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Ann Street Cottage: 1 Bedroom Short Term Rental in Key West FL

Cottage Rental in Key West Florida

Escape to Ann Street Cottage, a serene and romantic vacation rental in Key West, FL. Perfect for couples, this charming cottage offers modern amenities, including a private pool, for a relaxing and unforgettable getaway.

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Rates from
$250 / night
Additional fees may apply
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Rental overview

Why You'll Love This Rental

Ann Street Cottage is a 671 sq. ft. one-bedroom cottage in Key West’s Historic District, set in a quiet six-home compound on the waterfront (ocean) and near a beach. It sleeps two and is arranged for a simple, private stay with a king bed and an ensuite full bath, plus an additional half bath. A key differentiator is the shared garden setting with a free-form heated community pool, paired with an in-town location one block from Duval Street.

Inside, the cottage includes a fully equipped kitchen with major appliances (stove, oven, microwave, refrigerator, dishwasher, toaster) and a dining table for two. The living area has a TV, stereo, and DVD player, and the home includes air conditioning and internet access. French doors from both the living room and bedroom open to a private uncovered deck/patio with outdoor dining. A dedicated office nook with desk and chair sits behind the patio and also houses the in-unit washer/dryer. Street parking only; no reserved off-street space. Occupants must be age 16+ and the home is not pet-friendly.

Good fit for
Honeymoon
Heated Community Pool Shared compound includes a free-form heated community pool.
King Bed Suite One king bed with an ensuite full bathroom; plus a separate half bath.
Private Patio Access French doors from living room and bedroom open to a private uncovered patio.
In-Unit Laundry Washer/dryer located in the unit’s office space.
Duval Street Nearby Located one block from Duval Street in Key West’s Historic District.
At a glance

Property Highlights

Waterfront - OceanLocation Setting
Near a BeachBeach Access
1 BedroomBedrooms
1 Full, 1 Half BathroomsBathrooms
Sleeps 2Guest Capacity
671 sq. ft.Living Space
Pool (Community)Pool
Internet AccessInternet
TelevisionTelevision
YesAir Conditioning
YesWasher / Dryer
Location & nearby Explore the Area

Ann Street Cottage is in Key West’s Historic District within a quiet six-home compound. The setting is listed as waterfront (ocean) and near a beach. The property is one block from Duval Street, with Mallory Square and the Historic Seaport referenced as nearby in the source information. Parking is on-street only, with no reserved off-street space.

Plan your stay

Rates & Availability (USD)

Rates from
$250 per night
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Additional Rate Information

From: $190/Night

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About this rental

About This Rental

Ann Street Cottage is a one-bedroom, one-and-a-half-bath cottage in Key West, Florida Keys. The home sleeps two and is located in the Historic District within a shared compound of six residences. The setting is listed as waterfront (ocean) and near a beach, and the compound includes landscaped garden paths leading to a free-form heated community pool.

The interior layout is designed for a two-person stay. A living area sits alongside a small dining table for two and a fully equipped kitchen. Kitchen amenities include a stove, oven, microwave, refrigerator, dishwasher, toaster, dishes and silverware, cooking basics, and a coffee maker that supports both K-cup and drip brewing. A half bathroom is positioned near the kitchen for added convenience.

The bedroom features one king bed and an ensuite full bathroom. French doors open to a private uncovered deck/patio from both the bedroom and living room, with an outdoor dining table for meals or downtime outside. Behind the patio is a small office space with a desk and chair; the washer and dryer are located in this area.

Included amenities cover air conditioning, internet access, television, stereo, DVD player, towels/linens, hangers, shampoo and body wash, hair dryer, iron/ironing board, and safety items such as a smoke detector and fire extinguisher. Parking is street parking only, with no off-street or reserved space. The homeowners association requires all occupants to be 16 years and older, and the home is not pet-friendly.

Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. Both bathrooms have recently been remodeled and a private laundry is located in the unit.

The 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 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 heated pool tucked away in the far side of the gardens. 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 colors 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 ensuite bathroom. Calming hues and pops 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. The washer and dryer is in this office space as well.

Ann Street Cottage combines a peaceful hideaway with excellent location making it the perfect option for a couple looking to have the ultimate Key West experience.

(The Ann Street Compound Homeowners Association requires all occupants to be 16 + yrs. Regretfully, NO Children under 16 are allowed. This home is also not pet-friendly) STREET PARKING ONLY - Please note, parking is on-street. There is NO off-street, reserved parking spot for this property.

Bedding: 1 king bed
Before you book

Vacation Rental Policies

Check In

3:00 PM

Check Out

10:00 AM

Other Policies

HOUSE RULES
The following rules are a condition of this rental:

* MAXIMUM OCCUPANCY: Guest agrees to the maximum number of occupants previously stated and to register all occupants and visitors at the time the reservation is made. If there are any changes or substitutions in occupancy, RKWV must receive immediate notice.


* OCCUPANTS: No occupants under the age of 25 are allowed unless accompanied by a parent or other legal guardian. Non-compliance with this provision will result in denial of occupancy and forfeiture of all monies paid to date.

* QUIET HOURS: Guest and their visitors SHALL NOT DISTURB neighbors with loud noise, music or unlawful, unsafe or pollution-causing behavior. Should you allow or participate in any such use or behavior between the hours of 10PM to 7AM you will be asked to leave and will forfeit the remainder of your rental fee and deposit.

* SUBLETTING: Guest shall not sublet Property or allow anyone to share the Property without RKWV’s prior written consent.

* UNAUTHORIZED LATE CHECKOUT: Guest agrees to pay a late checkout fee of 1/3 of the daily rate per hour after 10AM UNLESS approval in writing for late checkout has been obtained from RKWV.

* KEYS: Unreturned keys and gate access devices will be assessed at a minimum of $25.00 per set or the higher amount set by a condominium/homeowners association for common area keys and/or gate access devices, currently as high as $250 per item.

* SMOKING / VAPING: Smoking and vaping is prohibited inside all rental units. Smoking and vaping may be permitted outside unless otherwise posted as restricted, provided all exterior doors and windows are closed. A fine of $750 will be charged against damage deposit or Guest credit card for anyone found in violation.

* NO GLASS IN OR AROUND THE POOL: Glass of any kind is not allowed inside or around the pool area. In the event that glass breaks in or around the pool, the pool will need to be drained and cleaned. If this occurs you must immediately notify the property manager. Draining and cleaning of the pool is valued at over $500

* CONDO / HOA RULES: Guest agree to abide by any condominium or homeowners association rules & regulations and sign any applications as required to seek association approval, where applicable. La Brisa, Beach Club and 1800Atlantic Condominiums require the completion of a registration form as a condition of rental.

* PETS: Pets are NOT ALLOWED unless prior arrangements have been made with RKWV. A pet fee will be charged as a condition of this authorization. Individual owners set the rules on pets for their individual property. All pet owners agree to pick up and properly dispose of pet waste regardless of pet designation. Guests found violating this, will be levied up to a $500 penalty.

* SERVICE ANIMALS: Rent Key West Vacations is ADA-compliant in offering accommodations to guests traveling with a service animal. Please let us know at the time of your reservation that you are traveling with a service animal and be prepared to provide information regarding the task the animal is trained to perform.

* EMOTIONAL SUPPORT ANIMALS: While Emotional Support Animals can be important travel companions, our properties do not make exceptions for Emotional Support Animals at non-pet friendly properties. If your trained animal is required due to a disability, please see Service Animals above.

* COMPLAINTS AND MAINTENANCE: RKWV will make all reasonable efforts to keep the property and facilities located within the property in good working order, with all inventories in a reasonably sufficient amount. In the event there is a maintenance problem with any of the facilities located within the property; the owner will take all reasonable steps to repair the problem as soon as possible after being notified in writing. No refund or rate adjustment will be made for unforeseen mechanical failures such as the supply of electricity, water, pool, air conditioning, television, appliances, etc. it is the guests responsibility to report any problems or damage immediately to RKWV. No refund or rate adjustment will be made for any construction projects being done in the neighboring houses, condos or townhomes.

* CARE OF PROPERTY: Guest is responsible for the care of the rented property and furnishings and to maintain the premise in a neat and sanitary condition. Guest will leave property in the same condition as at check-in, including furniture placement. All damage must be reported immediately.

* NEGLIGENCE: Guest shall be responsible for all conditions caused by negligent or wrongful act or omission of the Guest, including but not limited to any and all damage and to the Property. Guest agrees that RKWV may deduct charges for any damage, excessive cleaning fees or agreed fees from your damage deposit or by seeking other legal remedies. Deposits will be refunded as soon as all applicable bills have been received by RKWV.

* ACKNOWLEDGEMENTS: Guest acknowledges and agrees on guest behalf and on the behalf of all of guest’s family members, visitors, guests, and any other third parties occupying or using all or any part of the property that RKWV and property owner are in no way responsible for any personal injury or bodily harm that may occur for any reason whatsoever on the property including swimming pools/spa facilities. RKWV is not responsible for any damage or loss for any reason incurred by any of the aforementioned guests who may be present on the property. The guest hereby agrees to defend, indemnify and hold harmlessRKWV, and its employees and agents, from and against all claims, causes of action, lawsuits, damages, liabilities, and expenses (including reasonable attorneys’ fees) as may be incurred by indemnified parties because of guest failure to comply and/or cause the compliance of guests aforementioned acquaintances with the terms and conditions of this agreement.

* DRUGS AND HAZARDOUS MATERIALS: The guest, guest’s family, visitors, guests, and other members of such guests group are strictly prohibited from using or bringing onto the property any illegal substances, flammable fluids, explosives or other items deemed hazardous to, life, limb, or property, as determined by RKWV.

* PROPERTY FOR SALE: IF this property is for sale, Guest agrees to showings "by appointment only".

* PROPERTY USAGE: Guest agrees to use the property for residential accommodations use only. No special events, parties, commercial filming is permitted unless expressly granted in writing by the property owner.

~ HOA RULES:
* ANN STREET GARDENS COMPOUND RULES & REGULATIONS: Ann Street Gardens is not a hotel. There is no staff to take care of things or assist you. Please contact your Rent Key West Vacations if you have any questions. Please take care of our public spaces as you would your own home and respect the other residents and guests and their right to peaceful enjoyment of Ann Street Gardens, a special and unique place!

* GENERAL RULES: All music and other noise must be contained within the home. Please be quiet when using the walkways, gardens and courtyards. No noise after 11:00 PM. The homes are close, please be considerate.
No motorized vehicles (mopeds or scooters) inside the street gates. Please do not block pathways with bicycles.
There is no tenant parking permitted in the private parking space.

* POOL AND PATIO AREA RULES:
All persons using the pool do so at their own risk, as no lifeguard is provided.
Hours: Sunrise to 11:00 PM
Headsets must be used when playing music.
Cell phones conversations must be conducted away from other pool users.
Deck chairs and lounges cannot be reserved prior to occupancy.
No animals in pool, pool area or patio.
Drinks must be in plastic containers and absolutely no breakable objects.
Please take all trash back to your unit for disposal.
No diving or running.
Do not remove furniture from pool area.
No smoking allowed in the pool and patio area.
No nude or topless sun bathing.
No scuba tanks allowed in the pool, they will damage pool surface.

* LAUNDRY AREA:
Our laundry area is used by several of the homes, please be considerate. DO NOT OVER LOAD THE WASHER. Please move laundry along as soon as a load is completed. Do not leave laundry in washer or dryer. If another resident is waiting to use the appliances please alternate
laundry loads with them. Do not use dryer sheets. Please wipe off washer and dryer and clean dryer lint screen when finished. Turn off light when leaving the area.

* Please take all trash to the outdoor trash area daily. Ants and rodents can be a problem in our tropical climate. Key West is a green city. PLEASE RECYCLE. It is ok to mix glass, plastic, tin and paper..

* All Packages can be delivered to our rental office and available for pickup 7 days a week from 9 am 5 pm.

Things to enjoy

Activities and Special Interests

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

Beach
Boating
Fishing
Deep Sea Fishing
Honeymoon
Sailing
Scuba Diving
Spa
Hiking
Wind Surfing
Kayaking
Golfing
Biking

Other Activities and Special Interests

» Marinas, Boat Rentals & Excursions
» Museums
» Key West Aquarium
» Paddle Boarding
» Dolphin Watching
» Banana Boat Riding & Water Tubing
» Ocean Waterpark & Challenge Course
» Kite Boarding
» Pickleball
» Tennis
» Banks
» Grocery Stores
» Public Parks & Beaches
» Key West Historic Seaport
» Key West Tropical Forest & Tropical Garden
» Skydiving
» Southernmost Point Buoy
» Dry Tortugas National Park & Fort Jefferson
» Fort Zachary Taylor State Park & Beach
» Sunset Celebration at Mallory Square
» The Florida Reef - N. America’s only living coral barrier reef
» Key West Marine Park stretching from Higgs Beach to South Beach
» The Key West Butterfly & Nature Conservatory
» Dining Out
» Live Theater, Concerts & Entertainment
» Food Tours
» Ghost Tours
» Pub Crawls
» Your reservation guest portal will provide details
» Paint & Sip Art Classes
» Bird Watching
» Eco Tourism
» Shopping
» Fitness Centers
» Hospital
» Laundromats
» Jet Skiing
» Para-sailing
» Snorkeling
» Swimming
» Historic
» Romantic
What's included

Property Amenities

Featured Amenities

Air Conditioning
Internet Access
Dishwasher
Washer/Dryer
Television
Pool (Community)

Property Features

Towels/Linens
Microwave
Refrigerator
Toaster
Stove
Stereo
Hair Dryer
Oven

Entertainment

DVD Player

Other Property Amenities

» Hangers
» Kitchen
» Shampoo
» Body Wash
» Dishes & Silverware
» Fire Extinguisher
» Hot Water
» Smoke Detector
» Cooking Basics
» Not Necessary
» Essentials
» Iron & Ironing Board
» Area
» Historic District
» Street Parking
» Deck Patio Uncovered
» Dining table
» Coffee Maker - Kcup and Drip
Guest feedback

Testimonials

June 1, 2022 - Website
Exactly as Described by Recent Guest
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!Manager's ResponseThank you for your review of Ann Street Cottage and your recommendation. We are so glad that you enjoyed your stay and we look forward to welcoming you back soon!
Thank you for your review of Ann Street Cottage and your recommendation. We are so glad that you enjoyed your stay and we look forward to welcoming you back soon!

June 1, 2022 - Website
Fantastic little cottage! by Anthony A.
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 ResponseThank 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!
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!

May 1, 2022 - Website
Lovely cottage in great location by Michael B.
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 ResponseThanks 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!
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!

April 1, 2022 - Website
Excellent Location by Judy J.
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 ResponseThank 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!
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!
Helpful details

Frequently Asked Questions

Ann Street Cottage is located in Key West, Florida.

Ann Street Cottage accommodates up to 2 guests.

1 Bedroom and 1 Full, 1 Half Bathrooms.

The listed beach access for Ann Street Cottage is Near a Beach.

Yes. The property lists Pool (Community).

Ann Street Cottage is professionally managed by Rent Key West Vacations.
Local management

Professionally Managed By

Rent Key West Vacations
In business since 1996
View Manager Profile

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Property reference
#15890 · Ann Street Cottage
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