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Upper Matecumbe Key Vacation Rentals

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Our top choices for Upper Matecumbe Key vacation rentals

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (704 reviews)
"Enjoyed this place."
United States
Christopher
$127 nightly
The price is $143
Jul 7 - Jul 8
Total with taxes and fees
Breezy Palms Resort

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (77 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
$688 nightly
The price is $774
Jul 6 - Jul 7
Total with taxes and fees
The Islands of Islamorada

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
Jul 12 - Jul 13
Total with taxes and fees
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.8 out of 10, Exceptional, (7 reviews)
"Easy check in if you come After business hours. Kayaks and sport equipment available. Has a small beach which is unique to the Keys. Pool pretty much vacant at all times. Great views. Highly recommend."
United States
Dana
$275 nightly
The price is $309
Jul 13 - Jul 14
Total with taxes and fees
Caloosa Cove Resort by CoolVacay

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (162 reviews)
"Amazing stay!"
United States
Amanda
$260 nightly
The price is $293
Jul 6 - Jul 7
Total with taxes and fees
Treasure Harbor

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (172 reviews)
"Very nice small resort."
United States
Dan
$270 nightly
The price is $303
Aug 2 - Aug 3
Total with taxes and fees
Island Bay Resort

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (33 reviews)
"A comfortable little condo, conveniently located for exploring the Keys. There’s a nice pool and small beach area with a bar/restaurant that are well maintained."
United States
Stephen
$281 nightly
The price is $312
Jul 7 - Jul 8
Total with taxes and fees
Florida Keys Getaway - Slps 4 - Ocean View

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (50 reviews)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
$350 nightly
The price is $389
Jul 6 - Jul 7
Total with taxes and fees
Amazing Ocean view condo

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (115 reviews)
$399 nightly
The price is $443
Jul 9 - Jul 10
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.4 out of 10, Exceptional, (25 reviews)
$379 nightly
The price is $420
Jul 6 - Jul 7
Total with taxes and fees
Island Sanctuary Islamorada

Paradise in Key Largo, FL

Paradise in Key Largo, FL
Key Largo
9.8 out of 10, Exceptional, (75 reviews)
"Great place to stay everything was as stated. Everyone at campground was super friendly and pool was amazing. Would stay here again!!"
United States
Stacie B.
$280 nightly
The price is $311
Aug 3 - Aug 4
Total with taxes and fees
Paradise in Key Largo, FL

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (38 reviews)
"We stayed for 4 days over spring break. It was a good location between Key Largo and Islamorada. There were also plenty of places to eat nearby."
United States
Jared D.
$371 nightly
The price is $412
Jul 7 - Jul 8
Total with taxes and fees
Charming Home in Key Largo

Serene Oceanfront Keys Condo

Serene Oceanfront Keys Condo
Tavernier
10.0 out of 10, Exceptional, (41 reviews)
"We very much enjoyed our stay! The condo was comfortable and had most everything we needed. We loved the proximity to the pool and the small beach. Property was nice and clean and communicating with the owner was easy. "
United States
Christy W.
$408 nightly
The price is $452
Jul 6 - Jul 7
Total with taxes and fees
Serene Oceanfront Keys Condo

Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (71 reviews)
"Host was very responsive, location safe and wuiet."
United States
Tracey C.
$759 nightly
The price is $843
Jul 19 - Jul 20
Total with taxes and fees
Sunrise Escape - Ocean Front Villa - Sleeps 10

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Tavernier
9.8 out of 10, Exceptional, (47 reviews)
"We were two couples staying in this space with plenty of room. All the amenities on this property (pool, beach restaurant and bar)made this a terrific stay. "
United States
Donna B.
$417 nightly
The price is $463
Jul 6 - Jul 7
Total with taxes and fees
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Tavernier
10.0 out of 10, Exceptional, (22 reviews)
"Cute place! Plenty of room for our family with beautiful view from the balcony. The pool and beach were perfect. We’d stay again! "
United States
Erin G.
$462 nightly
The price is $514
Aug 3 - Aug 4
Total with taxes and fees
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

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, (158 reviews)
"The condo was nice and comfortable. The kitchen was great with everything you would need to cook. The patio was very small but still nice to step out and enjoy the ocean view. The location was very good, close to the pool."
United States
Katie H.
$431 nightly
The price is $469
Aug 5 - Aug 6
Total with taxes and fees
3212 Across from Pool * King & Queen/Twin Bunk Bed

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"Super clean and neat location!"
United States
Christopher R.
$405 nightly
The price is $440
Aug 4 - Aug 5
Total with taxes and fees
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (35 reviews)
"Loved the beach and pool."
United States
Haley P.
Lazy Daze Double King Suite Ocean Pointe 2310

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (169 reviews)
"Condo was beautiful would definitely stay here again."
United States
Dan M.
$417 nightly
The price is $463
Jul 8 - Jul 9
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

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 $143 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.

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