Top Cabins in Upper Matecumbe Key in 2026

A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.

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Recommended hotels in Upper Matecumbe Key

1. Chesapeake Beach Resort

Matecumbe

alicia

includes taxes & fees

24 Aug - 25 Aug

2. Cheeca Lodge & Spa

Matecumbe

Yuniel

includes taxes & fees

1 Sept - 2 Sept

3. Islander Resort

Matecumbe

Sarah

includes taxes & fees

30 Aug - 31 Aug

4. La Jolla Resort

Matecumbe

adrian

includes taxes & fees

12 Aug - 13 Aug

5. Pines & Palms Resort

Matecumbe

John

includes taxes & fees

12 Aug - 13 Aug

6. Bayside Villas by Islander Resort

Matecumbe

beata

includes taxes & fees

12 Aug - 13 Aug

Suite, 1 King Bed with Sofa bed, Ocean View | Exterior

7. La Siesta Resort & Villas

Matecumbe

Brianne

includes taxes & fees

12 Aug - 13 Aug

8. Amara Cay Resort

Matecumbe

Estefani

includes taxes & fees

19 Aug - 20 Aug

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Top Upper Matecumbe Key Hotel Reviews

Waterside Suites & Marina

10/10 Excellent

"Perfect stop to stay while diving!"

Lime Tree Bay Resort

10/10 Excellent

"Another amazing stay in the Florida Keys! 🌴☀️ This resort was absolutely beautiful. The beach was small, but it was still swimmable and perfect for relaxing by the water. The pool was a highlight—spacious, beautiful, and a great place to spend the day. A little tip: bring any essentials with you before you arrive. There is only one small store across the street, and while it's convenient, the selection is limited and the prices are quite high. We stayed in the two-bedroom, one-bathroom townhouse, and it was absolutely gorgeous—spacious, comfortable, clean, and perfect for our family. Overall, we had a fantastic stay and would definitely come back!"

Cheeca Lodge & Spa

10/10 Excellent

"I absolutely love the Florida Keys, and even though we only spent one day here, it was such a wonderful experience. The hotel is beautiful, the rooms are comfortable, and the amenities are fantastic. With multiple pools, a relaxing atmosphere, and amazing drinks, it was easy to unwind. The piña colada by the pool was hands down one of the best I've ever had! 🍹🌴 The only downside was the amount of sargassum on the beach. It was quite heavy and had a strong odor, which made it less enjoyable. Even so, the overall experience was excellent, and I would definitely come back to enjoy everything this beautiful property has to offer."

La Siesta Resort & Villas

10/10 Excellent

"The check in staff was amazing and helpful. There was a lot of included things to do that were really nice and easy to access. There was a strong fish smell, but that was likely because people catch/clean their fish at the dock and there was a bit of sea grass along the shore that likely contributed. We'd stay there again for sure!"

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cabin Rentals information

Number of reviews	6,629
Accommodation	2 Cabin Rentals
Lowest Price	£114
Highest Price	£2,869

Frequently asked questions

Are there cheap cabins in Upper Matecumbe Key?

Whether you want to stay steps from the water or on the top of a mountain, we have an awesome variety of cheap cabins in Upper Matecumbe Key to suit your budget and taste. Priced from £114 to £2,869 per night, your ideal cabin is waiting right here. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

What are the highest-rated cabins in Upper Matecumbe Key?

Expedia cabin travelers just keep coming back to Cabin - Sand Is The New Snow - New 4bedroom W. This top pick features a host of handy amenities including a private pool and a deck. It won't take you very long to see why Historic, Dog - Friendly Cottage In The Heart Of Key West W is also popular with vacationers. Conveniences such as a patio and a deck will help make your stay nice and comfortable.

Why should I book a cabin in Upper Matecumbe Key?

Affordability, outdoor attractions, rustic charm — there are countless great reasons to book an Upper Matecumbe Key cabin. Escape the noisy concrete jungle and wake up to the beautiful sounds of Mother Nature. There's so much adventure just around the corner too. Whether you're taking a break with friends, family or your partner, you'll find the perfect rental cabin on Expedia.

What are the top nature cabins in Upper Matecumbe Key?

Spend a few nights at Cabin - Sand Is The New Snow - New 4bedroom W and you'll be surrounded by nature. Amenities like a private pool and a deck help make this river cabin in Upper Matecumbe Key a top option. Historic, Dog - Friendly Cottage In The Heart Of Key West W is another place where you can escape the hustle and bustle and catch a few mindful moments by the water. Some of the conveniences here include a patio and a deck.

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Recommended hotels in Upper Matecumbe Key

1. Chesapeake Beach Resort

2. Cheeca Lodge & Spa

3. Islander Resort

4. La Jolla Resort

5. Pines & Palms Resort

6. Bayside Villas by Islander Resort

7. La Siesta Resort & Villas

8. Amara Cay Resort

9. Hadley Resort and Marina

10. Breezy Palms Resort

11. The Islands of Islamorada

12. Sands of Islamorada

13. Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite

14. Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room

15. Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite

16. Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite

17. Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

18. Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite

19. Casa Morada

20. Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite

Find holiday rentals that suit your style

Top Upper Matecumbe Key Hotel Reviews

Waterside Suites & Marina

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cabin Rentals information

Frequently asked questions

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