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A SUNRISE COTTAGE at The Truman Annex in Key West

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Pool
Living area
Exterior
Living area
Living area

Reviews

9.4 out of 10
Exceptional

Entire home

2 bedrooms2 bathroomsSleeps 61100 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Key West, FL
  • Place, Florida Keys National Marine Sanctuary
    ‪5 min walk‬
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Fort Zachary Taylor Historic State Park
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪13 min drive‬

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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 Ernest Hemingway Home and Museum. The vacation home includes a kitchen, a patio, and a sofa bed.
View more Vacation Homes in Key WestOpens in a new window

What's nearby

  • Florida Keys Eco - Discovery Center - 3 min walk - 0.2 miles
  • Florida Keys National Marine Sanctuary - 5 min walk - 0.3 miles
  • Duval Street - 6 min walk - 0.4 miles
  • Ernest Hemingway Home and Museum - 8 min walk - 0.4 miles
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.4 miles

Getting around

  • Key West Intl. Airport (EYW) - 19 min drive

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Rams Head Southernmost - ‬7 min walk
  • ‪Moondog Cafe & Bakery - ‬8 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.

A SUNRISE COTTAGE at The Truman Annex in Key West

This charming 2 story 2 bedroom with loft, two bath cottage in the Shipyard Condominiums is located just off the pool and gorgeous park. Both bathrooms have been recently updated! The first floor bedroom and bath are conveniently located just off the kitchen. Enjoy the very comfortable living room with a dining area that enjoys view through two sets of French doors to the rear deck and garden. The primary suite on the second floor enjoys a queen bed, plus a sitting area which includes a murphy bed. The large covered rear deck features out door dining and lounging and a back gate which provides quick access to the rest of the community and the park.
The Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s Old Town area. These condos are located just 2 blocks from Duval Street and all the Old Town Key West attractions including Fort Zachary Taylor State Park and Beach and the Truman Waterfront park. This property is outfitted with washer/dryer, pots/pans, towels, linens, central air conditioning, assigned off street parking, and access to a refreshing community pool.
Please note: This property will require a minimum of a 28 night stay.
The vacation home is air-conditioned and features a kitchen, 2 bathrooms, and a patio, and there's space to spread out with 2 bedrooms. Guests can expect to find free WiFi. Other standard amenities include a washer/dryer, a sofa bed, and a coffee maker.

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Bar (on property)
Southwinds Motel
Old Town Key West
  • Pool
  • Breakfast included
  • Restaurant
  • Air conditioning
8.6 out of 10, Excellent, 1,323 reviews
$233 nightly
The price is $262
May 10 - May 11
Total with taxes and fees
Southwinds Motel

Property amenities

Pool/Spa

  • Communal pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop

Bedrooms

  • 2 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 2 bathrooms
  • Shower
  • Towels provided

Outdoor areas

  • Garden
  • Patio

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

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

General

  • Garden
  • Gated community
  • Unit size: 1,100 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

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

  • 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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
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: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • 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 fire extinguisher, a smoke detector, and a deadbolt lock.

Property is also known as

A Sunrise The Truman Annex
Sunrise Cottage @ the Truman Annex
Sunrise Cottage in the Truman Annex
A Sunrise Cottage @ the Truman Annex Key West
20% Off Summer Special Sunrise Cottage @ the Truman Annex
A Sunrise Cottage @ the Truman Annex Private vacation home
2698-193337

Frequently asked questions

What is there to do around this vacation home?

This vacation home is situated in Old Town Key West within a 10-minute walk of Duval Street and Ernest Hemingway Home and Museum. You'll also find Florida Keys Beaches and Mallory Square less than a mile away.

Is parking available on site at A SUNRISE COTTAGE at The Truman Annex in Key West?

No, there isn't parking at this vacation home.

Is this vacation home adjacent to a casino?

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

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

What do couples enjoy most about A SUNRISE COTTAGE at The Truman Annex in Key West?

Couples staying at this vacation home will value amenities like a kitchen, a kitchen in some house, as well as a garden.

Does A SUNRISE COTTAGE at The Truman Annex in Key West have a hot tub?

No, this vacation home doesn't have a spa tub.

Does this vacation home provide breakfast?

No, this vacation home doesn't offer breakfast.

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

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

Does A SUNRISE COTTAGE at The Truman Annex in Key West have connecting rooms available?

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 (19 minutes by car).

Are there rooms with balconies that I can book at A SUNRISE COTTAGE at The Truman Annex in Key West?

Yes, every house at A SUNRISE COTTAGE at The Truman Annex in Key West comes with a patio.

A SUNRISE COTTAGE at The Truman Annex in Key West Reviews

Reviews

9.4

Exceptional

Rating 10 - Excellent. 44 out of 56 reviews
Rating 8 - Good. 8 out of 56 reviews
Rating 6 - Okay. 1 out of 56 reviews
Rating 4 - Poor. 2 out of 56 reviews
Rating 2 - Terrible. 1 out of 56 reviews

9.6/10

Cleanliness

10/10

Amenities

8.0/10

Property conditions & facilities

Reviews

8/10 Good

Lisa W.

Liked: Cleanliness
Host was great. The unit could use some upgrades in Kitchen - dishwasher was small and the range burners didn’t all really heat up to maximum heat. Overall we loved the layout of unit and location was great.
Stayed 14 nights in Dec 2025

10/10 Excellent

Jamie S., Seymour

Liked: Cleanliness
Great location.
Stayed 7 nights in Dec 2025

6/10 Okay

michael a.

Liked: Cleanliness
So whoever took the pictures and posted them online was not entirely honest about the beds in the bedrooms because we were surprised to find twin beds which my 6-ft 1 husband had to sleep on and and Murphy bed which was surprising and not in a good way
Stayed 7 nights in Oct 2025

10/10 Excellent

William F.

Liked: Cleanliness
We very much enjoyed our stay, the location was fantastic not only to everything to do in Key West but the pool was only steps from the front door.
Stayed 8 nights in Jul 2025

10/10 Excellent

KC C.

Liked: Cleanliness

Good times in KW

Great property, great location, and good time had by all.
Stayed 7 nights in May 2025

10/10 Excellent

Marian L., Ringoes, New Jersey, USA

Liked: Cleanliness

Construction 8am - HORRIBLE

Every morning there was 8 am construction couldn’t sit in the deck because of the falling debris. Kitchen drawer had no handle. The outside deck had no canopy like in the pictures. Other than that we had a great time.
Stayed 7 nights in Apr 2025

10/10 Excellent

Pat B.

Liked: Cleanliness

Vacationing in Paradise

The property was very clean, quiet and a very good location. Close to restaurants, shopping, and activities. The only issues with the condo was the upstairs toilet seat , bathroom hooks and toilet paper roll were loose. Was a little disappointed in the upstairs second bedroom which didn't have a bed or couch. Be sure to put security warning on the step out into this bedroom, drops suddenly. Water in downstairs toilet didn't fill high enough. But overall, we would stay here again.
Stayed 7 nights in Nov 2024

10/10 Excellent

John Mark

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
It has that 80’s beach house feel. Steps away from the pool and easy walk to town. Loved it!
Stayed 10 nights in Jul 2024

10/10 Excellent

Grabowski, A.

Liked: Cleanliness

Great Place to Stay

This was a great rental in a great location, and the management was very clear, helpful, and easy to reach. One thing to note is that the master suite does not have a door (as noted in other reviews), and the sound does travel from downstairs. Loved the location and the amenities.
Stayed 7 nights in May 2024

10/10 Excellent

Meg M.

Liked: Cleanliness

Great stay in Key West Truman Annex

Wonderful location, easy access to beach, old town, splash pad, pool. Really good for kids and adults alike.
Stayed 7 nights in Jun 2024

10/10 Excellent

JOseph P.

Liked: Cleanliness

Great Stay close to everything

Loved this property. Just as described. Would suggest renting bikes to get around everywhere. Beach is 5 min bike. sunset 2 min bike downtown key west 2 mins.
Stayed 7 nights in Mar 2024

10/10 Excellent

Kelley E.

Liked: Cleanliness

Nice getaway

We had a great week! The place was very clean and had updated bathrooms. We had no issues with anything. We did have 6 adults but the place would probably work better for a family of six based on only 2 bathrooms and the way the rooms are set up. Please also consider adding to the after hour check in instructions that the lock boxes are at the rental office not on the door. We did get an email but it went to spam so didn’t see it but that info isn’t included in the instructions in other places. Thanks for a great week!
Stayed 7 nights in Mar 2023

8/10 Good

Nancy H.

Liked: Cleanliness

Great location!

The property was very clean and actually looked better in person than online. looks like some recent updates may have been made. The location was perfect, we were able to walk to almost everything all week. Had a few questions regarding the property, management company was very helpful. Didn’t like the Master which was a loft, not private and all noises can be heard because it can’t be closed off. The only other issue we had was the pest control company knocked but then entered the property and wanted to spray. Would have been helpful if we had been advised. Overall, it was a good stay, enjoyed the week very much.
Stayed 7 nights in Jan 2023

10/10 Excellent

Steve G.

Liked: Cleanliness

Fun, Fun, Fun!!

Exactly as advertised! We had a blast! We will definitely be back!!
Stayed 8 nights in Dec 2022

10/10 Excellent

Mandy S.

Liked: Cleanliness

Great location and comfortable

Our family of 6 stayed here for a week and it was very enjoyable. Being here in July we knew it would be hot and humid with rain so we wanted to have space and comfort while indoors. Grandparents stayed in the bedroom downstairs while we stayed in the room upstairs. There’s a loft with a pull down full size bed. We brought an air mattress for our young kids and it was enough space in the loft for it instead of using the full size bed. Everything is as pictured. The dining room chairs are newer than pictured. The shower drain in the upstairs bathroom drains slower. The water hose in the back deck didn’t work. The microwave door handle was half broken. No major issues. Plenty of beach towels for us to use. Extra pillows and sheets. There were three beach chairs and some pool noodles we used for beach days. It also had puzzles, books, cards to play. Kitchen had cooking pots pans utensils. We didn’t cook so only used the plates and cups for take outs. Wine glasses are also available. Also had a cooler tote to carry some water to the beach. We really enjoyed our stay. Close to lots of attractions and short walk to the Truman water park which was free and there’s also a bus stop there for the free Duval loop bus. Would definitely consider this property again for future stays.
Stayed 7 nights in Jul 2022

8/10 Good

lisa h.

Liked: Cleanliness

Paint Me, Please the

Walls and door frames need painting and black around ceiling fans, some light fixtures and door frames need to be fixed. Is this mold? Pool rules are too strict and pool is too small for the size of the complex. All else was perfect. Thanks
Stayed 7 nights in May 2022

8/10 Good

Kimberly L., Denver, CO

Liked: Cleanliness

Very clean, great location!

We enjoyed our week. Would definitely stay again.
Stayed 7 nights in Apr 2022

10/10 Excellent

Gail H.

Liked: Cleanliness

Great location!

Excellent location close to everything but far enough away that it is very quiet. The kitchen lacks amenities for cooking, some of the linens were worn and some ceiling fans were inoperable. Overall experience was excellent and would stay there again...Highly recommend!
Stayed 7 nights in Jan 2022

10/10 Excellent

Rebecca B.

Liked: Cleanliness

Great place to stay!

My girlfriends and I stayed in this cottage for a week for our girls trip. This little cottage is so cute, was very clean and the back patio was perfect for sitting outside in the shade! It's within easy walking distance of Duval Street. We loved this place and would recommend it to others!
Stayed 7 nights in Oct 2021

10/10 Excellent

Donnette D.

Liked: Cleanliness

Beautiful Property

Just perfect for the 5 of us! We loved the property. The entire Truman Annex is beautiful. Literally a 10-15 minute walk to everything you need to see in downtown Key West. It was clean, had all the amenities and a wonderful patio that we had dinner on almost every night. I would recommend this place to anyone! Hope to come back again soon.
Stayed 8 nights in Aug 2021

10/10 Excellent

Brian L.

Liked: Cleanliness

Perfect Stay

Beautiful, quiet, and spacious 3 bedroom, 2 bath cottage. Close to all the tourist activities and great food. Will definitely pick this same cottage when we return.
Stayed 7 nights in Jul 2021

10/10 Excellent

Jennifer G.

Liked: Cleanliness

It was a lovely complex.

Very close to everything.
Stayed 7 nights in Jul 2021

10/10 Excellent

David J., Wyomissing, PA, USA

Liked: Cleanliness

What a truly wonderful cottage and location!

We had a wonderful time at the cottage and everything was as promised in the listing. We enjoyed it so much that we’ll be staying there again next year!
Stayed 10 nights in May 2021

10/10 Excellent

Thomas W.

Liked: Cleanliness

Truman annex

Overall we had a nice, relaxing time. The check in and out process was easy and when we had a dishwasher issue the office sent a repair person the next day to fix it. The covered outdoor patio was used a lot. Walking and biking was pleasant in that area. Truman annex overall was quiet and enjoyable. Pool area was crowded and some loud music played but security responded quickly. Key west overall during our stay was very pro-mask and health and safety conscious. Makes sense to protect the area and businesses. Saw a change when we were leaving w more spring breakers heading down.
Stayed 14 nights in Feb 2021

10/10 Excellent

Diane G.

Liked: Cleanliness

Incredible location

The Truman annex is a magical place- lush and tropical. Walking/biking distance to everything. Spent a lot of time at the state park beach. The unit had great accommodations for each of our 4 family members to sleep-- basically 3 bedrooms. 2 suggestions for upgrades that would have made our stay more enjoyable: hotter water in the showers (it was lukewarm) and better pillows (they were all flat and we were all a bit sore from using them). In general it was a wonderful place to spend 9 days!!
Stayed 9 nights in Jul 2020