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

Waterfront cottage with kitchen and balcony

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

Front of Cottage
Front of Cottage
Livingroom
Livingroom
Kitchen w/dishwasher

Reviews

10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 6116.1 sq m

Popular amenities

  • Dryer
  • Washer
  • Kitchen
  • Outdoor space

Explore the area

View map
  • Place, Duval Street
  • Place, Mallory Square
  • Place, Southernmost Point
  • Airport, Key West, FL (EYW-Key West Intl.)

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.
Starting Jan 2026 , this beautiful cottage will become monthly! Stays will have to be 28- 30 days. Discount of 10% for monthly stays. 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

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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 indicated that there are no carbon monoxide detectors or gas appliances on the property
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

This property does not have any lifts
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 cycling and ecotours nearby.
View more Cottages in Key WestOpens in a new window
Map
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

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Kaya Island Eats - ‬7 min walk
  • ‪Santiago's Bodega - ‬6 min walk
  • ‪Rams Head Southernmost - ‬7 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.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 188 out of 202 reviews
Rating 8 - Good. 14 out of 202 reviews
Rating 6 - Okay. 0 out of 202 reviews
Rating 4 - Poor. 0 out of 202 reviews
Rating 2 - Terrible. 0 out of 202 reviews

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

Reviews

10/10 Excellent

Todd G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful location and set up as always. Love staying here!
Stayed 7 nights in Oct 2025

10/10 Excellent

Joshua G.

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

Lisa W.

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

Dwayne K.

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

Randolph C.

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

Christian J.

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

Trisha P.

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

MICHAEL

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

ROSEMARIE V.

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

Jean O.

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

Pat W.

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

Key West Quiet & Relaxing

This is a great location! So convenient to everything but in a quiet neighborhood. We definitely enjoyed the upstairs deck and spent a great deal of time there enjoying coffee and books. It definitely had everything we could ask for.
Stayed 7 nights in Jan 2022

10/10 Excellent

Jill J.

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

Amazing location!!

We had a great stay! The house was everything it said it was and more. Very clean and location is awesome. Close to everything . We rented bikes and everything was within a 10 minute ride. Close to the beach, sunsets and Duval!!
Stayed 10 nights in Feb 2023

10/10 Excellent

Jenny B.

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

Would absolutely book again!!

The house was beautiful and central to everywhere we wanted to go. Any questions that came up, Jean answered us pretty quickly. Our stay was wonderful, the house and accommodations made it feel like our home away from home during our stay. When we come back to Key West we will definitely be looking to book with them again!
Stayed 7 nights in Oct 2023

10/10 Excellent

James T.

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

Key West for Family

Key West is built for small (4-6) family vacations. This property is well-suited to support that. Close to the action means lots of “walkability”. Well appointed with all the needed features. Easy check in, check out. Affordable.
Stayed 7 nights in Jun 2024

10/10 Excellent

Lori W.

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

Love Key West

Property was great, location was perfect. Jean was great at communicating. I wish they weren’t doing work on fences at 7:30 am. Pool was crowded, get there early. We had a great time! Would definitely stay there again!
Stayed 7 nights in Mar 2024

10/10 Excellent

Kristin S.

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

Becky G.

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

Great location and clean.

Enjoyed our stay. Wish we could stay longer. Loved the porch. Beds mostly comfortable. Bed in downstairs room was a bit lumpy on one side. Pool nice and needed. June is pretty humid and hot. Rules at pool were too restrictive but we enjoyed cooling off. I.e. no music. Overall a Lovely place. Lizards were entertaining!!
Stayed 7 nights in Jun 2024

10/10 Excellent

Dawn M.

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

Friends getaway to Key West

The whole Truman area was beautiful and the house was very nice! We loved the outside sitting area and spent a lot of time there. We enjoyed being within walking distance of many of the places that we wanted to go. We also appreciated being able to have a parking spot for the golf cart that we rented. The pool was our only disappointment due to its small size and the atmosphere. There were never any chairs available and many of the people in the pool were not very welcoming or friendly. There were also a lot of pool rules to follow!
Stayed 7 nights in Mar 2023

10/10 Excellent

Darci E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was perfect- no complaints. I would stay here again!
Stayed 4 nights in Oct 2025

10/10 Excellent

Stephanie C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything about this property was as exactly described, if not better. The location can't be beat in its proximity to Ft. Zach and the waterfront. We spent the majority of our time on the outside patio and only turned the tv on once or twice. Key West has too much to offer to be indoors and this property doesn't disappoint. Looking forward to staying here again.
Stayed 7 nights in Sep 2025

10/10 Excellent

Jenny B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely love staying here every time we come down to KW! The cottage is beautiful and comfortable, clean and central to every place in Old Town KW Will definitely book here again and highly recommend everyone we know to stay here!Thank you Jean & Lowell for providing such a great getaway!!
Stayed 7 nights in Oct 2025

10/10 Excellent

Stacey K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The location was perfect and the host was very responsive. We will definitely stay here again when we come back to Key West.
Stayed 7 nights in Aug 2025

10/10 Excellent

James J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Duplex outlets behind master bed wonky. Left side top outlet dead. Right side surge protector all dead.Had a little trouble with sugar ants on north baseboard of master b’room and east baseboard of 1st floor b’room.
Stayed 7 nights in Aug 2025

10/10 Excellent

Joshua

Liked: Cleanliness, property conditions & facilities
First time renting a home for me. Fortunately this particular property was great. Location is prime. Quiet location a few minutes walk to one of the cleanest and nicest beaches in the area. The walk into town depending on your destination can vary from 10-20 minutes. I Additional the property host was excellent and attentive beyond what they needed to be.This home was modern and clean. All though located in a crowded housing/condo complex this structure is detached from any other structural which is a bonus. Only cons are parking, which although free is a good distance from home and lacks convenienc. Additional unlike a hotel stay you are required to do some work relative to cleanup at the end of your stay. We where asked to start laundry and strip linenes off the bed at the end of our stay. You won't have convenience of free coffee or breakfast. But this is a fully functional unit where you can go shoppin and cook your own meals and brew your own coffee you buy. All in all very satisfied.
Stayed 7 nights in Jun 2025

10/10 Excellent

Kim P.

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

About the host

Hosted by Jean Kemp

Host profile image
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.

Languages:

English

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