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.
1 Hotel South Beach
South Beach
Price was $5,844, price is now $3,267 per person
$3,267
per person
Apr 8 - Apr 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,365 reviews)
Amazing hotel. Beyond our expectations. Rooms are huge. Modern and stylish
Lobby is fabulous as is the bars and restaurants
You must stay here !!! Total wow
Reviewed on Jan 21, 2026
Villas At Hawks Cay Resort
Save 100% on your flight
Price was $3,719, price is now $2,113 per person
$2,113
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (145 reviews)
Villa had a great few; toilets don’t flush well; handle on showered were backwards. Never came to clean at all during 5 day stay; had to text number to get anything needed; resort was understaffed; did two fishing charters and caught fish, nothing to bring home; rented paddle boards off site bc ones on site can only used in small area. Pools and hot tubs close at sunset which was a bummer we always live night swimming; golf cart was fun to rent a drive around looking at houses; no where to eat on island besides resort. Have to drive at least 20mins in either directions to get anything so if you like a variety of restaurants or happy hours this is not the place. Front desk is very understaffed; the line was always so long. Lots of people complaining about charges that weren’t theirs. We had it also happen to use. We avoided charging anything to the room bc if it.
Reviewed on Jan 4, 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.
Cheeca Lodge & Spa
Matecumbe
Save 100% on your flight
Price was $3,975, price is now $2,545 per person
$2,545
per person
Mar 9 - Mar 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (1,262 reviews)
This palce is awesome. Clean rooms. 2 large pools with a view. Covered garage spot.
Reviewed on Jan 22, 2026
1 Hotel South Beach
South Beach
Price was $5,844, price is now $3,267 per person
$3,267
per person
Apr 8 - Apr 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,365 reviews)
Amazing hotel. Beyond our expectations. Rooms are huge. Modern and stylish
Lobby is fabulous as is the bars and restaurants
You must stay here !!! Total wow
Reviewed on Jan 21, 2026
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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.
1 Hotel South Beach
South Beach
Save 100% on your flight
Price was $2,337, price is now $1,329 per person
$1,329
per person
Apr 20 - Apr 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,365 reviews)
Amazing hotel. Beyond our expectations. Rooms are huge. Modern and stylish
Lobby is fabulous as is the bars and restaurants
You must stay here !!! Total wow
Reviewed on Jan 21, 2026
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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.
Cavalier Hotel South Beach
South Beach
Price was $1,262, price is now $559 per person
$559
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
I had a wondeful time at this hotel (1/20-1/24/2026). The staff was polite, friendly and always ready to help. Room was clean and stylish exacly like the photo. The location is perfect: quiet and peaceful. And the same time not far from popular places.
I really enjoyed my stay and would definitely recommend this hotel to others.
Reviewed on Jan 26, 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.
9.6/10 Exceptional! (477 reviews)
Immaculate Our stay was outstanding. Would recommend 100%
Reviewed on Jan 22, 2026
Florida Keys Beach Getaway
Upper 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 ...
9.6/10 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
Beach Getaway in the Florida Keys
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 ...
8.2/10 Very Good! (7 reviews)
Amazing!
Amazing property and views. Tom was great and very helpful with places to go and things to do. Will definitely recommend!!
Reviewed on Mar 21, 2023
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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