Top Inns 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

Private beach, white sand, sun-loungers, beach towels

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

House, 3 Bedrooms, Ocean View, Oceanfront | Lanai

4. La Jolla Resort

Matecumbe

adrian

includes taxes & fees

10 Aug - 11 Aug

5. Breezy Palms Resort

Matecumbe

Tristan

includes taxes & fees

10 Aug - 11 Aug

6. Hadley Resort and Marina

Matecumbe

RAIBEL

includes taxes & fees

30 Aug - 31 Aug

Oceanfront Three Bedroom Villa | Premium bedding, iron/ironing board, free WiFi, individually decorated

7. Pines & Palms Resort

Matecumbe

John

includes taxes & fees

9 Aug - 10 Aug

Room, 1 King Bed with Sofa bed, Oceanfront, Lanai | View from room

8. Amara Cay Resort

Matecumbe

Estefani

includes taxes & fees

19 Aug - 20 Aug

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Top Upper Matecumbe Key Hotel Reviews

Baker's Cay Resort Key Largo, Curio Collection by Hilton

10/10 Excellent

"A wonderful family friendly resort! We had a great time and would def come back."

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 Inns information

Number of reviews	5,867
Accommodation	0 Inns
Lowest Price	£114
Highest Price	£2,869

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Room 1

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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. Breezy Palms Resort

6. Hadley Resort and Marina

7. Pines & Palms Resort

8. Amara Cay Resort

9. La Siesta Resort & Villas

10. Bayside Villas by Islander 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. Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite

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

19. Casa Morada

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

Top Upper Matecumbe Key Hotel Reviews

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Lime Tree Bay Resort

Cheeca Lodge & Spa

Hawks Cay Resort

La Jolla Resort

Pines & Palms Resort

The Islands of Islamorada

Sunset Inn

La Siesta Resort & Villas

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Inns information

Explore a world of travel with Expedia

Search Inns in Upper Matecumbe Key

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. Breezy Palms Resort

6. Hadley Resort and Marina

7. Pines & Palms Resort

8. Amara Cay Resort

9. La Siesta Resort & Villas

10. Bayside Villas by Islander 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. Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite

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

19. Casa Morada

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

Top Upper Matecumbe Key Hotel Reviews

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Inns information

Explore a world of travel with Expedia