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

Key West, Florida
$852 avg/night Minimum Stay 7 Nights
Bed 2

Bed

Bath 2

Bath

Home Condo

Property Type

Sleep 6

Max Sleeps

Night 7 nights

Min Stay

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.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    On The Beach
  • DINING

    Breakfast Available For A Fee Dining Table
  • SAFETY

    Deadbolt Lock Fire Extinguisher No Carbon Monoxide Detector (host Has Indicated There Is No Carbon Monoxide Detector Or Gas Appliances On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 1200 Sq Ft (111 Sq M)
  • KITCHEN

    Coffee/tea Maker Dishwasher Kitchen Island Microwave Oven Refrigerator Spices Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Not Required Onsite Parking Wheelchair-accessible Parking Available
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Garden
  • POOL/SPA

    Hot Tub Shared/communal Pool
  • BATHROOMS

    2 Bathrooms Hair Dryer Jetted Bathtub Shower Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • LANGS SPOKEN

    English French Spanish
  • THINGS TO DO

    Bicycle On Site Boat On Site Cycling Nearby Fishing Nearby Fitness Center Fitness Facilities Nearby Jet Skiing Nearby Kayak On Site Parasailing Nearby Scuba Diving Nearby Snorkeling Nearby Swimming Nearby Water Skiing Nearby Water Sports Equipment Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning
  • FAMILY FRIENDLY

    Playground
  • LOCATION HIGHLIGHTS

    Near The Ocean On The Waterfront
  • SERVICES AND CONVENIENCES

    Concierge Services Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    4 On-site Accessible Parking Spaces Elevator If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property Wheelchair Accessible Wheelchair-accessible Parking

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Rates & Availability

Review Review

  • Ed T.

    Submitted Feb 16, 2026

    Stayed Feb 7, 2026

    Great experience from beginning to end!

  • Carrie H.

    Submitted Apr 6, 2024

    Stayed Mar 30, 2024

    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.

  • Toni Michelle C.

    Submitted Oct 28, 2023

    Stayed Oct 21, 2023

    The location, rooms and staff make this resort the best in Key West.

  • Amy D.

    Submitted Apr 15, 2023

    Stayed Apr 8, 2023

    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

  • Patrick F.

    Submitted Jan 2, 2023

    Stayed Dec 24, 2022

    The unit was clean and great location for enjoying Key West

  • Laura B.

    Submitted Apr 9, 2022

    Stayed Apr 2, 2022

    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.

  • Submitted Jan 31, 2022

    Stayed Jan 22, 2022

    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,

  • Karah S.

    Submitted Aug 28, 2021

    Stayed Aug 21, 2021

    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!!

  • Toni Michelle C.

    Submitted Nov 7, 2018

    Stayed Dec 31, 1969

    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.

  • Jeffrey C.

    Submitted Mar 17, 2018

    Stayed Mar 10, 2018

    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.

Your dates are Available!

Total

Includes taxes and fees
$852+
View details