
Sugarloaf Key Pet-friendly Vacations
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Top Pet-friendly vacation packages in Sugarloaf Key
Price found within the past 48 hours. Click for updated prices.




Bay Breeze Premium Apartments By Eskape Collection
Save 100% on your flight
Price was $1,006, price is now $549 per person
$549
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (222 reviews)
The staff were very accommodating! The location was perfect. However, the apartment did not have basic kitchen items like dish soap, paper towels or spices, I had to DoorDash those items.
Reviewed on Jun 13, 2026

The 27 Wynwood
Wynwood Art District
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Price was $872, price is now $496 per person
$496
per person
Sep 5 - Sep 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
10/10 Exceptional! (12 reviews)
We were in a beautifully designed and furnished room (suite of two rooms/two baths) with all working and clean fixtures. Beautiful tiled bathroom/shower in one with the rainfall shower head; tub in the other. The furniture, bedding, kitchen appliances, and everything was new, and wonderful. The Bosch appliances, large, illy coffeemaker, and everything was top notch. Pool was clean and very nice, with hot tub and some cabanas for daytime, but our evening swim and the night lights view was terrific. The guest service staff was excellent. We had such a wonderful stay based at The 27 Wynwood and can't wait to return for another fun visit. p.s. Go to Maman and CoyoTaco when you go there.
Reviewed on Jun 18, 2026
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View all trips5* Pet-friendly vacations in Sugarloaf Key
Price found within the past 48 hours. Click for updated prices.



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View all trips3 Night Pet-friendly vacations in Sugarloaf Key
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Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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Price was $1,146, price is now $665 per person
$665
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (205 reviews)
Overall our stay was nice. We loved the shores pool, and paid extra for ocean view and balcony, which was ruined by the sargassum(out of resorts control of course). Also the balcony was not a private balcony attached to our room, it was just an extension off the walk way open to anyone really, so that part is kind of deceiving.
Also, not like a huge deal, but we are huge sports fans and we were trying to watch the FiFa and basketball championships game, and there was no cable.
Called to try and have it fixed, and they came and fixed it, but there was no directory and there were only 10 channels available, not nba championship game channel. And you had to shuffle through the 100 channels to find random channel that worked. (Again, not a huge deal breaker, but for price, should function)
There was also, black mold in the bathroom. I called and alerted front desk twice, they did not seem to care.
I had a “vip package” and was supposed to have a late checkout @1pm, and they told me no, that even though that was apart of my package I still was supposed to to call and request it.
I did like how close the resort was too a lot of things, and walking distance to good breakfast place frenchies cafe(great coffee)!
Reviewed on Jun 16, 2026


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View all trips4 Night Pet-friendly vacations in Sugarloaf Key
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Beach Plaza
South Beach
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Price was $1,008, price is now $548 per person
$548
per person
Aug 25 - Aug 29
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (169 reviews)
Great location, just a block from the beach and ocean drive. Easy check-in and check-out. Limited lockers to keep luggage if you arrive early and aren't able to check-in yet which was very convenient. Older building although the room itself was clean and well kept. A/c worked well. Did not have the chance to use the pool although towels were provided in the lobby. There does not appear to be staff regularly in the lobby although they do reply quickly via text (calling will prompt you to text them instead). There was security posted in the lobby during the night and we did notice a staff member by the door outside at night assisting guests to get into the lobby as after a certain time the front doors are locked and only accessible by code. Overall good value, would stay again.
Reviewed on Jun 16, 2026

Casablanca Miami Beach
North Beach
Price was $5,491, price is now $2,130 per person
$2,130
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.8/10 (324 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great.
It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.
Reviewed on Feb 22, 2026

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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 food and water bowls.
9.8/10 Exceptional! (585 reviews)
"The property was very clean and well laid out. Lot of great design thought went into the landscape architecture. That also applied to the rooms as well. From great lighting to a bathroom that was spacious, we felt quite at home. (Apparently, we are meant to stay in semi darkness and have a tiny shower ..."
Reviewed on Jun 15, 2026

Sugarloaf Key RV Resort & Cottages
311 Johnson Rd Summerland Key FL
Stay at this vacation home in Summerland Key. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
9.4/10 Exceptional! (14 reviews)
"First time staying here it won’t be our last!"
Reviewed on Jun 15, 2026

Florida Keys Beach Getaway
Sugarloaf Key FL
Stay at this vacation home in Summerland Key. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Florida Keys Beaches and Sugarloaf Beach ...
9.8/10 Exceptional! (28 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
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.
Things to do

Luxury Sandbar and Snorkeling trip in Key West
$1,200
per traveler
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