Top Cottages 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. Cheeca Lodge & Spa

Matecumbe

Yuniel

6.917.814 ₫ total

includes taxes & fees

18 Aug - 19 Aug

2. Hadley Resort and Marina

Matecumbe

RAIBEL

4.350.952 ₫ total

includes taxes & fees

30 Aug - 31 Aug

Premium bedding, in-room safe, desk, blackout curtains

3. Islander Resort

Matecumbe

Sarah

9.105.327 ₫ total

includes taxes & fees

30 Aug - 31 Aug

House, 3 Bedrooms, Ocean View, Oceanfront | Lanai

4. La Jolla Resort

Matecumbe

adrian

4.026.579 ₫ total

includes taxes & fees

10 Aug - 11 Aug

Deluxe Ocean View Two Queen Suite | Balcony

5. Chesapeake Beach Resort

Matecumbe

alicia

5.943.591 ₫ total

includes taxes & fees

17 Aug - 18 Aug

6. Bayside Villas by Islander Resort

Matecumbe

beata

8.885.675 ₫ total

includes taxes & fees

12 Aug - 13 Aug

7. Breezy Palms Resort

Matecumbe

Tristan

4.487.757 ₫ total

includes taxes & fees

1 Sept - 2 Sept

8. Pines & Palms Resort

Matecumbe

John

6.628.100 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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

9. Amara Cay Resort

Matecumbe

Estefani

6.890.470 ₫ total

includes taxes & fees

12 Aug - 13 Aug

10. La Siesta Resort & Villas

Matecumbe

Brianne

6.491.372 ₫ total

includes taxes & fees

12 Aug - 13 Aug

Suite, 1 King Bed with Sofa bed, Kitchenette, Oceanfront | Terrace/patio

11. Sands of Islamorada

Matecumbe

Virginia

6.711.897 ₫ total

includes taxes & fees

18 Aug - 19 Aug

Daily cooked-to-order breakfast for a fee

12. The Islands of Islamorada

Matecumbe

Christian

10.886.661 ₫ total

includes taxes & fees

16 Aug - 17 Aug

13. Casa Morada

Matecumbe

Lois

7.863.692 ₫ total

includes taxes & fees

10 Aug - 11 Aug

14. Fisher Inn Resort & Marina

Islamorada

MARC

4.099.007 ₫ total

includes taxes & fees

23 Aug - 24 Aug

15. Drift Hotel

Key Largo

oscar

3.296.168 ₫ total

includes taxes & fees

12 Aug - 13 Aug

16. Lime Tree Bay Resort

Long Key

Javier

4.549.453 ₫ total

includes taxes & fees

24 Aug - 25 Aug

Standard Room, 1 King Bed | In-room safe, iron/ironing board, free WiFi, bed sheets

17. Marina Del Mar Resort and Marina

Key Largo

Francisco

4.728.799 ₫ total

includes taxes & fees

12 Aug - 13 Aug

18. Drop Anchor

Islamorada

Noel

4.657.172 ₫ total

includes taxes & fees

12 Aug - 13 Aug

Two Queen Beds Water View | Egyptian cotton sheets, premium bedding, in-room safe, blackout curtains

19. Creekside Inn

Tavernier

Cristy

3.892.364 ₫ total

includes taxes & fees

27 Aug - 28 Aug

20. Dove Creek Resort & Marina, Trademark Collection by Wyndham

Key Largo

Mae L

3.733.381 ₫ total

includes taxes & fees

1 Sept - 2 Sept

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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 Cottages information

Number of reviews	12,183
Accommodation	2 Cottages
Lowest Price	3.296.168 ₫
Highest Price	10.886.661 ₫

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Recommended hotels in Upper Matecumbe Key

1. Cheeca Lodge & Spa

2. Hadley Resort and Marina

3. Islander Resort

4. La Jolla Resort

5. Chesapeake Beach Resort

6. Bayside Villas by Islander Resort

7. Breezy Palms Resort

8. Pines & Palms Resort

9. Amara Cay Resort

10. La Siesta Resort & Villas

11. Sands of Islamorada

12. The Islands of Islamorada

13. Casa Morada

14. Fisher Inn Resort & Marina

15. Drift Hotel

16. Lime Tree Bay Resort

17. Marina Del Mar Resort and Marina

18. Drop Anchor

19. Creekside Inn

20. Dove Creek Resort & Marina, Trademark Collection by Wyndham

Find holiday rentals that suit your style

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 Cottages information

Explore a world of travel with Expedia

Search Cottages in Upper Matecumbe Key

Change your mind

Treat yourself

Be picky

Check prices for these dates

Recommended hotels in Upper Matecumbe Key

1. Cheeca Lodge & Spa

2. Hadley Resort and Marina

3. Islander Resort

4. La Jolla Resort

5. Chesapeake Beach Resort

6. Bayside Villas by Islander Resort

7. Breezy Palms Resort

8. Pines & Palms Resort

9. Amara Cay Resort

10. La Siesta Resort & Villas

11. Sands of Islamorada

12. The Islands of Islamorada

13. Casa Morada

14. Fisher Inn Resort & Marina

15. Drift Hotel

16. Lime Tree Bay Resort

17. Marina Del Mar Resort and Marina

18. Drop Anchor

19. Creekside Inn

20. Dove Creek Resort & Marina, Trademark Collection by Wyndham

Find holiday rentals that suit your style

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 Cottages information

Explore a world of travel with Expedia