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





Reviews
9.6 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 6111.5 sq m
Popular amenities
Explore the area

Key West, FL
- Place, Florida Keys Beaches1 min walk
- Place, Duval Street5 min walk
- Place, Mallory Square6 min walk
- Airport, Key West, FL (EYW-Key West Intl.)14 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.
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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9.6 out of 10, Exceptional, (187 reviews)
House Rules
Check in after 4:00 PM
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Check-out instructions
The host requires you to complete the following before checking out:
Load and start the dishwasher
Gather used towels
Remove personal items and remove leftover food and drinks
Turn off the lights and lock the doors
This is a resort reservation, you will check in as you would at any resort. You can head to the front desk on your checkout day to get an itemized bill in regards to incidentals during your stay.
Failure to complete these may result in a negative review from the host.
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there are no carbon monoxide detectors or gas appliances on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
We should mention
A car is not required for transport to and from this property
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. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Key West, FL
What's nearby
- Florida Keys Beaches - 1 min walk - 0.0 km
- Duval Street - 5 min walk - 0.4 km
- Mallory Square - 6 min walk - 0.6 km
- Key West Aquarium - 6 min walk - 0.6 km
- Harry S. Truman Little White House - 9 min walk - 0.8 km
Getting around
Restaurants
- Conch Republic Seafood Company - 2 min walk
- Kermit's Key West Key Lime Shoppe - 4 min walk
- Schooner Wharf Bar - 5 min walk
- The Retro Room - 4 min walk
- Bagatelle - 5 min walk
Frequently asked questions
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 window9.6/10
Cleanliness
9.0/10
Check-in
8.8/10
Communication
10/10
Location
9.2/10
Listing accuracy
Reviews
Verified
28 October 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Oct 2023
Verified
10/10 Excellent
Patrick F.
2 January 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean, well located.
Patrick F.
Stayed 8 nights in Dec 2022
Verified
10/10 Excellent
Amy D.
15 April 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely beautiful
Amy D.
Stayed 7 nights in Apr 2023
Verified
8/10 Good
Carrie H.
6 April 2024
Liked: Cleanliness, check-in, location
Disliked: Listing accuracy
Bedroom configuration
Carrie H.
Stayed 7 nights in Mar 2024
Verified
10/10 Excellent
Tisha C.
10 March 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Tisha C.
Stayed 7 nights in Feb 2026
Verified
10/10 Excellent
Ed T.
16 February 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Ed T.
Stayed 7 nights in Feb 2026
Verified
6/10 Okay
Laura B.
9 April 2022
Liked: Cleanliness, location, listing accuracy
Disliked: Check-in
Almost Perfect
Laura B.
Stayed 7 nights in Apr 2022
Verified
10/10 Excellent
Verified traveller
31 January 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Week
Verified traveller
Stayed 7 nights in Jan 2022
Verified
10/10 Excellent
Karah S.
28 August 2021
Liked: Cleanliness, check-in, location, listing accuracy
Family of 5 Amazing Location
Karah S.
Stayed 7 nights in Aug 2021
Verified
10/10 Excellent
Toni Michelle C.
7 November 2018
The room and the view were absolutely spectacular!
Toni Michelle C.
Verified
10/10 Excellent
Jeffrey C.
17 March 2018
A Great Place!
Jeffrey C.
Stayed 7 nights in Mar 2018
About the host
Hosted by DashWeek by Dash Realty Group- Windermere, Florida
Our mission is to offer our guests guidance, peace of mind and personal service throughout the vacation rental process.
With more than 30 years of combined experience delivering luxury vacations through our premium hotel partners, you can trust the owners of Dash Realty Group to ensure your vacation is everything you expect. We are travelers helping travelers, our expertise on all of our destinations offer our guests travel planning without unanswered questions.
Travel has become more complex, with varying destination requirements and changing security measures, you can trust our staff to get you to your destination and back hassle free.
With more than 30 years of combined experience delivering luxury vacations through our premium hotel partners, you can trust the owners of Dash Realty Group to ensure your vacation is everything you expect. We are travelers helping travelers, our expertise on all of our destinations offer our guests travel planning without unanswered questions.
Travel has become more complex, with varying destination requirements and changing security measures, you can trust our staff to get you to your destination and back hassle free.
Why they chose this property
Unbeatable location in Key West, close to Duvall Street and Mallory Square. Marina rentals available for guests arriving by water!
What makes this property unique
Key West, Key West Rental, Florida Rental, Two Bedroom Rental, Florida Beach Rental, Rentals in Key West, Kid-Friendly, Summer Vacation Rental, Island Vacation, Florida Ocean Rental, Oceanviews, Lobster season rental.
Languages:
English, French, Spanish
Premier Host
They consistently provide great experiences for their guests
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