House
10.0(56 Reviews)
2 Bedrooms
4 Guests
Oceanfront
Hot Tub
Parking
Pool
US $933/Night
7 Nights - US $6,531
Upper Harbor Key Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Upper Harbor Key
10.0
House
10.0(1 Review)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $474/Night
7 Nights - US $3,316
House
10.0(1 Review)
1 Bedroom
- Parking
Balcony/Terrace
Internet
Pet Friendly
US $592/Night
7 Nights - US $4,142
House
10.0(55 Reviews)
2 Bedrooms
6 Guests
- Parking
Ocean View- Balcony/Terrace
View
US $652/Night
7 Nights - US $4,564
House
10.0(1 Review)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
Spa
US $424/Night
7 Nights - US $2,970
House
9.2(31 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
Air Conditioner- Internet
US $961/Night
7 Nights - US $6,727
House
10.0(51 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $321/Night
7 Nights - US $2,250
House
9.6(2 Reviews)
5 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $304/Night
7 Nights - US $2,128
Cottage
8.6(366 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $253/Night
7 Nights - US $1,772
House
10.0(47 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $321/Night
7 Nights - US $2,250
House
9.4(6 Reviews)
2 Bedrooms
7 Guests
- Parking
- Internet
- Pet Friendly
Child Friendly
US $310/Night
7 Nights - US $2,170
Cottage
10.0(47 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
Kitchen
US $282/Night
7 Nights - US $1,971
House
9.2(21 Reviews)
2 Bedrooms
5 Guests
Private Beach- Oceanfront
- Hot Tub
- Parking
US $495/Night
7 Nights - US $3,468
House
10.0(40 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $1,071/Night
7 Nights - US $7,494
House
10.0(13 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $645/Night
7 Nights - US $4,517
House
10.0(13 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $370/Night
7 Nights - US $2,592
House
10.0(12 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $481/Night
7 Nights - US $3,368
House
10.0(12 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $248/Night
7 Nights - US $1,735
House
10.0(10 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $500/Night
7 Nights - US $3,502
House
10.0(10 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $420/Night
7 Nights - US $2,942
House
10.0(10 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $379/Night
7 Nights - US $2,653
House
10.0(10 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $379/Night
7 Nights - US $2,650
House
10.0(9 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $903/Night
7 Nights - US $6,323
House
10.0(8 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $560/Night
7 Nights - US $3,920
About Casai's Private Villas and Holiday Rentals in Upper Harbor Key
Discover more than 1248 vacation rentals available in Upper Harbor Key. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Upper Harbor Key.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Upper Harbor Key, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Upper Harbor Key.
With Casai, finding and comparing holiday rentals in Upper Harbor Key is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
There are 1248 Upper Harbor Key, FL Holiday Rentals
- Prices for a holiday home in Upper Harbor Key start at US $68
- Top rated vacation home in Upper Harbor Key is Yellow Home - Receive 400 dollars towards a BOAT RENTAL!
- Most popular short term in Upper Harbor Key is Looe Key Reef Resort
- Cheapest place to stay in Upper Harbor Key is Charming shared 1-bedroom house with AC and WiFi also has a 37 foot dock
- Most expensive holiday rental in Upper Harbor Key is Florida Keys /Big Pine Key/ Dear Haven
Recently Booked Holiday Rentals in Upper Harbor Key
Frequently Asked Questions About Upper Harbor Key?
What are the top holiday rentals in Upper Harbor Key?
With numerous options available in Upper Harbor Key, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Upper Harbor Key:
- Yellow Home - Receive 400 dollars towards a BOAT RENTAL!
- Beautiful Oceanfront Home on Ramrod Key - Three Lots, Dock & Poolside Tiki Bar
- Barry Beach & Guesthouse
- Cozy Cottage
- Island Sunrise Resort- 3 acre estate with open water sunrises.
- Awesome Open Water View at Blue Heron Estate
- Post Card Point #319 - Ocean Views!
- A Tropical Luxury Getaway, Your own private resort!
- Oceanfront Home-Pool, Dock-Available Daily, Weekly or Monthly.
- Starfish - Ocean front with dock and pool
How many Casai.nz holiday rentals are available in Upper Harbor Key?
As of 2026, Casai boasts over 1248 properties listed in the Upper Harbor Key area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Upper Harbor Key.
Nearby Neighborhood (12)
| Neighborhood | Property Count |
|---|---|
| Cutthroat Harbor Estates Vacation Rentals in Florida | 71 |
| Breezeswept Beach Estates Vacation Rentals in Florida | 24 |
| Eden Pines Vacation Rentals in Florida | 454 |
| Doctor's Arm Vacation Rentals in Florida | 317 |
| Port Pine Heights Vacation Rentals in Florida | 114 |
| Pine Channel Estates Vacation Rentals in Florida | 493 |
| Sands Vacation Rentals in Florida | 371 |
| Cudjoe Gardens Vacation Rentals in Florida | 610 |
| Whispering Pines Vacation Rentals in Florida | 396 |
| Punta Brisa Vacation Rentals in Florida | 317 |
| Lambert Vacation Rentals in Florida | 301 |
| Tropical Bay Estates Vacation Rentals in Florida | 347 |
