The Galleon Resort

Key West, Florida

The Galleon Resort

Key West, Florida

Timeshare rentals

$250 - $1,250 /night

Starting at $250 /night

View all timeshare rentals

Timeshare resales

$21,585 - $70,000

Starting at $21,585

View all timeshare resales

Timeshare Owner?

Post your timeshare at The Galleon Resort for rent or sale in less than five minutes!

Overlooking the shimmering span of 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 Galleon Resort offers a multitude of accommodations in studio, one-bedroom and two-bedroom configurations. Studios house two people and are equipped with a small refrigerator, coffee maker and microwave oven. One-bedroom suites sleep up to four while most two-bedroom suites sleep up to six, while both include a full kitchen, dining area and decked out living area. Each is lovingly 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.

Room Types

Studio Efficiency

1 Bathroom, Partial kitchen, Sleeps 2

Room Details →

6 Rentals from $250/night No resales available

1 Bedroom Penthouse

1 Bathroom, Full kitchen, Sleeps 4

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No rentals or resales available

1 Bedroom Suite

1 Bathroom, Full kitchen, Sleeps 4

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1 Rental from $400/night No resales available

2 Bedroom Loft Penthouse

2 Bathrooms, Full kitchen, Sleeps 8

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No rentals or resales available

2 Bedroom Penthouse (1 Queen)

2 Bathrooms, Full kitchen, Sleeps 6

Room Details →

2 Rentals from $686/night 2 Resales from $29,500

2 Bedroom Penthouse (2 Twins)

2 Bathrooms, Full kitchen, Sleeps 6

Room Details →

2 Rentals from $600/night 2 Resales from $29,000

2 Bedroom Suite (1 Queen)

2 Bathrooms, Full kitchen, Sleeps 6

Room Details →

8 Rentals from $429/night 12 Resales from $22,000

2 Bedroom Suite (2 Twins)

2 Bathrooms, Full kitchen, Sleeps 6

Room Details →

7 Rentals from $457/night 8 Resales from $23,000


On-Site Features & Amenities

  • Boating
  • Elevator
  • Fishing
  • Fitness center
  • Internet access
  • Ocean
  • Outdoor pool
  • Restaurant
  • Sauna
  • Scuba diving
  • Shared laundry facilities
  • Spa services
  • Water skiing
  • Whirlpool/hot tub

Nearby Attractions

  • Golf
  • Grocery store
  • Live entertainment
  • Medical facilities
  • Security
  • Shopping area
  • Tennis

Policies

  • No Pets
  • No Smoking
  • Minimum check-in age: 21
  • Check-in time: 4:00 PM
  • Check-out time: 10:00 AM

Recently stayed at The Galleon Resort? Share any resort updates we should know about.

4.8 out of 5
  • 5

    (259)

  • 4

    (24)

  • 3

    (10)

  • 2

    (2)

  • 1

    (4)

  • Resort location
  • Staff/Service
  • Cleanliness
  • Sleep comfort
  • This is the premier time share resort in Key West. There are 1000,s of reasons these weeks are in demand always!

    Read more »
    By bn12 Updated Sep 13, 2022
    Helpful? 2 0
  • Once you have visited Key West, you will never stay further than 6 blocks north of Duval. By your second trip, you will realize the...

    Read more »
    By michaelv154 Jun 6, 2022
    Helpful? 1 0

Questions & Answers

The Pool is always heated in every season.
Albert P. answered Aug 12, 2024
Helpful?   1 0 Report
Best Italian food is at Onlywood. Their Pizza is beyond compare, For... Read more »
Albert P. answered Aug 12, 2024
Helpful?   1 0 Report
Free Weights, some machines, just enough to get some pump in.
Timothy H. answered Dec 2, 2025
Helpful?   1 0 Report

See more discussions in the The Galleon Resort forum →


Map & Address

617 Front St
Key West, Florida 33040
Accuracy not guaranteed. Contact the resort to confirm the address before making plans.

Timeshare Rentals

$250 - $1,250 /night

View all timeshare rentals

Timeshare Resales

$21,585 - $70,000

View all timeshare resales

Own a timeshare at The Galleon Resort?

Timeshare Rentals

Timeshares for rent at The Galleon Resort

Dec 27, 2025 – Jan 3, 2026 7 Nights
New!
$1,250/night $9,562 before tax
Mar 21–28, 2026 7 Nights
New!
$686/night $5,257 before tax
Jan 17–24, 2026 7 Nights
2 Bedroom Suite (2 Twins)
Sleeps: 6
$536/night $3,750 before tax
Rented!
Feb 21–28, 2026 7 Nights
RedWeek Verified
Studio Efficiency
Sleeps: 2
$295/night $2,065 before tax
Rented!
Jan 3–10, 2026 7 Nights
Verified & Protected
New!
$829/night $6,347 before tax

Timeshare Resales

Timeshares for sale at The Galleon Resort

Week: 41 (high)
Use: Annual, Type: Deed
New!
Price: $22,000
Maint. fee: $1,585
Week: 01 (high)
RedWeek Verified
Use: Annual, Type: Deed
New!
2 Bedroom Unit, Water view
Sleeps: 6
Price: $35,500
Maint. fee: $1,783
Week: 2 (high)
RedWeek Verified
Use: Annual, Type: Deed
New!
2 Bedroom Unit, Ocean view
Sleeps: 6
Price: $42,500
Maint. fee: $1,250
Week: 45 (high)
Use: Annual, Type: Deed
New!
Price: $50,000
Maint. fee: $1,300
Week: 24
Use: Annual, Type: Deed
New!
Price: $35,000
Maint. fee: $1,585