Entire home

Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex

Overview
Amenities
Policies
Location
Host

Exceptional

3 bedrooms2 bathroomsSleeps 61250 sq ft

Popular amenities

Dryer
Washer
Kitchen
Outdoor space

Explore the area

Key West, FL

Duval Street
‪6 min walk‬
Mallory Square
‪9 min walk‬
Southernmost Point
‪15 min walk‬
Key West, FL (EYW-Key West Intl.)
‪10 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Beds

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio

Porch or lanai

Kitchen

Balcony

Outdoor play area

Garden

Dining area

About this property

Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex

Sea Breeze Cottage Cottage is a private, tropical, stand alone cottage located in the prestigious Truman Annex. This is a weekly rental for the remainder of 2025.
Starting Jan 2026 , this beautiful cottage will become monthly! Stays will have to be 28- 30 days. Discount for monthly rental. Make plans to stay longer, relax or work remotely from paradise for a full month in 2026.
- King bed and Queen bed upstairs
- Twin beds downstairs can be converted to a king by request.
- Bathroom upstairs has double sinks and separate room with toilet and walk-in shower.
- Bathroom downstairs newly remodeled with walk-in shower, vanity w/sink and toilet.
- Fully equipped kitchen has everything you need for your stay.
- Washer & Dryer, towels & linens, including beach towels and beach chairs
- Central air & ceiling fans.
- Sea Breeze living area has 2 sets of double doors that opens to large covered deck with outdoor furniture seating for 6.
- Large deck upstairs off of queen bedroom with outdoor
furniture seating for 6.
- TV's in all bedrooms and living room with cable and Air Play
- Free Hi speed internet
- Assigned parking for 1 vehicle.
- Large heated pool for Shipyard guests only.

You are close to everything! Explore the Waterfront Park behind the complex. Take a stroll to the Waterfront Pier, watch sunsets and sailboats. Fort Zachary Park and Beach is a short walk or bicycle ride. Mallory Square where you can watch nightly Sunset Celebrations, local vendors and entertainment.
Just 2 blks to Duval Street, for dining, shopping, night clubs and museums. You are steps away to the Truman Annex heated pool.
Our Luxury Caribbean Cottage is Spacious & Quiet!!
There is much to do and see in this Southernmost City.

To see our other VRBO Key West listings:
Truman Annex Shipyard (1 bed, 1 bath) Island Escape vrbo.com/934388ha
Truman Annex Shipyard (2 bed, 1 bath) Conch Retreat vrbo.com/261681ha

Property manager

Jean Kemp

Premier Host

Languages

English

Add dates for prices

Amenities

Pool

Kitchen

Washer

Dryer

Free WiFi

Air conditioning

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Pool
Kitchen
Washer
Dryer

House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

No pets 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

On-site parties or group events are strictly prohibited

Long-term renters welcome

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 that there is a smoke detector on the property

Safety features at this property include a fire extinguisher and a first aid kit

We should mention

A car is not required for transport to and from this property

About the area

Key West

Located on the waterfront, this cottage is in Old Town Key West, a neighbourhood in Key West. Fort Zachary Taylor Historic State Park and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. USCGC Ingham Maritime Museum and Mel Fisher Maritime Museum are also worth visiting. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.

Key West, FL

What's nearby

Duval Street - 6 min walk - 0.5 km
Ernest Hemingway Home and Museum - 7 min walk - 0.7 km
Fort Zachary Taylor Historic State Park - 8 min walk - 0.7 km
Mallory Square - 9 min walk - 0.8 km
Southernmost Point - 15 min walk - 1.3 km

Getting around

Key West, FL (EYW-Key West Intl.) - 15 min drive

Restaurants

‪Margaritaville - ‬7 min walk
‪Blue Heaven - ‬8 min walk
‪Green Parrot Bar - ‬5 min walk
‪Willie T's - ‬6 min walk
‪Mangoes Restaurant & Island Cuisine - ‬6 min walk

Frequently asked questions

Does Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex have a pool?

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

Is Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex?

Check-in begins at 4:00 PM.

What time is check-out at Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex?

Checkout is at 10:00 AM.

Where is Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex located?

Located in Old Town Key West, this cottage is within a 10-minute walk of USCGC Ingham Maritime Museum, Duval Street and Fort Zachary Taylor Historic State Park. Ernest Hemingway Home and Museum and Florida Keys Beaches are also within 15 minutes.

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

9.8/10

Cleanliness

8.8/10

Amenities

10/10

Property conditions & facilities

6.0/10

Eco-friendliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

Kim P.

14 Jun, 2025

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

Great property - clean and well stocked. Host was fantastic. Close to everything. Nice pool

Stayed 7 nights in Jun 2025

10/10 Excellent

Randolph C.

20 Apr, 2025

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

Sea Breeze Cottage outstanding

Had another wonderful week at Sea Breeze Cottage. Perfect home, location, amenities, and host. Love going there.

Stayed 7 nights in Apr 2025

10/10 Excellent

Jeff S.

15 Apr, 2025

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

Perfect location, beautiful place

Great location, very clean, just as described. Jean is super responsive to any questions and very accomodating. We will definitely be back!

Stayed 7 nights in Apr 2025

8/10 Good

David P.

17 May, 2025

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

Vacation with friends

The home is very well maintained and great amenities. The location could not have been better. Short walk to the beach and Duval Street. The only negative thing I can come up with is that the bed pillows were too firm and gave us stiff necks.

Stayed 7 nights in May 2025

10/10 Excellent

Dwayne K.

8 May, 2025

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

Daughter's Wedding

Perfect location and perfect weather! What more could we ask for. Added an additional day with ease.

Stayed 3 nights in Apr 2025

10/10 Excellent

Becky B.

9 Apr, 2025

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

Sea Breeze Cottage

This condo is beautiful! We booked this condo because of the back porch table and seating. Location is within walking distance to all attractions and restaurants Looking forward to next year!

Stayed 7 nights in Mar 2025

10/10 Excellent

Linda S.

10 May, 2025

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

Great house during songwriters week

The house was beautiful and in a perfect location for us. We attended a concert at the Coffee Butler amphitheater and it was easy walking distance. the location is also easy walking distance to Duval and many bars and restaurants. The back decks are very peaceful for relaxing and enjoying the scenery. The owners were very easy to work with and helped us with any questions we had.We would definitely rent again.

Stayed 7 nights in Apr 2025

10/10 Excellent

Trisha P.

30 Apr, 2025

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

Anniversary trip

My husband and I took a trip to Key West for our 20th anniversary and even though this rental was a little more than we needed for just the 2 of us, we thoroughly enjoyed it. Booking was very easy and Jean was gracious enough to allow us to check in early so we didn’t have to cart our luggage around town. It was beautifully decorated and we loved the balcony in the evening! It really is a beautiful home and community. We would definitely stay again! Thanks!

Stayed 3 nights in Apr 2025

10/10 Excellent

Rick B.

14 Dec, 2024

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

Framily vacation

The property was exactly what we wanted and was clean, comfortable, and extended an unexpected level of privacy. The accommodation was perfect for our trip and the location was excellent.

Stayed 7 nights in Dec 2024

10/10 Excellent

Lisa W.

10 Jan, 2025

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

Fabulous

Loved our stay , perfect layout with everything we needed. Quiet location in Truman Annex. Hope to stay next year!

Stayed 7 nights in Dec 2024

10/10 Excellent

Joshua G.

6 Jul, 2024

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

Great location

Great location, perfect for family of 6.

Stayed 7 nights in Jun 2024

10/10 Excellent

Rebecca E.

28 Nov, 2024

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

Perfect vacation

We had such a wonderful time. The house was very clean and had everything we needed during our stay. We will definitely be returning in the future.

Stayed 7 nights in Nov 2024

10/10 Excellent

MICHAEL

2 Jan, 2025

Liked: Cleanliness, property conditions & facilities, communication

Great location for all activities, especially night life. Very attractive place inside & outside! Owner was excellent to work with. Very highly recommend this up to date, stand alone, 1.5 story cottage/house. Well stocked and secure place. A must place to stay, close enough to walk to grocery store and all your activities in Key West!

Stayed 7 nights in Oct 2024

10/10 Excellent

Christian J.

1 Dec, 2024

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

Cute little cottage

Walking/biking distance to everything! Enjoyed a week with 6 adults and it was a perfect home base. Little extras like beach chairs, towels and cooler a plus. Will definitely be back!!

Stayed 7 nights in Nov 2024

10/10 Excellent

Maureen N.

19 May, 2024

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

Perfect location

Spacious, close to the beach, restaurants, shops and bars. We’d love to return.

Stayed 7 nights in Apr 2024

10/10 Excellent

Matthew A.

27 Dec, 2023

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

Peace and quiet, but in the heart of it all.

Perfect location, lovely home, can’t wait to return!

Stayed 7 nights in Dec 2023

10/10 Excellent

Jean O.

21 Oct, 2024

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

Great Trip

The property is great location. Nice and clean. We really enjoyed stay. Pillows would be the only negative feedback. Need some softer ones.

Stayed 7 nights in Oct 2024

10/10 Excellent

ROSEMARIE V.

14 Jul, 2024

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

Family Vacation

Our family had a great time at the Seabreeze Cottage. It was equipped with everything we needed and was located in a beautiful and historic setting. Close to everything - the beach, shops and restaurants. We had an amazing time! Rose & Brian - Rochester, NY

Stayed 7 nights in Jul 2024

10/10 Excellent

Joseph D.

31 Jul, 2023

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

great stay

very nice

Stayed 7 nights in Jul 2023

10/10 Excellent

Randolph C.

24 Apr, 2023

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

Key West Lover

Outstanding vacation experience. We’ll maintained and supplied house in a convenient location.

Stayed 7 nights in Apr 2023

10/10 Excellent

Kristin S.

21 Nov, 2024

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

Favorite place

We enjoyed our stay . Very disappointed that the pool was closed.but updating was necessary. First three days very loud as boat owners set up on other side of fence.( Boat race week) would come back, not boat week!!

Stayed 7 nights in Nov 2024

10/10 Excellent

Christina O.

12 Aug, 2024

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

Wonderful family vacation

We truly enjoyed our stay! We got delayed by a day due to a tropical storm. Jean reached out to make sure we made it okay and that all was well. The accommodations were more spacious than we expected from the pictures, and our family of 5 had more than enough room. I would definitely stay here again!

Stayed 7 nights in Aug 2024

10/10 Excellent

Robert S.

25 Nov, 2023

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

Another great time in key west

Excellent and well worth the money.

Stayed 7 nights in Nov 2023

10/10 Excellent

traci f., Hoover,Alabama

27 Dec, 2020

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

Wonderful trip

We had a wonderful time staying at the Truman cottage. Everything is so convenient! The cottage was very well stocked and clean. We will definitely stay here again.

Stayed 14 nights in Dec 2020

10/10 Excellent

Jane R.

2 Apr, 2024

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

108

Great spot, quick walk to the beach and close to the Duval Loop. Manageable walk to the great food store.

Stayed 63 nights in Jan 2024

About the host

Hosted by Jean Kemp

When not in Key West my husband and I live and own a Powersports business in Kansas. We have 2 sons and 5 grandchildren. We have owned in Truman Annex Shipyard since 2001. After visiting a few times we fell in love and knew we had to own. It's a pleasure to share our cottage with others so they can also fall in love with this beautiful historic island. After all these years of visiting we still look forward to and enjoy everything Key West has to offer.

Why they chose this property

We love Truman Annex! Old Town Key West has everything. Cottage is private and relaxing with views. It's tropical foliage and gardens are pristine. The surroundings are relaxing and private. It's close to all the attractions and activities. The sunsets are breathtaking & celebrated.

What makes this property unique

Sea Breeze is unique in that it is the only stand alone cottage in the Shipyard Truman Annex! That means More Privacy. You have 2 decks. The rode to Fort Zachary Park & Beach and waterpark are behind the complex. Beautiful pier to chill and watch sunsets. You will have all the amenities, roominess, and a tranquil-secure place to stay.