Sugarloaf Key Pet-friendly Vacations
Book a Pet-friendly Hotel + Flight or Car together to unlock savings
Top Pet-friendly vacation packages in Sugarloaf Key
Price found within the past 48 hours. Click for updated prices.
Bahama Beach Club Pompano
Price was $1,291, price is now $628 per person
$628
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
10/10 Exceptional! (13 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
The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was $2,781, price is now $1,233 per person
$1,233
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.8/10 Exceptional! (39 reviews)
Really great stay, big thanks to Crispy and team! Hotel has a great atmosphere and location. I’ll be sure to visit again!
Reviewed on Oct 21, 2025
Bay Breeze Premium Apartments By Eskape Collection
Price was $2,035, price is now $1,067 per person
$1,067
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (185 reviews)
Great owner very helpful. Beautiful place.
Reviewed on Oct 13, 2025
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View all trips5* Pet-friendly vacations in Sugarloaf Key
Price found within the past 48 hours. Click for updated prices.
1 Hotel South Beach
South Beach
Save 100% on your flight
Price was $4,977, price is now $2,795 per person
$2,795
per person
Jan 14 - Jan 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,333 reviews)
I had an awesome view…. Got upgraded on check in so that I could see the ocean from my room… excellent service from everyone
Reviewed on Oct 21, 2025
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View all trips3 Night Pet-friendly vacations in Sugarloaf Key
Price found within the past 48 hours. Click for updated prices.
The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was $2,781, price is now $1,233 per person
$1,233
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.8/10 Exceptional! (39 reviews)
Really great stay, big thanks to Crispy and team! Hotel has a great atmosphere and location. I’ll be sure to visit again!
Reviewed on Oct 21, 2025
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View all trips4 Night Pet-friendly vacations in Sugarloaf Key
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Miami Beach
Mid Beach
Save 100% on your flight
Price was $1,104, price is now $567 per person
$567
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,118 reviews)
Lugar perfecto para pasarlo bien
Reviewed on Oct 22, 2025
The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was $2,436, price is now $1,095 per person
$1,095
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.8/10 Exceptional! (39 reviews)
Really great stay, big thanks to Crispy and team! Hotel has a great atmosphere and location. I’ll be sure to visit again!
Reviewed on Oct 21, 2025
1 Hotel South Beach
South Beach
Price was $6,302, price is now $3,338 per person
$3,338
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,333 reviews)
I had an awesome view…. Got upgraded on check in so that I could see the ocean from my room… excellent service from everyone
Reviewed on Oct 21, 2025
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View all tripsTop Pet-friendly Sugarloaf Key Hotels
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939, Summerland Key, FL
This oceanfront hotel is pet-friendly (fees apply) and offers amenities such as a dog park.
9.6/10 Exceptional! (443 reviews)
"This location had a variety of different things to do while your stay there and a very convenient public transportation stop to key west right outside the site. Very friendly staff. The rooms were very nice and clean. The doggy park was also clean. We felt very welcomed, we are definitely spreading ..."
Reviewed on Oct 19, 2025
Florida Keys Beach Getaway
Upper Sugarloaf Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Sugarloaf Beach and Lower Sugarloaf Sound ...
9.6/10 Exceptional! (27 reviews)
"The Online Property Manager almost pushed us to ask for a refund by telling us about loud dock construction between the hours of 10am -2pm every day immediately after he secured our final payment for the trip. Thankfully Tom who is the onsite manager was amazing and had the construction stopped for ..."
Reviewed on Oct 3, 2025
Palm - Beach Houses Key West
Upper Sugarloaf Key
Stay at this vacation home in Summerland Key. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Sugarloaf Beach and Lower Sugarloaf ...
10/10 Exceptional! (12 reviews)
"We had the most wonderful time staying in the Palm bungalow. It is just steps away from the pool oasis where we spent our days relaxing and grilling. We then drove into Key West in the evenings. Very convenient location where you get the best of both worlds of serenity and relaxation, but also close ..."
Reviewed on Aug 27, 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.