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

Search Cottages in Upper Matecumbe Key

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan
No exact matches found, but these alternatives could be just right

Recommended hotels in Upper Matecumbe Key

House, 3 Bedrooms, Ocean View, Oceanfront | Lanai

1. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
"Loved this place! driving in I wasn’t too sure but when we open the door to our King suite absolutely stunning clean smelled amazing and walk right up to the water. You can paddleboard kayak. We loved our stay."
United States
Tamara
The price is €132
includes taxes & fees
22 Sept - 23 Sept
La Jolla Resort
Premium bedding, in-room safe, desk, blackout curtains

2. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,116 reviews)
"Property is beautiful, staff is great and overall an amazing place to stay."
United States
Sonia
The price is €251
includes taxes & fees
27 Sept - 28 Sept
Islander Resort
Deluxe Ocean View Two Queen Suite | Balcony

3. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,773 reviews)
"Excellent location, nice breakfast."
United States
Suresh
The price is €196
includes taxes & fees
27 Sept - 28 Sept
Chesapeake Beach Resort
Balcony

4. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,430 reviews)
"Excellent hotel to spend good time with friends and family, just amazing."
United States
RAIBEL
The price is €210
includes taxes & fees
29 Sept - 30 Sept
Cheeca Lodge & Spa
Deluxe Cottage

5. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (748 reviews)
"Great resorts - will return again. Highly recommend"
United States
Lourdes
The price is €88
includes taxes & fees
30 Sept - 1 Oct
Breezy Palms Resort
View from room

6. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,312 reviews)
"Wonderful resort, very friendly staff, would definitely stay again!"
United States
Amy
The price is €214
includes taxes & fees
27 Sept - 28 Sept
Amara Cay Resort
Aerial view

7. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,000 reviews)
"Loved staying here and would stay again. Staff were so friendly and nice - made you feel like you knew them for years."
United States
Stephen
The price is €241
includes taxes & fees
21 Sept - 22 Sept
Pines & Palms Resort
Restaurant

8. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (462 reviews)
"Nice place very clean , quiet . Was great stay for us , thank you"
United States
beata
The price is €251
includes taxes & fees
28 Sept - 29 Sept
Bayside Villas by Islander Resort
Balcony view

9. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,000 reviews)
"Great location and good rates for the 2 nights that we stayed. Staff was great and helpful. Closed to shops, cafe, and restaurants."
United States
Pang
The price is €160
includes taxes & fees
27 Sept - 28 Sept
Hadley Resort and Marina
Daily cooked-to-order breakfast for a fee

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 €450
includes taxes & fees
27 Sept - 28 Sept
The Islands of Islamorada
Suite, 1 King Bed with Sofa bed, Kitchenette, Oceanfront | Terrace/patio

11. Sands of Islamorada

Sands of Islamorada
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (415 reviews)
"Great place to stay!"
United States
Virginia
The price is €200
includes taxes & fees
1 Oct - 2 Oct
Sands of Islamorada
Exterior

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

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Matecumbe
The price is €1,122
includes taxes & fees
24 Sept - 25 Sept
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Exterior

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

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Matecumbe
The price is €1,688
includes taxes & fees
24 Sept - 25 Sept
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Exterior

14. Charming Suite @Islamorada With Pool Access - Twilight Suite

Charming Suite @Islamorada With Pool Access - Twilight Suite
Matecumbe
The price is €2,242
includes taxes & fees
24 Sept - 25 Sept
Charming Suite @Islamorada With Pool Access - Twilight Suite
Outdoor dining

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

Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
Matecumbe
The price is €1,830
includes taxes & fees
24 Sept - 25 Sept
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
Exterior

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

Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
Matecumbe
The price is €3,376
includes taxes & fees
24 Sept - 25 Sept
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
Exterior

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

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
The price is €1,820
includes taxes & fees
24 Sept - 25 Sept
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Shangri-La Suite | Terrace/patio

18. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (457 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 €165
includes taxes & fees
6 Oct - 7 Oct
Casa Morada
Terrace/patio

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

Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
Matecumbe
The price is €1,122
includes taxes & fees
28 Sept - 29 Sept
Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
Exterior

20. Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite

Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
Matecumbe
The price is €2,130
includes taxes & fees
24 Sept - 25 Sept
Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upper Matecumbe Key Hotel Reviews

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

10/10 Excellent
"This is so peaceful. We have been 5x now and if you are looking for quaint and peaceful this is it. Very clean very nice people. Literally the only drawback is we cannot bring our jetskis, but get it."
kimberly 1-night trip
Posted 1 hour ago
The Pelican Key Largo Cottages

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cottages information

Number of reviews
5,651
Accommodation
28 Cottages
Lowest Price
€88
Highest Price
€3,376

Explore a world of travel with Expedia