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

Upper Matecumbe Key condominium resorts to rent from $139

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7
No exact matches found, but these alternatives could be just right

Recommended hotels in Upper Matecumbe Key

A beach with palm trees and lounge chairs.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,802 reviews)
"Great place"
United States
Phelicia
$188 nightly
The price is $212
Nov 11 - Nov 12
Total with taxes and fees
Chesapeake Beach Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

2. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,139 reviews)
"Amazing place would definitely recommend"
United States
Steven
$297 nightly
The price is $334
Oct 20 - Oct 21
Total with taxes and fees
Islander Resort
A beach with palm trees, thatched-roof huts, and lounge chairs.

3. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (767 reviews)
"Such a great place to stay!!"
United States
Gavin
$123 nightly
The price is $139
Oct 18 - Oct 19
Total with taxes and fees
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.

4. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,321 reviews)
"Super clean resort."
United States
Danielle
$208 nightly
The price is $234
Oct 18 - Oct 19
Total with taxes and fees
Amara Cay Resort
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

5. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,008 reviews)
"Nice hotel."
United States
Brett
$133 nightly
The price is $150
Oct 14 - Oct 15
Total with taxes and fees
La Jolla Resort
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

6. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,477 reviews)
"Staff is very helpful, rooms are clean, and there is a lot to do on the property!"
United States
Morgan
$250 nightly
The price is $281
Oct 14 - Oct 15
Total with taxes and fees
Cheeca Lodge & Spa
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

7. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,000 reviews)
"Great place to stay!"
United States
Brianne
$252 nightly
The price is $283
Nov 8 - Nov 9
Total with taxes and fees
La Siesta Resort & Villas
A balcony with a view of a beach, a pool, and a thatched-roof structure.

8. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,000 reviews)
"Great place"
United States
weder
$188 nightly
The price is $212
Nov 9 - Nov 10
Total with taxes and fees
Hadley Resort and Marina
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

9. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 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
$239 nightly
The price is $269
Oct 14 - Oct 15
Total with taxes and fees
Pines & 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
$558 nightly
The price is $626
Oct 15 - Oct 16
Total with taxes and fees
The Islands of Islamorada
A beachside lounge with a wooden deck, thatched roof, and tropical plants.

11. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 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!"
United States
Brian
$353 nightly
The price is $397
Oct 20 - Oct 21
Total with taxes and fees
Bayside Villas by Islander Resort
A beachside lounge area with sun loungers, a thatched structure, and a view of the ocean.

12. 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
$201 nightly
The price is $226
Oct 19 - Oct 20
Total with taxes and fees
Sands of Islamorada
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
$3,426 nightly
The price is $3,801
Oct 20 - Oct 21
Total with taxes and fees
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
Marina

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

Charming Suite @Islamorada With Pool Access - Twilight Suite
Matecumbe
$2,284 nightly
The price is $2,534
Oct 20 - Oct 21
Total with taxes and fees
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
$1,860 nightly
The price is $2,064
Oct 20 - Oct 21
Total with taxes and fees
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
An indoor wooden structure with a thatched roof, multiple hanging spherical lights, and a central seating area.

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

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
$1,849 nightly
The price is $2,051
Oct 20 - Oct 21
Total with taxes and fees
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
An indoor wooden structure with a thatched roof, multiple hanging spherical lights, and a central seating area.

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

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Matecumbe
$1,713 nightly
The price is $1,901
Oct 20 - Oct 21
Total with taxes and fees
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Marina

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

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Matecumbe
$1,142 nightly
The price is $1,267
Oct 20 - Oct 21
Total with taxes and fees
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Exterior

19. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (463 reviews)
"Very helpful staff and great location"
United States
David
$188 nightly
The price is $211
Oct 28 - Oct 29
Total with taxes and fees
Casa Morada
An indoor wooden structure with a thatched roof, multiple hanging spherical lights, and a central seating area.

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

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
Matecumbe
$2,282 nightly
The price is $2,532
Oct 20 - Oct 21
Total with taxes and fees
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

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

8/10 Good
"The hotel’s location is fantastic, right on the Gulf side with its own private beach, lounge chairs, and even a small pier. The sunsets were absolutely stunning, and waking up by the water was a real treat. Just a heads up: we booked the economy double room and it was really small; barely enough space for two people and luggage. Still, the outdoor areas more than made up for it."
Betul 1-night trip
Posted 12 hours ago
The Pelican Key Largo Cottages

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Condo Resorts information

Number of reviews
5,644
Accommodation
0 Condo Resorts
Lowest Price
$139
Highest Price
$3,801

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