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

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Beach nearby, beach towels - Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex (Key West)
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Marina - Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex (Key West)
Property grounds - Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex (Key West)
Escape to Sea Breeze Cottage in the exclusive Truman Annex, where a private tropical oasis awaits. Enjoy your spacious retreat with 3 bedrooms, fully equipped kitchen and washer/dryer. Unwind on one of two large covered decks or take a short stroll to Waterfront Park and Fort Zachary Beach.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 6116 sq m

Popular amenities

  • Ocean view
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

Add dates for prices

About this property

Entire place

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

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. LOCATION is what it's all about. No need for a car, everything is close. Upper deck looks out over the Waterfront Park.
- 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 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 amenities

Beach

  • Beach nearby
  • Beach towels

Pool/Spa

  • Communal pool
  • Fenced private pool
  • Heated pool
  • Outdoor pool

Internet

  • Available in the cottage: Free WiFi

Parking and transportation

  • Car not required
  • Wheelchair-accessible parking available

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Books
  • Smart TV with cable/satellite channels
  • Stereo

Outdoor areas

  • Balcony
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 1 accessible parking space
  • Upper floors accessible by stairs only
  • Wheelchair-accessible parking
  • Wheelchair-accessible path of travel
  • Smoking not allowed

Services and conveniences

  • Housekeeping (on request)
  • Iron/ironing board

Location highlights

  • In the city center
  • Near a hospital
  • Near the marina
  • Near the sea
  • On the waterfront

Things to do

  • Heated pool
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Windsurfing nearby

Safety features

  • No carbon monoxide detector or gas appliances (host has indicated there are no carbon monoxide detectors or gas appliances on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Garden
  • Housekeeping (on request)
  • Unit size: 1,250 square feet

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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

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

Pets

Pets not allowed

Children and extra beds

Children are welcome

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
Long-term renters welcome
Host has indicated there are no carbon monoxide detectors or gas appliances 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 first aid kit
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

We should mention

This property does not have elevators
A car is not required for transportation to and from this property

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.

How much is parking?

Onsite parking is available at the 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?

Check-out 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 Truman Waterfront Park, Duval Street, and Fort Zachary Taylor Historic State Park. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 15 minutes.

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Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 195 out of 209 reviews
Rating 8 - Good. 14 out of 209 reviews
Rating 6 - Okay. 0 out of 209 reviews
Rating 4 - Poor. 0 out of 209 reviews
Rating 2 - Terrible. 0 out of 209 reviews

9.8

Cleanliness

10

Location

10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Christopher B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A great place to stay in Paradise. Definitely located in a very walkable, safe neighborhood. Highly recommended.
Stayed 7 nights in Dec 2025
Verified

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
Verified

10/10 Excellent

Alice W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Comfortable, Clean and close to all Key West amenities, restaurants. We walked everywhere. Loved the state park access. Felt very safe. Hope to return
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

Devon W B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Iguanas, chickens and little lizards were friendlyand frogs
Stayed 7 nights in Nov 2025
Verified

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
Verified

10/10 Excellent

Randolph C.

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
Verified

10/10 Excellent

William F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was outstanding in all respects. It was completely as billed and even better than the pictures. The house was snuggly in the middle of the larger Truman Annex complex. The beds were very comfortable and the large screen TV was a nice family gathering spot. It was 2 blocks from the Green Parrot and 3 blocks from Duval Street so very walkable and convenient. Host was very prompt in addressing one need (laundry detergent) which was my bad as I just missed it.An overall great stay with my wife and grown children. 5 stars!
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

Rick B.

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
Verified

10/10 Excellent

Jeff S.

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
Verified

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
Verified

10/10 Excellent

Matthew A.

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
Verified

10/10 Excellent

Maureen N.

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
Verified

10/10 Excellent

Becky B.

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
Verified

10/10 Excellent

Rebecca E.

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
Verified

10/10 Excellent

Joseph H.

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

Late June stay

Was awesome! Clean, pool was close.
Stayed 7 nights in Jun 2024
Verified

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
Verified

8/10 Good

David P.

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
Verified

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
Verified

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
Verified

10/10 Excellent

Linda S.

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
Verified

10/10 Excellent

Dori N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay. Jean, the host, was incredibly accommodating when our family had a medical emergency. She was kind and understanding and worked with us to find a solution. Our stay was absolutely perfect. The park and splash pad were so convenient to our stay and our kids loved it. The location is perfect. The only few silly quirks we experienced were 1- the pool has a rule of no children that aren’t potty trained; 2- the toiletries provided were limited to bar soap and shampoo. 3- the checkout instructions include starting laundry but we couldn’t find any provided laundry detergent. We went out and bought some. Just good to know for future guests. We will absolutely be staying here again in the future.
Stayed 7 nights in Nov 2025
Verified

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
Verified

10/10 Excellent

Kelly M.

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

Key West week

This cute cottage had everything we needed. It was a great location - walkable to so many places we wanted to visit. We had one hiccup with technology that was quickly fixed. Any questions I had were answered promptly. Our only complaint would be the very firm bed pillows. Overall, a fantastic choice!
Stayed 7 nights in May 2025
Verified

10/10 Excellent

Jane R.

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
Verified

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