A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.

Upper Matecumbe Key Vacation Rentals

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Upper Matecumbe Key vacation rentals

A beach with palm trees, thatched-roof huts, and lounge chairs.

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (742 reviews)
"Great resorts - will return again. Highly recommend"
United States
Lourdes
$111 nightly
The price is $125
Sep 9 - Sep 10
Total with taxes and fees
Breezy Palms Resort
An indoor wooden structure with a thatched roof, multiple hanging spherical lights, and a central seating area.

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

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
$1,838 nightly
The price is $2,040
Sep 15 - Sep 16
Total with taxes and fees
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

3. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (173 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
$254 nightly
The price is $286
Oct 1 - Oct 2
Total with taxes and fees
Treasure Harbor
A beachside lounge with wooden lounge chairs and blue umbrellas, overlooking a calm sea and docked boats.

4. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (179 reviews)
"Amazing vacation spot!!"
United States
Katie Lyn
$227 nightly
The price is $256
Sep 29 - Sep 30
Total with taxes and fees
Island Bay Resort
A floating house with a thatched roof, large sliding glass doors, and a wooden deck with a chair.

5. Premium Floating Bungalow by Stay Ombi

Premium Floating Bungalow by Stay Ombi
3.5 star property
Key Largo
9.6 out of 10, Exceptional, (4 reviews)
"Great experience ! Will do it again"
United States
Deivys
$914 nightly
The price is $1,029
Sep 10 - Sep 11
Total with taxes and fees
Premium Floating Bungalow by Stay Ombi
A compact kitchen with a dishwasher, a microwave, and a sink. There is a window with a view of the outdoors, and a ceiling fan.

6. Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Tavernier
9.8 out of 10, Exceptional, (220 reviews)
"Very cute cozy house boat. Well equipped and close to restaurant. Enjoyable weekend stay. Heidi the host is very welcoming."
United States
Michelle P.
$392 nightly
The price is $435
Sep 9 - Sep 10
Total with taxes and fees
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
A beach with palm trees, a thatched-roof hut, and beach chairs.

7. Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo

Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo
Tavernier
9.6 out of 10, Exceptional, (233 reviews)
"Our stay was excellent. The home was immaculate and had everything we needed. We would definitely stay here again."
United States
Chris
$332 nightly
The price is $369
Sep 12 - Sep 13
Total with taxes and fees
Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo
A beach with rows of sun loungers, a wooden pier, and a thatched-roof structure.

8. 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
9.8 out of 10, Exceptional, (25 reviews)
"The property was in a great location, close to several beach bars and restaurants, the condo was so cute and the host was accessible throughout the entire process before and after our stay."
United States
Alicia
$464 nightly
The price is $515
Sep 19 - Sep 20
Total with taxes and fees
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

9. Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Tavernier
9.8 out of 10, Exceptional, (29 reviews)
"The space was family friendly and worked well for our stay. The pool area was very clean and the Island Grill on site was great for snacks and drinks while we swam."
United States
Miranda J.
$413 nightly
The price is $449
Sep 12 - Sep 13
Total with taxes and fees
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
A pool area with a palm tree, a showerhead, and blue lounge chairs.

10. Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
Tavernier
9.0 out of 10, Wonderful, (103 reviews)
"Great visit!"
United States
Leigh D. H.
$295 nightly
The price is $328
Sep 10 - Sep 11
Total with taxes and fees
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
A waterfront property with a dock, a house with a blue roof, and a marina with boats.

11. 2BR Oceanfront Suite w/ Beach & Marina Access

2BR Oceanfront Suite w/ Beach & Marina Access
Key Largo
10.0 out of 10, Exceptional, (1 review)
"This was a great place to stay. Incredibly clean and homey feel. I felt super safe walking the area after dinner at night"
United States
Alyssa H.
$238 nightly
The price is $264
Sep 14 - Sep 15
Total with taxes and fees
2BR Oceanfront Suite w/ Beach & Marina Access
A beachfront hotel with clear waters, palm trees, and a sandy beach.

12. Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
Tavernier
10.0 out of 10, Exceptional, (10 reviews)
"Such a beautiful condo! We loved our stay."
United States
Bethany B.
$413 nightly
The price is $449
Sep 9 - Sep 10
Total with taxes and fees
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
A beachside resort with a thatched umbrella, palm trees, and a dock.

13. Ocean View Corner Penthouse Ocean Pointe 5416

Ocean View Corner Penthouse Ocean Pointe 5416
Tavernier
9.8 out of 10, Exceptional, (18 reviews)
"Great place - love the location! "
United States
Ann C.
$476 nightly
The price is $521
Sep 9 - Sep 10
Total with taxes and fees
Ocean View Corner Penthouse Ocean Pointe 5416
A beachfront hotel with two palm trees, a flag, and a pool area with lounge chairs.

14. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (38 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
$284 nightly
The price is $315
Oct 4 - Oct 5
Total with taxes and fees
Florida Keys Getaway - Slps 4 - Ocean View
A wooden deck with thatched roof and benches overlooking the sea.

15. Serene Oceanfront Keys Condo

Serene Oceanfront Keys Condo
Tavernier
9.8 out of 10, Exceptional, (44 reviews)
"Condo was exactly as pictured. The location was great and close to everything we needed. The amenities and property grounds were beautiful and well kept. We thoroughly enjoyed spending time by the pool."
United States
Alexandra F.
$384 nightly
The price is $428
Sep 9 - Sep 10
Total with taxes and fees
Serene Oceanfront Keys Condo

16. Ocean View 2BR/2BA Sleeps 6

Ocean View 2BR/2BA Sleeps 6
Tavernier
10.0 out of 10, Exceptional, (136 reviews)
"Very clean and comfortable, wonderful amenities, great view of the ocean, fantastic location and the hosts were so accessible and helpful. We thoroughly enjoyed our stay!"
United States
Deborah D.
$408 nightly
The price is $443
Sep 9 - Sep 10
Total with taxes and fees
Ocean View 2BR/2BA Sleeps 6
A clear blue pool with lounge chairs and umbrellas, surrounded by palm trees and greenery.

17. Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (36 reviews)
"Loved the beach and pool."
United States
Haley P.
$413 nightly
The price is $449
Sep 10 - Sep 11
Total with taxes and fees
Lazy Daze Double King Suite Ocean Pointe 2310

18. Flamingo Flats Ocean Pointe 5306 2BR/2BA

Flamingo Flats Ocean Pointe 5306 2BR/2BA
Tavernier
9.6 out of 10, Exceptional, (9 reviews)
"Great location and prompt support with all questions we had. "
United States
Jim I.
$360 nightly
The price is $392
Sep 9 - Sep 10
Total with taxes and fees
Flamingo Flats Ocean Pointe 5306 2BR/2BA
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

19. Coral Penthouse Key Largo Ocean Pointe 4216

Coral Penthouse Key Largo Ocean Pointe 4216
Tavernier
10.0 out of 10, Exceptional, (21 reviews)
"The ocean view was perfect. The property was nicely situated for all the activities and restaurants in the upper keys. Would definitely stay here again"
United States
David C.
$404 nightly
The price is $438
Sep 9 - Sep 10
Total with taxes and fees
Coral Penthouse Key Largo Ocean Pointe 4216
A beach with clear shallow waters, a row of blue lounge chairs, and palm trees.

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (115 reviews)
"Everything was wonderful! We enjoyed our stay very much. "
United States
Colleen D.
$347 nightly
The price is $386
Sep 9 - Sep 10
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

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

10/10 Excellent
"Amazing"
Leilanis 1-night trip
Posted 2 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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 $125 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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