Upper Matecumbe Key Pet-friendly Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Flight and Pet-friendly hotel deals in Upper Matecumbe Key

Price found within the past 48 hours. Click for updated prices.
Park Central South Beach
Pelican Grand Beach Resort - A Noble House Resort
The Retreat Collection at 1 Hotel & Homes South Beach
EAST Miami
EAST Miami Residences
Don't see what you're looking for?
See all available trips from Columbus to Upper Matecumbe Key
View all trips

5* Pet-friendly holidays in Upper Matecumbe Key

Price found within the past 48 hours. Click for updated prices.
EAST Miami
The Retreat Collection at 1 Hotel & Homes South Beach
EAST Miami Residences
Don't see what you're looking for?
See all available trips from Columbus to Upper Matecumbe Key
View all trips

3 Night Pet-friendly holidays in Upper Matecumbe Key

Price found within the past 48 hours. Click for updated prices.
Park Central South Beach
Pelican Grand Beach Resort - A Noble House Resort
The Retreat Collection at 1 Hotel & Homes South Beach
Don't see what you're looking for?
See all available trips from Columbus to Upper Matecumbe Key
View all trips

4 Night Pet-friendly holidays in Upper Matecumbe Key

Price found within the past 48 hours. Click for updated prices.
Pelican Grand Beach Resort - A Noble House Resort
Riverside Hotel
Park Central South Beach
Don't see what you're looking for?
See all available trips from Columbus to Upper Matecumbe Key
View all trips

Pet-friendly Hotels in Upper Matecumbe Key

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
  • 10 min drive from Bud n' Mary's Dive Center
Stay at this 3.5-star beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9/10 Wonderful! (1,493 reviews)
"Morning breakfast was great. Staff was very attentive and pleasant. Room view was amazing. Very convenient for a person in our party that is disabled."

Reviewed on Aug. 21, 2025

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
  • 5 min walk from Bud n' Mary's Dive Center
Stay at this 4-star beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,237 reviews)
"Not the best hotel in the Florida Keys, but it’s OK for cooling off for a couple of days. For me the pool by the ocean and the tiki bar were the stars of the show. Rooms were meh"

Reviewed on Aug. 22, 2025

Amara Cay Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
  • 6 min drive from Bud n' Mary's Dive Center
Stay at this 4-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9/10 Wonderful! (1,001 reviews)
"We loved the resort atmosphere. It was peaceful and relaxing--just what we were looking for. The drinks are pretty expensive, but that was literally the only downside to the whole trip. It is close to anything you want to do in the Keys."

Reviewed on Aug. 22, 2025

Islander Resort
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.

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.