Book Hotels in Upper Matecumbe Key, FL

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Top Upper Matecumbe Key hotels

The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
$658 nightly
The price is $740 total per night from Jan 22 to Jan 23
$740 total
Jan 22 - Jan 23
Total with taxes and fees
2 outdoor pools, a 24-hour gym, and a hot tub are all featured at this smoke-free villa. Spend a day at the beach kayaking, or relax with sun loungers and beach ...
Beautiful accommodations and location, very clean, many activities available at resort

Reviewed on Nov 25, 2025

Opens in a new windowThe Islands of Islamorada
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$232 nightly
The price is $262 total per night from Jan 25 to Jan 26
$262 total
Jan 25 - Jan 26
Total with taxes and fees
A private beach, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind ...
Room was clean. Check in was fast and the staff was very friendly and welcoming.

Reviewed on Jan 18, 2026

Opens in a new windowChesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
$377 nightly
The price is $425 total per night from Feb 1 to Feb 2
$425 total
Feb 1 - Feb 2
Total with taxes and fees
This luxury resort features a private beach, a golf course, and a full-service spa. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...
Nice resort

Reviewed on Jan 19, 2026

Opens in a new windowCheeca Lodge & Spa
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
$332 nightly
The price is $374 total per night from Jan 22 to Jan 23
$374 total
Jan 22 - Jan 23
Total with taxes and fees
A private beach, 3 restaurants, and 2 outdoor pools are all featured at this hotel. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Families ...
Loved everything about this place!! &So many outdoor games to play.

Reviewed on Jan 19, 2026

Opens in a new windowIslander Resort
Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$208 nightly
The price is $234 total per night from Jan 27 to Jan 28
$234 total
Jan 27 - Jan 28
Total with taxes and fees
An outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A garden, a picnic area, and luggage storage ...
Air was loud. Very conveniently located. Friendly Bars nearby. Mangrove Mikes good for coffee and breakfast in the morning

Reviewed on Jan 9, 2026

Opens in a new windowSunset Inn
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway Islamorada FL
$152 nightly
The price is $171 total per night from Jan 26 to Jan 27
$171 total
Jan 26 - Jan 27
Total with taxes and fees
A private beach and an outdoor pool are featured at this smoke-free hotel. WiFi in public areas is free. A garden, a picnic area, and concierge services are ...
Lovely location

Reviewed on Jan 20, 2026

Opens in a new windowLa Jolla Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$273 nightly
The price is $308 total per night from Jan 26 to Jan 27
$308 total
Jan 26 - Jan 27
Total with taxes and fees
A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. If you want to take your pet along, this pet-friendly property offers everything ...
Amazing place to stay. Staff was great

Reviewed on Jan 16, 2026

Opens in a new windowAmara Cay Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$358 nightly
The price is $403 total per night from Feb 10 to Feb 11
$403 total
Feb 10 - Feb 11
Total with taxes and fees
The private beach and marina are among the highlights at this resort. Enjoy the outdoor pool and perks like a free area shuttle. There's a poolside bar on site, ...
Room was very clean

Reviewed on Jan 18, 2026

Opens in a new windowLa Siesta Resort & Villas
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$204 nightly
The price is $230 total per night from Jan 25 to Jan 26
$230 total
Jan 25 - Jan 26
Total with taxes and fees
This traditional hotel's private beach and marina are among the highlights. Enjoy a day at the beach kayaking, or relax with sun loungers. Families will appreciate ...
Clean room and beautiful view.

Reviewed on Jan 13, 2026

Opens in a new windowHadley Resort and Marina
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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.

Recent Upper Matecumbe Key hotel reviews by fellow wanderers

La Jolla Resort

La Jolla Resort

5 out of 5
Posted 14 hours ago
Travelocity Verified Review
"Lovely location "
A verified traveler stayed at La Jolla Resort
La Jolla Resort

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