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

  • 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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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
9.0 out of 10, Wonderful, (777 reviews)
"Such a great place to stay!!"
United States
Gavin
$123 nightly
The price is $138
Nov 3 - Nov 4
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
$1,849 nightly
The price is $2,051
Oct 30 - Oct 31
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, (180 reviews)
"Beautiful unique place"
United States
Laura
$244 nightly
The price is $275
Oct 25 - Oct 26
Total with taxes and fees
Treasure Harbor
A beachfront hotel with two palm trees, a flag, and a pool area with lounge chairs.

4. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (43 reviews)
"great stay and value! glad we went with this place for our trip, everyone loved it! beautiful, clean and the pool was great too!"
Canada
Nick
$300 nightly
The price is $333
Nov 3 - Nov 4
Total with taxes and fees
Florida Keys Getaway - Slps 4 - Ocean View
A wooden deck with a thatched roof, wooden chairs, and tables, overlooking a clear blue sea.

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (116 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
$329 nightly
The price is $365
Oct 25 - Oct 26
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
A modern kitchen with white cabinets, a black refrigerator, and a dining area with a black table and two black chairs.

6. Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"Very clean with everything you could need for your time in the Florida keys! The host was very responsive and helpful. Perfect place for a weekend with our dog."
United States
Anonymous traveler
$279 nightly
The price is $309
Oct 31 - Nov 1
Total with taxes and fees
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, and a covered pavilion in the background.

7. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (53 reviews)
"Excellent accommodations. Unit was even nicer than it looked in pictures, everything was clean and in working order. Enjoyed our stay very much and would definitely stay here again!"
United States
Jerad E.
$313 nightly
The price is $347
Oct 29 - Oct 30
Total with taxes and fees
Amazing Ocean view condo
Beach

8. Aqua Vista | Ocean View 2BR | Ocean Pointe 3307

Aqua Vista | Ocean View 2BR | Ocean Pointe 3307
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
$384 nightly
The price is $416
Nov 5 - Nov 6
Total with taxes and fees
Aqua Vista | Ocean View 2BR | Ocean Pointe 3307
A beach with a flagpole, palm trees, and beach chairs.

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (171 reviews)
"Perfect spot to stay in the keys! Great for fishing. The condo had everything you need to make your stay amazing. We will be back! Check in and out was a breeze, guards at gate were super friendly!"
United States
Pam K.
$324 nightly
The price is $360
Oct 28 - Oct 29
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
A resort with multiple buildings, a swimming pool, tennis courts, and a view of the ocean.

10. Paradise Palms | 2 Balconies | Ocean Pointe 1206

Paradise Palms | 2 Balconies | Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (8 reviews)
"Super clean and neat location!"
United States
Christopher R.
$396 nightly
The price is $430
Oct 25 - Oct 26
Total with taxes and fees
Paradise Palms | 2 Balconies | Ocean Pointe 1206
A pool area with a palm tree, a showerhead, and blue lounge chairs.

11. Ocean Pointe Ocean View w/heated pool beach marina

Ocean Pointe Ocean View w/heated pool beach marina
Tavernier
8.6 out of 10, Excellent, (13 reviews)
"Great location and host is great with communication!"
United States
Mary Katherine B.
$313 nightly
The price is $348
Oct 26 - Oct 27
Total with taxes and fees
Ocean Pointe Ocean View w/heated pool beach marina
A room with a view of the ocean, a balcony with a railing, and a table with a white box.

12. Ocean View Gem | 2 Balconies | Ocean Pointe 3406

Ocean View Gem | 2 Balconies | Ocean Pointe 3406
Tavernier
9.8 out of 10, Exceptional, (11 reviews)
"Clean and perfect location"
United States
Joanne P.
$395 nightly
The price is $429
Oct 31 - Nov 1
Total with taxes and fees
Ocean View Gem | 2 Balconies | Ocean Pointe 3406
Beach

13. Coastal Joy | Ocean View 2BR | Ocean Pointe 3412

Coastal Joy | Ocean View 2BR | Ocean Pointe 3412
Tavernier
9.4 out of 10, Exceptional, (3 reviews)
"Very clean. The view was amazing. Very comfortable beds. We are definitely coming back to this condo! "
United States
Jason U.
$393 nightly
The price is $426
Nov 10 - Nov 11
Total with taxes and fees
Coastal Joy | Ocean View 2BR | Ocean Pointe 3412
A waterfront property with a dock, a house with a blue roof, and a marina with boats.

14. 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.
$257 nightly
The price is $285
Nov 1 - Nov 2
Total with taxes and fees
2BR Oceanfront Suite w/ Beach & Marina Access
A balcony with a view of the sea, a chair, and a table with a lamp.

15. Boho Chic | Steps to Pool | Ocean Pointe 3214

Boho Chic | Steps to Pool | Ocean Pointe 3214
Tavernier
9.8 out of 10, Exceptional, (15 reviews)
"The condo was nice and clean. The view from the balcony is very nice. The property is also nice with things to do but not too busy. The host was great and responsive. "
United States
Anthony F.
$384 nightly
The price is $418
Oct 31 - Nov 1
Total with taxes and fees
Boho Chic | Steps to Pool | Ocean Pointe 3214
A spacious living room with a large TV, a white coffee table, and a balcony with a view of the ocean.

16. Corner Penthouse | Ocean Views | Ocean Pointe 5416

Corner Penthouse | Ocean Views | Ocean Pointe 5416
Tavernier
9.8 out of 10, Exceptional, (18 reviews)
"Great place - love the location! "
United States
Ann C.
$501 nightly
The price is $546
Oct 24 - Oct 25
Total with taxes and fees
Corner Penthouse | Ocean Views | Ocean Pointe 5416
A modern living room with a flat-screen TV, a black leather sofa, and a white ottoman.

17. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
10.0 out of 10, Exceptional, (41 reviews)
"Awesome house, convenient to everything we needed. Super clean and everything was pretty modern. I would definitely stay again and would definitely recommend this property"
United States
JOHN P.
$331 nightly
The price is $367
Oct 26 - Oct 27
Total with taxes and fees
Charming Home in Key Largo
A balcony with a view of the ocean, a chair, a sofa, and a decorative seahorse wall art.

18. Sunrise Sanctuary | Top Floor | Ocean Pointe 2415

Sunrise Sanctuary | Top Floor | Ocean Pointe 2415
Tavernier
9.8 out of 10, Exceptional, (19 reviews)
"Great stay"
United States
Blain R.
$391 nightly
The price is $424
Oct 26 - Oct 27
Total with taxes and fees
Sunrise Sanctuary | Top Floor | Ocean Pointe 2415
A balcony with a view of a green landscape, a potted plant, and a chair.

19. Sky Blue Escape | Ocean View | Ocean Pointe 1314

Sky Blue Escape | Ocean View | Ocean Pointe 1314
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"The place was exactly as advertised and the location was perfect! Our host was very informative and provided all the details for a seamless checkin."
United States
Bryan K.
$401 nightly
The price is $435
Oct 24 - Oct 25
Total with taxes and fees
Sky Blue Escape | Ocean View | Ocean Pointe 1314
A modern kitchen with a central island, white cabinetry, and a dining area with a sofa and ottoman.

20. 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.
$415 nightly
The price is $450
Oct 28 - Oct 29
Total with taxes and fees
Lazy Daze | Double King Suite | Ocean Pointe 2310
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upper Matecumbe Key Hotel Reviews

Islander Resort

Islander Resort

8/10 Good
"The place is beautiful. Staff is great. Unfortunately the high-end restaurant has a very poorly flavored food. The foor portions are ridiculously small, and the prices are extremely high. I would recommend eating elsewhere or in the bar."
Jorge 1-night trip
Posted 2 hours ago
Islander Resort

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 $138 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.

Explore a world of travel with Expedia