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.
Bay Breeze Premium Apartments By Eskape Collection
Save 100% on your flight
Price was $870, price is now $437 per person
$437
per person
Apr 25 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (189 reviews)
The staff was courteous and helpful. The apartment was equipped with basic essentials. The area was quiet. I would suggest adding oven mittens in the kitchen as there was nothing to use to take the pan out of the oven with.
Reviewed on Jan 21, 2026
Pelican Hotel
South Beach
Price was $1,246, price is now $555 per person
$555
per person
Apr 25 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (394 reviews)
A reasonably priced art deco hotel in a popular tourist area. Hotel and rooms are stylishly designed. Restaurant food was ok. Maria was a fabulous server. On the downside, there is no pool or fitness center.
Reviewed on Jan 12, 2026
The Marlin Hotel
South Beach
Save 100% on your flight
Price was $858, price is now $474 per person
$474
per person
Apr 25 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (1,002 reviews)
Amazingly helpful staff. Great room and an ideal location. Would be my top pick if staying in the area again.
Reviewed on Feb 10, 2026
Nomada Residences
Northeast Miami
Save 100% on your flight
Price was $1,171, price is now $663 per person
$663
per person
Apr 25 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (548 reviews)
Great time with family. Recommended by a coworker who does a long stay at the property. I would stay again.
Pro:
Near highway, free parking, convenient location. Beautiful pools and party room.
Con:
For the short stay I wished the management provide sponge as well for the dishes, extra pods for laundry.
The sofa (and sofa bed) could be more comfy, you feel the springs when you lie down. I was hoping the bathroom has dispenser of the soap and shampoo, but instead we have the little amenities.
Both tv are lagging, just be patience!
Air fryer could be a great addition to be honest.
Reviewed on Feb 8, 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.
Waterfront House with Boat Dock
Hammer Point
Save 100% on your flight
Price was $1,414, price is now $837 per person
$837
per person
Mar 23 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
6/10 (1 review)
Everything was fine except half way through the stay the water department came and shut off the water at the street. It came back on a few hours later, so it all worked out. The house was fine
Reviewed on Jan 9, 2026
1 Hotel South Beach
South Beach
Save 100% on your flight
Price was $5,738, price is now $3,254 per person
$3,254
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (1,365 reviews)
Clean room, great staff, wonderful amenities.
Reviewed on Feb 9, 2026
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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.
Nomada Residences
Northeast Miami
Save 100% on your flight
Price was $1,140, price is now $679 per person
$679
per person
Mar 29 - Apr 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (548 reviews)
Great time with family. Recommended by a coworker who does a long stay at the property. I would stay again.
Pro:
Near highway, free parking, convenient location. Beautiful pools and party room.
Con:
For the short stay I wished the management provide sponge as well for the dishes, extra pods for laundry.
The sofa (and sofa bed) could be more comfy, you feel the springs when you lie down. I was hoping the bathroom has dispenser of the soap and shampoo, but instead we have the little amenities.
Both tv are lagging, just be patience!
Air fryer could be a great addition to be honest.
Reviewed on Feb 8, 2026
The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was $1,590, price is now $936 per person
$936
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (56 reviews)
First day my room was behind the lift and I had a headache but staff did not refund me that stay . I am disappointed
Reviewed on Feb 8, 2026
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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.
Solé Miami, A Noble House Resort
Ocean Four
Price was $1,181, price is now $561 per person
$561
per person
Mar 30 - Apr 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,935 reviews)
The suite was clean and well prepared. Unfortunately, there was no furniture on the tbalcony and we had to bring out the chairs from the room
Reviewed on Feb 6, 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 ...
8.8/10 Excellent! (141 reviews)
Location cannot be beat and amenities were perfect we can’t wait to go back
Reviewed on Feb 3, 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! (1,001 reviews)
Very nice place !
Reviewed on Feb 3, 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.
8.6/10 Excellent! (1,009 reviews)
Loved this place
Reviewed on Feb 2, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
