Book Hotels in Upper Matecumbe Key, FL

Start date: Check-in selected.
To Date
End date: Check-out

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check prices for these dates

Tonight
Oct 6 - Oct 7
Tomorrow
Oct 7 - Oct 8
This weekend
Oct 10 - Oct 12
Next weekend
Oct 17 - Oct 19

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility

Top Upper Matecumbe Key hotels

Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $141 total per night from Oct 21 to Oct 22
$141 total
Oct 21 - Oct 22
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 ...
"Was great everything was perfect"

Reviewed on Sep 30, 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
$189 nightly
The price is $213 total per night from Oct 16 to Oct 17
$213 total
Oct 16 - Oct 17
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. ...
"Amazing!"

Reviewed on Oct 2, 2025

Opens in a new windowCheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$171 nightly
The price is $193 total per night from Oct 9 to Oct 10
$193 total
Oct 9 - Oct 10
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 ...
"Excellent recommendation for a small budget."

Reviewed on Sep 29, 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
$239 nightly
The price is $269 total per night from Oct 19 to Oct 20
$269 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 ...
"Stunning resort with great amenities and excellent service!"

Reviewed on Sep 28, 2025

Opens in a new windowIslander Resort
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 Oct 7 to Oct 8
$140 total
Oct 7 - Oct 8
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 ...
"Had an amazing time at this Hotel. The room was super nice; the facility had spectacular views and a great marina for my boat."

Reviewed on Sep 27, 2025

Opens in a new windowLa Jolla Resort
Pines & Palms Resort

Pines & Palms Resort

3 out of 5
80401 Old Hwy, Islamorada, FL
$178 nightly
The price is $200 total per night from Oct 7 to Oct 8
$200 total
Oct 7 - Oct 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 ...
"We had a full ocean view. The ocean was only a few steps away on beautiful white sand. The pool was ocean side as well. There are also piers to dock boats with sitting locations to watch the sunrise."

Reviewed on Sep 26, 2025

Opens in a new windowPines & Palms Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $210 total per night from Oct 14 to Oct 15
$210 total
Oct 14 - Oct 15
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 ...
"We had a room with an ocean view and it was great. There was a beautiful double rainbow over the water one of the days we were there."

Reviewed on Oct 4, 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
$186 nightly
The price is $210 total per night from Oct 20 to Oct 21
$210 total
Oct 20 - Oct 21
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 rooms"

Reviewed on Sep 20, 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
$136 nightly
The price is $153 total per night from Oct 7 to Oct 8
$153 total
Oct 7 - Oct 8
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 ...
"Nice location and very spacious suite!"

Reviewed on Sep 28, 2025

Opens in a new windowHadley Resort and Marina
Don't see what you're looking for?
See all available properties in Upper Matecumbe Key
View all properties
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

Amara Cay Resort

Amara Cay Resort

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"We had a room with an ocean view and it was great. There was a beautiful double rainbow over the water one of the days we were there."
A verified traveler stayed at Amara Cay Resort
Amara Cay Resort

Explore More Ways to Travel with Travelocity

Explore More Ways to Travel with Travelocity