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
9.6 out of 10, Exceptional, (75 reviews)
"What a wonderful venue for our last 2 nights in the Keys. This place is a hidden gem. The entire staff, especially Edith, the bartender, were fantastic."
United States
Michael
$627 nightly
The price is $705
May 14 - May 15
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, (671 reviews)
"Place was nicer inside than out. Great location."
United States
Marcos
$144 nightly
The price is $162
May 10 - May 11
Total with taxes and fees
Breezy Palms Resort

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
May 16 - May 17
Total with taxes and fees
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Sunset Access + Boat Basin | Walkable Islamorada

Sunset Access + Boat Basin | Walkable Islamorada
Matecumbe
10.0 out of 10, Exceptional, (45 reviews)
"Great location, stay, and nice to have the boat slip in the back yard. Will book again."
United States
Orion T.
$479 nightly
The price is $523
May 25 - May 26
Total with taxes and fees
Sunset Access + Boat Basin | Walkable Islamorada

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (153 reviews)
"Amazing stay!"
United States
Amanda
$267 nightly
The price is $300
May 10 - May 11
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, (2 reviews)
$926 nightly
The price is $1,042
Jun 1 - Jun 2
Total with taxes and fees
Premium Floating Bungalow by Stay Ombi

2 BR/2 BA Oasis w Kayak, Pool, Beach & Dock Rental

2 BR/2 BA Oasis w Kayak, Pool, Beach & Dock Rental
Key Largo
8.6 out of 10, Excellent, (92 reviews)
"Great stay for the price"
United States
William B J.
$289 nightly
The price is $321
May 27 - May 28
Total with taxes and fees
2 BR/2 BA Oasis w Kayak, Pool, Beach & Dock Rental

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (168 reviews)
"Very nice small resort."
United States
Dan
$280 nightly
The price is $315
Jun 7 - Jun 8
Total with taxes and fees
Island Bay Resort

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
Key Largo
9.6 out of 10, Exceptional, (127 reviews)
"Great place, great view, great hosts. No complaints about a thing. Publix is 2 minutes away, the campground is peaceful, house was clean. There were 4 of us and we had plenty of room. Will do that again"
United States
Joe J.
$432 nightly
The price is $482
May 10 - May 11
Total with taxes and fees
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Oceanside Kawama Villa R5

Oceanside Kawama Villa R5
Key Largo
9.2 out of 10, Wonderful, (180 reviews)
"Very very nice villa in a superb location… Abcolutely loved the property!"
United States
Ricardo G.
$575 nightly
The price is $636
May 11 - May 12
Total with taxes and fees
Oceanside Kawama Villa R5

LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Key Largo
9.4 out of 10, Exceptional, (66 reviews)
"Nice location with 5 min walk to ocean view. "
United States
Trevor P.
$517 nightly
The price is $574
May 10 - May 11
Total with taxes and fees
LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

Beautiful Kawama Townhouse

Beautiful Kawama Townhouse
Key Largo
9.8 out of 10, Exceptional, (147 reviews)
"The host, house and amenities were perfect. all praises.."
United States
Pete S.
$581 nightly
The price is $645
May 17 - May 18
Total with taxes and fees
Beautiful Kawama Townhouse

Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.8 out of 10, Excellent, (43 reviews)
"Rooms were spacious and a short drive to most of the attractions we wanted to do. Rooms and bathrooms were gorgeous!"
United States
Cindy
$390 nightly
The price is $432
May 11 - May 12
Total with taxes and fees
Ocean view condo with balcony/marina view

Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
Key Largo
9.6 out of 10, Exceptional, (137 reviews)
"My family and I had a great time. The place was very comfortable. Location was great and we enjoyed all the amenities. Great experience over all."
United States
Raul e.
$602 nightly
The price is $667
May 14 - May 15
Total with taxes and fees
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

3212 Across from Pool * King & Queen/Twin Bunk Bed

3212 Across from Pool * King & Queen/Twin Bunk Bed
Tavernier
9.8 out of 10, Exceptional, (157 reviews)
"Really enjoyed the location and the unit. "
United States
Teresa L.
$429 nightly
The price is $467
May 10 - May 11
Total with taxes and fees
3212 Across from Pool * King & Queen/Twin Bunk Bed

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Key Largo
10.0 out of 10, Exceptional, (54 reviews)
"super nice and modern house, really lovely host, the kitchen is equipped with all you need for cookingall decoration is so nice fits to the beach feelingall rooms are modern and nice decoratedwe could just recommend ! if we will come back to Florida this will be again our choice!"
United States
Anonymous traveler
$581 nightly
The price is $645
May 18 - May 19
Total with taxes and fees
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

Dazzling Ocean Pointe -OP-Main

Dazzling Ocean Pointe -OP-Main
Tavernier
9.0 out of 10, Wonderful, (95 reviews)
"Right in the heart of Key Largo but just off the beaten path. Clean, comfortable and cozy. The property has a beach, pool and restaurant which was convenient after a long day of travel."
United States
jodi
$294 nightly
The price is $327
May 11 - May 12
Total with taxes and fees
Dazzling Ocean Pointe -OP-Main

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Tavernier
9.8 out of 10, Exceptional, (240 reviews)
"Great place to stay"
United States
Llonda B.
$455 nightly
The price is $504
May 22 - May 23
Total with taxes and fees
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Key Largo Ocean Shore Villa 3 with pool & boat slip

Key Largo Ocean Shore Villa 3 with pool & boat slip
Key Largo
9.8 out of 10, Exceptional, (135 reviews)
"Beautiful, clean stay in Key Largo with views of the inlet, and kayaks on site to explore from! The unit had everything my family needed and we loved our 3 nights here."
United States
Heather W.
$529 nightly
The price is $586
May 13 - May 14
Total with taxes and fees
Key Largo Ocean Shore Villa 3 with pool & boat slip

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (165 reviews)
"Very nice place. Clean and easy to contact the host."
United States
Bonnie H.
$389 nightly
The price is $432
May 10 - May 11
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
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

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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.

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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 $162 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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