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
$749 nightly
The price is $843 total per night from Nov 12 to Nov 13
$843 total
Nov 12 - Nov 13
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 ...
i like the fact that there's beach area but it was difficult to walk in an out of it due to the rocks. The pool filter could have been cleaned during our stay as there was multiple days of debris caught in the drain trap. would have enjoyed more dining options. Room was available before check in ...

Reviewed on Oct 27, 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
$183 nightly
The price is $206 total per night from Nov 16 to Nov 17
$206 total
Nov 16 - Nov 17
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 ...
Beautiful location. The room was very comfortable and clean. The ocean view room with a balcony was perfect. The continental breakfast was great. I would highly recommend staying here.

Reviewed on Nov 9, 2025

Opens in a new windowChesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
$266 nightly
The price is $300 total per night from Nov 20 to Nov 21
$300 total
Nov 20 - Nov 21
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 ...
Awesome stay! Well recommended!

Reviewed on Nov 6, 2025

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
$159 nightly
The price is $179 total per night from Nov 12 to Nov 13
$179 total
Nov 12 - Nov 13
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 ...
Very spacious room with huge, comfortable bed. We were in Room 4 at the front of the property, so could hear noise from the busy highway outside. Swimming pool didn't appear to be heated, but is of a good size.

Reviewed on Nov 9, 2025

Opens in a new windowSunset Inn
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
$245 nightly
The price is $276 total per night from Nov 12 to Nov 13
$276 total
Nov 12 - Nov 13
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. ...
It was absolutely beautiful and the staff was always super nice!

Reviewed on Nov 8, 2025

Opens in a new windowCheeca Lodge & Spa
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway, Islamorada, FL
$124 nightly
The price is $140 total per night from Dec 2 to Dec 3
$140 total
Dec 2 - Dec 3
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 ...
Great place to stay lovely staff Easy to find

Reviewed on Nov 6, 2025

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
$207 nightly
The price is $233 total per night from Nov 30 to Dec 1
$233 total
Nov 30 - Dec 1
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 ...
Water Taxi is the best perk ever ..

Reviewed on Nov 6, 2025

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

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway, Islamorada, FL
$197 nightly
The price is $222 total per night from Dec 4 to Dec 5
$222 total
Dec 4 - Dec 5
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, ...
Great spot! Beautiful grounds and awesome rooms. Pool, beach and boats docks are great. Def will stay again **beer and wine only** at the bar. FYI. Pack accordingly 😂😂

Reviewed on Nov 5, 2025

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
$150 nightly
The price is $168 total per night from Dec 10 to Dec 11
$168 total
Dec 10 - Dec 11
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 ...
We came for a weekend getaway. Our room was clean but the floors were dusty and the water pressure in the bathroom was very low. The parking is a bit tight. However the location is great because it is around everything. (Publix, pharmacy, gas station, bait shop, etc.) The staff is very helpful and ...

Reviewed on Oct 24, 2025

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

Chesapeake Beach Resort

Chesapeake Beach Resort

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Beautiful location. The room was very comfortable and clean. The ocean view room with a balcony was perfect. The continental breakfast was great. I would highly recommend staying here. "
A verified traveler stayed at Chesapeake Beach Resort
Chesapeake Beach Resort

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