Ann Street Cottage: Vacation Rental Property in Key West FL

Ann Street Cottage: Vacation Rental Property in Key West FL

Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage, a charming one bedroom cottage.


Vacation Cottage in Key West Florida

Ann Street
Bedrooms: 1 Bedroom • Sleeps 2
Bed Arrangements: 1 King
Bathrooms: 1 Full, 1 Half Bathrooms
Location Setting: Waterfront - Nearby
Beach Access: Near a Beach
Air Conditioning: Yes
Pool: Pool (Community)
Internet: Internet Access
Television: Cable/Dish TV
Map of Key West

Rates & Availability  
(Displayed in USD)

  • Daily Rates from $270 to $422 per night

Availability details can be found on the Rent Key West Vacations - Key West Florida Accommodations, Property Management, and Real Estate Listings! website.

Book Direct through the website for maximum savings!

Availability Details

Additional Rate Information

From: $190/Night

Other Availability Information

Click on the Calendar button or the Book Direct button for the most updated rates and availability.

Property Description

This quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy Joe's, and Hog's Breath Saloon as well as a plethora of delicious restaurants. Venture just a short distance further to Mallory Square or the famous Historic Seaport. It's easy to see why this location is unbeatable. The shared compound, of 6 total homes, features a winding brick pathway surrounded by tropical foliage and flowers that lead to a free form unheated pool tucked away in the far side of the gardens. Adjacent to the pool area is a shared, coin-operated laundry facility. Take a refreshing dip, lounge and catch some sun, or enjoy a good book while being surrounded by beautiful trees and plants. This truly is a relaxing outdoor oasis!

Upon entering Ann Street Cottage you'll feel refreshed by the cool and relaxing decor. Neutral tones combine with pops of tropical color throughout to create an inviting atmosphere to relax in. Lounge in the living room while reading a great book or catch the morning news. Transom windows let in light and the vaulted ceiling creates a bright and airy atmosphere. A small dining table for two sits just off the fully equipped clean white kitchen. A half bathroom is conveniently located next to the kitchen. The bedroom combines island charm with boutique hotel style complete with full en-suite bathroom. Calming hues with accents of coral and teal will lull you to sleep after a busy day of exploring the island. French doors open out to the private patio with outdoor dining table from the bedroom and living room. A small office space with desk and chair are located behind the patio, in case you must get some work done.

Ann Street Cottage combines a peaceful hideaway with an unbeatable location, making it the perfect option for a couple looking to have the ultimate Key West experience. (The Homeowners Association requires all occupants to be 16+ yrs. Regretfully, NO children under 16 allowed. This home is also not pet-friendly.)

There is no off street parking available for this home. There is a daily lot around the corner or the City of Key West parking garage about 4 blocks away.


Activities and Special Interests

This property provides access to the following activities and special interests:

» Boating
» Honeymoon
» Sailing

Featured Amenities

» Air Conditioning
» Internet Access
» Pool (Community)
» Dishwasher
» Cable/Dish TV

Property Features

» Ceiling Fan(s)
» Gated Community
» Coffee Maker
» Dishes/Utensils
» Freezer
» Full Kitchen
» Microwave
» Oven
» Refrigerator
» Stove
» Deck/Patio/Porch

Other Property Amenities

Close to Town

Testimonials

Exactly as Described
June 2022
Recent Guest, canton, OH United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4
Property was conveniently close to everything, yet was quietly tucked away. Pool area was perfect for relaxing with beautiful landscaping. Cottage was clean and well equipped with everything we needed. Once we figured out the hot water in the shower, we were all set! Property management was very helpful when needed. Would highly recommend and would stay again in a heartbeat!

Key Lime Cottage
June 2022
Scott M., New Berlin, WI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
We can't say enough about how great a time we had in this key lime pie inspired cottage. The cottage had everything we needed right down to a few beach chairs, beach towels, and an umbrella.

Location, location, location... just one block from the heart of old town Key West and a half block from SunShine Scooter rentals (a must do activity). Despite the close proximity to Duval St we were surprised how quiet it was at night and throughout the day.

The pool is beautiful and private with a luxurious giant royal palm guarding and providing shade.

We will definitely be back!

Fantastic little cottage!
June 2022
Anthony A., Lombard, IL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
We were quite surprised at what a tropical oasis Ann St is. We were not expecting the lush tropical foliage as we walked up the path to the door, it got even better as we walked to the pool. Absolute relaxation, pool was the perfect temperature and had plenty of seating if you didn't want to relax in the pool.

The cottage itself was excellent, very clean and very comfortable with an AC unit in the living room area and one in the bedroom. And being a block and half off of Duval was extremely convenient to get to but also it was nice and quiet at the cottage.
We would absolutely pick this complex again with no hesitation.

Manager's Response
Thank you for your Five Star Review of Ann Street Cottage! We are so glad that you enjoyed your stay and we look forward to welcoming you back soon!

Lovely cottage in great location
May 2022
Michael B., Oak Ridge, NC United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Ann Street Cottage is located less than a block from Duval in its own private garden oasis. The cottage was quiet, roomy, and comfortable. The grounds are absolutely beautiful and well-maintained. The shared private pool was a welcome bonus. Duval Street, Mallory Square, the historic marina, restaurants, bars, sites, etc. are all an easy walk away. Unless you're lucky enough to get a free parking spot on Ann St., parking is not cheap at nearby lots but it's not difficult either. We'd recommend ditching the car and navigating Key West on foot or by bike! We were very happy with our stay at Ann St. Cottage and would definitely rent here again.

Manager's Response
Thanks so much for your review. We are very happy that you enjoyed your time at Ann Street Cottage and we look forward to your return!

Excellent Location
April 2022
Judy J., Fort Branch, IN United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4
Excellent location and very quiet. Property management offered to keep our luggage for us since we had a late flight so we could enjoy our last day on this beautiful island. Definitely will be back.

Manager's Response
Thank you for your review of Ann Street Cottage. We are so glad you enjoyed the cottage and its excellent, quiet location. We greatly appreciate your recommendation and look forward to welcoming you back soon!

Beautiful Place
March 2022
Edward F., DUBLIN, OH United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Ann Street Cottage was a great little property for my wife and I. Small complex with a beautiful, quiet, peaceful pool area and close to pretty much everything Key West.

Ann Street Cottage
February 2022
Anthony and Geraldine P., Olmsted Twp., OH United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
We just love all the cottages! This was our first stay in Ann Street Cottage, because we usually stay in Ann Street Tranquility. We love the location! Having two bathrooms was a real plus for us!

Amazing tranquil oasis
December 2021
Sonesh C., Key Biscayne, FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
This property was amazing -- great location, peaceful, immaculate, charming, filled with foliage, and somehow quiet though a hop, skip and a jump from Duval. Will definitely come back!

Great location
December 2021
Amy B., Allegan, MI United States

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
3
Location is key for this quaint little cottage. We stayed here without a vehicle and was within walking distance to everything we wanted to do. The cottage was comfortable but showing its age. For example....some cracked floor tiles, porch doors that were warped and almost impossible to open and close. The bed was comfy and the kitchen had everything in it we needed to cook a few small meals. The cottage was very quiet at night despite its close proximity to night life. We would recommend staying here if you want to be close to Duval, it’s nightlife, and the harbor/Mallory square.

Quiet little place in the middle of eveything!
November 2021
JILL Y., Natrona Heights, PA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Surprisingly quiet little cottage considering the location. Really enjoyed and would definitely come back to this location given the right price.

Twice the Charm
October 2021
Recent Guest, CARROLLTON, GA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4
This was our 2nd visit to the Ann St Cottage. It's a perfect little place for a couple in a great location. We will definitely stay here again and the air conditioning will freeze you out:)

Loved it!
September 2021
Recent Guest, Phoenix, AZ United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Lovely property. Very relaxing area but still close to the action. Wish my vacation was longer, but it really was delightful. Would definitely reboot at this property.

Location Location Location
July 2021
LANCE J., Amarillo, TX United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Very nice cottage. Great Location! Just right for a couple.

Quiet, great location
June 2021
Melissa A., Pinellas Park, FL United States

Overall
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
4
The unit was clean and super well stocked. Loved having two bathrooms and the washer and dryer were a huge plus! We would have brought a duffle bag instead of checking luggage had we realized what an asset that would be. So nice after a hot sweaty day to wash your clothes. Staff was nice. Only complaint was the shower didn't get hot. We noticed that it had been redone recently and it could just be that the valve needs adjusted. Would definitely stay here again. You couldn't ask for a more convenient location to everything

Amazing rental
June 2021
Recent Guest, CHARLESTON, WV United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
The place we rented was amazing and very close to things to do. I definitely recommend it if you get the chance to rent this property. The pool area was beautiful and so was the rest of the property.

Back in paradise.
May 2021
judith g., Port Chester, NY United States

Overall
5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
5
Perfect private quiet little house. Has everything you need- very well supplied.

Much Needed Getaway in Secluded KW Paradise
April 2021
Palmer H., Cherryville, NC United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
We could not be happier with our week at Ann Street Cottage, and we will only stay here for our future KW visits. We stayed at Bali Hideaway (located in the same compound) 11 years ago, and we also enjoyed it very much. However, we do prefer this cottage due to the larger king size bed, extra half bath, private courtyard patio, and private laundry. The location is within easy walking distance to all of our favorite spots in Old Town. It is amazing that you can enjoy such peace and quiet literally just steps away from the Duval Street party scene. We had no need to contact management the entire week, so that speaks volumes for the preparation of the cottage. Honestly, it was tough leaving this place to head back home! This might be KW's best kept secret, so don't tell anyone. ;)

Made for the perfect getaway
April 2021
Recent Guest, Chapel Hill, NC United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Couldn't have been happier with the experience. Great unit and spectacular location. Wish we had stayed an extra night or two.

Fun in Key West
March 2021
Recent Guest, Dublin, OH United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Beautiful home plenty of space comfortable king sized bed
Pool is gorgeous

Awesome stay!
February 2021
Alison H., Wilmington, NC United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Would definitely rent this place again. Perfect location! One block from Duval Street so it was easy to walk everywhere and enjoy the night life, but was also far enough away that it was private and quiet. This is a perfect little cottage for two with a full kitchen and extra half bath. The private courtyard patio was our breakfast spot and we spent much time by the pool which sometimes we had by ourselves and sometimes not. My only suggestion to property management is there is no blanket. My husband was hot and I was cold, there was no blanket. Other than that simply perfect. Would highly recommend! We will be back.

Quiet, private, and perfect location
January 2021
Blaine C., Evansville, IN United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
This is the perfect cottage for two, in the perfect location. We did not use the kitchen, but everything else was fantastic and exactly what we needed!! Bike rental company just around the corner makes Fort Zachary Taylor only a 10 minute ride away. Older Key West is just a 10-15 minute walk. Couldn't believe how close we were to Duval without all the commotion and noise. Can easily Uber to further destinations if needed. We were thankful we didn't have a car to mess with parking. Check-in and out was a breeze. It was nice to have a keypad lock and not worry about keys. We already plan to stay here again! Thank you!

(sidenote to rental company: the master bedroom door sticks pretty bad in the upper corner--we were worried it would break with trying to get out in the mornings! Could easily be shaved down or something)

Best location!
January 2021
Recent Guest, Tampa, FL United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
3
We have stayed at several of the places on Ann Street, and will keep coming back!

Relaxing cottage
November 2020
Recent Guest, Marietta, GA United States

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Overall, it was a pleasant stay. Cottage was clean, more than enough for our needs. I would only say an e tea blanket would be nice. We like it cool at night, but the thin cover & sheet was not enough. Everything else was very nice. Except the weather! Oh well!

Escape to Key West
June 2020
Thomas H., Houston, TX United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
We were very happy with the cottage. It was very clean and well prepped for our visit. The location is perfect for walking around town. We plan to stay there on our next visit.

Home away from home
March 2020
Recent Guest, Devon, PA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4
Outstanding!!!

Home away from home
March 2020
Ken S., Devon, PA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4
Outstanding!!!

Ann Street 2 a home away
February 2020
James and Patricia C., Wildwood, MO United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Our second year in this cottage and we know we will be back. Lovely and spacious, this cottage feels like home and has everything needed for your stay. Close to Duval but closed in and peppered with the tropics you enjoy the pool and the quiet. Joyce our agent is welcoming and most helpful. We have also stayed at Bali on Ann Street and although smaller, still is great!!

Ann Street 2 a home away
February 2020
James C., Wildwood, MO United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Our second year in this cottage and we know we will be back. Lovely and spacious, this cottage feels like home and has everything needed for your stay. Close to Duval but closed in and peppered with the tropics you enjoy the pool and the quiet. Joyce our agent is welcoming and most helpful. We have also stayed at Bali on Ann Street and although smaller, still is great!!

Ann Street 2 a home away
February 2020
Recent Guest, Wildwood, MO United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Our second year in this cottage and we know we will be back. Lovely and spacious, this cottage feels like home and has everything needed for your stay. Close to Duval but closed in and peppered with the tropics you enjoy the pool and the quiet. Joyce our agent is welcoming and most helpful. We have also stayed at Bali on Ann Street and although smaller, still is great!!

Schroder's review
February 2020
Glenn S., NEWTON, NH United States

Overall
4
Services from rental manager
5
Cleanliness
5
Location
4
Property condition
4
Great location. Right in the thick of the action, but a little quiet oasis to yourself. Best of both worlds. Parking was a *****. Glad we lucked out by finding a spot a few streets away but it was only by luck. Place was clean and relaxing. Pool was nice also. Great stay!

Great location & property
February 2020
Recent Guest, Warrenville, IL United States

Overall
4
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4
Cottage location was perfect and loved the pool and privacy. The cottage was very clean and brightly decorated as shown. The bathrooms and kitchen were outdated, but also very clean. The location couldn't be any better within walking distance to just about everything and 1.5 blocks from the free Duval Loop shuttle bus. If there was one drawback, it would be the bathrooms age. If I was the owner I would update them.

Loved Ann St. Cottage
January 2020
Connie S., Chattanooga, TN United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Loved Ann St. Cottage and look forward to my next stay. Location is perfect along with privacy. Well decorated, clean and very comfortable. Rent KW was very attentive to one maintenance issue. The only drawback is no parking space.

Loved Ann St. Cottage


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