Upper Matecumbe Key Vacation Rentals

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Our top choices for Upper Matecumbe Key vacation rentals

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (70 reviews)
"Amazing stay, can’t wait to stay there again!"
United States
Anonymous traveler
$602 nightly
The price is $677
Jan 28 - Jan 29
Total with taxes and fees
The Islands of Islamorada

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (615 reviews)
"Friendly staff, beautiful peaceful beach, great room with a big comfy bed and all that you might need. "
United States
Alexander
$226 nightly
The price is $254
Jan 28 - Jan 29
Total with taxes and fees
Breezy Palms Resort

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Matecumbe
$1,142 nightly
The price is $1,267
Feb 2 - Feb 3
Total with taxes and fees
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite

Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room

Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
Matecumbe
$1,142 nightly
The price is $1,267
Feb 2 - Feb 3
Total with taxes and fees
Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Matecumbe
$1,713 nightly
The price is $1,901
Feb 2 - Feb 3
Total with taxes and fees
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
$1,849 nightly
The price is $2,051
Feb 2 - Feb 3
Total with taxes and fees
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite

Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
Matecumbe
$1,860 nightly
The price is $2,064
Feb 2 - Feb 3
Total with taxes and fees
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite

Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite

Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
Matecumbe
$2,169 nightly
The price is $2,406
Feb 2 - Feb 3
Total with taxes and fees
Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
Matecumbe
$2,282 nightly
The price is $2,532
Feb 2 - Feb 3
Total with taxes and fees
Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite

Charming Suite @Islamorada With Pool Access - Twilight Suite

Charming Suite @Islamorada With Pool Access - Twilight Suite
Matecumbe
$2,284 nightly
The price is $2,534
Feb 2 - Feb 3
Total with taxes and fees
Charming Suite @Islamorada With Pool Access - Twilight Suite

Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite

Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
Matecumbe
$3,426 nightly
The price is $3,801
Feb 2 - Feb 3
Total with taxes and fees
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (127 reviews)
"There were a few problems with the room when we arrived but the staff took care of it promptly. The stay was very relaxing. Manatees off the bow of the boat every day. It was our second trip here and hope to come back again. "
United States
Lamar
$259 nightly
The price is $292
Jan 30 - Jan 31
Total with taxes and fees
Treasure Harbor

Premium Floating Bungalow by Stay Ombi

Premium Floating Bungalow by Stay Ombi
3.5 star property
Key Largo
10.0 out of 10, Exceptional, (1 review)
$1,259 nightly
The price is $1,417
Jan 27 - Jan 28
Total with taxes and fees
Premium Floating Bungalow by Stay Ombi

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.8 out of 10, Exceptional, (14 reviews)
"It exceeded our expectations, and we are so glad we found this location!"
United States
Jenn H.
$372 nightly
The price is $413
Jan 27 - Jan 28
Total with taxes and fees
Island Sanctuary Islamorada

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (43 reviews)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
$352 nightly
The price is $391
Feb 4 - Feb 5
Total with taxes and fees
Amazing Ocean view condo

Beachfront Retreat w Pool, Boat Ramp & Dock Rental

Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Key Largo
10.0 out of 10, Exceptional, (6 reviews)
$343 nightly
The price is $381
Feb 1 - Feb 2
Total with taxes and fees
Beachfront Retreat w Pool, Boat Ramp & Dock Rental

Beautiful Kawama Townhouse

Beautiful Kawama Townhouse
Key Largo
9.8 out of 10, Exceptional, (141 reviews)
"Great location, well stocked kitchen, bathrooms, etc. Excellent host, had a great time in a beautiful community. The lagoon is a great feature."
United States
jannet p.
$1,054 nightly
The price is $1,170
Feb 15 - Feb 16
Total with taxes and fees
Beautiful Kawama Townhouse

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (30 reviews)
"Great location. Very clean very nice, stay there again"
United States
Mark B.
$461 nightly
The price is $513
Feb 21 - Feb 22
Total with taxes and fees
Charming Home in Key Largo

Spacious 4BR/3BA • 8 Beds • Mariner’s Club Community • Perfect for Large Groups

Spacious 4BR/3BA • 8 Beds • Mariner’s Club Community • Perfect for Large Groups
Rock Harbor
10.0 out of 10, Exceptional, (71 reviews)
"Well organized, clean, beds and pillows were very comfortable, quit and very relaxing.If you are looking for a place to stay while diving, I would highly recommend staying here."
United States
Tracy M.
$1,205 nightly
The price is $1,337
Feb 12 - Feb 13
Total with taxes and fees
Spacious 4BR/3BA • 8 Beds • Mariner’s Club Community • Perfect for Large Groups

The place to go when you want to get away!

The place to go when you want to get away!
Key Largo
10.0 out of 10, Exceptional, (72 reviews)
"Perfect spot!"
United States
Jennifer A.
The place to go when you want to get away!
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 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 $254 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.