Upper Matecumbe Key Pet-friendly Vacations
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Top Pet-friendly vacation packages in Upper Matecumbe Key
Price found within the past 48 hours. Click for updated prices.
Hotel Colonnade Coral Gables, Autograph Collection
Coral Gables Section
Price was $1,278, price is now $521 per person
$521
per person
Nov 21 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (1,006 reviews)
Es un hotel estupendo muy bien situado y el personal es fantástico!!
Reviewed on Oct 14, 2025
The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was $2,986, price is now $1,335 per person
$1,335
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.8/10 Exceptional! (31 reviews)
Great hotel. Clearly freshly refurbished and excellent facilities. Staff were extremely attentive - everyone we bumped into in the lift, for example, even junior team members, asked how we were and whether there was anything that they could do to improve our stay. Shows a great culture! Only downsides are a bar that shuts very early (10pm) and a LOT of mosquitoes in the outdoor pool area - they give bug spray it we had to retreat late afternoon or after rain.
Reviewed on Oct 6, 2025
Bahama Beach Club Pompano
Price was $1,283, price is now $578 per person
$578
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
10/10 Exceptional! (12 reviews)
Such a cute property with lots of charm and a great pool. We loved being able to walk to absolutely everything! The owners were so helpful in guiding us in things to do and how to best get around. We can’t wait to return.
Reviewed on Oct 15, 2025
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View all trips5* Pet-friendly vacations in Upper Matecumbe Key
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View all trips3 Night Pet-friendly vacations in Upper Matecumbe Key
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Park Central South Beach
South Beach
Save 100% on your flight
Price was $1,906, price is now $1,058 per person
$1,058
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (116 reviews)
The bed and sheet are not clean
Reviewed on Oct 16, 2025
The Shelborne By Proper, a Member of Design Hotels
South Beach
Save 100% on your flight
Price was $2,163, price is now $1,066 per person
$1,066
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.8/10 Exceptional! (31 reviews)
Great hotel. Clearly freshly refurbished and excellent facilities. Staff were extremely attentive - everyone we bumped into in the lift, for example, even junior team members, asked how we were and whether there was anything that they could do to improve our stay. Shows a great culture! Only downsides are a bar that shuts very early (10pm) and a LOT of mosquitoes in the outdoor pool area - they give bug spray it we had to retreat late afternoon or after rain.
Reviewed on Oct 6, 2025
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View all trips4 Night Pet-friendly vacations in Upper Matecumbe Key
Price found within the past 48 hours. Click for updated prices.
Bentley Hotel South Beach
South Beach
Save 100% on your flight
Price was $2,304, price is now $1,208 per person
$1,208
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (334 reviews)
The staff very friendly and helpful,
Reviewed on Oct 15, 2025
The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was $2,986, price is now $1,335 per person
$1,335
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.8/10 Exceptional! (31 reviews)
Great hotel. Clearly freshly refurbished and excellent facilities. Staff were extremely attentive - everyone we bumped into in the lift, for example, even junior team members, asked how we were and whether there was anything that they could do to improve our stay. Shows a great culture! Only downsides are a bar that shuts very early (10pm) and a LOT of mosquitoes in the outdoor pool area - they give bug spray it we had to retreat late afternoon or after rain.
Reviewed on Oct 6, 2025
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View all tripsTop Pet-friendly Upper Matecumbe Key Hotels
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Enjoy hiking or biking trails near this oceanfront resort, where dogs are treated to pet-friendly amenities, like food and water bowls. Fees apply for pets.
8.8/10 Excellent! (1,254 reviews)
"Room was spacious, clean with a great balcony."
Reviewed on Oct 7, 2025
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
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. ...
9.2/10 Wonderful! (1,543 reviews)
"Love this place. Great beach/pool. Lovely room with great bathroom. Unbelievable view of the sunrise over the water from our balcony"
Reviewed on Oct 14, 2025
Islander Resort
82100 Overseas Highway, Islamorada, FL
Hiking and biking trails are ready for you to explore near this oceanfront hotel, where dogs and cats can stay for an additional fee.
9/10 Wonderful! (1,009 reviews)
"Amazing property! We’ve been going for years!!"
Reviewed on Oct 11, 2025
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.