Book Hotels in Upper Matecumbe Key, FL

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Top Upper Matecumbe Key hotels

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $188 total per night from Dec 3 to Dec 4
$188 total
Dec 3 - Dec 4
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 ...
Great place

Reviewed on Nov 28, 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
$271 nightly
The price is $305 total per night from Dec 4 to Dec 5
$305 total
Dec 4 - Dec 5
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 ...
Everything was delightful!

Reviewed on Nov 26, 2025

Opens in a new windowIslander Resort
Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy Islamorada FL
$116 nightly
The price is $131 total per night from Dec 16 to Dec 17
$131 total
Dec 16 - Dec 17
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 ...
Great staff, spotless roomy room...great stay!

Reviewed on Nov 25, 2025

Opens in a new windowSunset Inn
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
$240 nightly
The price is $271 total per night from Dec 17 to Dec 18
$271 total
Dec 17 - Dec 18
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. ...
We stayed in the newest section of the Cheeca Lodge. It is so incredibly nice! We had other family staying in the lagoon area. We enjoyed all the activities on the property as well. My nephew especially loved the par3 golf course. I really loved the staff at Cheeca Lodge too. Shelia, Amber and David ...

Reviewed on Nov 26, 2025

Opens in a new windowCheeca Lodge & Spa
Pines & Palms Resort

Pines & Palms Resort

3 out of 5
80401 Old Hwy Islamorada FL
$188 nightly
The price is $212 total per night from Dec 7 to Dec 8
$212 total
Dec 7 - Dec 8
Total with taxes and fees
The private beach and marina are among the highlights at this hotel. Enjoy a day at the beach snorkeling, or relax with sun loungers. Enjoy the outdoor pool ...
Bed and bedding were clean and super comfortable. Kitchen had everything we needed to make our dinner on the grill (which was delivered 😊). View was specular! Right on the beach. Front desk staff was welcoming and helpful.

Reviewed on Nov 29, 2025

Opens in a new windowPines & Palms Resort
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway Islamorada FL
$101 nightly
The price is $114 total per night from Dec 18 to Dec 19
$114 total
Dec 18 - Dec 19
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 ...
A lucky lucky find ... old florida style, staff couldn't do more ... free loan of everything , free bait, free fruit and snacks

Reviewed on Nov 22, 2025

Opens in a new windowLa Jolla Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
$207 nightly
The price is $233 total per night from Dec 4 to Dec 5
$233 total
Dec 4 - Dec 5
Total with taxes and fees
A private beach and a restaurant are featured at this resort. If you want to take your pet along, this pet-friendly property offers everything you'll need for ...
Loved the resort

Reviewed on Nov 21, 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
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $224 total per night from Dec 4 to Dec 5
$224 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, ...
The cottages on the beach are fantastic!

Reviewed on Nov 22, 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
$129 nightly
The price is $145 total per night from Dec 3 to Dec 4
$145 total
Dec 3 - Dec 4
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 ...
Everything was excellent

Reviewed on Nov 26, 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

Pines & Palms Resort

Pines & Palms Resort

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Bed and bedding were clean and super comfortable. Kitchen had everything we needed to make our dinner on the grill (which was delivered 😊). View was specular! Right on the beach. Front desk staff was welcoming and helpful. "
A verified traveler stayed at Pines & Palms Resort
Pines & Palms Resort

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