Upper Matecumbe Key Hotels, Resorts, and Rentals

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

The Islands of Islamorada
FromZA R13,616 per night
|
9.5 (20 Reviews)
24 Bedrooms 50 Guests
The Caribbean Resort
FromZA R10,944 per night
|
10.0 (166 Reviews)
1 Bedroom 2 Guests
Casa Morada
FromZA R9,853 per night
|
9.0 (119 Reviews)
16 Bedrooms 32 Guests
Casa Morada
FromZA R9,527 per night
|
9.4 (430 Reviews)
1 Bedroom 2 Guests
Keys Villa
FromZA R6,228 per night
10.0 (7 Reviews)
2 Bedrooms 6 Guests
La Jolla Resort
FromZA R4,626 per night
8.8 (906 Reviews)
22 Bedrooms 60 Guests
Chesapeake Beach Resort
FromZA R7,138 per night
|
9.2 (1676 Reviews)
1 Bedroom 2 Guests
Sunset Inn
FromZA R2,809 per night
|
8.6 (1298 Reviews)
31 Bedrooms 16 Guests
Cheeca Lodge & Spa
FromZA R7,483 per night
|
9.2 (1307 Reviews)
1 Bedroom 2 Guests
Sands of Islamorada
FromZA R4,607 per night
8.6 (320 Reviews)
9 Bedrooms 30 Guests
Islander Resort
FromZA R14,835 per night
|
9.2 (1007 Reviews)
1 Bedroom 2 Guests
Topsider Resort
FromZA R9,248 per night
8.6 (12 Reviews)
2 Bedrooms 6 Guests
Sunset Inn
FromZA R4,552 per night
|
9.2 (1004 Reviews)
1 Bedroom 2 Guests
The Ocean View Inn
FromZA R4,213 per night
|
8.4 (303 Reviews)
7 Bedrooms 7 Guests
Pines & Palms Resort
FromZA R12,290 per night
|
9.2 (1002 Reviews)
1 Bedroom 2 Guests
Breezy Palms Resort
FromZA R2,858 per night
|
8.3 (1557 Reviews)
54 Bedrooms 30 Guests
La Jolla Resort
FromZA R5,277 per night
9.2 (1001 Reviews)
1 Bedroom 2 Guests
Matecumbe Resort
FromZA R3,665 per night
8.3 (341 Reviews)
32 Bedrooms 26 Guests
Coconut Cove Resort and Marina
FromZA R7,495 per night
|
9.0 (223 Reviews)
1 Bedroom 2 Guests
La Siesta Resort & Villas
FromZA R4,116 per night
|
8.2 (311 Reviews)
55 Bedrooms 136 Guests
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
|
9.0 (166 Reviews)
1 Bedroom 2 Guests
Coconut Cove Resort & Marina
FromZA R3,768 per night
8.1 (265 Reviews)
20 Bedrooms 13 Guests
The Ocean View Inn & Pub
FromZA R5,832 per night
9.0 (17 Reviews)
1 Bedroom 2 Guests
Treasure Harbor
FromZA R4,182 per night
|
8.1 (125 Reviews)
13 Bedrooms 45 Guests
Amara Cay Resort
FromZA R6,038 per night
|
8.8 (1268 Reviews)
1 Bedroom 2 Guests
Amara Cay Resort
FromZA R4,355 per night
|
7.9 (594 Reviews)
110 Bedrooms 84 Guests
Drop Anchor
FromZA R5,107 per night
|
8.8 (1010 Reviews)
1 Bedroom 2 Guests
Fisher Inn Resort & Marina
FromZA R3,523 per night
|
7.7 (927 Reviews)
37 Bedrooms 38 Guests
La Siesta Resort & Villas
FromZA R8,750 per night
|
8.8 (1004 Reviews)
1 Bedroom 2 Guests
Hadley Resort and Marina
FromZA R3,472 per night
|
7.2 (642 Reviews)
30 Bedrooms 30 Guests
Breezy Palms Resort
FromZA R4,632 per night
8.8 (630 Reviews)
1 Bedroom 2 Guests
Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water views!
|
10.0 (2 Reviews)
3 Bedrooms 6 Guests
Bayside Villas by Islander Resort
|
8.8 (412 Reviews)
1 Bedroom 2 Guests
Pineapple Beach
FromZA R42,816 per night
10.0 (1 Review)
1 Bedroom 10 Guests
Sands of Islamorada
FromZA R4,712 per night
8.8 (401 Reviews)
1 Bedroom 2 Guests
Anglers Reef Paradise
FromZA R6,851 per night
|
9.6 (19 Reviews)
2 Bedrooms 6 Guests
Matecumbe Resort
FromZA R3,285 per night
8.8 (99 Reviews)
1 Bedroom 2 Guests
Islamorada Paradise Overlooking the Fabulous Florida Bay.
|
9.5 (9 Reviews)
3 Bedrooms 6 Guests
Fisher Inn Resort & Marina
FromZA R4,692 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
FromZA R4,995 per night
|
7.6 (1008 Reviews)
1 Bedroom 2 Guests
Anglers Reef Vacation Rental
FromZA R8,478 per night
|
9.5 (2 Reviews)
2 Bedrooms 6 Guests
The Islands of Islamorada
FromZA R16,339 per night
|
9.8 (72 Reviews)
1 Bedroom 4 Guests
Ragged Edge Resort & Marina
FromZA R4,680 per night
9.1 (157 Reviews)
14 Bedrooms 35 Guests
Ragged Edge Resort & Marina
FromZA R4,248 per night
9.6 (222 Reviews)
1 Bedroom 2 Guests
Pines & Palms Resort
FromZA R8,529 per night
|
9.0 (762 Reviews)
24 Bedrooms 44 Guests
Treasure Harbor
FromZA R5,686 per night
|
9.0 (139 Reviews)
1 Bedroom 2 Guests
Islander Resort
FromZA R9,711 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
FromZA R10,961 per night
|
New
5 Bedrooms 12 Guests
Beacon Reef 222
FromZA R4,316 per night
|
New
2 Bedrooms 4 Guests
Beacon Reef 310
FromZA R3,528 per night
|
New
2 Bedrooms 4 Guests
Escape to the Keys
FromZA R3,460 per night
|
New
1 Bedroom 8 Guests
Executive Bay Club Condo M-1
FromZA R2,261 per night
|
New
2 Bedrooms 6 Guests
Palms 317
FromZA R2,038 per night
|
New
1 Bedroom 3 Guests
Beacon Reef 306
FromZA R3,288 per night
|
New
2 Bedrooms 4 Guests
Little Bay Compound
FromZA R276,131 per night
New
6 Bedrooms 18 Guests
Little Bay Prime
FromZA R18,822 per night
New
4 Bedrooms 12 Guests

About Upper Matecumbe Key Vacation Rentals

There are more than 1383 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 701.29 ft² on average, with prices averaging ZA R13,250 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 1383 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 636