See all properties
Entire home

5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free.

Choose dates to view prices

Photo gallery for 5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free.

Outdoor pool, a heated pool
Smart TV, DVD player, stereo
Terrace/patio
4 bedrooms, desk, iron/ironing board, free WiFi
Terrace/patio

Reviews

9.8 out of 10
Exceptional

Entire home

4 bedrooms1 bathroomSleeps 81800 sq ft

Popular amenities

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

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪5 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪9 min walk‬
  • Place, Mallory Square
    ‪11 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪15 min drive‬

Room options

You may also like

Ad
Bar (on property)

Southwinds Motel

Old Town Key West
  • Pool
  • Breakfast included
  • Restaurant
  • Air conditioning
8.6 out of 10, Excellent, 1,355 reviews
$164 nightly
The price is $185
Jun 16 - Jun 17
Total with taxes and fees
Southwinds Motel

About the neighborhood

Key West

Located in Old Town Key West, this vacation home is within a 10-minute walk of popular sights such as Duval Street and Fort Zachary Taylor Historic State Park. The vacation home includes a private pool, a kitchen, and a patio.
View more Vacation Homes in Key WestOpens in a new window

What's nearby

  • Duval Street - 5 min walk - 0.3 miles
  • Florida Keys National Marine Sanctuary - 8 min walk - 0.4 miles
  • Ernest Hemingway Home and Museum - 9 min walk - 0.5 miles
  • Mallory Square - 11 min walk - 0.6 miles
  • Fort Zachary Taylor Historic State Park - 11 min walk - 0.6 miles

Getting around

  • Key West Intl. Airport (EYW) - 14 min drive

Restaurants

  • ‪Green Parrot Bar - ‬5 min walk
  • ‪Margaritaville - ‬8 min walk
  • ‪Blue Heaven - ‬9 min walk
  • ‪Wendy's - ‬9 min walk
  • ‪Kermit’s Key West Key Lime Shoppe - ‬10 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.

5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free.

Our calendar is updated in real time and our rates are accurately displayed. You can book instantly without waiting for owner approval. Flexible cancellation policy. We try to beat rates of all of the other houses in Truman Annex.

Millionaires Row – Welcome to Island Living. Cozy, but upscale.

Truman Annex is the most exclusive private residential community in Old Town Key West, located just off the main drag of Duval Street. Quiet streets lined with palms and beautiful Old Florida Homes. The entrance has a 24 hour staffed guard gate.

Unplug and recharge in wonderful Key West, stop and smell the flowers and the salt air. You will be located only 1 block from mile ZERO.

Truman Annex Waterfront Park is only 2 blocks away and comes complete with a family friendly playground and splash pad, and the Amphitheater where you can enjoy lots of live concerts and events.

If you want sand between your toes instead of the private pool, the beautiful beach at Fort Zachary Taylor Park is just at the end of the street. Enjoy a tour of the fort, snorkeling, fishing, or just sunning and watch the yachts go by.

You will have every luxury and convenience you might want. Large flat screen TV in the living room and flat screens also in other parts of the property. Complimentary, secure Wi-Fi service. Our home is meticulously maintained and immaculate.

First floor is an open floor plan overlooking the private cocktail pool. There is dining space for 10. There is also a first floor bedroom with twin beds and a computer desk.

Upstairs you will find the Owner’s bedroom which is spacious with vaulted ceilings, a king size bed, ample closet and storage area, flat screen TV, and ensuite bath.

There is also a third bedroom upstairs, which is split from the Main bedroom, with a queen bed and flat screen TV. Another bath is adjacent.

The unique guest cottage is complete with vaulted ceilings, queen bed, flat screen TV, full bath, microwave, coffee maker, and refrigerator. It has its own private entrance.

The pool is surrounded by tropical plants and mood lighting.

When you are ready to venture out, walk over to Mallory Square where there is free entertainment every single night before sunset. Great viewing area for Key West’s famous sunsets that set into the ocean. Also within walking distance is The Aquarium, Little White House, The Key West Lighthouse, the Hemingway house, the Audubon House, and Mel Fisher’s Maritime Museum.

You will also be in walking distance to boutique shopping and many art galleries. Be sure to check out the gourmet restaurants and live music venues everywhere.

Nearby there is parasailing, snorkeling trips, fishing charters, and wonderful sunset cruises.
The vacation home is air-conditioned and features a kitchen and a patio, and there's space to spread out with 4 bedrooms. Guests can expect to find free WiFi and a Smart TV with a DVD player. Other standard amenities include a private pool, a washing machine, and a sofa bed.

Similar properties

2 outdoor pools, open 7:00 AM to 10:00 PM, cabanas (surcharge)
Blue Flamingo Resort Key West
New Town
  • Pool
  • Hot tub
  • Pet friendly
  • Free WiFi
8.4 out of 10, Very Good, 2,388 reviews
$184 nightly
The price is $207
Jun 16 - Jun 17
Total with taxes and fees
Blue Flamingo Resort Key West

Property amenities

Beach

  • Beach towels

Pool/Spa

  • Heated pool
  • Hot tub
  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Car not required
  • Onsite parking options include a garage

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 0.5 bathroom
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • DVD player
  • Smart TV with cable/satellite channels
  • Stereo

Outdoor areas

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

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Area rugs in public areas
  • Hardwood flooring in public areas
  • No elevator
  • Tile flooring in public areas
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near a health/beauty spa
  • Near a hospital
  • Near the marina
  • Near the sea

Things to do

  • Heated pool
  • Optional golf privileges
  • Birdwatching nearby
  • Cycling nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Whale watching nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Garden
  • Unit size: 1,800 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 21

Check-out

Check-out before 10:00 AM
Contactless check-out available

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

Rules

See rental agreement for cancellation policy, some refunds. This is a private nicely furnished home, not a party house.
No oversized cars or trucks Vehicles over 15 feet long or 80 inches wide strictly prohibited. They will be towed, they must fit in garage.

Pets

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

Events

No events allowed

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 21

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a deadbolt lock.

Additional information about polices, regulations, and more:

  • There are no elevators.

Property is also known as

Pool Home Reduced!!!
Truman Annex Pool Home + Cottage = Fun
NEW TO Market 5 Star Property 4/3 1/2 Pool Wifi Renovated

Frequently asked questions

What's there to do within easy reach of this vacation home?

This vacation home is situated in Old Town Key West within a 10-minute walk of Duval Street, Fort Zachary Taylor Historic State Park, and Ernest Hemingway Home and Museum. You'll also find Florida Keys Beaches and Southernmost Point less than a mile away.

Is parking available on site at 5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free.?

Yes, there is a garage.

Is this vacation home associated with a casino?

No, this vacation home is not connected to a casino.

Is there an indoor pool at this vacation home?

No, this vacation home doesn't have an indoor pool; however, there are an outdoor pool and a hot tub.

Is 5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free. good for couples?

This historic vacation home offers many amenities for couples such as a private pool, a private pool in some house, as well as an outdoor pool.

Are there hot tubs at 5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free.?

No, but guests can enjoy a heated pool at this vacation home.

Does this vacation home include breakfast service?

No, this vacation home doesn't offer breakfast.

Does this vacation home allow pets to stay free of charge?

No, pets aren't allowed at this vacation home.

Are there connecting rooms at 5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free.?

No, this vacation home doesn't feature connecting guestrooms.

How far is the airport from this vacation home?

The closest major airport to this vacation home is Key West Intl. Airport (EYW), which is 4.1 mi away (14 minutes by car).

Are there rooms with balconies that I can book at 5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free.?

Yes, every house at 5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free. comes with a patio.

5 STAR HOME 3/2 1/2 + 1/1 cottage, pool, buy 3 weeks get 4th week free. Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 57 out of 64 reviews
Rating 8 - Good. 6 out of 64 reviews
Rating 6 - Okay. 0 out of 64 reviews
Rating 4 - Poor. 0 out of 64 reviews
Rating 2 - Terrible. 1 out of 64 reviews

9.8/10

Cleanliness

8.0/10

Amenities

10/10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

John L.

Liked: Cleanliness, check-in, communication, listing accuracy
Great location, very comfortable floor plan – everything about it was perfect!
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

Colin B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice home. Great location. Would stay again.
Stayed 7 nights in Sep 2025
Verified

10/10 Excellent

Stacey V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home, very comfortable. A great location - you can’t beat it. Host was responsive to questions but honestly we didn’t need anything! Check in was easy, Penny was great. Would love to stay again when in Key West. THANK YOU!
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

Cheryl S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location. Wonderful house. Loved our daily pool time.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Megan H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful time during our stay in Key West. Penny's home was beautiful and well kept. Great location, close top everything but in a nice quiet neighborhood. The pool was pristine and a lifesaver in the Florida heat. We will definitely be back!
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Trudy S.

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

Family Vacation

We enjoyed our stay, will be back one day.
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Mark L.

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

Family vacation

We had four generations for the week. Accommodations worked out great. Owner responded to all questions and resolved issues quickly. Walked to all restaurants and parks. Great vacation
Stayed 7 nights in Apr 2025
Verified

10/10 Excellent

Tisha P.

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

Great Location Very Quiet

Our stay was great. Host was very responsive to a couple of unexpected issues that came up. We let our 4 kids (18, 19, 19 and 19) stay in the main house. My husband and I stayed in the "guest house" in back yard. That was perfect, we had so much privacy, it was like we were on a seperate vacation. The pool was perfect, we relaxed daily in it.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Michael J.

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

Key West Is Best

Great setup for us with 3 generations of family all under one roof. Great access to walk to all the hot spots on the island. Great stay and we’d book again in the future.
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Jeff B.

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

Great location in Key West

Everything was as expected and look forward to coming back in the future.
Stayed 12 nights in Jan 2023
Verified

8/10 Good

Darby S.

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

Wonderful Stay in a Prime Location

We had a fantastic time staying at this home! The location couldn't be better—just a short walk to Duval Street and Fort Zachary Taylor State Park, which made exploring Key West so convenient. The house itself was spotless and nestled in a beautiful, quiet neighborhood that felt both welcoming and private.We were initially concerned that the pool might be too small, but it turned out to be just right. It was perfect for a refreshing midday dip to cool off and relax. Overall, this place exceeded our expectations and was ideal for our trip.
Front of house
Neighborhood
Stayed 9 nights in May 2025
Verified

10/10 Excellent

Audrey C.

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

Family Time 3

This was one of the most lovely and accommodating properties we have ever stayed at. The photos didn't do justice to how beautiful and spacious it truly was. Especially the cottage. The house was perfect for our family of 6 to both come together, and spread out. There's even some small details that show how much love has gone into the comfort of this home. Many wonderful memories were made during our stay.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Joe M.

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

Just like home

beautiful home in great condition and in a great location. We look forward to a return visit.
Stayed 7 nights in Feb 2020
Verified

10/10 Excellent

Ron B.

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

Perfect Spot

We thoroughly enjoyed our week! Penny was responsive and we couldn't have been happier with our choice in houses.
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

Joseph B.

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

Fabulous, Fabulous

In the heart of the Truman Annex, literally steps from major Key West attractions. Georgeous neighborhood, beautiful house, with pool and casita. WONDERFUL.....
Stayed 6 nights in Feb 2020
Verified

10/10 Excellent

KATHIE S.

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

Wonderful location

The property was great. We had a non urgent problem with the pool and the owners had someone to fix the problem within 2 hours. The house is beautiful and highly recommend it
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Christine R.

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

High school Graduation present trip

My son wanted to go to Key West for his grad trip (we were supposed to travel Europe but Covid19 happen) so, I happened to find this cute lil home and we booked it.. beautiful neighborhood, felt safe, very close to everyone walking distance. The guest cottage was absolutely perfect. Would definitely stay here again (if we don’t buy one for us😁)
Stayed 7 nights in Aug 2020
Verified

10/10 Excellent

Christina S.

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

Such a great Experience

Everything was just perfect! The location is so ideal for all ages. We had a few littles that live the short walk to the splash pad. Our 19 year old loved the proximity to the park for her workouts and the adults enjoyed the location to mid Duval making it ideal for quick shopping and dining in either location. The house was perfect size and the pool was nice and private! We loved every minute of our stay!
Stayed 8 nights in Jun 2023
Verified

10/10 Excellent

jay t.

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

Great location

Super location with easy walk to Mallory Square, Duval, Hemmingway House and Southern Point. Plunge pool was great for cool off. Some plumbing issues were solved timely. Penny was great communicator.
Stayed 7 nights in Feb 2023
Verified

10/10 Excellent

RICHARD T.

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

Family Vacation

Property and location were beautiful as described. We had a couple challenges but Penny the owner handled them right away. After researching many properties we were glad we chose this one. The Main house, pool and guest house gave us 7 adults plenty of room. Truly made a memorable vacation! Thank You!
Stayed 6 nights in Jul 2020
Verified

10/10 Excellent

Phillip F.

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

Awesome home.

The house was as advertised. The kitchen had most things needed for a week long stay. The bedrooms were very nice and we had plenty of room. The location was perfect, close to most things Key West had to offer. Only thing I would change is adding a second gate key so more than one person could have one.
Stayed 7 nights in Jun 2020
Verified

10/10 Excellent

karyn r.

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

Wonderful location, beautiful property

First stay in Truman Annex and it was wonderful. The location was quiet but two blocks from the action. Private space with pool for afternoon cocktails and beautiful front porch for morning coffee and watching the "doggy" parade! Property is very spacious and you immediately appreciate the details that make you feel at home. Penny was immediately responsive to any questions we had. Would not stay anywhere else in Key West!!
Stayed 7 nights in Feb 2022
Verified

8/10 Good

Carole G.

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

Good place to stay

My family enjoyed the home and cottage. The home was furnished with everything we needed in the kitchen to be able to cook meals. The pool size was disappointing. Also, there was not much sunlight in the pool area. Only had about 3 hours of full sun to be able to sit by pool.My family enjoyed the fact that we could walk to many things in the area.I enjoyed the cottage and being able to have my own private place to relax in. The shower being so small was very challeging, but I made it work.
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Marge O.

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

The BEST place to stay on Key West!

This property has it all!! First, the location cannot be beat. You will be within walking distance of all the best restaurants, Duval Street shopping, Mallory Square, beaches, and historical sites, parks, and museums. The house is even more beautiful in person too! - the decor and amenities add a personal touch to make you feel instantly welcome and at home. Penny is a great communicator, and accommodating to our needs. The neighborhood is quiet, friendly, and beautifully landscaped. We especially enjoyed a cool dip in the pool and relaxing on the front porch after the day's activities. We've been to Key West many times over the past 10 years, staying in luxury hotels, and this is our favorite rental!
Stayed 6 nights in Feb 2025
Verified

10/10 Excellent

Pam

Liked: Cleanliness, amenities, property conditions & facilities, communication
The property is in a great location with easy walking to tourist attractions, restaurants, and playgrounds. It is a very comfortable home with ample space so that you can enjoy being with your fellow housemates. The pool was enjoyable even though the temperatures in Key West were much cooler than normal. I did have an issue when I first arrived, but the owner answered my text promptly and the issue was resolved. I would highly recommend this property.

Hotels