Upper Matecumbe Key Hotels, Resorts, and Rentals

Compare HOTELS, RESORTS, AND RENTALS in Upper Matecumbe Key, Florida, USA

The Islands of Islamorada
FromCA $936 per night
|
9.2 (24 Reviews)
24 Bedrooms 50 Guests
The Caribbean Resort
FromCA $880 per night
|
10.0 (166 Reviews)
1 Bedroom 2 Guests
Keys Villa
FromCA $501 per night
10.0 (7 Reviews)
2 Bedrooms 6 Guests
Casa Morada
FromCA $793 per night
|
9.0 (119 Reviews)
16 Bedrooms 32 Guests
Islander Resort
FromCA $597 per night
|
9.4 (1014 Reviews)
1 Bedroom 2 Guests
La Jolla Resort
FromCA $372 per night
8.8 (853 Reviews)
22 Bedrooms 60 Guests
Casa Morada
FromCA $766 per night
|
9.4 (430 Reviews)
1 Bedroom 2 Guests
Sunset Inn
FromCA $258 per night
|
8.6 (1298 Reviews)
31 Bedrooms 16 Guests
Chesapeake Beach Resort
FromCA $415 per night
|
9.2 (1678 Reviews)
1 Bedroom 2 Guests
Sands of Islamorada
FromCA $371 per night
8.6 (320 Reviews)
9 Bedrooms 30 Guests
Cheeca Lodge & Spa
FromCA $602 per night
|
9.2 (1307 Reviews)
1 Bedroom 2 Guests
Topsider Resort
FromCA $744 per night
8.6 (12 Reviews)
2 Bedrooms 6 Guests
Sunset Inn
FromCA $366 per night
|
9.2 (1004 Reviews)
1 Bedroom 2 Guests
The Ocean View Inn
FromCA $339 per night
|
8.4 (316 Reviews)
7 Bedrooms 7 Guests
Pines & Palms Resort
FromCA $617 per night
|
9.2 (1002 Reviews)
1 Bedroom 2 Guests
Breezy Palms Resort
FromCA $230 per night
|
8.3 (1557 Reviews)
54 Bedrooms 30 Guests
The Ocean View Inn & Pub
FromCA $457 per night
9.2 (22 Reviews)
1 Bedroom 2 Guests
Matecumbe Resort
FromCA $243 per night
8.3 (341 Reviews)
32 Bedrooms 26 Guests
La Jolla Resort
FromCA $347 per night
9.0 (1005 Reviews)
1 Bedroom 2 Guests
Coconut Cove Resort & Marina
FromCA $417 per night
8.3 (272 Reviews)
20 Bedrooms 13 Guests
Coconut Cove Resort and Marina
|
9.0 (238 Reviews)
1 Bedroom 2 Guests
La Siesta Resort & Villas
FromCA $574 per night
|
8.2 (311 Reviews)
55 Bedrooms 136 Guests
Treasure Harbor
FromCA $336 per night
|
8.1 (125 Reviews)
13 Bedrooms 45 Guests
Amara Cay Resort
FromCA $486 per night
|
8.8 (1268 Reviews)
1 Bedroom 2 Guests
Amara Cay Resort
FromCA $530 per night
|
7.9 (594 Reviews)
110 Bedrooms 84 Guests
Drop Anchor
FromCA $538 per night
|
8.8 (1000 Reviews)
1 Bedroom 2 Guests
Fisher Inn Resort & Marina
FromCA $283 per night
|
7.7 (871 Reviews)
37 Bedrooms 38 Guests
Breezy Palms Resort
FromCA $368 per night
8.8 (652 Reviews)
1 Bedroom 2 Guests
Hadley Resort and Marina
FromCA $279 per night
|
7.2 (642 Reviews)
30 Bedrooms 30 Guests
Bayside Villas by Islander Resort
|
8.8 (413 Reviews)
1 Bedroom 2 Guests
Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water views!
|
10.0 (2 Reviews)
3 Bedrooms 6 Guests
Sands of Islamorada
FromCA $379 per night
8.8 (401 Reviews)
1 Bedroom 2 Guests
Pineapple Beach
FromCA $3,445 per night
10.0 (1 Review)
1 Bedroom 10 Guests
Matecumbe Resort
FromCA $264 per night
8.8 (99 Reviews)
1 Bedroom 2 Guests
Anglers Reef Paradise
FromCA $551 per night
|
9.6 (19 Reviews)
2 Bedrooms 6 Guests
La Siesta Resort & Villas
FromCA $416 per night
|
8.6 (1003 Reviews)
1 Bedroom 2 Guests
Islamorada Paradise Overlooking the Fabulous Florida Bay.
|
9.5 (9 Reviews)
3 Bedrooms 6 Guests
Fisher Inn Resort & Marina
FromCA $378 per night
|
8.2 (1009 Reviews)
1 Bedroom 2 Guests
Key Lime Cottage in the heart of Islamorada
|
9.5 (4 Reviews)
2 Bedrooms 5 Guests
Hadley Resort and Marina
FromCA $402 per night
|
7.6 (1008 Reviews)
1 Bedroom 2 Guests
Anglers Reef Vacation Rental
FromCA $682 per night
|
9.5 (2 Reviews)
2 Bedrooms 6 Guests
The Islands of Islamorada
FromCA $1,314 per night
|
9.8 (72 Reviews)
1 Bedroom 4 Guests
Ragged Edge Resort & Marina
FromCA $376 per night
9.1 (136 Reviews)
14 Bedrooms 39 Guests
Ragged Edge Resort & Marina
FromCA $347 per night
9.6 (242 Reviews)
1 Bedroom 2 Guests
Pines & Palms Resort
FromCA $686 per night
|
9.0 (762 Reviews)
24 Bedrooms 44 Guests
Treasure Harbor
FromCA $457 per night
|
9.0 (139 Reviews)
1 Bedroom 2 Guests
Islander Resort
FromCA $979 per night
|
8.7 (1439 Reviews)
107 Bedrooms 68 Guests
Angler's Reef Resort by KeysCaribbean
|
9.0 (14 Reviews)
2 Bedrooms 4 Guests
Hidden Gem Duplex in Heart of Islamorada Sleeps 8
|
New
4 Bedrooms 8 Guests
Oceanfront Islamorada Townhome with Dock and Pool
|
New
3 Bedrooms 7 Guests
Sandglass 4
FromCA $882 per night
|
New
5 Bedrooms 12 Guests
Beacon Reef 222
FromCA $347 per night
|
New
2 Bedrooms 4 Guests
Beacon Reef 310
FromCA $284 per night
|
New
2 Bedrooms 4 Guests
Escape to the Keys
FromCA $278 per night
|
New
1 Bedroom 8 Guests
Executive Bay Club Condo M-1
FromCA $182 per night
|
New
2 Bedrooms 6 Guests
Palms 317
FromCA $164 per night
|
New
1 Bedroom 3 Guests
Beacon Reef 306
FromCA $265 per night
|
New
2 Bedrooms 4 Guests
Little Bay Compound
FromCA $22,215 per night
New
6 Bedrooms 18 Guests
Little Bay Prime
FromCA $1,514 per night
New
4 Bedrooms 12 Guests

About Upper Matecumbe Key Vacation Rentals

There are more than 1390 places to stay in Upper Matecumbe Key that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Upper Matecumbe Key.

Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Upper Matecumbe Key, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Upper Matecumbe Key. Places to stay near Upper Matecumbe Key are 701.71 ft² on average, with prices averaging CA $1,060 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Upper Matecumbe Key with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.

Frequently Asked Questions About Upper Matecumbe Key?

What are the top hotels or resorts in Upper Matecumbe Key?

You have a lot of choices in or near Upper Matecumbe Key. If you need a hotel in the Upper Matecumbe Key area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Upper Matecumbe Key:

How many hotels, resorts, or rentals are available in Upper Matecumbe Key?

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2026 is over 1390 in the Upper Matecumbe Key area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Upper Matecumbe Key.

Nearby Neighborhood (1)

NeighborhoodProperty Count
Coral Cove Hotel & Resort Deals in Florida 643