Upper Matecumbe Key Holiday Rentals

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Holiday Rentals in Upper Matecumbe Key

Breezy Palms Resort

2.5 star property
Matecumbe
8.8 out of 10, Excellent, (562)
"This is one of my top 5 spot to stay in the keys, clean, friendly and budget friendly, mimi is awesome "
United States
franklin
The price is NZ$216
includes taxes & fees
16 Nov - 17 Nov
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (68)
"Beautiful property!"
United States
Betty
The price is NZ$1,448
includes taxes & fees
13 Nov - 14 Nov
The Islands of Islamorada

Treasure Harbor

3.0 star property
Islamorada
9.0 out of 10, Wonderful, (109)
"Unique House boat experience, friendly staff. "
United States
Luis
Treasure Harbor

Island Bay Resort

2.5 star property
Tavernier
10.0 out of 10, Exceptional, (135)
"Beautiful, well maintained, small resort with a nice beach area. "
United States
Robert
The price is NZ$495
includes taxes & fees
17 Nov - 18 Nov
Island Bay Resort

Key Largo Cottages

2.5 star property
Key Largo
9.6 out of 10, Exceptional, (26)
"Tropical paradise the way it's supposed to be! The staff are super friendly and helpful. They make you feel at home."
United States
Pamela P
Key Largo Cottages

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Key Largo
9.6 out of 10, Exceptional, (81)
"Very cozy tiny home"
United States
Kristen H.
The price is NZ$646
includes taxes & fees
18 Nov - 19 Nov
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Paradise in Key Largo, FL

Key Largo
9.6 out of 10, Exceptional, (60)
"Beautiful property. We uh, I very much enjoyed our stay highly recommend we will stay here again"
United States
George D.
The price is NZ$523
includes taxes & fees
18 Nov - 19 Nov
Paradise in Key Largo, FL

BEACHFRONT POOL HOME

Key Largo
9.6 out of 10, Exceptional, (106)
"We spent an amazing week celebrating our 50th wedding anniversary one of our daughters 24th wedding anniversary one of our granddaughters 21st birthday!! Our group of 13 enjoyed the spa/pool and swimming on the beach along with very comfortable evenings cooking, visiting, and sleeping in the spacious home. "
United States
Clayton S.
BEACHFRONT POOL HOME

Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches

Duck Key
9.6 out of 10, Exceptional, (25)
"Loved our stay!"
United States
Jessica B.
Waterfront, dog-friendly home with beautiful canal view & 2 shaded porches

Piece of Paradise located at Hawks Cay in Duck Key

Duck Key
9.8 out of 10, Exceptional, (6)
"Great place and it’s a well kept unit. The owner was very helpful. Having our pool was great for the little ones. "
United States
Joe S.
Piece of Paradise located at Hawks Cay in Duck Key

Mariners Club Oceanfront Condo, Water views from every room, Tennis & Pickleball

Rock Harbor
10.0 out of 10, Exceptional, (134)
"Great place to stay!"
United States
Nicole P.
Mariners Club Oceanfront Condo, Water views from every room, Tennis & Pickleball

Oceanfront Community, Luxury,Beach,Pools, TOP AMENITIES & VALUE in FLORIDA KEYS

Key Largo
10.0 out of 10, Exceptional, (195)
"Nice accommodations. "
United States
Jill M.
Oceanfront Community, Luxury,Beach,Pools, TOP AMENITIES & VALUE in FLORIDA KEYS

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Key Largo
9.6 out of 10, Exceptional, (123)
"Great location, friendly staff, awesome overall experience. Place was well kept and just what we were looking for. Will have to come back! "
United States
Baxter M.
The price is NZ$784
includes taxes & fees
18 Nov - 19 Nov
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,

Marathon
10.0 out of 10, Exceptional, (181)
"We spent four days with plenty of room. The house was spotless and any questions we had we addressed immediately. I highly recommend this location!"
United States
Pamela A.
Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,

Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.

Tavernier
9.6 out of 10, Exceptional, (60)
"Lovely Stay - clean, comfortable, cool AC, just the right amenities I needed."
United States
Kathleen P.
Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.

Condo with Pool and Beach Access

Tavernier
10.0 out of 10, Exceptional, (25)
"Easy check-in, clean and newly renovated condo. Well equipped/great communication from owners. Wonderful quick trip in the upper keys."
United States
bethany h.
Condo with Pool and Beach Access

Florida Keys Luxury Houseboat, Unique living on the Water WiFi

Tavernier
9.8 out of 10, Exceptional, (209)
"It was an amazing stay ,the onwer was great hostand it was great location"
United States
Alisha B.
The price is NZ$731
includes taxes & fees
16 Nov - 17 Nov
Florida Keys Luxury Houseboat, Unique living on the Water WiFi

Paradise in Key Largo Florida 2

Key Largo
9.8 out of 10, Exceptional, (41)
"The marina was very clean and the staff was friendly. Beautiful area."
United States
Mark F.
The price is NZ$516
includes taxes & fees
13 Nov - 14 Nov
Paradise in Key Largo Florida 2

Charming Home in Key Largo

Key Largo
9.8 out of 10, Exceptional, (26)
"Great location. Very clean very nice, stay there again"
United States
Mark B.
The price is NZ$813
includes taxes & fees
18 Nov - 19 Nov
Charming Home in Key Largo

New Key Largo Home in resort

Key Largo
9.2 out of 10, Wonderful, (43)
"House was fantastic. Just as advertised. Perfect for a large group."
United States
MICHAEL D.
New Key Largo Home in resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Upper Matecumbe Key Hotel Reviews

Find out more about Upper Matecumbe Key

Everything you need to know about Upper Matecumbe Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Upper Matecumbe Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Upper Matecumbe Key holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Upper Matecumbe Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Upper Matecumbe Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upper Matecumbe Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upper Matecumbe Key holiday rentals we have selected for you start as low as NZ$216 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Upper Matecumbe Key rentals

At Expedia, we put the best Upper Matecumbe Key holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Upper Matecumbe Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Upper Matecumbe Key holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upper Matecumbe Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.