Windley Key Pet-friendly Vacations
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Top Pet-friendly vacation packages in Windley Key
Price found within the past 48 hours. Click for updated prices.
Private Apartment at the Congress
South Beach
Save 100% on your flight
Price was $587, price is now $344 per person
$344
per person
Aug 26 - Aug 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.6/10 (11 reviews)
Really friendly staff, easy check in and even accommodated early check in. Roof top pool was clean and spacious with a nice bar.
Reviewed on Jul 9, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was $11,810, price is now $5,620 per person
$5,620
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
The E11 Luxury Residences
Downtown Miami
Save 100% on your flight
Price was $1,451, price is now $951 per person
$951
per person
Oct 4 - Oct 11
found 3 hours ago
Roundtrip non-stop flight included
New York (NYC) to Miami (MIA)
6/10 (2 reviews)
Everything went well ! Nice propertyyy i enjoyed my stay , just be prepared to not be able to speak w the host.
Reviewed on Jul 8, 2026
1 Hotel South Beach
South Beach
Save 100% on your flight
Price was $1,993, price is now $1,312 per person
$1,312
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,577 reviews)
An excellent hotel overall, simple as.
Reviewed on Jul 19, 2026
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See all available trips from Columbus to Windley Key
View all trips5* Pet-friendly vacations in Windley Key
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was $11,810, price is now $5,620 per person
$5,620
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
1 Hotel South Beach
South Beach
Save 100% on your flight
Price was $1,993, price is now $1,312 per person
$1,312
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,577 reviews)
An excellent hotel overall, simple as.
Reviewed on Jul 19, 2026
Don't see what you're looking for?
See all available trips from Columbus to Windley Key
View all trips3 Night Pet-friendly vacations in Windley Key
Price found within the past 48 hours. Click for updated prices.
Private Apartment at the Congress
South Beach
Save 100% on your flight
Price was $587, price is now $344 per person
$344
per person
Aug 26 - Aug 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.6/10 (11 reviews)
Really friendly staff, easy check in and even accommodated early check in. Roof top pool was clean and spacious with a nice bar.
Reviewed on Jul 9, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was $12,199, price is now $6,532 per person
$6,532
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
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See all available trips from Columbus to Windley Key
View all trips4 Night Pet-friendly vacations in Windley Key
Price found within the past 48 hours. Click for updated prices.
The Marlin Hotel
South Beach
Save 100% on your flight
Price was $1,004, price is now $492 per person
$492
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
9.2/10 Wonderful! (1,002 reviews)
Perfect location for South Beach. One block off Ocean Drive with bars, restaurants, clubs, etc. all within walking distance & a great Italian restaurant on-property too.
Reviewed on Jul 13, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was $11,810, price is now $5,620 per person
$5,620
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
Casablanca Miami Beach
North Beach
Price was $1,730, price is now $873 per person
$873
per person
Sep 5 - Sep 9
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
5.8/10 (324 reviews)
This was a very disappointing stay. The apartment was dirty, dusty, and hot. The temperature stayed around 77–78°F all night, yet the only bedding provided was thick comforters, making it impossible to sleep comfortably.
When I simply asked for thin bed sheets, the host became argumentative instead of trying to help. They kept saying they were a private owner, as if that somehow excused poor customer service or making guests uncomfortable. It wasn’t until I contacted Expedia that the host responded by providing what I initially asked for.
I didn’t want to spend my vacation dealing with unnecessary conflict, so we checked out after the first night instead of staying for the remaining five nights of our six-night reservation. I would not stay here again.
Reviewed on Jul 2, 2026
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View all tripsTop Pet-friendly Windley Key Hotels
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
This family-friendly, oceanfront resort welcomes dogs (fees apply) with pet-friendly perks such as food and water bowls. While you're here, explore nearby hiking ...
9/10 Wonderful! (231 reviews)
"The whole staff was discriminating from start to finish. From the moment of check in the staff had a look on their faces like they didn’t want to be there or at least with us. We saw them treat other guests with smiles and pleasantry until it came to us. None of the restaurants or amenities opens ..."
Reviewed on Jul 19, 2026
Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
Dogs are welcome to join you (fees apply) for a pet-friendly getaway at this family-friendly, oceanfront motel.
8.2/10 Very Good! (1,005 reviews)
"No cumplió mis expectativas"
Reviewed on Jul 19, 2026
Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
Hiking and biking trails are ready for you to explore near this oceanfront hotel, where dogs can stay for an additional fee.
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.
