Upper Matecumbe Key Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Upper Matecumbe Key vacation rentals

Aparthotel in Matecumbe

Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (637 reviews)
"We enjoyed our stay! This was a better experience than the more expensive house one I paid in Key West. "
United States
Wendy
$239 nightly
The price is $268
Mar 24 - Mar 25
Total with taxes and fees
Breezy Palms Resort

Villa in Matecumbe

The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (72 reviews)
"Beautiful accommodations and location, very clean, many activities available at resort"
United States
Janet
$748 nightly
The price is $842
Apr 13 - Apr 14
Total with taxes and fees
The Islands of Islamorada
$3,426 nightly
The price is $3,801
Mar 23 - Mar 24
Total with taxes and fees
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
$2,284 nightly
The price is $2,534
Mar 23 - Mar 24
Total with taxes and fees
Charming Suite @Islamorada With Pool Access - Twilight Suite
$2,282 nightly
The price is $2,532
Mar 23 - Mar 24
Total with taxes and fees
Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
$2,169 nightly
The price is $2,406
Mar 23 - Mar 24
Total with taxes and fees
Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
$1,860 nightly
The price is $2,064
Mar 23 - Mar 24
Total with taxes and fees
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
$1,849 nightly
The price is $2,051
Mar 23 - Mar 24
Total with taxes and fees
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
$1,713 nightly
The price is $1,901
Mar 23 - Mar 24
Total with taxes and fees
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
$1,142 nightly
The price is $1,267
Mar 23 - Mar 24
Total with taxes and fees
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
$1,142 nightly
The price is $1,267
Mar 23 - Mar 24
Total with taxes and fees
Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room

Houseboat in Islamorada

Treasure Harbor
3.0 star property
9.0 out of 10, Wonderful, (144 reviews)
"Staff was great, rooms clean, views excellent"
United States
Diane
$272 nightly
The price is $307
Mar 29 - Mar 30
Total with taxes and fees
Treasure Harbor

Mobile Home in Key Largo

Paradise in Key Largo, FL
9.8 out of 10, Exceptional, (66 reviews)
"We really enjoyed our stay here .. the place was clean — had everything we needed… thanks for sharing your place.."
United States
brenda b.
$278 nightly
The price is $309
Mar 22 - Mar 23
Total with taxes and fees
Paradise in Key Largo, FL

Houseboat in Tavernier

Island Sanctuary Islamorada
9.8 out of 10, Exceptional, (18 reviews)
"An amazing place to switch gears. Great host. Win/win."
United States
Alex Z.
$380 nightly
The price is $421
Mar 27 - Mar 28
Total with taxes and fees
Island Sanctuary Islamorada

Aparthotel in Tavernier

Island Bay Resort
2.5 star property
10.0 out of 10, Exceptional, (152 reviews)
"Wonderful property and staff. Quite and beautiful!. "
United States
Ethan
$314 nightly
The price is $354
Apr 16 - Apr 17
Total with taxes and fees
Island Bay Resort
9.6 out of 10, Exceptional, (7 reviews)
"Great area"
United States
Yesenia
$458 nightly
The price is $499
Mar 23 - Mar 24
Total with taxes and fees
Reel Key Largo Escape Ocean Pointe 5209

Vacation Home in Key Largo

Charming Home in Key Largo
9.8 out of 10, Exceptional, (33 reviews)
"Very nice place and definitely would stay there again! Very nice host and redponded on time."
United States
Amey P.
$384 nightly
The price is $426
Mar 29 - Mar 30
Total with taxes and fees
Charming Home in Key Largo
9.6 out of 10, Exceptional, (46 reviews)
"I really enjoyed our stay at the campsite. The home is right on the water with plenty of activities to do. Also the grocery store and places to eat are only a few minutes away. "
United States
Everett S.
$365 nightly
The price is $406
Apr 14 - Apr 15
Total with taxes and fees
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
9.8 out of 10, Exceptional, (152 reviews)
"Great stay lovely home "
United States
Yezenia
$458 nightly
The price is $499
Mar 23 - Mar 24
Total with taxes and fees
3212 Across from Pool * King & Queen/Twin Bunk Bed
8.6 out of 10, Excellent, (90 reviews)
"It was very clean. Pet friendly. Everybody at the campground is wonderful."
United States
Tammie F.
$314 nightly
The price is $350
Apr 14 - Apr 15
Total with taxes and fees
2 BR/2 BA Oasis w Kayak, Pool, Beach & Dock Rental
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Upper Matecumbe Key Hotel Reviews

Find out more about Upper Matecumbe Key

Everything you need to know about Upper Matecumbe Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Upper Matecumbe Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Upper Matecumbe Key vacation 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 low season months. For more hustle and bustle, you may prefer to visit Upper Matecumbe Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $268 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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.