Hotels in Upper Matecumbe Key

Free cancellation options if plans change
Earn rewards on every night you stay
Save more with Member Prices

Check prices for these dates

Tonight
12 Jul - 13 Jul
Tomorrow
13 Jul - 14 Jul
Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul

Where to stay in Upper Matecumbe Key?

Islander Resort
Relax in comfort on the beach with lounge chairs and enjoy the ocean views.

Islander Resort

4.0 star property
9.2 out of 10, Wonderful, (1015)
The price is ₹17,846
₹25,868 total
includes taxes & fees
4 Aug - 5 Aug
Islander Resort
Sunset Inn
Relax by the pool surrounded by palm trees and lounge chairs, with umbrellas providing shade.

Sunset Inn

3.0 star property
9.2 out of 10, Wonderful, (1002)
The price is ₹12,278
₹14,779 total
includes taxes & fees
15 Jul - 16 Jul
Sunset Inn
Cheeca Lodge & Spa
Relax on the beach with lounge chairs, a shaded hut, and a long pier extending into the calm sea.

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1136)
The price is ₹17,074
₹25,000 total
includes taxes & fees
12 Aug - 13 Aug
Cheeca Lodge & Spa
The Islands of Islamorada
Relax by the pool surrounded by palm trees and enjoy stunning ocean views.

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (61)
The price is ₹47,107
₹57,717 total
includes taxes & fees
20 Jul - 21 Jul
The Islands of Islamorada
Pines & Palms Resort
Relax on the beach with a clear view of the ocean from a wooden pier, surrounded by palm trees and comfortable lounge chairs.

Pines & Palms Resort

3.0 star property
9.2 out of 10, Wonderful, (1001)
Pines & Palms Resort
La Jolla Resort
Relax on the beach with lounge chairs and umbrellas at La Jolla Resort.

La Jolla Resort

2.5 star property
9.0 out of 10, Wonderful, (1002)
La Jolla Resort
Casa Morada
Relax by the ocean with a tranquil view of the sunset from our poolside lounge chairs.

Casa Morada

3.5 star property
9.4 out of 10, Exceptional, (402)
The price is ₹19,536
₹24,177 total
includes taxes & fees
13 Jul - 14 Jul
Casa Morada
Breezy Palms Resort
Relax on the beachfront lawn with lounge chairs, enjoy the tranquil atmosphere, and take in the views of the calm sea.

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (488)
The price is ₹7,785
₹10,126 total
includes taxes & fees
15 Jul - 16 Jul
Breezy Palms Resort
Chesapeake Beach Resort
Relax on the beach with a tranquil ocean view and comfortable sun loungers.

Chesapeake Beach Resort

3.5 star property
9.2 out of 10, Wonderful, (1489)
The price is ₹21,111
₹28,575 total
includes taxes & fees
23 Jul - 24 Jul
Chesapeake Beach Resort
Islander Bayside Villas and Boatslips
Restaurant

Islander Bayside Villas and Boatslips

3.5 star property
8.8 out of 10, Excellent, (368)
The price is ₹20,592
₹28,957 total
includes taxes & fees
10 Aug - 11 Aug
Islander Bayside Villas and Boatslips
Sands of Islamorada
Enjoy the serene ocean views from this expansive deck, surrounded by palm trees and overlooking the sandy beach.

Sands of Islamorada

2.5 star property
8.8 out of 10, Excellent, (384)
The price is ₹15,615
₹20,463 total
includes taxes & fees
13 Jul - 14 Jul
Sands of Islamorada
Hadley Resort and Marina
Enjoy waterfront views and access to boat rentals and guided tours from this serene dock.

Hadley Resort and Marina

3.5 star property
7.8 out of 10, Good, (1004)
The price is ₹10,866
₹15,024 total
includes taxes & fees
11 Aug - 12 Aug
Hadley Resort and Marina
Amara Cay Resort
Relax in a serene outdoor seating area with Adirondack chairs around a central fire pit, surrounded by palm trees and ocean views.

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1236)
The price is ₹16,666
₹24,445 total
includes taxes & fees
10 Aug - 11 Aug
Amara Cay Resort
La Siesta Resort & Villas
Relax by the uniquely shaped pool surrounded by palm trees and shaded by umbrellas.

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1000)
The price is ₹14,736
₹22,273 total
includes taxes & fees
15 Jul - 16 Jul
La Siesta Resort & Villas
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Relax by the oceanfront pool surrounded by palm trees and lounge chairs.

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

3.5 star property
9.0 out of 10, Wonderful, (47)
The price is ₹23,264
₹31,868 total
includes taxes & fees
11 Aug - 12 Aug
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
The Ocean View Inn & Pub
Relax in style with two Adirondack chairs on a patio, adjacent to a building with a sliding glass door.

The Ocean View Inn & Pub

2.0 star property
9.8 out of 10, Exceptional, (6)
The price is ₹13,667
₹15,375 total
includes taxes & fees
22 Jul - 23 Jul
The Ocean View Inn & Pub
Coconut Cove Resort and Marina
Exterior

Coconut Cove Resort and Marina

3.0 star property
7.6 out of 10, Good, (801)
The price is ₹14,594
₹16,419 total
includes taxes & fees
14 Jul - 15 Jul
Coconut Cove Resort and Marina
Fisher Inn Resort & Marina
Relax by the pool or on the beach, with lounge chairs and a dock leading into the ocean.

Fisher Inn Resort & Marina

3.5 star property
8.0 out of 10, Very good, (1007)
The price is ₹9,772
₹13,794 total
includes taxes & fees
23 Jul - 24 Jul
Fisher Inn Resort & Marina
Drop Anchor
Relax in a semi-circular seating area overlooking the beach, surrounded by palm trees and a thatched umbrella.

Drop Anchor

3.0 star property
8.8 out of 10, Excellent, (1005)
Drop Anchor
Ragged Edge Resort & Marina
Relax on the beach with comfortable lounge chairs and a serene ocean view.

Ragged Edge Resort & Marina

2.5 star property
9.4 out of 10, Exceptional, (183)
Ragged Edge Resort & Marina
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.
Showing deals for:25 Jul - 27 Jul

Image gallery for Chesapeake Beach Resort

Beach

Chesapeake Beach Resort

3.5 star property
Islamorada
9.2/10Wonderful (1,489 reviews)
7% off
Price is ₹34,047
₹86,259 total
includes taxes & fees
Chesapeake Beach Resort

Top landmarks in Upper Matecumbe Key

Florida Keys Brewing Co.

Florida Keys Brewing Co.

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

See properties in Florida Keys Brewing Co.
Florida Keys Brewing Co.

Learn more about Upper Matecumbe Key

Upper Matecumbe Key is applauded for its cultural attractions such as History of Diving Museum and MoradaWay Arts & Cultural District.

See all hotels in Upper Matecumbe Key

Check out reviews of Upper Matecumbe Key hotels guests love

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"We loved the property grounds and attention to detail from the walking paths to the lagoon and the tiki torches. Our favorite time was spent in the evening on the beach as it was so calm and peaceful. We wish the beach was more usable and swimmable however. Even getting the kayaks into the water was unpleasant, I would definitely not recommend swimming there. The staff were all very attentive and friendly, Stephanie K did a wonderful job cleaning our room and the kids loved finding their stuffies organized when returning to the room. Speaking of rooms, the 1 bedroom suite was perfect! We stayed in a few resorts/ hotels during this trip and it was so nice to have a full kitchen, separate bedroom, and massive bathroom with a separate tub. We don’t normally visit the same resort twice just to be able to experience new places but Cheeca is one resort we will come back to!"
Lisanne 3-night trip
Posted 9 hours ago
Cheeca Lodge & Spa

Frequently asked questions

What accommodations do travelers like in Upper Matecumbe Key?
The Caribbean Resort, Pines & Palms Resort and Cheeca Lodge & Spa are all accommodations that are popular with guests.
Can I book a refundable accommodation in Upper Matecumbe Key?
If you need the flexibility to change your travel plans to Upper Matecumbe Key, most hotels offer refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Which Upper Matecumbe Key hotels do our guests like for their great location?
Travelers like these properties for their convenient location: Chesapeake Beach Resort, Islander Resort and Hadley House Islamorada.
Where can I stay in Upper Matecumbe Key if I want a budget-friendly accommodation?
Two inexpensive options worth considering are Chesapeake Beach Resort and La Jolla Resort.
Where can I stay in Upper Matecumbe Key if I want a vacation rental instead of a traditional hotel?
If you're looking for a good alternative to a hotel, browse our selection of 115 vacation homes. In addition, there are 9 apartments and 13 condos.
Why should I book my Upper Matecumbe Key accommodation with Hotels.com?
There are lots of reasons to book your Upper Matecumbe Key trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

Keep exploring

Keep exploring