Stock Island Pet-friendly Vacations

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Top Pet-friendly vacation packages in Stock Island

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

$504
per person
Sep 23 - Sep 26
found 18 hours ago
Roundtrip non-stop flight included
Spokane (GEG) to Key West (EYW)
9.4/10 Exceptional! (1,329 reviews)
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

$740
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Key West (EYW)
9/10 Wonderful! (1,841 reviews)
Good: Staff was extremely nice and helpful, the concierge knows everything, the property itself is very nice and the marina is fairly scenic. Beds were comfortable, the A/C goes down to 67 and felt great, the pools are bathwater warm, and the balcony was cozy. Having a shuttle was helpful to get downtown (only has one stop though at the furthest end of town from the Southernmost Point of the US marker - a mile or so away). There's a small gym you can use, and the Tiki Hut has some fun stuff going on (plastic hatchet throwing, shell decorating, pay as you go canoe experiences). The on-site Yellow Fin restaurant is excellent. Bad: Bathroom had no lock on the door, surprise fees for parking and "resort fee" total maybe $70 extra per night (might be mentioned but I didn't notice). Breakfast in the package deal is only free for 2 people per day though (?), leaving us a $40 bill + tip for every breakfast. One whole building is currently undergoing upgrades, so drill, hammer noises, etc, plus big blue tarps all over it.

Reviewed on Aug 24, 2026

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3 Night Pet-friendly vacations in Stock Island

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

$504
per person
Sep 23 - Sep 26
found 18 hours ago
Roundtrip non-stop flight included
Spokane (GEG) to Key West (EYW)
9.4/10 Exceptional! (1,329 reviews)
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

$740
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Key West (EYW)
9/10 Wonderful! (1,841 reviews)
Good: Staff was extremely nice and helpful, the concierge knows everything, the property itself is very nice and the marina is fairly scenic. Beds were comfortable, the A/C goes down to 67 and felt great, the pools are bathwater warm, and the balcony was cozy. Having a shuttle was helpful to get downtown (only has one stop though at the furthest end of town from the Southernmost Point of the US marker - a mile or so away). There's a small gym you can use, and the Tiki Hut has some fun stuff going on (plastic hatchet throwing, shell decorating, pay as you go canoe experiences). The on-site Yellow Fin restaurant is excellent. Bad: Bathroom had no lock on the door, surprise fees for parking and "resort fee" total maybe $70 extra per night (might be mentioned but I didn't notice). Breakfast in the package deal is only free for 2 people per day though (?), leaving us a $40 bill + tip for every breakfast. One whole building is currently undergoing upgrades, so drill, hammer noises, etc, plus big blue tarps all over it.

Reviewed on Aug 24, 2026

Don't see what you're looking for?
See all available trips from Columbus to Stock Island
View all trips

4 Night Pet-friendly vacations in Stock Island

Price found within the past 48 hours. Click for updated prices.
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

$863
per person
Oct 24 - Oct 28
found 20 hours ago
Roundtrip non-stop flight included
Richmond (RIC) to Key West (EYW)
9/10 Wonderful! (1,841 reviews)
Good: Staff was extremely nice and helpful, the concierge knows everything, the property itself is very nice and the marina is fairly scenic. Beds were comfortable, the A/C goes down to 67 and felt great, the pools are bathwater warm, and the balcony was cozy. Having a shuttle was helpful to get downtown (only has one stop though at the furthest end of town from the Southernmost Point of the US marker - a mile or so away). There's a small gym you can use, and the Tiki Hut has some fun stuff going on (plastic hatchet throwing, shell decorating, pay as you go canoe experiences). The on-site Yellow Fin restaurant is excellent. Bad: Bathroom had no lock on the door, surprise fees for parking and "resort fee" total maybe $70 extra per night (might be mentioned but I didn't notice). Breakfast in the package deal is only free for 2 people per day though (?), leaving us a $40 bill + tip for every breakfast. One whole building is currently undergoing upgrades, so drill, hammer noises, etc, plus big blue tarps all over it.

Reviewed on Aug 24, 2026

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

$941
per person
Oct 24 - Oct 28
found 20 hours ago
Roundtrip non-stop flight included
Richmond (RIC) to Key West (EYW)
9.4/10 Exceptional! (1,329 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Stock Island
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Top Pet-friendly Stock Island Hotels

Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

5950 Peninsular Avenue Key West FL
  • 23 min walk from Key West Golf Club
Dogs are welcome (fees apply) at this luxury, oceanfront hotel, which offers pet-friendly amenities, like food and water bowls, to four-legged guests.
9/10 Wonderful! (1,849 reviews)
"Good: Staff was extremely nice and helpful, the concierge knows everything, the property itself is very nice and the marina is fairly scenic. Beds were comfortable, the A/C goes down to 67 and felt great, the pools are bathwater warm, and the balcony was cozy. Having a shuttle was helpful to get ..."

Reviewed on Aug 24, 2026

Hilton Key West Resort & Marina
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

7001 Shrimp Road Key West FL
  • 14 min walk from Key West Golf Club
Dogs can accompany you (fees apply) at this pet-friendly, seaside hotel, where they will enjoy pet-approved amenities, like a dog park.
The Perry Hotel & Marina Key West
Miss Serenity your Marine Expreience

Miss Serenity your Marine Expreience

7005 Shrimp Rd Key West FL
  • 16 min walk from Key West Golf Club
This pet-friendly cruise ship welcomes dogs and cats for free.
7.4/10 Good! (24 reviews)
"Boat itself wasn’t terrible, but Teddy, the guy running things, defrauded my credit card and steals from his one employee. The Marina the boat was at had so many complaints from guests about Miss Serenity, that they kicked them out of the marina on 6 May 2019. Don’t go anywhere near this boat ..."

Reviewed on May 7, 2019

Miss Serenity your Marine Expreience
See all 3,067 properties in Stock Island
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.

Things to do

Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

$79
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Combo image of activity in Key West

Key West Rum & Reggae: Snorkel & Sunset Sail Combo

$69
per adult
88% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$45
per adult
88% of travellers recommend
Key West Conch Tour Train
See all activities in Stock Island

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.