Windley Key Pet-friendly Vacations
Book a Pet-friendly Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Pet-friendly vacation packages 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
$13,722
per person
Dec 1 - Dec 6
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
Icon Brickell Luxe Stays by IliosRentals
Brickell
$2,712
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
7.8/10 Good! (7 reviews)
no communication after i emailed them and messaged them on Expedia app, lot of thing broken in the unit. It was okay stay.
Reviewed on Oct 8, 2026
Don't see what you're looking for?
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
$13,722
per person
Dec 1 - Dec 6
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
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.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$12,664
per person
Dec 31 - Jan 3
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
Icon Brickell Luxe Stays by IliosRentals
Brickell
$2,712
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
7.8/10 Good! (7 reviews)
no communication after i emailed them and messaged them on Expedia app, lot of thing broken in the unit. It was okay stay.
Reviewed on Oct 8, 2026
Don't see what you're looking for?
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 Local House
South Beach
$634
per person
Dec 9 - Dec 13
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (1,001 reviews)
The hotel has a great atmosphere. The check in lady was very nice she explained everything on details . Beach was just a block from the hotel . Love this hotel and definitely recommend it . Restaurant is downstairs too and very convenient
Reviewed on Oct 5, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$15,577
per person
Dec 24 - Dec 28
found 11 hours ago
Roundtrip flight included
New York (NYC) 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
President Hotel Villa
South Beach
$761
per person
Dec 3 - Dec 7
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
Buen lugar excelente ubicación cerca de todo
El único detalle es que las instalaciones son un poco antiguas, adicional no nos hicieron limpieza un dia en la habitación
Reviewed on Oct 11, 2026
Don't see what you're looking for?
See all available trips from Columbus to Windley Key
View all tripsTop Pet-friendly Windley Key Hotels
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
- 10 min walk from Theater of the Sea
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! (291 reviews)
"this was the nicest place i have ever stayed. the staff was so incredibly helpful and the amenities they provide are amazing. will definitely stay here again. 10/10"
Reviewed on Oct 12, 2026
Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
- 5 min walk from Theater of the Sea
Dogs are welcome to join you (fees apply) for a pet-friendly getaway at this family-friendly, oceanfront motel.
8.2/10 Very Good! (1,004 reviews)
"It was EXACTLY what I was looking for. Thank you! I wish I had more time to enjoy the super adorable room."
Reviewed on Oct 12, 2026
Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
- 8 min walk from Theater of the Sea
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.
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
