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

Search Villas in Upper Matecumbe Key

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan
No exact matches found, but these alternatives could be just right

Recommended hotels in Upper Matecumbe Key

A bathroom with a large bathtub, a view of the sea, and a pier with boats.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,451 reviews)
"Excellent hotel to spend good time with friends and family, just amazing."
United States
RAIBEL
The price is Rp2.659.203
Rp4.296.754 total
includes taxes & fees
24 Sept - 25 Sept
Cheeca Lodge & Spa
A beach with palm trees and lounge chairs.

2. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,783 reviews)
"Excellent location, nice breakfast."
United States
Suresh
The price is Rp2.682.346
Rp4.016.528 total
includes taxes & fees
23 Sept - 24 Sept
Chesapeake Beach Resort
A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.

3. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,123 reviews)
"Great palace to stay at a reasonable price"
United States
John
The price is Rp3.493.550
Rp5.134.917 total
includes taxes & fees
29 Sept - 30 Sept
Islander Resort
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

4. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,005 reviews)
"The room was very nice and neat !"
United States
Leslie
The price is Rp1.956.924
Rp2.703.576 total
includes taxes & fees
23 Sept - 24 Sept
La Jolla Resort
A beachside lounge with a wooden deck, thatched roof, and tropical plants.

5. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (464 reviews)
"Nice place very clean , quiet . Was great stay for us , thank you"
United States
beata
The price is Rp4.377.347
Rp6.123.181 total
includes taxes & fees
23 Sept - 24 Sept
Bayside Villas by Islander Resort
A balcony with a view of a beach, a pool, and a thatched-roof structure.

6. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,004 reviews)
"Great place"
United States
weder
The price is Rp2.108.623
Rp2.954.549 total
includes taxes & fees
28 Sept - 29 Sept
Hadley Resort and Marina
A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.

7. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,317 reviews)
"amazing clean stay."
United States
MICHAEL
The price is Rp2.758.700
Rp4.408.689 total
includes taxes & fees
27 Sept - 28 Sept
Amara Cay Resort
A beachside resort with a pool area, lounge chairs, and palm trees.

8. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,002 reviews)
"It was a great time staying at the resort. Really enjoyed that they had a bartender at the pool in the evenings."
United States
Colt
The price is Rp2.077.686
Rp3.316.396 total
includes taxes & fees
24 Sept - 25 Sept
Pines & Palms Resort
A covered outdoor area with a wooden deck, palm trees, and a view of the beach.

9. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (749 reviews)
"It was very cozy. I was able to relax while I was celebrating my anniversary with my wife. The bed was super comfortable. The shower was excellent, and the staff was very friendly."
United States
Dionisio
The price is Rp1.224.661
Rp1.662.448 total
includes taxes & fees
29 Sept - 30 Sept
Breezy Palms Resort
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

10. The Islands of Islamorada

The Islands of Islamorada
5.0 star property
Matecumbe
9.6 out of 10, Exceptional, (81 reviews)
"Love this property! Our family had the most amazing time in the villas. The location is great and the property is really well kept with amazing staff. We enjoyed the pool, the kids game area, pickle ball and relaxing in the home. Highly recommend!!"
United States
Christian
The price is Rp7.351.812
Rp9.396.734 total
includes taxes & fees
1 Oct - 2 Oct
The Islands of Islamorada
A wooden deck with a view of the beach and ocean.

11. Sands of Islamorada

Sands of Islamorada
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (416 reviews)
"Very small, Was quiet and relaxing."
United States
Nicolas
The price is Rp3.426.624
Rp4.095.887 total
includes taxes & fees
1 Oct - 2 Oct
Sands of Islamorada
A view from a window overlooking a beach with palm trees and a wooden pier.

12. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (458 reviews)
"The hotel was in the mist of redoing it's landscaping by adding gaint palm trees and some new boat docks, but it didn't interfere with the overall feel of the place. We enjoyed the free paddle boards and pool. Its also located on a beautiful part of the Keys"
United States
Lois
The price is Rp2.794.840
Rp3.344.974 total
includes taxes & fees
19 Oct - 20 Oct
Casa Morada
A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.

13. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,003 reviews)
"Love that they have a food truck on the property!"
United States
Alexandra
The price is Rp1.956.924
Rp2.783.888 total
includes taxes & fees
23 Sept - 24 Sept
Fisher Inn Resort & Marina
A clear blue pool with palm trees and a white fence in the background.

14. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (293 reviews)
"Excellent stay! Love this place and will definitely be back!"
United States
Hailey Ritch and Patrick
The price is Rp2.659.203
Rp2.991.603 total
includes taxes & fees
23 Sept - 24 Sept
Coconut Cove Resort and Marina
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

15. Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (276 reviews)
"Beautiful place Great beds Lots of dining options"
Canada
Eslita
The price is Rp3.555.122
Rp5.304.664 total
includes taxes & fees
29 Sept - 30 Sept
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A balcony with a view of a river, a wooden cabinet, and a door leading to a shower.

16. Creekside Inn

Creekside Inn
2.5 star property
Tavernier
7.8 out of 10, Good, (1,021 reviews)
"Great place to stay for the night."
United States
Terry
The price is Rp2.541.170
Rp2.859.038 total
includes taxes & fees
29 Sept - 30 Sept
Creekside Inn
A beach with palm trees, a thatched-roof hut, and beach chairs.

17. Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.6 out of 10, Excellent, (1,000 reviews)
"Great location,"
United States
Marianela
The price is Rp2.136.033
Rp3.027.682 total
includes taxes & fees
24 Sept - 25 Sept
Drop Anchor
A bedroom with a large bed, a sliding glass door to a balcony, a wooden cabinet, and a kitchen area with a microwave.

18. The Ocean View Inn & Pub

The Ocean View Inn & Pub
2.0 star property
Islamorada
9.2 out of 10, Wonderful, (32 reviews)
"Very friendly staff"
United States
Maria
The price is Rp3.324.896
Rp3.740.374 total
includes taxes & fees
27 Sept - 28 Sept
The Ocean View Inn & Pub
A covered outdoor area with a view of a beach and palm trees.

19. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,186 reviews)
"Absolutely lovely resort, we always have a wonderful stay ♥️"
United States
Tia
The price is Rp1.796.222
Rp2.020.750 total
includes taxes & fees
24 Sept - 25 Sept
Rock Reef Resort
A swimming pool with lounge chairs and umbrellas, a fenced area, and a building with a door.

20. Waterside Suites & Marina

Waterside Suites & Marina
3.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,489 reviews)
"The place was clean, and the staffs were nice and helpful. We enjoyed our staying."
United States
Thuc
The price is Rp2.176.243
Rp2.947.650 total
includes taxes & fees
27 Sept - 28 Sept
Waterside Suites & Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Great beach for the keys and great breakfast! The bar food is minimal and they don’t always open but Wahoo next door is amazing. Would definitely come back to this hotel."
Julia 1-night trip
Posted 4 hours ago
Chesapeake Beach Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Villas information

Number of reviews
12,562
Accommodation
6 Villas
Lowest Price
Rp1.662.448
Highest Price
Rp9.396.734