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Entire home

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

Vacation 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!

Fridge, microwave, oven, stovetop - ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool in Truman Annex! (Key West)
Fridge, microwave, oven, stovetop - ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool in Truman Annex! (Key West)
Outdoor dining - ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool in Truman Annex! (Key West)
Exterior - ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool in Truman Annex! (Key West)
Terrace/patio - ISLE AZURE ~ Charming 3 Bed/3 Bath with Private Pool in Truman Annex! (Key West)
Truman Annex neighborhood, this townhome retreat is set steps from the lively action on Duval St. Equipped with charm and modern amenity perks, this home awaits the creation of your tropical vacation. Enjoy an outdoor oasis with a private pool heated during cooler months and covered porch seating for 4 to enjoy a meal or crafted cocktail.

Reviews

9.4 out of 10
Exceptional

Entire home

3 bedrooms3 bathrooms1608 sq ft

Popular amenities

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

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.

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...

Property amenities

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Living room

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Concierge services
  • Iron/ironing board

Location highlights

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

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
  • Water skiing nearby
  • Windsurfing 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

  • Garden
  • Unit size: 1,608 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

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

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
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 there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
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
Property Registration Number 25230-127405

Property is also known as

Vrbo Property
2450-178688

About the neighborhood

Map
Key West, FL

What's nearby

  • Duval Street - 5 min walk - 0.3 miles
  • Mallory Square - 8 min walk - 0.5 miles
  • Ernest Hemingway Home and Museum - 9 min walk - 0.5 miles
  • Fort Zachary Taylor Historic State Park - 9 min walk - 0.5 miles
  • Southernmost Point - 17 min walk - 0.9 miles

Getting around

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

Restaurants

  • ‪Green Parrot Bar - ‬5 min walk
  • ‪Margaritaville - ‬8 min walk
  • ‪Willie T's - ‬7 min walk
  • ‪Blue Heaven - ‬9 min walk
  • ‪Santiago's Bodega - ‬7 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.

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!?

Check-out 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 vacation 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.

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

Reviews

9.4

Exceptional

Rating 10 - Excellent. 63 out of 84 reviews
Rating 8 - Good. 16 out of 84 reviews
Rating 6 - Okay. 2 out of 84 reviews
Rating 4 - Poor. 2 out of 84 reviews
Rating 2 - Terrible. 1 out of 84 reviews

9.8/10

Cleanliness

Reviews

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

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
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

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

Mel M.

Great place and perfect 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: The house was very clean. The beds were comfortable. Any questions were handled quickly. We would stay in this home again.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Terry C.

Isle Azure

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 a beautiful rental home. It is equipped with everything to make your stay comfortable. We especially liked it’s location in Truman Annex which is in walking distance to practically everything you would want to do in Key West. Looking forward to visiting again.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

OMG Best Birthday Ever

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 was awesome. Centrally located and a great place to come home to after a hot day. Pool was perfect! It was nice to each have our own bedroom/bathroom. I traveled with 2 ladies to celebrate my big 50 for a week!
Stayed 7 nights in Jun 2020
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Donald W.

Return to Key West

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: Retuned to "ISLE AZURE" for the 2nd time.Love the location & house. Property is well maintained & any issue we had was addressedby the manager. House is an easy walk to down-town. Would recommend this property to family & friends with no problem at all .

8/10 Good

Robert E., Altoona, USA

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

Great place to stay

The property was very nice and a great location to walk to nearly everything. There was also a parking space off the street with was great because we had a car. Improvements need to be made on the pool to make it look clean. I think it was but looked dirty. Also you couldn’t heat the hot tub unless you shut off the house AC. It blew the breaker if both ran. This was a disappointment to our group. We had to have the AC on so we didn’t get to use the hot tub but once. Overall it was a good experience.
Stayed 7 nights in Feb 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kaleija I.

5 Star Rental, highly Recommend!

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: What you see is what you get with this rental. It is a beautiful property located in the nicest neighborhood in Key West, so you can expect to have a comfortable stay and to be close to everything Key West has to offer. The house is a short 10-minute walk away from the water, fort Zachary/ beach, and Duval St.The house had more items available for use than any other rental I have stayed in previously. This included a fully stocked kitchen, board games, beach chairs, toiletries, and much more. The house was clean, the backyard was an oasis, and there was designated on-site parking which was huge in this area.Melanie, the property manager, made sure we had all the information we needed before arriving so check-in was smooth. She was incredibly responsive and she made herself available 24/7 to answer questions if anything came up during the stay. When we return to Key West there is no doubt that this property will be number 1 on our list of places to stay if it is available.
Stayed 7 nights in Nov 2023

10/10 Excellent

Kristina K.

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

Everything we could ask for

This place had everything we needed and more! The space was comfortable and clean. Kitchen was fully equipped and appliances were brand new. Plenty of toilet paper. Beds were cozy. Our only concern was the upstairs outdoor balcony - the railing/banister was very wobbly and we let management know in hopes it will be fixed for safety reasons, but that didn’t impact our stay. This place had plenty of room for 4 adults and 2 kids. The best part was the pool/hot tub. We got a lot of use out of those, especially the kids. Some had mentioned the debris in the pool due to the foliage around it but that was to be expected and an easy fix just using the provided pool net until the pool guy came on Thursday (and he was super nice). We also had an iguana stop at the pool twice which was exciting to watch. The location was quite most of the time and perfect walking distance from all the fun of Key West. We walked to Mallory Square most mornings for coffee at Cuban Queen and it was a perfect stroll for starting the day. We easily walked to Faustos for groceries and CVS as needed. For evening activities, Duvall is only 2 blocks away - just keep in mind the community gate closest to the house locks at 6pm and you have to walk a little farther to the other gate and around to get back. Overall this was a stay to remember.
Stayed 7 nights in Dec 2022
This review comes from a trusted partner site and has not been verified.

2/10 Terrible

Bridget B.

Isle Azure Vacation

Rating Details: The property manager was somewhat unhelpful. The vacation rental was somewhat dirty. I was 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: Overall, we had a nice time in Key West. However, our rental was very disappointing - especially for the price we paid for it. I carefully read the reviews on this property and noticed that the pool wasn't working properly. However, I also saw that the issue was fixed. I was mistaken. The heater for both the spa and pool worked for literally 12 hours of our rental and that was it. Several repair people came to look at it but issue was not resolved. I only rented this place because of the pool & spa. I had 3 teens with me who never used the pool during our stay due to it being extremely cold and shaded. Extremely disappointed with how the mgt company never resolved the issue nor did they offer any compensation for our inconvenience.
Stayed 7 nights in Mar 2021
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!

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

8/10 Good

Alice N.

Liked: Cleanliness, check-in, location
Disliked: Communication, listing accuracy

Great location!

Great location as quiet and near Duval street and the action of Key West. It’s not a full house as it appears on site, it’s a duplex. The neighbors were smoking cigars a lot and we couldn’t be outside by the pool much. For the price I was expecting more. They didn’t have any way to make tea and there was limited kitchen supplies. They don’t leave any items from previous guest so when you food shop, you have to buy everything you need. When I contacted the management about the missing items I was told to use the microwave to make tea and to use a knife to peel potatoes!!! I wasn’t asking for any out of the ordinary items. It’s a great place if you’re interested in having an ice maker but forget about making hot tea. The rooms are small but nice. It’s a great location but you do not get a full house. And if you have more then one car, you have to pay for parking and move the car often.
Stayed 8 nights in Dec 2024
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.

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
This review comes from a trusted partner site and has not been verified.

4/10 Poor

Joe G.

A Series of Unfortunate Events at the Isle Azure

Rating Details: The property manager was adequately helpful. The vacation rental was very 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: Unfortunately outside of the location, we were not satisfied with this property. We stayed at a different property in Truman Annex in April 2024 and had a lovely experience. We were excited to hear our room was ready at 11:00 am rather than 4:00 PM however would have preferred the place was cleaned. We experienced numerous cockroaches, hair in all of the showers, bed covers yellow stained with a crusty sand like material, leftover tape on cabinets which makes us infer place was not cleaned, clogged drains in the shower cause water pooling and hair back up from shower, the hot tub was not functional & the third set of keys did not have a key to the Truman Annex gate. Guests in the yellow room experienced bites which we do not believe to be bed bugs but maybe cockroaches?The pools had iguana feces however I will say the pool man did an excellent job.
Stayed 7 nights in Nov 2024
This review comes from a trusted partner site and has not been verified.

8/10 Good

Carmen M.

Key West Vacation

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: Isle Azure is a very spacious townhouse. The kitchen, eating area, and living area are all one large room together which we enjoyed for eating and playing games. There was a side bar with a mini fridge and an ice maker. Bedrooms were large with lots of windows, seating area and plenty of storage for clothes. The location is the best with many things in walking distance from the house. Melanie the property manager was wonderful and helped us with anything we needed. The pool and hottub are right out the living area and are heated. Very nice sitting area by the pool with plenty of chairs and a table. The house came with many amenities- the pool is maintained weekly, someone came by and put out the trash and recyclables, etc. Overall we enjoyed staying in this townhouse.Cons:The a/c went out twice. Melanie was quick to get the unit fixed on the days it went out. The hottub did not work while we were there so Melanie refunded our money for this. The house needs some TLC on the inside- some of the blinds/shades do not work, one blind in the bathroom was too short for the window, and some drawers are missing knobs.
Stayed 15 nights in Sep 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Samantha S.

Relax

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! Quiet and clean space. Close to everything. Great place to relax and reset!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Samantha S.

Relax

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! Quiet and clean space. Close to everything. Great place to relax and reset!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Thomas M.

Perfect family 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: Nice quite location, feel very safe as it's in a gated community, with8n walking distance of many attractions.
Stayed 7 nights in Jul 2024

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
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.