Unveil the magic of Upper Matecumbe Key, Florida, by staying at one of our top-rated resorts. Upper Matecumbe Key offers a variety of activities and scenic spots, making it a hotspot for families, groups and solo travelers alike. From lush landscapes to vibrant local culture, Upper Matecumbe Key promises an enriching experience for all.

Not sure if a resort is right for you? Dive into a world of adventure. Boasting an array of recreational activities, including water sports, hiking trails, and organized excursions. These resorts cater to all - families, groups, or solo travelers alike.

With something for everyone, you are sure to find the ideal resort for your vacation in Upper Matecumbe Key. Our selection of resorts have been specially curated to ensure that you can find somewhere in Upper Matecumbe Key to suit your vacation needs.

Top Amenities: Internet / Wifi, Air conditioner, Kitchen or Kitchenette, Parking and TV

Points of Interest: Everglades National Park, Everglades Alligator Farm, Florida Keys Aquarium Encounters, Theater of the Sea and Crane Point Hammock

Why wait? Book your dream resort in Upper Matecumbe Key today and experience the vacation you've always wanted. Limited spots available!

Top resorts in Upper Matecumbe Key

Beachfront
Bird's eye view
4.5
Excellent(875 Reviews)
Pines & Palms Resort
Resort
 in Islamorada
1 king bed, 1 sofa bed
Garden · Pool · Kitchen or Kitchenette

Discover the beauty of Upper Matecumbe Key with a stay at Pines & Palms Resort, a top rated Resort with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Beachfront
Property view
4.3
Excellent(1,590 Reviews)
Islander Resort
Resort
 in Islamorada
1 king bed
Garden · Pool · Pets allowed
Most favorited

Indulge in a peaceful retreat at Islander Resort, our elegant Resort in Upper Matecumbe Key. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Beachfront
Bedroom
4.1
Excellent(244 Reviews)
Islander Bayside Villas & Boatslips
Resort
 in Islamorada
2 king beds, 1 sofa bed
Pool · Pets allowed · Kitchen or Kitchenette

Nestled in Upper Matecumbe Key, this Resort is perfect for your next vacation. Enjoy Islander Bayside Villas & Boatslips's top-rated amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Beachfront
Beach
4.0
Good(873 Reviews)
Chesapeake Beach Resort
Resort
 in Islamorada
1 king bed
Pool · Pets allowed · Kitchen or Kitchenette

Looking to create some memories in Upper Matecumbe Key? Look no further than our Resort, Chesapeake Beach Resort. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Beachfront
Swimming pool
4.3
Excellent(1,062 Reviews)
Cheeca Lodge & Spa
Resort
 in Islamorada
2 queen beds
Garden · Pool · Kitchen or Kitchenette
Most favorited

Indulge in a peaceful retreat at Cheeca Lodge & Spa, our elegant Resort in Upper Matecumbe Key. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Exterior
4.4
Excellent(1,230 Reviews)
Amara Cay Resort
Resort
 in Islamorada
1 king bed, 1 sofa bed
Garden · Pool · Air conditioner

Indulge in a peaceful retreat at Amara Cay Resort, our elegant Resort in Upper Matecumbe Key. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Property grounds
5.0
Outstanding(6 Reviews)
Custom-Built Oceanfront Caribbean Home w/ Incredible Ocean & Sunrise Views
Resort
 in Islamorada
8 guests · 3 bedrooms · 3 baths
Pool · Kitchen or Kitchenette · Air conditioner

This attractive Resort in Upper Matecumbe Key, $1,819 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Exterior
4.4
Excellent(1,244 Reviews)
Amara Cay Resort
Resort
 in Islamorada
2 guests · 1 bedroom · 1 bath
Garden · Pool · Air conditioner

Nestled in Upper Matecumbe Key, this Resort is perfect for your next vacation. Enjoy Amara Cay Resort's top-rated amenities, including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Outdoor pool, sun loungers
4.3
Excellent(1,004 Reviews)
La Siesta Resort & Villas
Resort
 in Islamorada
2 guests · 1 bedroom · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

The best choice in Upper Matecumbe Key for Resort, for $318 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Outdoor pool, sun loungers
4.2
Excellent(1,005 Reviews)
La Siesta Resort & Villas
Resort
 in Islamorada
1 king bed, 1 queen bed
Pool · Kitchen or Kitchenette · Air conditioner

When traveling to Upper Matecumbe Key, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $318 per night.

$$$$
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Property grounds
5.0
Outstanding(5 Reviews)
Beautifully Renovated Home w/ Custom Furnishings, Chef's Kitchen, & Veranda
Resort
 in Islamorada
9 guests · 3 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

The best choice in Upper Matecumbe Key for Resort, for $1,173 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Private beach, sun loungers, beach umbrellas, beach towels
5.0
Outstanding(1 Review)
Cheeca Lodge & Spa
Resort
 in Islamorada
2 guests · 1 bedroom · 1 bath
Garden · Pool · Air conditioner

Looking for a memorable stay in Upper Matecumbe Key? Our Resort might just be what you're looking for. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more during your stay.

$$$$
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Resorts with internet & wifi in Upper Matecumbe Key

Property grounds
5.0
Outstanding(5 Reviews)
Caribbean-Style Family Home w/ Kitchen, WiFi, Outdoor Veranda, & Washer-Dryer
Resort
 in Islamorada
6 guests · 2 bedrooms · 1 bath
Pool · Kitchen or Kitchenette · Air conditioner

Looking to create some memories in Upper Matecumbe Key? Look no further than our Resort, Caribbean-Style Family Home w/ Kitchen, WiFi, Outdoor Veranda, & Washer-Dryer. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property grounds
5.0
Outstanding(5 Reviews)
Cozy Caribbean-Style Home w/ Outdoor Veranda - Steps to Beach-Entry Pool
Resort
 in Islamorada
4 guests · 1 bedroom · 1 bath
Pool · Kitchen or Kitchenette · Air conditioner

Indulge in a peaceful retreat at Cozy Caribbean-Style Home w/ Outdoor Veranda - Steps to Beach-Entry Pool, our elegant Resort in Upper Matecumbe Key. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Property grounds
4.8
Outstanding(4 Reviews)
Custom-Built Oceanfront Caribbean Home w/ Gorgeous Ocean & Sunrise Views
Resort
 in Islamorada
8 guests · 3 bedrooms · 3 baths
Pool · Kitchen or Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Upper Matecumbe Key? This Resort offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property grounds
5.0
Outstanding(2 Reviews)
Caribbean-Style Family Home w/ Full Kitchen, WiFi, Veranda, & Full Washer-Dryer
Resort
 in Islamorada
8 guests · 2 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

This attractive Resort in Upper Matecumbe Key, $728 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property grounds
5.0
Outstanding(2 Reviews)
Caribbean-Style Family Home w/ Full Kitchen, WiFi, Veranda, & Washer-Dryer
Resort
 in Islamorada
8 guests · 2 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

Looking to create some memories in Upper Matecumbe Key? Look no further than our Resort, Caribbean-Style Family Home w/ Full Kitchen, WiFi, Veranda, & Washer-Dryer. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property grounds
5.0
Outstanding(2 Reviews)
Oceanfront Home w/ Patio, Kitchen, & WiFi - Steps to Marina & Activity Center
Resort
 in Islamorada
4 guests · 1 bedroom · 1 bath
Pool · Kitchen or Kitchenette · Air conditioner

Nestled in Upper Matecumbe Key, this Resort is perfect for your next vacation. Enjoy Oceanfront Home w/ Patio, Kitchen, & WiFi - Steps to Marina & Activity Center's top-rated amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property grounds
5.0
Outstanding(2 Reviews)
Large Caribbean-Style Home w/ Full Kitchen, WiFi, Grill, & Outdoor Veranda
Resort
 in Islamorada
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

Indulge in a peaceful retreat at Large Caribbean-Style Home w/ Full Kitchen, WiFi, Grill, & Outdoor Veranda, our elegant Resort in Upper Matecumbe Key. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Private beach, sun loungers, beach umbrellas, beach towels
5.0
Outstanding(1 Review)
Cheeca Lodge & Spa
Resort
 in Islamorada
2 queen beds
Garden · Pool · Air conditioner

Looking for a Resort in Upper Matecumbe Key, this Resort for $324 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

$$$$
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Property grounds
Breezy Caribbean-Style Home w/ Kitchen, WiFi, & Wraparound Outdoor Veranda
Resort
 in Islamorada
8 guests · 2 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

The best choice in Upper Matecumbe Key for Resort, for $763 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property grounds
Bright Caribbean-Style Home w/ Kitchen, WiFi, & Wraparound Outdoor Veranda
Resort
 in Islamorada
4 guests · 1 bedroom · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

Looking to create some memories in Upper Matecumbe Key? Look no further than our Resort, Bright Caribbean-Style Home w/ Kitchen, WiFi, & Wraparound Outdoor Veranda. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Property grounds
5.0
Outstanding(1 Review)
Caribbean-Style Family Home w/ Full Kitchen, WiFi, Grill, & Outdoor Veranda
Resort
 in Islamorada
8 guests · 2 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

Are you ready to indulge in a relaxing getaway? Our Resort in Upper Matecumbe Key has everything you need for a rejuvenating stay. Treat yourself to Caribbean-Style Family Home w/ Full Kitchen, WiFi, Grill, & Outdoor Veranda's exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.

$$$$
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Property grounds
5.0
Outstanding(1 Review)
Spacious Caribbean-Style Home w/ Kitchen, WiFi, & Wraparound Outdoor Veranda
Resort
 in Islamorada
8 guests · 2 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Upper Matecumbe Key? This Resort offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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