Upper Matecumbe Key Cottages

Upper Matecumbe Key Cottages
Islamorada
Florida
United States of America
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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

A covered outdoor area with a wooden deck, palm trees, and a view of the beach.

A view of a beachfront property with a parking area, palm trees, and a clear sky.

A beach with palm trees, thatched-roof huts, and lounge chairs.

A covered outdoor area with a view of the beach, a pool, and a patio with chairs.

1. Breezy Palms Resort

Breezy Palms Resort

2.5 star property

Matecumbe

9.0 out of 10, Wonderful, (777 reviews)

9.0/10

Wonderful

(777 reviews)

"Such a great place to stay!!"

Gavin

The price is €116

€116

includes taxes & fees

3 Nov - 4 Nov

Breezy Palms Resort

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.

A hotel room with a sofa, a small round table, a desk with a chair, and a view of the sea through large windows.

A balcony with a view of a beach, palm trees, and a pool.

A beach with palm trees, a dock, and lounge chairs.

2. Amara Cay Resort

Amara Cay Resort

4.0 star property

Matecumbe

8.8 out of 10, Excellent, (1,324 reviews)

8.8/10

Excellent

(1,324 reviews)

"Great location as well."

Amir

The price is €235

€235

includes taxes & fees

15 Nov - 16 Nov

Amara Cay Resort

A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.

A balcony with two blue chairs and a small table, overlooking a beach with palm trees and a clear blue sky.

A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

A hotel room with a bed, a bedside table with a lamp, a small table with a basket, a blue and white striped ottoman, and a balcony with a view of palm trees and the ocean.

3. Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 star property

Matecumbe

9.4 out of 10, Exceptional, (1,804 reviews)

9.4/10

Exceptional

(1,804 reviews)

"Nice beach walkable property Great breakfast made to order"

kent brian

The price is €203

€203

includes taxes & fees

3 Nov - 4 Nov

Chesapeake Beach Resort

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

A balcony with a view of palm trees and the sea, a white railing, and a table with chairs.

A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.

A tropical resort with a swimming pool, palm trees, and a waterfall.

4. Cheeca Lodge & Spa

Cheeca Lodge & Spa

5.0 star property

Matecumbe

9.2 out of 10, Wonderful, (1,496 reviews)

9.2/10

Wonderful

(1,496 reviews)

"Great place. Phenomenal food!"

Brandon

The price is €248

€248

includes taxes & fees

8 Nov - 9 Nov

Cheeca Lodge & Spa

A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

A bedroom with a bed, two chairs, a sofa, a TV, and a large window with a view of the ocean.

A beachfront property with a white building, a balcony with a white railing, and palm trees.

5. La Jolla Resort

La Jolla Resort

2.5 star property

Matecumbe

9.2 out of 10, Wonderful, (1,004 reviews)

9.2/10

Wonderful

(1,004 reviews)

"Loved the beach area! Bed was comfortable, kitchenette well appointed, and there were enough electrical outlets!"

Jane

The price is €152

€152

includes taxes & fees

4 Nov - 5 Nov

La Jolla Resort

A patio with a wooden table and chairs, a sofa, and a striped ottoman. There are palm trees and a view of the beach.

A bar area with a wooden counter, bar stools, and potted plants.

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

A wooden pier leading to a beach with palm trees and a row of beach huts.

6. Islander Resort

Islander Resort

4.0 star property

Matecumbe

9.4 out of 10, Exceptional, (1,160 reviews)

9.4/10

Exceptional

(1,160 reviews)

"The entire resort was clean, staff very friendly, bar and restaurant and pools were fabulous! Would definitely stay there again!"

DEBORAH

The price is €299

€299

includes taxes & fees

3 Nov - 4 Nov

Islander Resort

A balcony with a view of a beach, a pool, and a thatched-roof structure.

A beach scene with two yellow beach chairs and a person lying on one.

A balcony with a view of the beach, lounge chairs, and a palm tree.

A pier with boats docked, a thatched-roof structure, and signs indicating tours and rentals.

7. Hadley Resort and Marina

Hadley Resort and Marina

3.5 star property

Matecumbe

7.6 out of 10, Good, (1,000 reviews)

7.6/10

Good

(1,000 reviews)

"Can’t wait to stay again in the spring. Amazing property."

Jason

The price is €174

€174

includes taxes & fees

15 Nov - 16 Nov

Hadley Resort and Marina

A resort with a pool surrounded by palm trees and a view of the ocean.

A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

A row of colorful beach huts with palm trees in the background.

A beach with colorful buildings, kayaks, and lounge chairs.

8. La Siesta Resort & Villas

La Siesta Resort & Villas

4.0 star property

Matecumbe

8.6 out of 10, Excellent, (1,000 reviews)

8.6/10

Excellent

(1,000 reviews)

"Great place to stay!"

Brianne

The price is €221

€221

includes taxes & fees

15 Nov - 16 Nov

La Siesta Resort & Villas

A wooden deck with a view of the beach and ocean.

A spacious living area with a round dining table, a sofa, and a TV mounted on the wall.

A beachside lounge area with sun loungers, a thatched structure, and a view of the ocean.

A beach with an American flag, palm trees, and a barbecue area.

9. Sands of Islamorada

Sands of Islamorada

2.5 star property

Matecumbe

8.8 out of 10, Excellent, (416 reviews)

8.8/10

Excellent

(416 reviews)

"Very small, Was quiet and relaxing."

Nicolas

The price is €206

€206

includes taxes & fees

16 Nov - 17 Nov

Sands of Islamorada

A beachside resort with a pool area, lounge chairs, and palm trees.

A modern two-story beachfront property with balconies, a pool, and a sandy beach area.

A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

10. Pines & Palms Resort

Pines & Palms Resort

3.0 star property

Matecumbe

9.2 out of 10, Wonderful, (1,001 reviews)

9.2/10

Wonderful

(1,001 reviews)

"We have stayed here multiple times and always have a good stay."

Michael

The price is €242

€242

includes taxes & fees

4 Nov - 5 Nov

Pines & Palms Resort

A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

A balcony with two wooden chairs and a small table, overlooking a beach with palm trees and the ocean.

A beachfront hotel with multiple-story buildings, a pool, and palm trees.

11. The Islands of Islamorada

The Islands of Islamorada

5.0 star property

Matecumbe

9.6 out of 10, Exceptional, (83 reviews)

9.6/10

Exceptional

(83 reviews)

"We had an AMAZING stay! The staff was wonderful, providing excellent customer service and providing local recommendations for activities and dining. The property is pristine and gorgeous. My only critique would be a lack of on property food options. We will definitely be back."

Catherine

The price is €755

€755

includes taxes & fees

30 Nov - 1 Dec

The Islands of Islamorada

An outdoor dining area with wooden furniture, tables, and chairs, overlooking a beach and ocean.

A resort with a central swimming pool surrounded by palm trees and a view of the ocean.

A bar area with a counter, stools, and potted plants.

A balcony with a TV, wicker furniture, and a view of the sea.

12. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort

3.5 star property

Matecumbe

9.0 out of 10, Wonderful, (468 reviews)

9.0/10

Wonderful

(468 reviews)

"Had a blast in the keys! This property gave us every reason to stay on property! Fishing provided! Bait provided! Games, bikes, excellent staff and the vibes are worth every booking moment! Definitely coming back! FYI: we stay in the townhomes and still had access to all of the amenities! Book your stay! Let’s go!"

Brian

The price is €307

€307

includes taxes & fees

3 Nov - 4 Nov

Bayside Villas by Islander Resort

A two-story building with a covered porch and a pathway leading to it, surrounded by lush greenery and palm trees.

A pool with a view of a bridge and umbrellas in the background.

An indoor wooden structure with a thatched roof, multiple hanging spherical lights, and a central seating area.

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

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

Matecumbe

The price is €3,291

€3,291

includes taxes & fees

8 Nov - 9 Nov

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

A kitchen area with white cabinets, a green countertop, and various kitchen items.

A bathroom with a toilet, a sink, a mirror, and a shower area.

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

Charming Suite @Islamorada With Pool Access - Twilight Suite

Matecumbe

Charming Suite @Islamorada With Pool Access - Twilight Suite

A covered outdoor area with a white railing, a table with a straw hat, and a bench.

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

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

Matecumbe

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

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

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite

Matecumbe

The price is €1,095

€1,095

includes taxes & fees

8 Nov - 9 Nov

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite

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

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

Matecumbe

The price is €1,775

€1,775

includes taxes & fees

8 Nov - 9 Nov

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

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

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

Matecumbe

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

A view from a window overlooking a beach with palm trees and a wooden pier.

A balcony with two white cups on saucers, overlooking a beach with palm trees and the ocean.

19. Casa Morada

Casa Morada

3.5 star property

Matecumbe

9.2 out of 10, Wonderful, (466 reviews)

9.2/10

Wonderful

(466 reviews)

"Very helpful staff and great location"

David

The price is €195

€195

includes taxes & fees

4 Nov - 5 Nov

Casa Morada

A room with a sofa, a small wooden table, a bed, and a kitchen area.

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

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite

Matecumbe

The price is €2,187

€2,187

includes taxes & fees

8 Nov - 9 Nov

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana 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.

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Top Upper Matecumbe Key Hotel Reviews

Waterside Suites & Marina

8/10 Good

"It was dark when we arrived and pouring rain when we left, so no amenities used. It was great for a short stay."

Mary 1-night trip

Posted 4 hours ago

Waterside Suites & Marina

Pines & Palms Resort

10/10 Excellent

"Great trip, this is a very nice place to visit. Highly recommend it."

Michelle 7-night trip

Posted 12 hours ago

Pines & Palms Resort

The Pelican Key Largo Cottages

8/10 Good

"Quaint cottages. Well kept, very clean. Parking right in front of the cottage. The office staff was helpful and friendly."

Connie 2-night trip

Posted 13 hours ago

The Pelican Key Largo Cottages

The Caribbean Resort

10/10 Excellent

"Everything was wonderful."

Karl 2-night trip

Posted 1 day ago

The Caribbean Resort

Chesapeake Beach Resort

10/10 Excellent

"The property had bikes, kayaks, paddle boards and fishing rods you can use at no charge. The breakfast was omelettes made to order, pancakes and a variety of other breakfast items ( no meats) and a nice area to sit outside and enjoy breakfast. It was a very nice place. We will definitely stay there again."

Carol 5-night trip

Posted 1 day ago

Chesapeake Beach Resort

Hadley Resort and Marina

8/10 Good

"Was there for my annual fishing trip. The rooms were quiet, and the ac worked well. The pool was good and so was the small beach."

Casandra 2-night trip

Posted 5 days ago

Hadley Resort and Marina

Breezy Palms Resort

10/10 Excellent

"Right on the ocean. Beautiful views. Very relaxing. Not busy this time of year and it was great."

Judy 3-night trip

Posted 10 days ago

Breezy Palms Resort

Casa Morada

10/10 Excellent

"."

angela 3-night trip

Posted 2 weeks ago

Casa Morada

Find out more about Upper Matecumbe Key