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Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21

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A modern kitchen with white cabinetry, a central island with bar stools, and a wooden ceiling with exposed beams. - Old Town Caribbean Estate Key West -  Great for Groups - Private Pool - Sleeps 21 (Key West)
A pool area with a hammock, palm trees, and a covered patio with outdoor furniture. - Old Town Caribbean Estate Key West -  Great for Groups - Private Pool - Sleeps 21 (Key West)
A wooden cabin bedroom with two beds, a ceiling fan, and a large window with curtains. - Old Town Caribbean Estate Key West -  Great for Groups - Private Pool - Sleeps 21 (Key West)
A covered porch with green chairs and a table, surrounded by lush tropical plants. - Old Town Caribbean Estate Key West -  Great for Groups - Private Pool - Sleeps 21 (Key West)
An attic room with a wooden ceiling, a golden statue, and a patterned mat on the floor. - Old Town Caribbean Estate Key West -  Great for Groups - Private Pool - Sleeps 21 (Key West)
Close to Duval Street and Mallory Square, Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21 provides a garden, laundry facilities and more. Stay connected with free in-room WiFi.

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

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About this property

Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21

  • The Old Town Caribbean Estate is a masterful combination of a classic Key West Victorian home with an exotic Caribbean-style guest house. These two beautifully renovated historic structures provide 10 bedrooms and 7.5 bathrooms. This is a remarkable place for family and friends to stay together in a Key West weekly rental. Spacious and luxurious, this estate is gated and fenced with a pool, decks, and tropical gardens. To top it off, the property is located in the sought after 19th century Historic Seaport area.

    The picturesque Key West Seaport is just 3 short streets away. Strolling to the harbour takes you past grand wooden homes and adorable cottages hand-built by seafaring merchants. Narrow island streets and lanes line the area punctuated with white picket fences.

    A Bit of History

    The Key West Historic Seaport area was the first area to be developed on Key West. Most don`t realise that the bravest of these early builders were 1700`s British loyalist settlers of the Bahamas. These forefathers and mothers created an established sailing route between the sleepy Green Turtle Key in the Bahama Bahamas and the growing trade centre of Key West.

    Over the ensuing 150 years, many British settlers gradually relocated to Key West. Rather than leave home behind, some literally disassembled their wooden houses, and floated them over to Key West and rebuilt them. This remarkable time established architectural roots that still bind the two island cultures together.

    During the early 19th century building frenzy, the seaport became a major world trade centre. Regrettably old growth heart pinewood forests in the Florida Keys were decimated by rakish settlers. In return for being cut down, trees were milled into boards that still remain nearly imperviable.

    The loss of the old pine forests was partially reconciled with the wooden structures built near the Key West Historic Seaport. Skilled carpenters milled the trees and fashioned the gold coloured boards into craftsman structures - from warehouses, to sail lofts, to merchant shops, to hotels, to domiciles. What remain standing in the wake, is a cherished collection of one-of-a kind wooden buildings. Fortunately, unlike the old growth trees, the historic Old Town Key West houses are now permanently protected. They will sustain the changing times.

    More than a century has past since most of the buildings were constructed. While many of the structures still stand, their private and commercial use has changed with the times. Sail lofts, warehouses, canneries, and stables have been transformed into a new wave of fashionable enterprises. While the outside of the structures held their original form, inside they`ve been transformed into remarkable places.

    LAYOUT

    Main House:

    Located at the front of the property, the 7BR 5.5BA Classic Key West Estate is the perfect place for your group to gather. For a full description of this 2-story Victorian home, please follow this link. The common rooms on the 1st floor provide a spacious living room / media / dining room that connects with a renovated blue and white kitchen with stainless steel appliances and earth-tone granite worktops.

    The kitchen is located at the back of the house. Two sets of French doors, at the back corner of the kitchen, lead to the pool deck and garden. Easy access to the kitchen makes the setting ideal for entertaining. The pool deck provides an elegant backyard lounging and dining area. A flat screen TV is placed on the exterior wall above the table for outside media entertainment.

    All bedrooms in the main Victorian house are spacious with 12 ft ceilings, and each provides a king size bed. There are 2 bedrooms and 1.5 bathrooms on the ground floor and 4 bedrooms and 3 bathrooms on the 2nd floor.

    Across the pool deck there`s a free-standing poolside cottage bedroom that provides 2 full size beds and 1 full bathroom. The privacy fence at the back of the pool deck has a gate that leads to the Private Caribbean Guest House. Open the gate for a seamless access between the two dwellings.

    Caribbean Guest House:

    The 3BR 2BA Caribbean Guest House is exotic, private, and luxurious! Situated at the back of the estate property, it was completely renovated in 2021. The renovation expanded this estate to provide 10 bedrooms and 7.5 bathrooms total.

    This private guest house provides a special space for the persons who desire privacy from the rest of the larger group. The property owner designed it as a luxurious peaceful retreat, with spaces to relax, read, and quietly enjoy hydrotherapy in an exotic setting.

    Entering from the pool deck, the front entrance of the guest house steps into the open concept great room. Dark mahogany floors and white walls throughout the integrate the spaces throughout the house. Ceilings in many of the rooms are lined with bamboo paper, creating an exotic-tropical feel.

    In the living room, bright green banana leaf print wallpaper is featured on one wall. A modern furniture grouping provides a sofa, two easy chairs, and large flat screen TV mounted on wall. For a surprise, look up! Overhead you`ll notice the unusual hammock netting stretched across part of the ceiling. Look closer for a peek-a-boo view of an unsurpassed meditation loft above.

    The modern kitchen also makes an impressive statement. Bright white cabinets with an L-shape breakfast counter and top-of-the line stainless steel appliances complete the space. The kitchen ceiling is finished up to the gable roof line and lined with bamboo paper and contrasting mahogany ceiling beams.

    Leaving the great room, an L-shape hallway leads to the three bedrooms and two bathrooms. All bathrooms are elegant. The first bathroom is close to the main entrance door. Decorated in bright white with black fixtures, it offers a deep oval-shaped bathtub and a single vanity sink with three drawers. An oval mirror above the sink reflects the nature light that streams in from the three windows above the bathtub.

    All bedrooms painted bright white and minimally furnished using tropical textures of bamboo, seagrass, and wicker. Each bedroom offers different bed sizes and unique features and tropical designs.

    Bedroom One: Immediately to the left, the first bedroom is furnished with a full-size (double) bed with sea grass headboard. A custom spiral bright yellow metal ladder leads to the meditation loft above.

    The meditation loft is set with seat pillows and lit with artistic lighting. A Buddha statue is placed on one end of the meditation room, backlit by a gable window at the front of the house. Guests are asked to use this unique space respectfully and agree to follow the posted rules, according to the rental contract.

    Directly across the hallway from bedroom one, a modern design bathroom is finished in white-on-white tile and marble. The single vanity is topped with a moulded sink. The shower is oversized with a rain shower and a wand; all bathroom fixtures are an elegant gold tone.

    Bedroom Two: Directly across the hall from bedroom one, the second bedroom is furnished with modern walnut tone furnishings. A platform queen size bed, featuring an abstract headboard, sits as a centre piece in the bright white room. Matching end tables on either side of the bed, and a bureau complete the set. Plantation shutters on the four tall sash windows add to the minimalist island style. An exterior door to the left of the bed, leads to the swimming porch.

    Bedroom Three: The third bedroom is at the end of the hallway. Larger than the other two bedrooms and providing a king size bed, it is considered the master bedroom. Golden bamboo furnishings blend beautifully with the bamboo and mahogany ceiling. French doors to the left of the bed, lead to the swimming porch.

    Exotic Swimming Porch: The Caribbean-style outdoor covered swimming porch is a fabulous feature of the house. Here you enjoy an exotic swimming setting for two - with two deep clawfoot bathtubs surrounded by louvered plantation shutters. If you prefer to shower instead, there is an open shower at the end of the swimming room. The bamboo ceiling is carried to the swimming room, and louvered walls provide plenty of privacy. Hanging orchids and potted palm trees punctuate the tropical design.

    Grounds:The estate grounds are fenced and gated, with curb views of each house. The back yard the connects the dwellings is completely decked. There is a swimming pool off the back deck closest to the main house. Covered front porches on the 1st and 2nd floor of the main house provide views of famous Fleming St. The 2nd floor verandah on the back of house provides a view of the pool garden below and creates a covered loggia off the pool deck. Mature palm trees and foliage create a romantic tropical setting.

    Bedding Summary

    Main House:

    First Floor - Bedroom One - 1 Queen Murphy bed; Bedroom Two - 1 King size bed

    Second Floor - Bedroom Three - 1 King size bed; Bedroom Four - 1 King size bed; Bedroom Five - 1 King size bed; Bedroom 6 - 1 King size bed

    Pool-side Cottage - 2 full size (double) beds.


    Guest House:


    Bedroom One; Full (Double) Bed

    Bedroom Two; Queen Size Bed

    Master Bedroom; King Size Bed


    Amenities: Swimming pool, large deck, tropical gardens, expansive porches, and privacy fences. Fully equipped kitchen, central a/c, telephone, TV, stereo, washing machine / dryer. Linens and towels are provided. Reimbursement for parking of 1 vehicle.

    Restrictions: While this property is ideal for families and groups to unite, is not suitable for staging loud parties. Smoking permitted outside only. No pets please. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.

    PAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.
    PARKING: We reimburse for 1 vehicle.

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About the area

Located in Key West, this holiday home is in the city centre. 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. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. Discover the area's water adventures with power boating and swimming nearby, or enjoy the great outdoors with ecotours. Visit our Key West travel guide
View more Holiday homes in Key West
Map
Key West, FL

What's nearby

  • A stone angel statue with outstretched wings, set against a clear blue sky with scattered clouds.
    Key West Cemetery
    6 min walk - 0.6 km
  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    8 min walk - 0.7 km
  • A sign reading "Welcome to Mallory Square" with an American flag, a red and white striped awning, and a statue of a man in a blue shirt and straw hat.
    Mallory Square
    13 min walk - 1.2 km
  • A historical marker for The Little White House, built in 1890, used by American Navy officers, and listed on the National Register of Historic Places in 1974.
    Harry S. Truman Little White House
    14 min walk - 1.2 km
  • A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.
    Ernest Hemingway Home and Museum
    15 min walk - 1.3 km

Getting around

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

Restaurants

  • Kermit's Key West Key Lime Shoppe
    8 min walk
  • Cuban Coffee Queen Waterfront
    5 min walk
  • Schooner Wharf Bar
    7 min walk
  • Half Shell Raw Bar
    5 min walk
  • The Breakfast Club, Too
    9 min walk

Frequently asked questions

Does Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21 have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21 pet-friendly?

No, pets are not allowed at this property.

How much is parking at Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21?

On-site parking is available at the property.

What time is check-in at Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21?

Check-in begins at 4:00 PM.

What time is check-out at Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21?

Checkout is at 10:00 AM.

Where is Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21 located?

Located in Old Town Key West, this holiday home is within a 10-minute walk of The Kite House and Duval Street. Florida Keys Beaches and Mallory Square are also within 15 minutes.

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Reviews

Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21 Reviews

9.0

Wonderful

9.6

Cleanliness

10

Location
Rating 10 - Excellent. 5 out of 8 reviews
Rating 8 - Good. 2 out of 8 reviews
Rating 6 - Okay. 1 out of 8 reviews
Rating 4 - Poor. 0 out of 8 reviews
Rating 2 - Terrible. 0 out of 8 reviews

Reviews

Verified review

10/10 Excellent

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

Wedding in Key West

We all wanted to stay together for a family wedding. It’s difficult to find a place to fit everyone. The home has a lot of historical charm, plenty of bedrooms and is convenient to downtown. Would definitely stay there again.
Stayed 4 nights in Nov 2024
Verified review

10/10 Excellent

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

Amazing Experience

This beautiful property was perfect for a girls weekend! We were able to all meet in the mornings for coffee in the main house but still have privacy when needed! The location was perfect for walking to dinner and shopping. Look forward to staying here again for our next girls trip! Thank you!
Stayed 3 nights in Dec 2024
Verified review

8/10 Good

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

Fun Family getaway with 17 guests

We loved the property! The 3 houses (2 cottages and one large house) made it so we could have privacy and be super close with our large family group. Its super close to everything we wanted to do! Parking was 2 blocks away, so plan ahead, but its doable. The pool is smaller but deep, and the kids had a blast. The outdoor shower and bath tubs were really fun. The kitchen had two leaks, but the staff was quick to talk with and fix them, so they didn't affect our trip. We had a miscommunication about late check out that left a bad taste, but that was the only down side. Overall, we had a great time, and with 17 guests, we had plenty of space.
Stayed 8 nights in Jan 2024
Verified review

6/10 Okay

Liked: Cleanliness, check-in, communication, location

Good…mostly

A beautiful property with awesome accommodations in a great location. We had a large family group stay here and had a good time overall. BUT, for paying as much as we did, the details were lacking. Over the course of the week, uncovered problems included: a shower door was missing parts and a doorknob had fallen off. The house iPad didn’t work, the WiFi didn’t work upstairs, a cabinet door was broken in the cottage, and the fridge water dispenser was very moldy. A fire alarm of some sort was beeping in the attic ALL DAY AND NIGHT and the cottage had no hot water whatsoever. Luckily one of our members has a background in property maintenance and with the great help of the management company, they talked us through fixing the hot water. I understand these things happen, but was told that these are a recurring set of complaints. Thus, the owner has failed to fix reported problems. This is what I had issue with. You could tell that problems had been neglected for some time now for this many to stack up. Nobody showed up to fix the issues, so I had to reset the water heater breaker multiple times a day for the remainder of the week to avoid cold showers for our family. So once again, a beautiful place. But for 20k, not nearly as kept as it should have been.
Stayed 7 nights in Mar 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect get away for a 40th birthday trip. Place could not have been better
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 4 nights in Jun 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Jan 2025