Bedrooms
2 Baths
4 Guests
850 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
£520/Night
7 Nights - £3,639
House
10.0(18 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
£493/Night
7 Nights - £3,449
House
10.0(18 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
£150/Night
7 Nights - £1,051
House
10.0(13 Reviews)
2 Bedrooms
2 Baths
4 Guests
1300 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
£279/Night
7 Nights - £1,955
House
10.0(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
£360/Night
7 Nights - £2,523
House
10.0(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
990 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
£182/Night
7 Nights - £1,277
House
10.0(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
864 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
£369/Night
7 Nights - £2,582
House
10.0(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
£289/Night
7 Nights - £2,021
House
10.0(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
1141 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
£283/Night
7 Nights - £1,979
House
10.0(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
861 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
£279/Night
7 Nights - £1,952
