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 $118

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Check prices for these dates

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

Recommended hotels in Upper Matecumbe Key

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,458 reviews)
"Excellent hotel to spend good time with friends and family, just amazing."
United States
RAIBEL
$190 nightly
The price is $214
Oct 4 - Oct 5
Total with taxes and fees
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, (1,785 reviews)
"Excellent location, nice breakfast."
United States
Suresh
$186 nightly
The price is $209
Oct 6 - Oct 7
Total with taxes and fees
Chesapeake Beach Resort
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

3. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,004 reviews)
"Loved the amenities"
United States
Kayla
$105 nightly
The price is $118
Sep 29 - Sep 30
Total with taxes and fees
La Jolla Resort
A beach with palm trees, thatched-roof huts, and lounge chairs.

4. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (753 reviews)
"Great Florida style resort, clean and nice staff. Close to everything in Islamorada!"
United States
Debra
$107 nightly
The price is $120
Sep 29 - Sep 30
Total with taxes and fees
Breezy Palms Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

5. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,127 reviews)
"Great palace to stay at a reasonable price"
United States
John
$297 nightly
The price is $334
Sep 29 - Sep 30
Total with taxes and fees
Islander Resort
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

6. 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
$268 nightly
The price is $302
Sep 28 - Sep 29
Total with taxes and fees
Pines & 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.

7. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,323 reviews)
"amazing clean stay."
United States
MICHAEL
$208 nightly
The price is $234
Sep 30 - Oct 1
Total with taxes and fees
Amara Cay Resort
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, (1,003 reviews)
"Great place"
United States
weder
$147 nightly
The price is $166
Sep 28 - Sep 29
Total with taxes and fees
Hadley Resort and Marina
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

9. The Islands of Islamorada

The Islands of Islamorada
5.0 star property
Matecumbe
9.6 out of 10, Exceptional, (80 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
$466 nightly
The price is $523
Oct 1 - Oct 2
Total with taxes and fees
The Islands of Islamorada
A beachside lounge with a wooden deck, thatched roof, and tropical plants.

10. 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
$355 nightly
The price is $399
Sep 28 - Sep 29
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.

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
$204 nightly
The price is $230
Oct 1 - Oct 2
Total with taxes and fees
Sands of Islamorada

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

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
Matecumbe
$1,073 nightly
The price is $1,198
Oct 4 - Oct 5
Total with taxes and fees
Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite
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
$3,236 nightly
The price is $3,611
Oct 4 - Oct 5
Total with taxes and fees
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
An indoor wooden structure with a thatched roof, multiple hanging spherical lights, and a central seating area.

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

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Matecumbe
$1,618 nightly
The price is $1,806
Oct 4 - Oct 5
Total with taxes and fees
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon 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
$1,756 nightly
The price is $1,960
Oct 4 - Oct 5
Total with taxes and fees
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
A deck with a white railing, a lounge chair, a blue towel, and a large umbrella.

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

Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
Matecumbe
$1,073 nightly
The price is $1,198
Oct 4 - Oct 5
Total with taxes and fees
Romantic Suite With Jacuzzi & Garden Oasis @Islamorada - Jungles Suite Room
An indoor wooden structure with a thatched roof, multiple hanging spherical lights, and a central seating area.

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

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Matecumbe
$1,747 nightly
The price is $1,949
Oct 4 - Oct 5
Total with taxes and fees
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

18. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (460 reviews)
"Very helpful staff and great location"
United States
David
$186 nightly
The price is $210
Oct 6 - Oct 7
Total with taxes and fees
Casa Morada

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

Charming Suite @Islamorada With Pool Access - Twilight Suite
Matecumbe
$2,157 nightly
The price is $2,407
Oct 4 - Oct 5
Total with taxes and fees
Charming Suite @Islamorada With Pool Access - Twilight Suite
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
$2,155 nightly
The price is $2,405
Oct 4 - Oct 5
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Loved the kayak, and breakfast and the view! Everything!"
Sebastian 1-night trip
Posted 11 hours ago
Chesapeake Beach Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Condo Resorts information

Number of reviews
5,123
Accommodation
0 Condo Resorts
Lowest Price
$118
Highest Price
$3,611

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