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ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool in Truman Annex!

Holiday home with private pool, 8-minute walk to Duval Street

Photo gallery for ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool in Truman Annex!

Private outdoor oasis
Lush tropical views all around
Beautiful Truman Annex community
Front porch lounging
Hardwood flooring all around

Reviews

9.4 out of 10
Exceptional
3 bedrooms3 bathroomsSleeps 61608 sq ft

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Kitchen
  • Barbecue grill

Explore the area

View in a map
Key West, FL
  • Place, Harry S. Truman Little White House
    ‪3 min walk‬
  • Place, Duval Street
    ‪5 min walk‬
  • Place, Mallory Square
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪9 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Queen Bed

3 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Garden
Dining area

About this property

ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool in Truman Annex!

PLEASE BE AWARE...
We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nights if your arrival is 12/22 or before.

QUINTESSENTIAL OLD TOWN CHARM…
Imagine pulling up to a picture-perfect gated community, lined by white picket fences and swaying palm trees in the breeze. Set within the attractive Truman Annex neighborhood, this townhome retreat is conveniently located steps from the lively action on Duval St. Equipped with the perfect combination of charm and modern amenity perks, this home awaits the creation of your tropical vacation!
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE

DETAILS AND AMENITIES…
Step inside to find your updated island escape featuring an open floor plan with wood flooring, ceiling fans and cheery tropical views of your outdoor oasis. A fully equipped kitchen with top of the line appliances, granite counters, custom cabinetry and a full wet bar create an enjoyable space for meal preparation. Seating for 4 can be found at the banquet dining table which neighbors the cozy living area full of plentiful seating and a flat screen TV for movie nights.

SLEEPING ARRANGEMENTS…
Enjoy convenience on the first floor guestroom featuring a queen bed and en suite full bathroom with a shower that can also be entered by the hallway. The upstairs master king suite boasts tall cathedral ceilings and features an en suite full bathroom with a shower. Open the French doors to the balcony with seating for 2 as you marvel over the lush and vibrant community beyond. Across the hall lies the 3rd guestroom equipped with a king bed, en suite bathroom with a shower and a writing table for mapping out your island adventures. All rooms come with ceiling fans, storage space and flat screen TVs.

OUTDOOR LIVING…
Bring the indoor/outdoor space together by perching open the French doors from the living area to fully appreciate island life. A private pool that comes heated during the cooler months is surrounded by colorful foliage all around. A covered porch seats 4 at the dining table to enjoy a well-deserved crafted cocktail and your fresh catch of day grilled out on the BBQ grill. Soak up the breeze in the comfortable loungers and let your worries wash away. This home is just a short distance to Fort Zachary State Park, The Truman Little White House and all the other iconic Key West museums and attractions.

PARKING...
A covered carport for one car adds to the convenience for those venturing past the downtown area. No vehicle length over 18’ long, including trailer hitches, or 80” wide is allowed on property.

PETS...
This is not a pet friendly home.

MULTI MONTH RESERVATIONS...
For monthly reservations, the following fees will be added PER MONTH:
Mid-stay clean
Pool Heat
Pet fee (if applicable)

BOOKING DATES...
This home is only available as a monthly rental (28 night minimum) as of Dec 23, 2025. We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.

CONCIERGE SERVICES...
Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!

CANCELLATION...
Bookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.

PARADISE AWAITS...

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
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
Property Registration Number 25230-127405
Property # 9382082

About the area

Key West

Located by the sea, this holiday home 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 Smathers 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 ecotours and cycling nearby.
Map
Key West, FL

What's nearby

  • Harry S. Truman Little White House - 3 min walk - 0.3 km
  • Duval Street - 5 min walk - 0.4 km
  • Mallory Square - 8 min walk - 0.7 km
  • Ernest Hemingway Home and Museum - 9 min walk - 0.8 km
  • Fort Zachary Taylor Historic State Park - 9 min walk - 0.8 km

Getting around

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

Restaurants

  • ‪Margaritaville - ‬8 min walk
  • ‪Green Parrot Bar - ‬5 min walk
  • ‪Willie T's - ‬7 min walk
  • ‪Blue Heaven - ‬9 min walk
  • ‪Jack Flats - ‬8 min walk

Frequently asked questions

Is ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool in Truman Annex! pet-friendly?

No, pets are not allowed at this property.

How much is parking at ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool in Truman Annex!?

On-site parking is available at the property.

What time is check-in at ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool in Truman Annex!?

Check-in begins at 4:00 PM.

What time is check-out at ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool in Truman Annex!?

Checkout is at 10:00 AM.

Where is ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool in Truman Annex! located?

Located in Old Town Key West, this holiday home is within a 10-minute walk of We Cycle Key West, Duval Street and Fort Zachary Taylor Historic State Park. Ernest Hemingway Home and Museum and Mallory Square are also within 15 minutes.

Reviews

9.4

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. 65 out of 86 reviews
Rating 8 - Good. 16 out of 86 reviews
Rating 6 - Okay. 2 out of 86 reviews
Rating 4 - Poor. 2 out of 86 reviews
Rating 2 - Terrible. 1 out of 86 reviews

9.8/10

Cleanliness

9.8/10

Check-in

9.6/10

Communication

10/10

Location

9.4/10

Listing accuracy

Reviews

10/10 Excellent

Heather S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This place was so great and amazing! Perfect! Besides the pool, best part was the beverage fridge and tje giant ice maker. 1st time we didn't have to buy ice! 10 out of 10.
Stayed 8 nights in Oct 2025

10/10 Excellent

Roger O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was very comfortable. It was so nice having bathrooms in every bedroom. Kitchen provided many amenities I.e. microwave, dishwasher, ice maker. Washer and dryer came in handy, making it so you didn’t need as many clothing. Close to Duval making it easier to get to establishments. Host responded quickly when contacted, providing feedback.
Stayed 7 nights in Oct 2025

10/10 Excellent

Judy C.

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

Great location and very comfortable

Very nice property, easy living. Great location, comfortable.
Stayed 7 nights in Apr 2025

10/10 Excellent

Inez C.

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

Key West Trip

Our stay was perfect from start to finish ! It fit our needs exactly . We would definitely stay at this property again !
Stayed 7 nights in Apr 2025
This review comes from a trusted partner site and has not been verified.

8/10 Good

Jean C.

Great spot for a week in Key West

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: Loved the location - a nice quiet neighborhood. The house was very comfortable for two adult couples. Having a little pool to cool off in was great!
This review comes from a trusted partner site and has not been verified.

8/10 Good

Allison B.

Great Location & Private Paradise!

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 home was just perfect for the four of us! Beautifully decorated and very comfortable and clean! The only glitch we experienced on our very first night was the parking of our rental car and rental golf cart under the carport. We received a violation the next morning for having both in the carport but our property manager, Dan, immediately helped us with a solution. If we had known how strict the HOA was, we would’ve followed the rules, had we known this ahead of time. Next time, no golf cart rental needed!

8/10 Good

Roselle E.

Liked: Cleanliness, check-in, communication, listing accuracy
Property was very nice overall. Had trouble with allergies due to feather pillows on the couch cushions (?). Otherwise, nice. Although we were unable to use the pool several times due to nearby smell of marijuana.
Stayed 7 nights in Jul 2025

10/10 Excellent

Pamela S.

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

Secret gem!!!!

Awesome place. House was stocked with everything you could think of. Location was great, able to walk everywhere. Strongly recommend staying here.
Stayed 7 nights in Dec 2024

10/10 Excellent

Lora C.

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

Perfect place to stay with your family

This place is in the best location in Key West. Walking distance to everything.
Stayed 7 nights in Aug 2022

10/10 Excellent

Vittorio P.

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

Spacious , updated and conveniet location!

Spacious , clean , and very accommodating necessities . Proximity to all the island has to offer made our vacation a 100% success and enjoyable! Will be back for sure!!
Stayed 7 nights in Jul 2024

10/10 Excellent

Mary W.

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

Key West with Friends

We had an incredible experience. Location, amenities and service were impeccable. We would highly recommend staying here on your visit to Key West.
Stayed 7 nights in Jun 2021

10/10 Excellent

Julie L.

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

Summer paradise

The place is beautiful, inside and out. I read out by the pool, it was the most relaxing vacation I think I’ve ever had. A lot of walking around Key West, I just love it!
Stayed 7 nights in Mar 2024

10/10 Excellent

Michael G.

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

Loved it!

The townhouse had everything we needed and more. One of the best we’ve ever stayed in. Beds were comfy and plenty of space in living room and kitchen. Pool was great too! Can’t beat the location in Truman Annex. Already booked it again for next year!
Stayed 7 nights in Apr 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Eric K.

Great time!

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: Great location, great house!
Stayed 7 nights in Nov 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kimberly T.

Key West Family Holiday

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 family arrived from 3 different states and had a wonderful time. The neighborhood is just lovely. And very convenient to everything. We especially enjoyed the day trip to Cuba through the concierge. The only drawback was the hot tube was still not fixed in december from the summer.

8/10 Good

Andy, Chicago

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

Location location location

Awesome location! Close to everything. Great house and amenities. Pool area was not clean, probably due to all the close vegetation, and the spa didn’t work, but otherwise great.
Stayed 7 nights in Oct 2022

10/10 Excellent

Bette C.

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

Happy family getaway

All great! Had a great week in the beautiful house with 2 adult children snd their spouses. Perfect space for 3 couples. Property manager was attentive and very quickly responsive. Great quiet location in town.
Stayed 7 nights in Jan 2021

10/10 Excellent

natalie E.

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

Great place

Great location to Duval st. Easy to walk to shops and restaurants. This place is very clean and spacious, the rooms are a great size also has a small personal pool and spa which is nice. I would definitely recommend this place and I would book again. Easy communication with check in and out. The building manager is around with any issues as well.
Stayed 7 nights in Jul 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Michael G.

Family Vacation Spot

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 house was perfect for our family of 6. The pool, spa and pool area was a great place for the kids and adults. It’s our second time at Isle Azure and won’t be our last.

10/10 Excellent

Jane K.

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

Great house in Truman Annex

Comfortable, spacious, clean, and well appointed house in the annex near Fort Zachary and Duval Street. It is perfect for a family of four but could accommodate more. No complaints at all. Hope to return.
Stayed 8 nights in Dec 2020
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

John F.

Perfect 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: Perfect unit for our family of six, Truman Annex is not only a lovely location but perfectly situated for access to all activities!
Stayed 7 nights in Jul 2020

10/10 Excellent

Angelia N.

Liked: Cleanliness, check-in, communication, location

Girls week

Clean Beautiful Perfect
Stayed 7 nights in Aug 2022
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Julia M.

Beautiful & relaxing

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 was a very clean, well stocked, great location, and a very central location to everything. The property manager was very helpful with all request. I would definitely stay here again.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Truly Wonderful

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 house was exactly as described, clean and inviting. Truman Annex is always a wonderful area to stay.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Stefanie T.

Fantastic Rental

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: Isle Azure is an amazing rental. Perfect house, great location, and the pool is a such a bonus. I can’t recommend it enough.

About the host

Hosted by Wendy Zintsmaster & Team

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Languages:

English

Premier Host

They consistently provide great experiences for their guests