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OCEAN BREEZE at The Truman Annex in Key West

Top rated by guests

Outdoor dining

Private kitchen

Private kitchen

Private kitchen

Interior

8.6Excellent

(20 Ratings)

The property manager was very helpful, the vacation rentals were clean, and the locations were great. Overall, the reviewers highly recommend these vacation rentals.

From real guest reviews summarized by AI

Don't miss out! Price and availability may change

8.6 / 10.0

Excellent(20 Ratings)

Apartment in Key West, FL

2 guests · 2 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Top-tier experienceA high end property in this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this apartment rental

Gorgeous open water views from this 2-bedroom, 2.5 bath condominium in Harbour Place in the award-winning Truman Annex! | Directly facing the ocean, where the Gulf of Mexico and Atlantic Ocean meet, this nicely furnished condominium enjoys a large waterfront plaza with chaise lounges and front row seating for sunset. | There is a beautiful community pool, covered off street parking and convenient access to Mallory Square! | The Truman Annex is a gated community, in the heart of Old Town with a quick walk to Duval Street, shopping, dining and watersports!
“Beginning January 2026, all properties in the Truman Annex will require a minimum of a 28 night stay”

Amenities at OCEAN BREEZE at The Truman Annex in Key West

Family friendly

Map of Key West, FL

city location on map

Nearby attractions

The Key West Butterfly and Nature Conservatory

Southernmost Point of the Continental U.S.A.

The Hemingway Home and Museum

Things to know

Additional fees to expect

Cleaning & other feesWe include all stay related fees in the Cleaning Fee line, which may include cleaning, property manager, resort, tourism and other stay related fees. All Vrbo properties are professionally cleaned after each stay.

Booking feeNo booking fees, easy credit card payments.

Service feeThis helps Vrbo provide a safer and more secure booking experience.

TaxesTaxes on accommodation such as Occupancy Tax, VAT, or GST. May also include tourism fees.

Customer support

Customer support is handled by our partner Vrbo

$$$$

Top rated by guests

8.6Excellent

(20 Ratings)

The property manager was very helpful, the vacation rentals were clean, and the locations were great. Overall, the reviewers highly recommend these vacation rentals.

From real guest reviews summarized by AI

Don't miss out! Price and availability may change

$$$$

8.6 / 10.0

Excellent(20 Ratings)

Apartment in Key West, FL

2 guests · 2 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Top-tier experienceA high end property in this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

Map of Key West, FL

city location on map

Nearby attractions

The Key West Butterfly and Nature Conservatory

Southernmost Point of the Continental U.S.A.

The Hemingway Home and Museum

About this apartment rental

Gorgeous open water views from this 2-bedroom, 2.5 bath condominium in Harbour Place in the award-winning Truman Annex! | Directly facing the ocean, where the Gulf of Mexico and Atlantic Ocean meet, this nicely furnished condominium enjoys a large waterfront plaza with chaise lounges and front row seating for sunset. | There is a beautiful community pool, covered off street parking and convenient access to Mallory Square! | The Truman Annex is a gated community, in the heart of Old Town with a quick walk to Duval Street, shopping, dining and watersports!
“Beginning January 2026, all properties in the Truman Annex will require a minimum of a 28 night stay”

Amenities

Family friendly

Things to know

Additional fees to expect

Cleaning & other feesWe include all stay related fees in the Cleaning Fee line, which may include cleaning, property manager, resort, tourism and other stay related fees. All Vrbo properties are professionally cleaned after each stay.

Booking feeNo booking fees, easy credit card payments.

Service feeThis helps Vrbo provide a safer and more secure booking experience.

TaxesTaxes on accommodation such as Occupancy Tax, VAT, or GST. May also include tourism fees.

Customer support

Customer support is handled by our partner Vrbo

Ratings and reviews

8.6 / 10.0

Excellent(20 Ratings)

Summary of reviews

The property manager was very helpful, the vacation rentals were clean, and the locations were great. Overall, the reviewers highly recommend these vacation rentals.

From real guest reviews summarized by AI

10.0 / 10.0

Awesome patio to look over the the boardwalk. The condo was super clean and nicely appointed with everything we needed. Short walk to fabulous restaurants, a grocery store, musemums, and Duval Street. The neighborhood is super quiet at night. Covered place to park your vehicle. Very good secuity to get into the neighborhood and complex. The hosts went out of their way to make everything easy to understand. Highly recommend.

10.0 / 10.0

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: perfect location - great security - all amenities - quiet - good parking - perfect location - westerly water view - three-minute walk to Duval - perfect location

8.0 / 10.0

Rating Details: The property manager was very helpful. The vacation rental was clean. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Excellent

8.0 / 10.0

Ocean breeze stay

Ocean breeze stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our stay at Ocean Breeze was Great! The condo was clean and set up perfectly for our family of 5. The location was accessible to Duval Street and many restaurants and shops. The only negative thing about the condo was the bedroom with the king size bed did not have window coverings to block out the parking lot street lights at night.

10.0 / 10.0

Key West Experience

Key West Experience

Great property Close to town, restaurants and a gated community

10.0 / 10.0

Ocean breeze

Ocean breeze

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Very nice condo

8.0 / 10.0

OB Vaca

OB Vaca

Rating Details: The property manager was more than helpful. The vacation rental was clean. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Awesome

10.0 / 10.0

Trip to Key West in Ocean Breeze

Trip to Key West in Ocean Breeze

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The location of these units is perfect. They are quiet, close to the ocean and in a gated community. 2 blocks from Duval, a very short walk to a coffee shop, and even a semi close walk to the southern shore of the island. Being two blocks from Duval I figured we'd see more traffic but that is not the case, it's very private. Access to the pool is easy, although the heater was broken for the entirety of our trip and the water was very cold. The only negative I would say is that it is a big pain to get down to the park/boardwalk below the deck. To get to it you have to walk all the way around the fence, there is no way to get through from these units. Maybe a key for a gate would be nice?

Thanks for being part of the wonderful time in Key West.

10.0 / 10.0

My Happy Place

My Happy Place

Rating Details: The property manager was very helpful. The vacation rental was clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The Ocean Breeze at Truman Annex was a perfect place for our January trip to Key West. My parents stayed in this unit for the winters for many years and it was fun to come back to it. The unit has not been updated but it was clean (except for the rugs needed cleaned) and comfortable with a fantastic view. It is a perfect location to enjoy the fun of Mallory Square and Duval street and then return to the quiet of the annex.

10.0 / 10.0

Paradise!

Paradise!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Beautiful condo!! Great location! The view from the pool and the deck outside the condo is breathtaking. Realtor office was east to work with. The only problem we had was the night we got there. There has to be a better way!! Dropped off in the dark in a unfamiliar place. After going the wrong way a person who lives there came out and helped us find the office. Then in the dark we had to find the condo. Needs to be easier to find. Other than that the trip was amazing.

10.0 / 10.0

Lovely visit

Lovely visit

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a wonderful 7 day stay at Harbourside in Key West.

10.0 / 10.0

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The location of these units is perfect. They are quiet, close to the ocean and in a gated community. 2 blocks from Duval, a very short walk to a coffee shop, and even a semi close walk to the southern shore of the island. Being two blocks from Duval I figured we'd see more traffic but that is not the case, it's very private. Access to the pool is easy, although the heater was broken for the entirety of our trip and the water was very cold. The only negative I would say is that it is a big pain to get down to the park/boardwalk below the deck. To get to it you have to walk all the way around the fence, there is no way to get through from these units. Maybe a key for a gate would be nice?Thanks for being part of the wonderful time in Key West.

10.0 / 10.0

Great place to stay

Great place to stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Wonderful as usual

10.0 / 10.0

Great location, helpful staff, perfect homebase

Great location, helpful staff, perfect homebase

Traveled with family of 4+ mother-in-law, great pool, quick walk to most of the activities. It was a tight fit for five people but would be perfect for four. Nice balcony, very helpful to have towels and other beach gear and washer / dryer in the unit. Staff was very helpful, including coming to the condo at eight in the evening when I accidentally locked myself out.

8.0 / 10.0

Truman Annex

Truman Annex

Beautiful property in a great location. It was really easy to get to all of the great shops and restaurants. All were in a very short walking distance. I highly recommend this location and property. Oh.... and the sunset views were off the chart!

4.0 / 10.0

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We have stayed in Truman Annex for several years. We love the location. On Wednesday before we were to check in on Saturday, we received a call that the unit we had chosen would not be available for check in due to owner repairs not being finished. Michelle with Compass called and said they were moving us to this unit in the Harbor Breeze condos in Truman and this would be an upgrade due to it's size and oceanfront view. It is a great location and the view is beautiful. Condo was clean and well appointed but very outdated. It was not the location or the unit that we wanted & it was pretty much all we were offered at the last minute so that kind of put a damper on our week!

4.0 / 10.0

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was more than happy with the location. I was somewhat dissatisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: We recently stayed at this vacation rental and unfortunately, we were quite disappointed with our experience based on the price. The property is in dire need of renovation as the interior was outdated and in need of some TLC. The beds were extremely uncomfortable and made it difficult to get a good night's sleep.Additionally, the outdoor furniture was dry rotted and in poor condition, making it impossible to enjoy the beautiful outdoor space. It was clear that the property had not been maintained. With a little bit of investment, and attention to detail, this property could be a nice getaway.

6.0 / 10.0

Rating Details: The property manager was very helpful. The vacation rental was somewhat dirty. I was very happy with the location. I was very dissatisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: The layout of the unit is very good and the view is terrific, but it needs a lot of upkeep. Many of the window shades lack wands, the couches are a mess (dirty and springs/webbing are shot). throw rugs are filthy, towels, bedding and pillows are virtually thread bare, towel rack in bathroom was broken, kitchen lacks a real toaster and table ware is a cobbled together mess. In other words--unit is very good but insides are neglected and need a work.

10.0 / 10.0

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Watching an unobstructed view of the sunset, followed by a short walk to all things fun in Key West. Comfortable unit with security and conveniences.

8.0 / 10.0

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: The view was spectacular! The location was close to lots of things which was nice. The place itself was a bit tired.

10.0 / 10.0

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Facility was outstanding and the sunsets from the patio were magnificent! Highly recommend.

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