Upper Harbor Key Oceanfront Vacation Rentals
864 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
ZA R15,703/Night
For 7 Nights ZA R109,927
2798.62 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Villa
- Private Beach
- Oceanfront
- Hot Tub
ZA R13,287/Night
For 7 Nights ZA R93,015
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
ZA R17,975/Night
For 7 Nights ZA R125,823
888 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
ZA R6,760/Night
For 7 Nights ZA R47,311
753.47 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Pool
ZA R7,438/Night
For 7 Nights ZA R52,063
1200 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Pool
- Ocean View
ZA R7,884/Night
For 7 Nights ZA R55,193
861.11 ft²
5 Guests
2 Bedrooms
2 Bathrooms
House
- Private Beach
- Oceanfront
- Hot Tub
ZA R4,975/Night
For 7 Nights ZA R34,823
1200 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
ZA R9,055/Night
For 7 Nights ZA R63,387
850.35 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Villa
- Private Beach
- Oceanfront
- Hot Tub
ZA R14,880/Night
For 7 Nights ZA R104,159
1200 ft²
6 Guests
1 Bedroom
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
ZA R8,610/Night
For 7 Nights ZA R60,273
1194.79 ft²
30 Guests
10 Bedrooms
15 Bathrooms
Ocean View
House
- Private Beach
- Oceanfront
- Fireplace/Heating
ZA R9,562/Night
For 7 Nights ZA R66,927
1200 ft²
6 Guests
2 Bedrooms
4 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
ZA R9,919/Night
For 7 Nights ZA R69,434
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.
Explore and book the perfect rental in Upper Harbor Key
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!
- 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!
- Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!
- ISLAND PARADISE
- Oceanfront Rental With Heated Pool, Dock & Tiki Hut
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
721.18 ft²
4 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Resort
- Private Beach
- Oceanfront
- Hot Tub
ZA R4,410/Night
For 7 Nights ZA R30,874
960 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
ZA R2,612/Night
For 7 Nights ZA R18,288
700 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Ocean View
- Balcony/Terrace
ZA R8,784/Night
For 7 Nights ZA R61,486
864 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
ZA R9,477/Night
For 7 Nights ZA R66,337
1296 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
ZA R8,119/Night
For 7 Nights ZA R56,832
864 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
ZA R7,148/Night
For 7 Nights ZA R50,031
ZA R4,870/Night
For 7 Nights ZA R34,086
850 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Fireplace/Heating
ZA R10,876/Night
For 7 Nights ZA R76,136
1152 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
ZA R4,231/Night
For 7 Nights ZA R29,612
1000 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
ZA R3,045/Night
For 7 Nights ZA R21,320
1300 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
ZA R5,906/Night
For 7 Nights ZA R41,346
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
ZA R7,290/Night
For 7 Nights ZA R51,031
