Welcome to Key West, Florida’s southernmost city known for its vibrant culture, conch-style houses, clear waters, and Old Town neighborhood. Originally founded in 1996, Rent Key West Vacations is one of the longest standing vacation rental companies on the island of Key West. Our office is located right on Duval street, just one block from the Ernest Hemingway Museum. This position at the center of Old Town Key West allows our team to manage both short and long-term rentals for many of Key West’s most famous homes. We connect with every guest to ensure that you find the right place for your Key West Vacation.

Key West's Best Rental Company

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

Ann Street Cottage

Bedroom

This is a SAMPLE of the customized agreement that you will be sent upon booking. 

 
;
1075 DUVAL STREET #C-11 • KEY WEST • FL • USA • 33040 
(800) 833-RENT • (305) 294-0990 • FAX • (305) 768-0146
 SHORT TERM RENTAL AGREEMENT
{{formatDate date "medium"}}
RESV #: {{reservation.id}}
BOOKING DATE: {{formatDate reservation.rescreated "medium"}}
GUEST INFORMATION:
{{contact.name}}
{{contact.address1}}
{{contact.address2}}
{{contact.locality}}, {{contact.region}} {{contact.postal}}
{{contact.country}}
Phone#: {{contact.cellPhone}}
Email: {{contact.email}}
Total # of Guests:  {{reservation.guests}} 
RENTAL: {{unit.name}}
RENTAL ADDRESS: {{unit.streetAddress}}, Key West, FL 33040
RENTAL PHONE: {{unit.phone}}
PARKING INFO: 
ARRIVAL: {{formatDate reservation.checkin "medium"}} 3:00 - 5:00 PM
DEPARTURE: {{formatDate reservation.checkout "medium"}} 10:00 AM

RENTAL TERMS & CONDITIONS: This Short Term Rental Agreement (Agreement) is made by and between Rent Key West Vacations, Inc. (hereinafter designated as “RKWV”), agents of the owner(s), and the Guest as listed above:
ADVANCED DEPOSIT: RKWV will reserve this property up to 3 days from issuance of this Agreement during which Guest must sign and return this Agreement with payment terms specified. Bookings made more than 60 days before arrival require payment of 50% of the rent & taxes within 3 days of booking. The final payment of 50% is due 60 days before arrival. Within 60 days of arrival, payment in full is required within 3 days of booking. Acceptable methods of payment include personal checks, E-Checks, Credit Cards, Cashier's Checks, or Money Orders in US dollars. No checks of any kind will be accepted within 45 days of your arrival. We accept VISA, MASTERCARD, AMEX, or DISCOVER but require authorization to charge.
CANCELLATION POLICY: All notices of cancellations must be received in writing. For Agreements cancelled more than 60 days before arrival, your prepayment will be refunded less a $200 cancellation fee and reservation fee. On cancellations received WITHIN 60 days of your scheduled arrival, no refund is possible unless we are able to re-rent the property for your original dates and comparable rents. Prorated refunds are issued for any nights re-rented. Mandatory evacuation due to hurricane (issued by Monroe County Emergency Management) is considered a cancellation and rental fees will not be refunded.
TRAVEL INSURANCE: The optional premium for CSA Guest Protect Travel Insurance has been included on the reservation quote page of your short term rental agreement.  Guest Protect reimburses for pre-paid non-refundable expenses due to certain unforeseeable circumstances that may cause you to cancel, interrupt or delay your trip (including mandatory hurricane evacuation).  Please review our cancellation policy above.  Residents of NewYork and Hawaii, may not accept the insurance here, but may purchase on the following link: CSA Travel Protection.You must accept coverage on your rental agreement for this protection and the cost will be added to the total due on the iniital payment. Travel insurance & reservation fees are non-refundable once paid. Questions concerning CSA Guest Protect can be obtained by reviewing the certificate of insurance on their website http://www.vacationrentalinsurance.com or calling 866-999-4018. If you have purchased CSA Guest Protect and need to file a claim, please contact them at 800-554-9839 to begin your claim.
SECURITY DEPOSITS & DAMAGE COVERAGE:  In and effort to maintain the property in its best condition for all of our rental guests, unintentional damage coverage is included as part of the Reservation Fee paid. This damage plan covers unintentional damages to the rental unit that occur during your stay that are immediately disclosed to management prior to check-out. This does not cover lost keys, gate cards or remotes. The policy will pay a maximum benefit of $3,000. Guests failure to report damage, automatically denies the claim and assigns responsibiilty to the Guest. Any unreported or intentional damages or damages that exceed $3,000 will be charged to the credit card on file.
Some property owners, espcially large properties (4 bedroom or greater) and rental stays (any property) less than 6 nights may require additional refundable Security Deposits, which are collected with the final payment. This deposit is held until approximately two weeks following the departure of your reservation to cover any intentional damage, excess unintentional damage or excess cleaning charges during the agreement term. By no means does the amount of the security deposit limit guest's responsibility for damages and charges exceeding security deposit amount. By signing this written agreement Guest authorizes Rent Key West Vacations to charge such fees to the credit card on file. All credit cards must be valid for 60 days following departure.
Please note multiple Deposits (Security, Pet and/or Utilities) may be required on one reservation.
Guest Initials: {i:sR:____}
GUEST RESPONSIBILTIES:
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.
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, whether by credit card or cash. Cash deposits will be refunded as soon as all applicable bills have been received by RKWV.
Smoking is prohibited inside all rental units. Smoking may be permitted outside provided all exterior doors are closed. A fine of $750 will be charged against damage deposit or Guest credit card for anyone found in violation.
Unreturned keys/gate cards & remotes will be assessed at $25.00 per key or a higher amount set by a condominium/homeowners association for common area keys, currently as high as $250 per key.
Guest agrees to pay a late checkout fee of 1/5 of the daily rate per hour after 10AM unless approval in writing for late checkout has been obtained from RKWV.
Guest agrees to use the property for residential/accommodations use only. No special events or functions are permitted in private residences without prior written permission of RKWV. Guests 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, you will be asked to leave and will forfeit the remainder of your rental fee and deposit.
As a condition of use of the pool/spa, Guest agrees to forever discharge, waive and release RKWV for all accounts of bodily or mental injury, death and/or property damage from any mishap, accident, loss, injury or damage suffered by you or your guests resulting from, connected with or caused by Rental swimming poo/spa facilities, including but not limited to mechanical defects or failure of equipment.  By signing this contract, Guest declares that you and the other guests, including children, are in good medical & physical health and that the use of the pool/spa poses no danger to your health.  Guest further understands that participation in pool/spa activities is at your own risk.
Guest shall not sublet Property or allow anyone to share the Property without RKWV’s prior written consent.
Guest agrees to abide by any condominium or homeowners association rules & regulations and sign any applications as required to seek association approval, where applicable.
IF this property is for sale, Guest agrees to showings "by appointment only".
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.
PETS ARE NOT ALLOWED unless prior arrangements have been made with RKWV. Individual owners set the rules on pets for their individual property. Guest found violating this, will be levied a $500 penalty. RKWV acknowledges permission to have a pet by including a “pet fee” in the rental terms of this agreement. Pets to be included under the terms of this agreement are: Breed: ______________________________  Name: __________________ Weight:_______
Guest agrees to the maximum number of occupants previously stated and to register all occupants and visitors at the time the reservation is made, which may include providing photo identification for all non-minor occupants. If there are any changes or substitutions in occupancy, RKWV must receive immediate notice. Please list all occupant names & ages here:
1{t*:sR:___________________________}
5.{t*:sR:_________________________}
9.
{t*:sR:__________________________}
2.{t:sR:___________________________}
6.{t*:sR:_________________________}
10.
{t*:sR:__________________________}
3.{t*:sR:__________________________}
7.{t*:sR:_________________________}
11.
{t*:sR:__________________________}
4.{t*:sR:__________________________}
8.
{t*:sR:__________________________}
12.
{t*:sR:__________________________}

RENT KEY WEST VACATIONS, INC. RESPONSIBILITIES
RKWV agrees to provide the Property in a clean condition and to provide maintenance and repairs as required. RKWV relies on independent contractors to provide these services and are dependent on their availability.
RKWV reserves the right to substitute like properties in the event of circumstances beyond our control.
NEITHER THE OWNER NOR RKWV is responsible for loss, theft or personal injury sustained by you or persons accompanying you.
THIS AGREEMENT IMPOSES an obligation of good faith in its performance and enforcement. If you default in the performance of any of the obligations contained herein, Rent Key West Vacations, Inc., shall be entitled to recover all costs and expenses, including court costs and reasonable attorney fees.
THIS AGREEMENT shall be construed to conform to the Chapter 509 Florida Statutes.
  *
Guest Signature: {s:sR:______________________}
Date: {d:sR:_____________}
 
     1075 Duval Street Suite C11 Key West Florida 33040 USA
 


ARRIVAL
DEPARTURE
DATE RESERVED
{{reservation.dowcheckin}}
{{formatDate reservation.checkin "medium"}}{{formatTime reservation.checkintime "short"}}
{{reservation.dowcheckout}}
{{formatDate reservation.checkout "medium"}}  {{formatTime reservation.checkouttime "short"}}
{{formatDate reservation.rescreated "medium"}}

Booking Charges:
 
Rent Charges Total
{{formatCurrency reservation.totalrent currency}}
 
 {{#reservation.fees}}{{name}}:
{{#reservation.fees}}{{name}}: {{formatCurrency value currency}}
{{/reservation.fees}} 
 
 Taxes (12.5%)
{{formatCurrency reservation.totaltaxes currency}} 
 
 Travel Insurance
{{formatCurrency reservation.insurance currency}} 
 
Booking Total
 {{formatCurrency reservation.totalinsurance currency}} 


Guest Protect Plan offered by RKWV through CSA Travel Protection includes:
Valuable benefits before, during and after your vacation
Reimbursement of non-refundable trip costs if you must cancel your trip or cut it short due to covered sickness, injury or other events.
- Up to 150% of the trip cost coverage for covered trip interruptions.
- 24/7/365 emergency assistance hotline, plus access to a global network of physicians.
Residents of NY & HI may purchase insurance here: CSA Travel Protection
This insurance will only cover Covid related illness & infections, not travel restrictions by government authorities or employers.
See attached information sheet.
Please initial one of the following:
{c*:sR:____}Accept{{formatCurrency reservation.insurance currency}}
{c*:sR:____}Decline coverage
{c*:sR:____}Purchased thru VRBO or third party website: I acknowledge that I/we have purchased travel insurance 

By signing this agreement:
Guest accepts the quoted reservation costs and optional service plans as part of the short term rental agreement with Rent Key West Vacations.
Accepted by:
Guest Signature: {s:sR:______________________}
Date: {d:sR:_____________}
RES-{{reservation.id}}{{reservation.agent.name}}
     1075 Duval Street Suite C11 Key West Florida 33040 USA
 


Guest Information:
Credit Card Billing information  (if different
 {{contact.name}}
{{contact.address1}}
{{contact.address2}}
{{contact.locality}}, {{contact.region}} {{contact.postal}}
{{contact.country}}
{t*:sR:__________________________________________}
{t*:sR:__________________________________________}
{t*:sR:__________________________________________}

Booking Charges:
 
Rent Charges Total
{{formatCurrency reservation.totalrent currency}}
 
 {{#reservation.fees}}{{name}}:
{{#reservation.fees}}{{name}}: {{formatCurrency value currency}}
{{/reservation.fees}} 
 
 Taxes (12.5%)
{{formatCurrency reservation.totaltaxes currency}} 
 
 Travel Insurance
{{formatCurrency reservation.insurance currency}} 
 
Booking Total
 {{formatCurrency reservation.totalinsurance currency}} 

 
PAYMENT METHODS:
 
{c*:sR:____} CHECK / MONEY ORDER / WIRE TRANSFER
 
{c*:sR:____} CREDIT CARD: 
CC#: {{reservation.lastfour}}{t*:s________________________________________________}
Exp:  {t*:sR:_______}
CVV: {t*:sR:_______}



By signing this agreement:
Guest authorizes Rent Key West Vacations, Inc. to charge the amounts listed above on the dates designated.
Guest authorizes Rent Key West Vacations, Inc. to charge the credit card (on file) for any damages or charges to the property during the lease period as per the Deposit policies previously stated in this agreement.
Guest is verifying that they are the authorized signer of the credit card listed above and that all of the information is correct as provided to the credit card issuer.
Accepted by:
Guest Signature:    {s:sR:______________________}
Date: {d:sR:_____________}
RES-{{reservation.id}}{{reservation.agent.name}}

Ann Street Cottage

Ann Street Cottage

House hosted by Rent Key West Vacations

About The Property

Sleeping Arrangements

Amenities

Rent Key West Vacations

Key West, FL 33040

Safety & Inspections

Additional Details