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DOLPHIN WATCH at the Truman Annex in Key West

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Outdoor dining - DOLPHIN WATCH at the Truman Annex in Key West (Key West)
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A heated pool - DOLPHIN WATCH at the Truman Annex in Key West (Key West)
In the heart of downtown Key West, this luxurious waterfront home offers a tranquil retreat with private pool and fantastic ocean views from its balcony. With 4 bedrooms, including 2 king master ensuites and a spacious open living area, it's perfect for relaxation or entertaining.

Reviews

9.4 out of 10
Exceptional

Entire home

4 bedrooms3 bathroomsSleeps 81840 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

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About this property

Entire place

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

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

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre
  • Near the ocean
  • 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
  • Snorkelling nearby
  • Swimming nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Unit size: 1,840 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in and check-out are available

Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

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

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
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 deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

About the area

Located on the waterfront, this holiday home is in Old Town Key West, a neighbourhood 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. 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. Visit our Key West travel guide
View more Holiday homes in Key West
Map
Key West, FL

What's nearby

  • Harry S. Truman Little White House
    Harry S. Truman Little White House
    3 min walk - 0.2 miles
  • Duval Street
    Duval Street
    6 min walk - 0.4 miles
  • Mallory Square
    Mallory Square
    9 min walk - 0.5 miles
  • Fort Zachary Taylor Historic State Park
    Fort Zachary Taylor Historic State Park
    11 min walk - 0.6 miles
  • Florida Keys National Marine Sanctuary
    8 min walk - 0.4 miles

Getting around

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

Restaurants

  • Green Parrot Bar
    7 min walk
  • Margaritaville
    7 min walk
  • Key Lime Pie Factory
    6 min walk
  • The Bull & Whistle Bar
    6 min walk
  • La Concha Bar
    5 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 at DOLPHIN WATCH at the Truman Annex in Key West?

On-site 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?

Checkout is at 10:00 AM.

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

Located in Old Town Key West, this holiday 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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DOLPHIN WATCH at the Truman Annex in Key West Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers 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.
More informationOpens in a new window
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

10

Cleanliness

10

Location

Reviews

Verified

10/10 Excellent

Ann N.

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

Patti J.

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

A guest from Horseheads, NY

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

10/10 Excellent

Todd K.

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

10/10 Excellent

Richard W.

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

8/10 Good

Jose P.

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
Verified

10/10 Excellent

Drew D.

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

Dawn C.

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

8/10 Good

Michael B.

Amazing view, perfect location!

Rented the house for 4th of July week. Had some other couples join my wife and I. The view of water and cruise ships was fantastic. Truman Annex is a unique spot just blocks from all the action on Duval Street. Convenient parking place for unloading bags/groceries. The upstairs master bedroom is great, along with living room/dining area on 2nd floor. There is a new park being finished adjacent to the annex. Looks awesome. The only issues we had with the property; a TV from the 90's in the living room needs to be updated. Ice maker in the fridge didn't work. The guest bathroom downstairs is dated. Weeds (including poison ivy) next to the pool deck need attending. The pool itself could use some work as well. We're looking to be back next year. Just may rent an HD TV if need be. I understand that some owners won't put money into their place as long as it stays booked, which is a shame because this place could be perfect!
Stayed 7 nights in Jul 2018
From a partner site

10/10 Excellent

Vicki M.

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

Fred S.

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

Vicki M.

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

Suzanne D.

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

10/10 Excellent

Amy A.

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

8/10 Good

Robert R.

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

Ed C.

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

Karen S.

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

Jeff L.

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

10/10 Excellent

Willow F.

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

10/10 Excellent

Pat B.

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

10/10 Excellent

Sue S.

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

10/10 Excellent

tammi d.

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

10/10 Excellent

Katie G.

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

8/10 Good

Karen V.

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

10/10 Excellent

SANDRA T.

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