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DOLPHIN WATCH at the Truman Annex in Key West

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A covered outdoor seating area with two Adirondack chairs and a small table, overlooking a golf course and palm trees. - DOLPHIN WATCH at the Truman Annex in Key West (Key West)
A pool with a white fence, palm trees, and a view of the beach. - DOLPHIN WATCH at the Truman Annex in Key West (Key West)
A spacious kitchen with a large island, a dining area, and a view of the outdoors. - DOLPHIN WATCH at the Truman Annex in Key West (Key West)
A two-story house with a swimming pool, white railings, and a flag. - DOLPHIN WATCH at the Truman Annex in Key West (Key West)
A spacious living area with a large sofa, a dining table, and a kitchen with wooden cabinets and a central island. - DOLPHIN WATCH at the Truman Annex in Key West (Key West)
A short walk from Duval Street and Mallory Square, DOLPHIN WATCH at the Truman Annex in Key West provides a water park, laundry facilities, and more. Stay connected with free in-room WiFi.

Reviews

9.4 out of 10
Exceptional

Popular amenities

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

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About this property

DOLPHIN WATCH at the Truman Annex in Key West

  • VERY LUXURIOUS water front home located in the heart of downtown Key West within walking distance to all downtown attractions and the famous Fort Zachary Taylor Beach. This home has 2 master ensuites with king beds, and there is a total of 4 bedrooms and 3 baths. The second level offers open living and kitchen area, master bedroom with ensuite bath and a great view of the ocean. From the second floor you can enjoy the fantastic view of the harbor and sunsets from the balcony that also has a spiral staircase that leads to the private pool area. Downstairs you have the 2nd king master bedroom with ensuite bath that leads directly to the pool and 2 additional guest bedrooms and full bath. The first guest room has a queen bed and the second guest room has two twin beds that can be converted into a king. Don't miss out on this home as it is one of the few Private Homes in Key West that has a view of the water and located in the Prime Location area here at the Truman Annex Community!

    Please note: This property has a 28 night minimum stay

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About the neighborhood

Located near the beach, this vacation home is in Old Town Key West, a neighborhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. 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. Visit our Key West travel guide
View more Vacation Homes in Key West
Map
FL, Key West

What's nearby

  • A military jet flying low over a concrete path surrounded by vegetation.
    Key West Naval Station
    2 min walk - 0.2 km
  • A historical marker for The Little White House, built in 1890, used by American Navy officers, and listed on the National Register of Historic Places in 1974.
    Harry S. Truman Little White House
    3 min walk - 0.3 km
  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    6 min walk - 0.6 km
  • A sign reading "Welcome to Mallory Square" with an American flag, a red and white striped awning, and a statue of a man in a blue shirt and straw hat.
    Mallory Square
    8 min walk - 0.7 km
  • A coastal fortification with a staircase leading to a higher platform, overlooking the sea.
    Fort Zachary Taylor Historic State Park
    11 min walk - 0.9 km

Getting around

  • Key West Intl. Airport (EYW)
    14 min drive

Restaurants

  • Margaritaville
    7 min walk
  • Green Parrot Bar
    7 min walk
  • Key Lime Pie Factory
    6 min walk
  • Wendy's
    5 min walk
  • The Bull & Whistle Bar
    6 min walk

Frequently asked questions

Does DOLPHIN WATCH at the Truman Annex in Key West have a pool?

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

Is DOLPHIN WATCH at the Truman Annex in Key West 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 DOLPHIN WATCH at the Truman Annex in Key West?

Check-in begins at 4:00 PM.

What time is check-out at DOLPHIN WATCH at the Truman Annex in Key West?

Check-out is at 10:00 AM.

Where is DOLPHIN WATCH at the Truman Annex in Key West located?

Located in Old Town Key West, this vacation home is within a 10-minute walk of Truman Waterfront Park, Duval Street, and Mallory Square. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 15 minutes.

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Reviews

DOLPHIN WATCH at the Truman Annex in Key West Reviews

9.4

Exceptional

10

Cleanliness

10

Location
Rating 10 - Excellent. 20 out of 27 reviews
Rating 8 - Good. 6 out of 27 reviews
Rating 6 - Okay. 0 out of 27 reviews
Rating 4 - Poor. 0 out of 27 reviews
Rating 2 - Terrible. 1 out of 27 reviews

Reviews

Verified review

10/10 Excellent

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

Dolphin Watch

Clean, lots of room, walking distance to everything. Pool was great. Would stay again. Highly recommend
Stayed 7 nights in Nov 2024
From a partner site

10/10 Excellent

Fabulous View and Location

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 view and great location! This is a very clean house with exceptional views of the water! Fabulous location so having a car or golf cart is not necessary. The property manager was very easy to work with and responded promptly. We definitely look forward to staying here next time!!!!
From a partner site

10/10 Excellent

Beautiful View

Rating Details: The property manager was very helpful. The vacation rental was very 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: This property has a beautiful view from the upstairs porch. Perfect for sunrise or sunset watching..Location perfect. Close to everything, yet quiet and private. Sleeps 8 comfortably.. I’d stay here again.
Verified review

10/10 Excellent

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

Out Stay at Dolphin Watch

Perfect Location. It is in a quiet Private Neighborhood just a few blocks from Duval.
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

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

What a view

I absolutely loved this place, it’s a 5 minute walk to almost anything u want to do yet nice and quiet. Pool was great, there was enough amenities in the house to make it feel like a home. If u need a great place to stay, stay here u won’t regret it.
The view off the porch
Sunset off the cruise ship pier
Stayed 7 nights in Jun 2025
Verified review

10/10 Excellent

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

Key West Paradise

Location Location Location! You won’t need a car or golf cart! You are in the middle of all the day and night time action!
Stayed 7 nights in May 2023
From a partner site

10/10 Excellent

Best Rental in Key West

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: This is the 2nd time renting this house and it is the best! Best views, best location, best amenities, best everything!
Verified review

8/10 Good

Liked: Cleanliness, check-in, location, listing accuracy
Great location and comfortable space. Communication w management wasn't bad except with checkout time. There were some glitches with the time allotted but it all worked out in the end.
Stayed 10 nights in Aug 2025
From a partner site

10/10 Excellent

Our fall getaway

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 have rented annually for 3 years and love this property. We would request extra kitchen towels (more than one please!!) and garbage bags. See you next year!
From a partner site

10/10 Excellent

a wonderful place

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: overall no problems and very nice--all provided for and wonderful sunsets on deck
From a partner site

10/10 Excellent

A wonderful vacation

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: We had four couples stay in this beautiful home - everything was great. Could use more towels and beach towels, but we managed! Beautiful views, pool was wonderful, plenty of chairs outside and a great location! We will be back next year!
From a partner site

10/10 Excellent

Dolphin Hideaway

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: It was great. Accommodation was beautiful and in a great location. Plenty to do in Key West to stay busy.
From a partner site

10/10 Excellent

Peaceful sunsets

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 booking process was easy. We needed a property that would accommodate 3 couples. The space and layout worked well. The property was clean and as described. The sunsets from the porch were delightful.
From a partner site

8/10 Good

Recommend Dolphin Watch

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: The house was perfect for our group of 6. Would stay here again. Only issues were that the pool is smaller than appears in pictures, but still was well maintained. Only other issue was that the house next door was going through a full renovation, with lots of hammering and music. I'm sure if you stay in the future this will not be an issue. Highly recommend. Outside chairs could use a pressure washing. But that's still pool side.
From a partner site

2/10 Terrible

Very noisy! Next door to major renovation. Saws start at 8AM.

Rating Details: The property manager was more than helpful. The vacation rental was very clean. I was more than happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: Hoping for a quiet escape but didn’t get told by Compass that the house next door is going thru a 1/2 year renovation! They totally tore off the 2nd floor deck and back siding during our visit. Loud noise all day. Can’t use back deck or pool bec of noise & Mexican radio. Don’t stay here! No construction discount either.
From a partner site

10/10 Excellent

Wonderful Family Vacation

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: This property was ideal for our 3 generation family getaway. Truman Annex is conveniently located for sightseeing, dining, and other activities. The Dolphin Watch property was very comfortably furnished with everything we wanted and needed. We especially enjoyed the pool area.Compass Realty is very easy to interact with, from reservation to check out.We'd definitely like to stay here again!
From a partner site

10/10 Excellent

Beautiful home and location

Rating Details: The property manager was adequately 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: The location/view can't be beat! Easy walking distance to Mallory Square and Duval Street (you can also watch the sunset from your balcony), lovely decor, very clean. Love the plunge pool! Great place for our extended family. The home only has one parking spot. Since it sleeps 8, we had two cars. It would have been nice if free and paid parking options for a second car were provided so we didn't have to figure that out on our own. (Yes, there are free street parking options!)Suggestions for improvement include a better-equipped kitchen. The basics were there, but for the price and the number of people the house sleeps, we expected things like a large frying pan, storage containers for leftovers, serving dishes, an ice cream scoop, and other things most guests are used to at home. Another suggestion is shelving in the twin bedroom closet, as there is not room for a dresser in the room. Can't say much about the managers because we had no real contact from them. We checked in on a weekend, picking up the key from a lockbox because the office is only open M-F. (Surprised there isn't an electronic lock for security, and so guests don't have to pick up/drop off the key.) A hurricane/tropical storm was forecast, the house faces the water, but no one reached out to ask if we had concerns/needed guidance. The wifi went out on a weekday, but no one answered the phone or called us back (the wifi came back on a few hours later, so was probably a cable company issue). That said, overall it's a great place! Would stay here again.
Verified review

10/10 Excellent

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

Excellent Location

Our entire party enjoyed staying at this property. The house is nice and the location is close enough to Duval to walk, but still very quiet and peaceful. Great view of the water to watch boats come and go. We had 5 people and everyone was comfortable both inside and out. The downstairs master bed still had the stripped sheets from the previous renters laying on it when we arrived, but if having to make a bed upon arrival is the worst thing that happens on vacation, then you’re doing good. We would stay here again for sure.
Stayed 11 nights in Oct 2021
Verified review

10/10 Excellent

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

Perfect Location

The house was great. Very comfortable and spacious. Walking distance from many great places and restaurants. We barely used the card. Love hearing the Star Spangled Banner in the mornings. The view from the terrace was just perfect.
Stayed 7 nights in Aug 2021
Verified review

10/10 Excellent

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

Wonderful Stay in KW

This was our 3rd time staying at this property in Key West and it was, again, an excellent stay! The location can’t be beat...within walking distance to everything, clean and secure within the Truman Annex, and the home itself is wonderful! Great pool, amazing views and plenty of space for everyone. Working with Compass was a very smooth process as well and they were always prompt when I had questions. We would highly recommend this property to any group traveling to Key West. Can’t wait to return for trip #4!
Stayed 7 nights in May 2021
Verified review

10/10 Excellent

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

Beautiful house perfect for 7 adults

We absolutely loved our stay at Dolphin Watch. We were 7 adults and it was the perfect size. The view from the balcony is beautiful. The pool was wonderful and we used it every day. Its the perfect location; close to everything. We rented bicycles and either rode them or walked. We did have some confusion with getting the gate keys but got that resolved the 2nd day. Would highly recommend this property however, we noticed the price has gone up considerably since our booking.
Stayed 7 nights in Oct 2020
Verified review

10/10 Excellent

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

Perfect location with lots of space

We stayed 11 days at Dolphin Watch. The property was perfect for our two families, the house came with everything you might need during your stay. We will definitely be back.
Verified review

8/10 Good

Liked: Cleanliness, location

wonderful

House was comfortable, beautiful view, well designed and decorated. Convenient location for walking to town and biking the park. Beds are super comfortable. Gave 4 star instead of 5 because some supplies were minimal or not there. Example, only 2 wine glasses in the house. No paper or pen. No laundry basket. Inconvenient to carry loads of laundry up and down the stairs.
Stayed 7 nights in Jun 2019
Verified review

10/10 Excellent

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

Dolphin Watch Stay June 2010

First time using VRBO. Was very impressed and pleased with the the process. Completely satisfied with the property and had a great vacation. Photographs of the property were exactly what the property was and then some. Lots of storage space, plenty of extra bedding available in the closets, washer and dryer worked very well (although both could have been larger) and kitchen appliances were very good. The only item we could have used were some pool instructions and we would have gladly cleaned the pool since we used it every day. We did find it difficult to get into the facility and finding the entrance after picking up the keys (but then again we had 6 people giving instructions on how to get to the property). Would not hesitate on using this facility again.
Stayed 7 nights in Jun 2019
Verified review

8/10 Good

Perfect location, beautiful home.

This home is beautiful on the inside and has a beautiful view. A couple of issues: Foundational problems that caused large cracks (actually had to tell my daughter not to step on them and enter her bed from the other side) in the tile in two of the downstairs bedrooms. Master bedroom has open windows on the stairway so there is no privacy from a noise perspective even when everything is closed. Pool needs to be resurfaced as my friend scraped herself up pretty badly. Despite all of my complaints, it's a very beautiful and comfortable home. Big thumbs up on the oversupply of cushy beach towels as well. I would definitely stay here again.