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

Upper Matecumbe Key Hotels

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
18 Aug - 19 Aug
Tomorrow
19 Aug - 20 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

Filter by

Star rating

Guest rating

Our top choices for Upper Matecumbe Key hotels

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
Jessica
€208
includes taxes & fees
19 Aug - 20 Aug
Cheeca Lodge & Spa

2. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
United States
Rey
€195
includes taxes & fees
19 Aug - 20 Aug
Chesapeake Beach Resort

3. La Jolla Resort

La Jolla Resort
Matecumbe
United States
adrian
€140
includes taxes & fees
19 Aug - 20 Aug
La Jolla Resort

4. Islander Resort

Islander Resort
Matecumbe
United States
Chris
€276
includes taxes & fees
31 Aug - 1 Sept
Islander Resort

5. Pines & Palms Resort

Pines & Palms Resort
Matecumbe
United States
Isabel
€188
includes taxes & fees
19 Aug - 20 Aug
Pines & Palms Resort

6. Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
United States
RAIBEL
€135
includes taxes & fees
7 Sept - 8 Sept
Hadley Resort and Marina

7. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
Estefani
€226
includes taxes & fees
23 Aug - 24 Aug
Amara Cay Resort

8. Breezy Palms Resort

Breezy Palms Resort
Matecumbe
United States
roger
€113
includes taxes & fees
1 Sept - 2 Sept
Breezy Palms Resort

9. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
Matecumbe
United States
beata
€287
includes taxes & fees
24 Aug - 25 Aug
Bayside Villas by Islander Resort

10. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
United States
Brianne
€213
includes taxes & fees
23 Aug - 24 Aug
La Siesta Resort & Villas

11. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
United States
Christian
€404
includes taxes & fees
19 Aug - 20 Aug
The Islands of Islamorada

12. Casa Morada

Casa Morada
Matecumbe
United States
Lois
€171
includes taxes & fees
14 Sept - 15 Sept
Casa Morada

13. Sands of Islamorada

Sands of Islamorada
Matecumbe
United States
Virginia
€225
includes taxes & fees
24 Aug - 25 Aug
Sands of Islamorada

14. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
United States
MARC
€135
includes taxes & fees
1 Sept - 2 Sept
Fisher Inn Resort & Marina

15. Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
United States
Ana
€264
includes taxes & fees
25 Aug - 26 Aug
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

16. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
United States
Lisa C
€145
includes taxes & fees
31 Aug - 1 Sept
Coconut Cove Resort and Marina

17. Drop Anchor

Drop Anchor
Islamorada
United States
Marianela
€123
includes taxes & fees
19 Aug - 20 Aug
Drop Anchor

18. Rock Reef Resort

Rock Reef Resort
Rock Harbor
United States
manuel
€101
includes taxes & fees
13 Sept - 14 Sept
Rock Reef Resort

19. Drift Hotel

Drift Hotel
Key Largo
United States
Sheily
€104
includes taxes & fees
19 Aug - 20 Aug
Drift Hotel

20. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
Islamorada
United States
Lauren
€132
includes taxes & fees
9 Sept - 10 Sept
Ragged Edge Resort & Marina
View all properties
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Upper Matecumbe Key attractions

A marina with boats docked, a motel, and a cafe.

Bud n' Mary's Dive Center

8.8/10 (504 reviews)
Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this family-friendly area.
See properties
A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Florida Keys Brewing Co.

9.2/10 (520 reviews)
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.
See properties
A building with a blue facade, a large mural of a diving scene, and a statue of a diver.

History of Diving Museum

9.0/10 (177 reviews)
Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.
See properties

Islamorada Brewery & Distillery

9.4/10 (8 reviews)
You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.
See properties

MoradaWay Arts & Cultural District

Enjoy an outing to MoradaWay Arts & Cultural District during your stay in Islamorada.
See properties

beach near Islamorada

Why not spend a lazy afternoon at beach near Islamorada during your trip to Islamorada?
See properties

Keys History & Discovery Center

You can spend time studying the exhibits at Keys History & Discovery Center during your trip to Islamorada.
See properties

Lorelei Restaurant & Cabana Bar

After visiting Lorelei Restaurant & Cabana Bar, make a plan to see the other sights and activities in Islamorada.
See properties

Learn more about Upper Matecumbe Key

Venture to sights like Bud n' Mary's Dive Center and Florida Keys Brewing Co. as you discover Upper Matecumbe Key.

See all hotels in Upper Matecumbe Key
A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.
Photo by Cameron Abbott

Top Upper Matecumbe Key Hotel Reviews

Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"We loved our stay. The rooms were beautiful and well maintained and the staff were amazing! It was the most professional team that I have interacted with in quite some time. Kyle was super helpful! We loved all of the amenities and the restaurant was really good also. I definitely recommend this resort."
George 3-night trip
Posted less than an hour ago
Lime Tree Bay Resort
Hawks Cay Resort

Hawks Cay Resort

8/10 Good
"We had a great time! The pool, lagoon and restaurants were amazing. The only downside was our villa was in need of some upkeep and a good deep clean. We found someone’s under garments by our washer and the corners of the tub and walls throughout were dirty. We only had one wash cloth when we checked in for three people and had to get more from the front desk. Also, the kitchen equipment in the villa was sub par. Only one pan to cook on and it was warped and scratched, no baking sheets, no pot holders, no can opener or pizza cutter. The staff however, was top notch and very friendly."
Ebony 7-night trip
Posted less than an hour ago
Hawks Cay Resort
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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

10/10 Excellent
"Recommend!"
Fares 2-night trip
Posted 1 hour ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"Our stay at Waterside Suites and Marina was absolutely wonderful! From beginning to end, everything exceeded our expectations. The property was enjoyable, clean, comfortable, and very well maintained. The location was perfect, and the marina and surrounding views made the experience even more special. The staff was incredibly friendly, helpful, and welcoming. You could truly tell that they care about their guests and want everyone to have a great experience. Everything was exactly what we hoped for, and we felt comfortable and relaxed throughout our entire stay. We traveled with our family, including our two children and my parents, and it was a wonderful place for everyone. We enjoyed the peaceful atmosphere and having everything we needed right there. We would absolutely stay at Waterside Suites and Marina again without hesitation. We highly recommend this place to anyone looking for a beautiful, relaxing, clean, and family-friendly stay in the Keys. Thank you for making our vacation such a wonderful experience! We loved every moment and cannot wait to come back! ❤️🌴🌊"
Isabel C 3-night trip
Posted 1 hour ago
Waterside Suites & Marina
Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Perfect getaway spot"
John 2-night trip
Posted 20 hours ago
Cheeca Lodge & Spa
Hadley Resort and Marina

Hadley Resort and Marina

10/10 Excellent
"All good"
Jon 3-night trip
Posted 20 hours ago
Hadley Resort and Marina
Chesapeake Beach Resort

Chesapeake Beach Resort

8/10 Good
"The welcome staff were personable and our room was clean. The garden view left much to be desired- no garden or landscaping. (Maybe due to renovations) The free breakfast was a pleasant experience along with the staff."
Paula 3-night trip
Posted 21 hours ago
Chesapeake Beach Resort
Islander Resort

Islander Resort

10/10 Excellent
"This property is beautiful. Each room has a patio that leads that has a scenic route that leads ti the pool. The staff was exceptional and I would recommend this resort for families with small children."
Aisha 1-night trip
Posted 2 days ago
Islander Resort
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent
"The number 1 resort in our book to date.. Food was amazing, staff were kind and helpful, facility was clean and very well maintained!!"
Jessica 3-night trip
Posted 2 days ago
Playa Largo Resort & Spa, Autograph Collection

More cheap stays in Upper Matecumbe Key

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL
€96
23 Aug - 24 Aug
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
The Pelican Key Largo Cottages
Drift Hotel

Drift Hotel

95320 Overseas Hwy Key Largo FL
€104
19 Aug - 20 Aug
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
Drift Hotel
Breezy Palms Resort

Breezy Palms Resort

80015 Overseas Highway Islamorada FL
€113
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (727 reviews)
Breezy Palms Resort
Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay

102400 Overseas Hwy Key Largo FL
€127
25 Aug - 26 Aug
includes taxes & fees
Hampton Inn Key Largo Manatee Bay
Creekside Inn

Creekside Inn

90611 Old Highway Tavernier FL
€128
20 Aug - 21 Aug
includes taxes & fees
7.8/10 Good! (1,015 reviews)
Creekside Inn
Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

527 Caribbean Drive Key Largo FL
€157
16 Sept - 17 Sept
includes taxes & fees
8.6/10 Excellent! (1,874 reviews)
Marina Del Mar Resort and Marina

Explore a world of travel with Expedia