Choose from 411 vacation rentals located in Upper Matecumbe Key, Florida. Top filters in Upper Matecumbe Key include Internet / Wifi, Air conditioner, and TV. Prices range from $122 to $15,878 per night. Our most popular vacation rental types near Upper Matecumbe Key are Hotel and RV.

Top vacation rentals in Upper Matecumbe Key

Lake
5.0 / 5.0
Outstanding(98 Ratings)
RELAX in your PRIVATE Oceanfront Cottage!
Cottage
 in Islamorada
4 guests · 1 bedroom · 1 bath
Pets allowed · Kitchen or Kitchenette · Air conditioner

This inviting Cottage in Upper Matecumbe Key can fit your needs for many types of vacations, at $277 per night.

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Property grounds
5.0 / 5.0
Outstanding(109 Ratings)
WATERFRONT FISHING COTTAGE/ DOCKAGE + Walking distance to world famous Lorelei
Cottage
 in Islamorada
2 guests · 1 bedroom · 1 bath
Garden · Pets allowed · Kitchen or Kitchenette

Indulge in a peaceful retreat at WATERFRONT FISHING COTTAGE/ DOCKAGE + Walking distance to world famous Lorelei, our elegant Cottage in Upper Matecumbe Key. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Beachfront
Swimming pool
4.1 / 5.0
Excellent(684 Ratings)
Amara Cay Resort
Hotel
 in Islamorada
4star
1 queen bed, 1 sofa bed
Garden · Pool · Pets allowed
Most favorited

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 $205 per night.

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Beachfront
Bird's eye view
4.5 / 5.0
Excellent(875 Ratings)
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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Search by amenity

Explore vacation rentals with the most popular amenities in Upper Matecumbe Key

Vacation rentals with internet & wifi in Upper Matecumbe Key

Pool
5.0 / 5.0
Outstanding(89 Ratings)
Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay
Villa
 in Islamorada
6 guests · 3 bedrooms · 2 baths
Garden · Pets allowed · Kitchen or Kitchenette

This attractive Villa in Upper Matecumbe Key, $305 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Beachfront
Beach
4.3 / 5.0
Excellent(878 Ratings)
La Jolla Resort
Inn
 in Islamorada
1 king bed, 2 single beds, 1 sofa bed
Garden · Pool · Kitchen or Kitchenette

Discover the beauty of Upper Matecumbe Key with a stay at La Jolla Resort, a top rated Inn with amenities such as Air conditioner, Internet / Wifi and Smoking allowed, and more.

$$$$
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Beachfront
Beach
4.1 / 5.0
Excellent(437 Ratings)
La Siesta Resort & Villas
Hotel
 in Islamorada
4star
1 sofa bed, 2 queen beds
Garden · Pool · Pets allowed

Looking for a Hotel in Upper Matecumbe Key, this Hotel for $207 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

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Beachfront
Swimming pool
4.3 / 5.0
Excellent(1,062 Ratings)
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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Upper Matecumbe Key

Upper Matecumbe Key travel guide

Let us help you plan your perfect Upper Matecumbe Key vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Upper Matecumbe Key, and more.

Frequently asked questions

What is the price range for rentals in Upper Matecumbe Key?

Vacation rentals in Upper Matecumbe Key have a price range between $122-$15,878. The average price for rentals in Upper Matecumbe Key is $486 per night.

What are the most popular vacation rental amenities in Upper Matecumbe Key?

  • Internet / Wifi
  • Air conditioner
  • TV

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