
Raccoon Key Pet-friendly Vacations
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Top Pet-friendly vacation packages in Raccoon Key
Price found within the past 48 hours. Click for updated prices.


Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $2,367, price is now $1,380 per person
$1,380
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Everything was great. Suites were spacious, clean and well designed. Staff was friendly, helpful and courteous in additional knowledgeable. The views were great. Excellent job!
Reviewed on Dec 14, 2025

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,584, price is now $1,551 per person
$1,551
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,044 reviews)
Staff was exceptional. At check in we found one of the rooms musty (Winslow bungalow 21), asked to be moved. The check in lady was very accommodating, great customers service. The second bungalow #38 was very noisy in the morning as its close to the breakfast serving area and adjacent to the staff entrance for supplies. You can hear the door slamming behind the staff each time they go in and out. I raised the concern to the 2 staff members stocking the room, and promptly they must have reported it to their supervisor, as one came out to speak to me within 5 min of reporting the issue. I didnt ask to speak with a manager, but was pleasantly suprised that the staff took my concern seriously and took initiative to resolve it. The manager was pleasant and had some quick solutions and also said she will escalate the issue so that a permanent solution can be put in place. I give all the staff we encountered, 5*, from check in, to the bartender, they really know customer service. The property and its lush pathways are beautiful. Its quiet and quaint and the location and proximity to Duval street can't be beat.
Reviewed on Dec 12, 2025

Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $2,361, price is now $1,505 per person
$1,505
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,844 reviews)
It was rather deceiving to me when i booked the room regarding the view. Yes it was walkable however we had view of a parking lot with a lot of outside noise. Room itself was nice and clean. Also i was told breakfast not included however then i heard it was. Kinda disappointed for my first stay at Keywest. I probably will not return after this experience.
Reviewed on Dec 15, 2025

Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $3,522, price is now $2,285 per person
$2,285
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,006 reviews)
Excellent staff, property, view, and amenities. Did not like the switch to a cashless system.
Reviewed on Dec 15, 2025
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See all available trips from Columbus to Raccoon Key
View all trips3 Night Pet-friendly vacations in Raccoon Key
Price found within the past 48 hours. Click for updated prices.

Oceans Edge Key West Resort, Hotel & Marina
Price was $1,299, price is now $834 per person
$834
per person
Jan 31 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Everything was great. Suites were spacious, clean and well designed. Staff was friendly, helpful and courteous in additional knowledgeable. The views were great. Excellent job!
Reviewed on Dec 14, 2025

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Price was $1,626, price is now $1,065 per person
$1,065
per person
Jan 31 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,044 reviews)
Staff was exceptional. At check in we found one of the rooms musty (Winslow bungalow 21), asked to be moved. The check in lady was very accommodating, great customers service. The second bungalow #38 was very noisy in the morning as its close to the breakfast serving area and adjacent to the staff entrance for supplies. You can hear the door slamming behind the staff each time they go in and out. I raised the concern to the 2 staff members stocking the room, and promptly they must have reported it to their supervisor, as one came out to speak to me within 5 min of reporting the issue. I didnt ask to speak with a manager, but was pleasantly suprised that the staff took my concern seriously and took initiative to resolve it. The manager was pleasant and had some quick solutions and also said she will escalate the issue so that a permanent solution can be put in place. I give all the staff we encountered, 5*, from check in, to the bartender, they really know customer service. The property and its lush pathways are beautiful. Its quiet and quaint and the location and proximity to Duval street can't be beat.
Reviewed on Dec 12, 2025

Southernmost Beach Resort and Guesthouses
Old Town Key West
Price was $1,406, price is now $931 per person
$931
per person
Jan 31 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,844 reviews)
It was rather deceiving to me when i booked the room regarding the view. Yes it was walkable however we had view of a parking lot with a lot of outside noise. Room itself was nice and clean. Also i was told breakfast not included however then i heard it was. Kinda disappointed for my first stay at Keywest. I probably will not return after this experience.
Reviewed on Dec 15, 2025
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See all available trips from Columbus to Raccoon Key
View all trips4 Night Pet-friendly vacations in Raccoon Key
Price found within the past 48 hours. Click for updated prices.

Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,417, price is now $840 per person
$840
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
Found a roach in room
Reviewed on Dec 14, 2025

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $3,202, price is now $1,896 per person
$1,896
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Being right on Duval Street if city noise bothers you you might want to stay a block or two off Duval. But if you want all the action then this place is fantastic. Staff is great and the room was nicely appointed and very comfortable.
Reviewed on Dec 12, 2025

Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,554, price is now $924 per person
$924
per person
Feb 22 - Feb 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Excellent place to stay on Key West, spacious apartment, nice view, quiet area, great pool area and billiard table, mini market inside property. Just 10 min drive to famous Duvall Street and different restaurants walking distance from the hotel.
Reviewed on Dec 15, 2025
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See all available trips from Columbus to Raccoon Key
View all tripsTop Pet-friendly Raccoon Key Hotels

Altair House at Lunara Bay
Key West Florida
Stay at this vacation home in Key West. Enjoy private pools, a fitness center, and a garden. Popular attractions Duval Street and Smathers Beach are located ...
9.8/10 Exceptional! (11 reviews)
Great house. Large space, everything you need is there.
Reviewed on Aug 11, 2025

Capmar House by Brightwild Huge Home Pool
Key West FL
Stay at this vacation home in Key West. Enjoy free parking and a garden. Popular attractions Duval Street and Smathers Beach are located nearby.
10/10 Exceptional! (1 review)
Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay
Reviewed on Jan 20, 2025

Brand New The Greenmoor House With Pool
Key West FL
Stay at this vacation home in Key West. Enjoy free parking and a garden. Popular attractions Duval Street and Smathers Beach are located nearby.
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.


















