Condo

The Galleon Resort, Waterfront Location, Well-equipped Two Bedroom Villa!

Photo gallery for The Galleon Resort, Waterfront Location, Well-equipped Two Bedroom Villa!

Marina
Pool
This is an oceanfront room, please ask what view is available for your dates.
Miscellaneous
Private kitchen

Reviews

9.6 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 6

Popular amenities

  • On beach
  • Swimming pool
  • Hot tub on site
  • Onsite parking available
  • Kitchen
  • Washing machine

Explore the area

View in a map
Key West, FL
  • Place, Florida Keys Beaches
    ‪4 min walk‬
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Mallory Square
    ‪7 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪15 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Living Room 1

1 Double Sofa Bed

2 bathrooms

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Toilet · Shower only · Jetted bathtub

Spaces

Deck or patio
Kitchen
Balcony
Number of living rooms
Outdoor play area
Garden
Dining area

About this property

The Galleon Resort, Waterfront Location, Well-equipped Two Bedroom Villa!

Please choose a Saturday check-in, all rentals will be in seven night increments.
Bedding configuration may vary, depending upon your travel week and the villa available, please inquire prior to booking.
Thank you for your interest in booking with Dash Realty Group, Windermere Florida.
Dash Realty Group is registered in Florida as a licensed Fla. Seller of Travel Ref. No. ST42435.

Overlooking the Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with friends new and old at the Tiki Bar, or relax and unwind in the swimming pool. The resort's observation deck guarantees a stunning view from sunrise to sunset, and even to gaze at the stars. Rent a boat for a private viewing of the Keys or take a jetski for a spin right from the resort's marina. Work up a sweat at the on-site exercise room and afterwards, relax your body and mind in the sauna.

The resort's 90-slip marina accommodates boats up to 150 feet and hosts a variety of water activities. After you've had your fill of fun on the water, stretch out on the private beach or outdoor pool. If you want to venture out and explore the island, there are local attractions, art galleries, shopping and restaurants within walking distance of the resort's doorstep.

A two-bedroom suite sleep up to six, and include a full kitchen, dining area and decked out living area. Villa is furnished with sandy earth tones, rattan furniture and tropical prints that perfectly set the mood for your stay in Key West.

The Galleon Resort is perfectly positioned, sitting only two blocks from Duval Street - a legendary road that boasts top-notch restaurants, dazzling nightlife and non-stop soirees. Party until dawn at a carnival, swing by a cuban cigar stand or bring your camera to the exotic butterfly conservatory, all located on this versatile street that's earned its reputation. At the northwest end of Duval Street lies Mallory Square, a plaza which is famous for its "Sunset Celebration" - tourists gaze at the sunset while arts and crafts displays and entertainers amuse the gatherers. Key West's oldest attraction, the Key West Aquarium is a hit with families - everyone will enjoy scoping out the menagerie of rainbow-hued fish.

Large waterfront swimming pool
Private beach
Boardwalk
Observation deck with a 360-degree panoramic view
of Key West ... one of a kind
Dock Café
Tiki Bar
Sauna
Diving & Snorkeling
Sun Bathing
Sunset Cruises
Exercise Room
24 hour security
Wireless Internet

The Galleon's Marina offers dockage space to accommodate boats and yachts up to 140 feet. Outside of being the most highly protected harbor for your vessel, they also offer exclusive marina and resort amenities when renting a boat slip in the Marina. Wet slips are available for both seasonal and transient rentals.

Fishing Charters, Sunset Cruises, Parasailing, Snorkeling, Dolphin Watching, Glass Bottom Boat Jet Ski Rental, Scooter rentals, all available onsite or nearby.

THE BOOK IT NOW FEATURE IS A REQUEST FOR RESERVATIONS, NOT A CONFIRMED STAY. Please do not reserve your airfare until you have communicated with us and have an executed rental agreement

Booking through VRBO is fast and easy. Dash Realty Group will email you the updated confirmation once you book thru VRBO. Please note that VRBO provides an instant quote that may not be accurate and may require us to send an adjusted price quote and adjusted dates based on what is available for your requested dates.
This is based on higher demand weeks and resorts that may be higher than the initial quote. The VRBO calendar does help provide instant availability and estimated price quote. However, because availability and rates vary constantly, the calendar feature and instant quote feature is not always 100% accurate.

The photos are a good representation of what your villa will look like. Layouts may vary. The resort updates and maintains the villas at this resort and your villas is assigned upon check-in.

Add dates for prices

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About the area

Key West

Located on the beach, this condo is in Key West Historic District, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. Key West Shipwreck Museum and Mel Fisher Maritime Museum are also worth visiting. Discover the area's water adventures with jet skiing, kayaking and scuba diving nearby, or enjoy the great outdoors with cycling.
Map
Key West, FL

What's nearby

  • Florida Keys Beaches - 4 min walk - 0.4 km
  • Duval Street - 6 min walk - 0.6 km
  • Mallory Square - 7 min walk - 0.7 km
  • Key West Aquarium - 8 min walk - 0.7 km
  • Audubon House and Tropical Gardens - 9 min walk - 0.8 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 14 min drive

Restaurants

  • ‪Conch Republic Seafood Company - ‬2 min walk
  • ‪Schooner Wharf Bar - ‬5 min walk
  • ‪Kermit's Key West Key Lime Shoppe - ‬4 min walk
  • ‪The Retro Room - ‬4 min walk
  • ‪Bagatelle - ‬5 min walk

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 11 out of 13 reviews
Rating 8 - Good. 1 out of 13 reviews
Rating 6 - Okay. 1 out of 13 reviews
Rating 4 - Poor. 0 out of 13 reviews
Rating 2 - Terrible. 0 out of 13 reviews

9.8/10

Cleanliness

9.0/10

Check-in

9.0/10

Communication

10/10

Location

9.4/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Tisha C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay and love the location.
Stayed 7 nights in Feb 2026
Response from VrboOwner on 10 Apr, 2026
Thank you for taking the time to leave a review! We’re so glad you enjoyed your time in Key West and hope to welcome you back again soon!
Verified

10/10 Excellent

Amy W.

Liked: Cleanliness, check-in, communication, listing accuracy
This room has an unobstructed view of the water and access to the deck below. It was an awesome view and very relaxing to sit on our balcony and watch the boats and sunset. We would highly recommend this place. The room itself was spacious
Stayed 7 nights in Mar 2026
Verified

10/10 Excellent

Robert M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, condo well outfitted, overlooking the marina. Balcony you can relax. All within walking distance of great restaurants and activities. Never need a car.
Stayed 7 nights in Mar 2026
Verified

10/10 Excellent

Ed T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great experience from beginning to end!
Stayed 7 nights in Feb 2026
Response from VrboOwner on 10 Apr, 2026
Thank you so much! We truly appreciate your kind words and would love to assist you with your future travel plans anytime!
Verified

10/10 Excellent

Toni Michelle C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Thr best place tostay in Key West.

The location, rooms and staff make this resort the best in Key West.
Stayed 7 nights in Oct 2023
Response from VrboOwner on 10 Apr, 2026
Thank you so much for your kind words! We’re thrilled you enjoyed the location, rooms, and staff. We’d love to assist you again on your next trip to Key West!
Verified

10/10 Excellent

Patrick F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Clean, well located.

The unit was clean and great location for enjoying Key West
Stayed 8 nights in Dec 2022
Response from VrboOwner on 10 Apr, 2026
Thank you for your kind words! It was truly a pleasure working with you, and I’m so glad you enjoyed the clean unit and great location. We’d love to help you plan your next Key West getaway!
Verified

10/10 Excellent

Amy D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Absolutely beautiful

Great location. We could see the sunset from our balcony. Could also see the pool and beach area. Very clean and comfortable. Close to the attractions and restaurants. Loved the master suite
Stayed 7 nights in Apr 2023
Response from VrboOwner on 10 Apr, 2026
Thank you so much for your kind review! We’re so glad you enjoyed the beautiful sunset views, convenient location, and the comfort of the master suite. It was a pleasure hosting you, and we hope to welcome you back again soon!
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Week

Great time at The Galleon. Our first visit at The Galleon, over looking the Marina, perfect spot. Very much to do in Key West, all within walking distance. Plan to visit again. Cheers,
Stayed 7 nights in Jan 2022
Verified

8/10 Good

Carrie H.

Liked: Cleanliness, check-in, location
Disliked: Listing accuracy

Bedroom configuration

Very disappointed with bed listings. We chose this location because it was listed a king and 2 twin beds and I had asked a few times to make sure that was the plan and it ended up not being that configuration. My family was not satisfied with our non solution.
Stayed 7 nights in Mar 2024
Response from VrboOwner on 10 Apr, 2026
We’re very sorry to hear about the bedding issue and understand how frustrating that was. Bedding configurations can vary by unit, and while we do our best to keep our listings as accurate and up to date as possible, we rely on the resort for final assignments. We always do our best to communicate guest requests, and we truly regret that we were unable to secure the setup you were expecting. Your feedback is appreciated and helps us continue improving.
Verified

10/10 Excellent

Karah S.

Liked: Cleanliness, check-in, location, listing accuracy

Family of 5 Amazing Location

This property is a hidden gem in all of Old Town Key West! This particular room has an incredible view of the small private beach (perfectly large enough to enjoy for all ages, even with 3 children ages 8, 6 & 4), the Gulf of Mexico and the pool. It's located right on the marina where the water adventures & fishing trips load in and out of. There are lots of restaurants surrounding the marina as well! Also, The Galleon is only a 2 min walk to Duval Street and a 2 min walk to Mallory Square!! Additionally, basically right on the same property, you can rent a golf cart and sightsee for the day or keep it for a week! My kids (and my hubby and I too) loved riding all over Key West on the 6-seater golf cart! Our stay was Aug 21 to Aug 28 and we felt like we had the town to ourselves. We'll definitely be staying at the Galleon on future trips to Key West and we'll be sure to visit at this time of year!!
Stayed 7 nights in Aug 2021
Response from VrboOwner on 10 Apr, 2026
Thank you so much for the wonderful review! We’re thrilled you and your family enjoyed the views, location, and all the fun nearby. It sounds like the golf cart adventures were a highlight! Your detailed feedback is so helpful to future guests, and we truly appreciate you sharing your experience. We look forward to welcoming you back to The Galleon on your next Key West getaway.
Verified

6/10 Okay

Laura B.

Liked: Cleanliness, location, listing accuracy
Disliked: Check-in

Almost Perfect

Had stayed at this property last year and came back because of the location and walkability to the town. This year everything was good except our room was on the end of the unit next to the Hyatt property. The Hyatt used the lot next to our building to drop an empty Dumpster at 5 am and then proceed to drop stuff and garbage in it for the next two nights and days. After that every 18 wheeler and delivery truck backed in with their reverse horns beeping every morning before sunrise. These delivery trucks woke us every morning before sunrise!! The other downfall was that they wouldn’t let us check in until after 6 pm but insisted we checked out by 10 am. The pros of the unit were, for sure, the air conditioning unit, the kitchen, bathrooms and the washer and dryer. The beds were just average but acceptable. The pool and tiki/bar hut on premises were very nice. You can’t beat the sunsets at this location. All in all, I would probably stay again, but just not on the side by the Hyatt.
Stayed 7 nights in Apr 2022
Response from VrboOwner on 10 Apr, 2026
Thank you for sharing such detailed, helpful insight. We’re so glad you enjoyed the property, sunsets, and amenities, but we truly apologize for the noise disturbances and the inconvenience with your check-in time. Your feedback is incredibly valuable, especially regarding room placement, and will help future guests make the best choice for their stay. We’d love to welcome you back again for an even more relaxing experience next time!
Verified

10/10 Excellent

Toni Michelle C.

The room and the view were absolutely spectacular!

We have been staying at the the Galleon for years however I must say that this particular condo was absolutely spectacular. We were able to have a view from our bedroom that had was on the corner which enabled us too have two balconies on both sides of the water. The unobstructed view was to die for. The staff and ease of walking to everything was perfect. I will be requesting this room again.
Verified

10/10 Excellent

Jeffrey C.

A Great Place!

We found this unit on VRBO and were pleased and impressed. The view from our unit was great overlooking the water and the pool. We were on the 4th floor of a five floor building. The unit was well appointed with cable and high speed internet. Although, we found the internet to be slow and sometimes couldn’t stream Netflix. The complex is located in a great part of key West. It’s right next to a large marina and very close to the action on Duval Street. This was our first time to Key West and we would definitely go back. The restaurants are great with a lot of variety. We took a restaurant walking tour which I would recommend. You get a good feel for the Cuban influence on the community and we ate some great food. Next time we will try to fly directly in to Key West rather than Fort Lauderdale. The drive was very long and we found that once in Key West we walked everywhere and didn’t use the rental car.
Stayed 7 nights in Mar 2018
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