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BEAUTIFUL SANCTUARY PRIVATE ISLAND CONNECTED BY BRIDGE TO KEY WEST

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Outdoor pool
Interior
Smart TV, foosball
Property grounds
Exterior

Reviews

9.8 out of 10
Exceptional

Entire home

9 bedrooms9 bathroomsSleeps 208000 sq ft

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

Explore the area

View in a map
Key West, FL
  • Place, Key West Tropical Forest and Botanical Garden
    ‪15 min walk‬
  • Place, Key West Golf Club
    ‪20 min walk‬
  • Place, Fort East Martello Museum and Gallery
    ‪3 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪4 min drive‬

Room options

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Outdoor dining
Harbor Walk Hideaways | Group Compound In Old Town, Pool!
  • Pool
  • Kitchen
  • Pet friendly
  • Air conditioning
4.9 out of 5, Exceptional, 12 reviews
$1,960 nightly
The price is $2,175
Feb 23 - Feb 24
Total with taxes and fees
Harbor Walk Hideaways | Group Compound In Old Town, Pool!

About the neighborhood

Key West

When you stay at this vacation home in Key West, you'll be on the waterfront, within a 5-minute drive of Smathers Beach and Florida Keys Beaches. .This vacation home is 3.5 mi (5.7 km) from Duval Street and 3.6 mi (5.8 km) from Southernmost Point.
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What's nearby

  • Key West Tropical Forest and Botanical Garden - 15 min walk - 0.8 miles
  • Key West Golf Club - 20 min walk - 1.1 miles
  • Fort East Martello Museum and Gallery - 3 min drive - 1.5 miles
  • Key West Art and Historical Society - 4 min drive - 1.7 miles
  • Key West Naval Station - 5 min drive - 1.9 miles

Getting around

  • Key West Intl. Airport (EYW) - 2 min drive

Restaurants

  • ‪McDonald's - ‬17 min walk
  • ‪El Siboney Stock Island - ‬4 min drive
  • ‪Bad Boy Taqueria & Tequila - ‬5 min drive
  • ‪Toasted Coconut - ‬16 min walk
  • ‪Starbucks - ‬15 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

BEAUTIFUL SANCTUARY PRIVATE ISLAND CONNECTED BY BRIDGE TO KEY WEST

A Castle on an Island On A Privately Owned Key West Island

Private Bridge for Cars and Trucks connected to Key West

From the Era of the Great Gatsby, in 1926, one of the richest men in South Florida, his family owned 45 percent of the land in Key West and most all of the shrimp and fishing boats in the Keys, married a beautiful young New York socialite and wanted her to move to Key West to live with him. "Honey", I will only move to Key West if you build me a Castle on an Island. So it was!!

For almost a century, this special Island has hosted a presidents, governors and business leaders for meetings, celebrations and parties. This historical property has been restored to its original beautiful stately manner , furnished in modern hip hop Gatsby Style from the recent movie, and now is available for you to host your colleagues, families, and friends for business meetings, educational conferences, and special family events,.

This is one of the most historic, beautiful and expensive properties in Key West, A 35 million dollars private Island, connected to Key West by a bridge and only 8 short minutes to Duval Street. This is a controlled access, gated island community.

Your friends, family and colleagues can make your private island, their meeting place for time in the Key West and the Florida Keys. On your own secluded and secure gated Island,, only 10 minutes to the downtown area, you can enjoy the refreshing trade winds while you meet with your group. The properties boasts some 25 rooms to host your activities, whether formal meetings or just a simple game of teambuilding Volleyball and then a swim in either the salt water pool or fresh water pool, you will enjoy the best the Florida Keys has to offer.

OTHER AMENITIES

FULL AIR CONDITIONING

PRIVATE SMALL BEACH AREA

5 ACRE SECURE GATED ISLAND

4 KAYAKS,

2 PADDLEBOARDS

JACUZZI

POOLVOLLEYBALL COURT (Sand)

DOCK AND BOAT SLIPS WITH FISHING and FISH CLEANING AREA

TENNIS COURT (OFF SITE)

BASKETBALL HOOP

POOL TABLE

10 FLAT SCREENS

MULTIPLE WIFI (INCLUDING 5G) NETWORKS

RACKETBALL COURT (OFFSITE /OPTIONAL)

2 LARGE OCEANVIEW PORCHES

Bedroom and Sleep Info

The VERY LARGE MASTER is 600 sq. feet with a private bathroom, shower and tub, and has 2 king beds.

The Coral Room, about the size of an average master has a king bed with private bath, shower and tub

The Ocean Room has a king bed and private bathroom with tub and shower.

The Turtle Room has a king bed with private bathroom with shower

The Gatsby Room has a king bed with bathroom and shared shower.

INCLUDED NO EXTRA CHARGE The Mango Tree Cottage had a large living room, a full kitchen, 2 larger bedrooms with kings, and 2 private bathrooms with showers.



OPTIONAL EXTRA FEE

The Mermaid's Cottage is very modern with a small living area and small full kitchen, very large bedroom with a king bed and a bathroom with shower.

OPTIONAL EXTRA FEE BEACH COTTAGE

The Beach Cottage is very modern with a small living area, very large bedroom with a king bed and a bathroom with shower.

PLEASE CALL FOR MORE INFO
Thanks Andrew cell 305 923 6480
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Complimentary wireless internet access keeps you connected, and a Smart television is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.
Don't miss out on recreational opportunities including an outdoor pool and a hot tub.
Guests will find features like internet access and onsite parking.

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Hot tub
  • Outdoor pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 9 bedrooms
  • Bedsheets provided

Bathroom

  • 8.5 bathrooms
  • Bathtub
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Smart TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the ocean
  • On the waterfront

Things to do

  • Billiards/pool table
  • Foosball table
  • Kayak

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Garden
  • Unit size: 8,000 square feet

Policies

Check-in

Check-in time starts at 4:00 PM

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome
Note from host: ALL CHILDREN ARE COUNTED FOR MAX OCCUPANCY

Events

Events allowed: family gatherings, birthday parties, weddings
PEOPLE ATTENDING NOT STAYING SUBJECT TO ADDED FEE

Smoking

Smoking is not permitted

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
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 99
Note from host: PEOPLE ATTENDING NOT STAYING SUBJECT TO ADDED FEE
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

BEAUTIFUL SANCTUARY PRIVATE ISLAND CONNECTED BY BRIDGE TO KEY WEST Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 16 out of 18 reviews
Rating 8 - Good. 2 out of 18 reviews
Rating 6 - Okay. 0 out of 18 reviews
Rating 4 - Poor. 0 out of 18 reviews
Rating 2 - Terrible. 0 out of 18 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Rosalynn M.

Liked: Cleanliness
Excellent property. The host was very accommodating and anticipated every need.
Stayed 2 nights in Jan 2026

10/10 Excellent

Kathy D.

Liked: Cleanliness
We had a wonderful family Christmas stay here at this charming, historic home! Loved the location as it is close to the airport, grocery, the beach and has a beautiful water view. We traveled with my 86 year old mom and I’d like to caution others that this is an old house that is not handicap accessible and does not have a shower on the main floor. For the younger ones, however, it was nice being on an island where they could talk and laugh and not bother any neighbors and there was a lot for them to do. Andrew is a very nice, accommodating, responsive host. Scott was great with orientation and any needs we had throughout the week. Overall a very positive stay!
Stayed 7 nights in Dec 2025

10/10 Excellent

Piero F.

Liked: Cleanliness

Awesome Experience

Andrew and Co. are the best. They make you feel right at home and can connect you with local businesses if you are looking to plan some fun when in KW
Stayed 2 nights in May 2025

10/10 Excellent

Kyle L.

Stayed 3 nights in Nov 2024

10/10 Excellent

Tyler C.

Liked: Cleanliness

Memorable stay

The Thompson Island home was amazing for us to celebrate our wedding! Thanks so much to the host for being responsive and helpful. It was a great experience all around
Stayed 2 nights in Dec 2024

10/10 Excellent

Marcus M.

Liked: Cleanliness

Happy Get Together

Wonderful communication. Lovely home. Thoroughly enjoyed our time and would return
Stayed 6 nights in Aug 2024

10/10 Excellent

Debbie V.

Liked: Cleanliness

Incredible & Perfect!

We hosted an executive leadership retreat and rented the entire property. It was the most positive experience from beginning to end! The host's communication and the grounds team that greeted us were impeccable. The house & cottages were beautiful and surpassed our expectations. There is everything you need: kayaks, paddle boards, bikes, volleyball! I can't say enough how much we all enjoyed it. Thank you so much!! Highly recommend!
Stayed 4 nights in Apr 2024

10/10 Excellent

Paige H., Hunt Valley, MD

Liked: Cleanliness

Beautiful property for a large group.

We had an amazing time on Thompson Island for my big birthday! Plenty of room for our 15 friends. The property was clean and the kitchen was well stocked. We really enjoyed our stay.
Stayed 4 nights in Feb 2024

10/10 Excellent

Peter K., Temecula California

Liked: Cleanliness

Amazing spot in the Keys for a professional meeting and social event.

We had a group of 20 dentists and meet ever year in a tropical or snow setting. The accomodations were ideal for us on Thompson island. Staff and owners were very attentive. One of our guest misplaced her wallet and phone. The staff located it and she was able to get it before flying out. First class!
Stayed 3 nights in Feb 2024

10/10 Excellent

Vincent Y.

Liked: Cleanliness

Our Island Off the Island

I had a milestone birthday and had family celebrate with me. Andrew's estate was conveniently close to the airport and was easy to find. All fifteen adults had comfortable beds and use of seven and a half bathrooms. We especially loved the size of the dining room and how we were all able to sit at the same table. The home itself is close to 100 years old, so do not expect perfection. It has its unique charm and a compelling history that is worth knowing. Everyone had a great stay in Key West, thanks in good part to this property.
Stayed 4 nights in Jan 2024

10/10 Excellent

Edward S.

Liked: Cleanliness

Wedding celebration weekend

The property is large and private. It gears to large groups looking to celebrate any occasion. Water access is provided for kayaking and paddle boarding.
Stayed 2 nights in Nov 2023

10/10 Excellent

Brittany Z.

Liked: Cleanliness

Wedding of our dreams

We got married on Thompson Island and it was truly the wedding of our dreams. We got to have our closest friends and family stay on the Island with us for a long weekend and it was absolutely the best weekend ever. The place was so beautiful to take pictures at as well. And Andrew and his wife are so sweet and helpful. Couldn’t recommend enough.
Stayed 3 nights in Sep 2023

10/10 Excellent

Cynthia M.

Liked: Cleanliness

We had such a GREAT time!

My whole family and I stayed for a week. Everything was so perfect that besides going to the grocery store we didnt leave the house the whole time.
Stayed 4 nights in Sep 2023

10/10 Excellent

Dave G.

Liked: Cleanliness

Perfect property for family, friends and wedding party

Thompson Island, private island, estate was just perfect for housing our friends and wedding guests of 20 people, and Andrew and Scott were super accommodating and easy to work with. Perfect combination of soaking in Key West and all that it has to offer, and a private estate to relax in and enjoy connections with those that you love.
Stayed 4 nights in Jul 2023

10/10 Excellent

Michael G.

Liked: Cleanliness

Spectacular location and property

The property manager was wonderful to work with from the moment we booked to the moment we left always was extremely responsive and professional the property itself is just wow wow wow what a location all the amenities all the kids stayed busy I would recommend this property to anyone that is looking for a dream vacation in the keys thank you Andrew to you and your staff a real Jem thank you.
Stayed 3 nights in May 2023

8/10 Good

Diane G.

Liked: Cleanliness

Key West Wedding Weekend

We rented this home for our son And daughter in law to “tie the knot” on a sunset sailboat with just 16 family members. This home was perfect for what we needed so we could all hang out and Celebrate the weekend and getting to get to know each other’s family. The home is very large with a lot of space. If you like history then this home has it but you need to understand the home is close to 100 years old and not updated but had a lot of Charm. The owner was extremely easy to work with and very helpful and answered all questions very quickly.
Stayed 3 nights in Oct 2022

8/10 Good

Carlie Z.

Liked: Cleanliness

Historic Key West Vibe with Gatsby Flare

Very nice property with appropriate accoutrements to the time and period for the property. Very quiet location with excellent views. This is not a property for a party with anyone with accessibility needs.
Stayed 3 nights in Jul 2022

10/10 Excellent

Jason A.

Liked: Cleanliness

Historical bliss

Thompson island was an absolute perfect setting for my wife’s 40th. The week there was filled with so much activities(both on and off the island) and the history of the home was beautiful.
Stayed 5 nights in Jul 2022