
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.



Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Save 100% on your flight
Price was $1,387, price is now $786 per person
$786
per person
Jun 5 - Jun 9
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (181 reviews)
We loved everthing about this resort! We just wish we had stayed longer! We stayed in The Cove. It was secluded and quiet! A perfect get away!
Reviewed on Apr 16, 2026

1 Hotel South Beach
South Beach
Save 100% on your flight
Price was $2,460, price is now $1,421 per person
$1,421
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,471 reviews)
Our stay started off on a frustrating note due to issues with housekeeping. Room service didn’t come on the first day, and on the second day we had to call reception around 5pm to follow up. After speaking with the manager, we agreed on a specific daily time for housekeeping for the remainder of our 8-day stay. Unfortunately, even after this arrangement, the room was not serviced at the agreed time the following day, and we once again had to contact reception.
While the staff did offer a room credit as a gesture, the repeated inconvenience did affect the overall holiday experience and made it difficult to fully relax thereafter.
That said, the hotel itself has a lot going for it. The room was excellent, and the amenities were of a high standard. The rooftop area is a highlight, although it can get quite crowded—on one occasion we weren’t able to get chairs, which was disappointing.
Overall, a property with great potential and strong facilities, but the inconsistency in service needs improvement to match the otherwise high standard.
Reviewed on Apr 18, 2026

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View all trips5* Pet-friendly vacations in Windley 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 $2,460, price is now $1,421 per person
$1,421
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,471 reviews)
Our stay started off on a frustrating note due to issues with housekeeping. Room service didn’t come on the first day, and on the second day we had to call reception around 5pm to follow up. After speaking with the manager, we agreed on a specific daily time for housekeeping for the remainder of our 8-day stay. Unfortunately, even after this arrangement, the room was not serviced at the agreed time the following day, and we once again had to contact reception.
While the staff did offer a room credit as a gesture, the repeated inconvenience did affect the overall holiday experience and made it difficult to fully relax thereafter.
That said, the hotel itself has a lot going for it. The room was excellent, and the amenities were of a high standard. The rooftop area is a highlight, although it can get quite crowded—on one occasion we weren’t able to get chairs, which was disappointing.
Overall, a property with great potential and strong facilities, but the inconsistency in service needs improvement to match the otherwise high standard.
Reviewed on Apr 18, 2026


Nobu Hotel Miami Beach
Mid Beach
Save 100% on your flight
Price was $3,652, price is now $2,242 per person
$2,242
per person
Jul 2 - Jul 9
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (1,354 reviews)
The hotel was decent. It wasn't as special as I thought it should be. Plus, it's the same place as another hotel, they share a lobby and probably everything else. It was clean and the staff were helpful. The walls were kinda thin. But, it served it's purpose.
Reviewed on Apr 13, 2026
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View all trips3 Night Pet-friendly vacations in Windley Key
Price found within the past 48 hours. Click for updated prices.

Miami Downtown Condos
Downtown Miami
Price was $1,201, price is now $447 per person
$447
per person
Jul 5 - Jul 8
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
8.2/10 Very Good! (135 reviews)
Everybody was very nice, helpful and friendly they answered All my questions right away helped me right away the condo was so clean and nice my balcony loved it beautiful view I’m definitely coming back they get 10 stars from go book them I asked for a late check out they answered right away and gave it to me I love them I’m definitely coming back
Reviewed on Apr 14, 2026


Hotel Riu Plaza Miami Beach
Mid Beach
Save 100% on your flight
Price was $1,387, price is now $774 per person
$774
per person
Jun 20 - Jun 23
found 1 day ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
8/10 Very Good! (1,141 reviews)
Breakfast was excellent, room was clean, staff were friendly and efficient.
Reviewed on Apr 13, 2026
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View all trips4 Night Pet-friendly vacations in Windley Key
Price found within the past 48 hours. Click for updated prices.


Casablanca Miami Beach
North Beach
Price was $5,545, price is now $2,234 per person
$2,234
per person
Jul 14 - Jul 18
found 2 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
5.8/10 (322 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 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! (185 reviews)
We loved everthing about this resort! We just wish we had stayed longer! We stayed in The Cove. It was secluded and quiet! A perfect get away!
Reviewed on Apr 16, 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! (1,004 reviews)
Beautiful view of the ocean
Reviewed on Apr 18, 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.
8.8/10 Excellent! (1,001 reviews)
Great room. Staff was very helpful and kind. Enjoyed the beachfront
Reviewed on Apr 15, 2026
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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