Book Hotels in Upper Matecumbe Key, FL

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Oct 16 - Oct 18
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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
$187 nightly
The price is $211 total per night from Oct 18 to Oct 19
$211 total
Oct 18 - Oct 19
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 ...
"Un lugar muy tranquilo y una vista hermosa. Excelente para relajarse, meditar y descansar."

Reviewed on Oct 10, 2026

Opens in a new windowChesapeake Beach Resort
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $142 total per night from Oct 21 to Oct 22
$142 total
Oct 21 - Oct 22
Total with taxes and fees
A marina and an outdoor pool are featured at this aparthotel. WiFi in public areas is free. Self parking, a terrace, and a picnic area are also offered.
"This fun little place was a great stopover on our way to Key West. This is not a new property, but it has been redone so well. We stayed in a bungalow and were really struck by how well it had been renovated. Great vibe and decor."

Reviewed on Oct 11, 2026

Opens in a new windowBreezy Palms Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$204 nightly
The price is $230 total per night from Oct 20 to Oct 21
$230 total
Oct 20 - Oct 21
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 ...
"Very clean resort. The pool was fabulous. The tiki bar was great. Stall friendly and helpful. Truly enjoyed my stay!"

Reviewed on Oct 6, 2026

Opens in a new windowAmara Cay 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
$195 nightly
The price is $219 total per night from Oct 12 to Oct 13
$219 total
Oct 12 - Oct 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. ...
Opens in a new windowCheeca Lodge & Spa
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$297 nightly
The price is $334 total per night from Oct 19 to Oct 20
$334 total
Oct 19 - Oct 20
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 ...
Opens in a new windowIslander Resort
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway Islamorada FL
$137 nightly
The price is $154 total per night from Oct 13 to Oct 14
$154 total
Oct 13 - Oct 14
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 ...
Opens in a new windowLa Jolla Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
$252 nightly
The price is $283 total per night from Nov 8 to Nov 9
$283 total
Nov 8 - Nov 9
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, ...
Opens in a new windowLa Siesta Resort & Villas
Casa Morada

Casa Morada

3.5 out of 5
82200 overseas HWY Islamorada FL
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $211 total per night from Oct 28 to Oct 29
$211 total
Oct 28 - Oct 29
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Spend a day at the beach kayaking, or relax with sun loungers and beach ...
Opens in a new windowCasa Morada
The Islands of Islamorada

The Islands of Islamorada

5 out of 5
82779 Old Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$558 nightly
The price is $626 total per night from Oct 15 to Oct 16
$626 total
Oct 15 - Oct 16
Total with taxes and fees
A marina, 2 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Spend a day at the beach kayaking, or relax with sun loungers and beach ...
Opens in a new windowThe Islands of Islamorada
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See all available properties in Upper Matecumbe Key
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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

Breezy Palms Resort

Breezy Palms Resort

5 out of 5
Posted 5 hours ago
Travelocity Verified Review
"This fun little place was a great stopover on our way to Key West. This is not a new property, but it has been redone so well. We stayed in a bungalow and were really struck by how well it had been renovated. Great vibe and decor."
A verified traveler stayed at Breezy Palms Resort
Breezy Palms Resort

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