Cocktails & Dreams

Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterpark, Beach & Pool!

2 BR
1 Bath
Sleeps 4

Welcome to "Cocktails & Dreams," an impeccably updated second-floor condo located in the coveted Shipyard Condominiums. Positioned at one of Key West's prime locations, this residence offers you an unparalleled Key West experience. Just a short 2-block stroll from the vibrant energy of Duval Street, Cocktails & Dreams places you at the heart of Key West's renowned dining, nightlife, and shopping. Explore a plethora of restaurants, bars, and unique boutiques, immersing yourself in the dynamic spirit of the island. Venture to Truman Waterfront Park for a day of family enjoyment, creating cherished memories. If relaxation is your goal, the soft sands and inviting turquoise waters of Fort Zachary Taylor Park are only moments away, offering a tranquil escape. When the allure of the complex beckons, retreat to your private front or rear balcony. Begin your day with a cup of coffee and the soothing morning breeze, or unwind in the afternoon with a cocktail as you soak in the island vibes. For those seeking refreshment, the community pool offers a delightful way to beat the heat. Take a leisurely dip, enjoy the sun's warmth, and relish the ease of having your relaxation needs met right on-site. Inside, Cocktails & Dreams is meticulously updated, providing you with modern comfort amidst the vibrant island atmosphere. Discover a harmonious blend of convenience and style that enhances your Key West stay. Whether you're an adventurer or a leisure seeker, Cocktails & Dreams places all the wonders of Key West within your grasp. Uncover the magic of this island paradise, knowing you have a comfortable haven to return to. Discover the essence of Key West living at "Cocktails & Dreams." Experience the luxury of convenience and the allure of the island lifestyle. Book your stay now and let your Key West dreams come to life!

Please be aware of the following essential policies for your stay at Cocktails & Dreams:

Age and Occupancy Requirements: Booking tenant must be 25 years of age or older and must occupy the property for the entire duration of the booking. Furthermore, this property is exclusively available as a vacation rental and is not available for worker housing.

No Smoking: Smoking is strictly prohibited within the property. For the comfort and safety of all guests, please refrain from smoking indoors.

Pets Policy: Pets are not permitted for guest bookings less than 30 days per the HOA. For guest bookings 30 days or more, dogs weighing 25 lbs or less will be considered with the payment of a pet fee of $15 per night and registration of the dog through our third-party pet screening service, which incurs a $20 fee. Please note that all guests bringing a dog must complete the registration process with our third-party pet screening service, and a link will be provided after booking.

Mandatory Mid-Stay Cleaning: A mandatory mid-stay cleaning is required for all bookings 28 nights or more to ensure the quality and cleanliness of the property.

Bedroom 1: Queen Bed, Smart TV

Bedroom 2: Two Twin Size Beds, Smart TV

Living Room: Sofa With Pull Out Bed, Two Chairs, Smart TV

Kitchen: Nicely Equipped (everything needed to prepare and serve meals)



- Shared Pool

- One Designated Parking Space

- Linens and towels provided

- Please be aware that a security camera (Ring camera) is located at the front door.

- Military Discount: A 10% discount is offered to active duty, retired, or reserve armed forces personnel with a valid military ID.- 0.2 miles to Duval Street

- 0.3 miles to Fort Zachary Taylor State Park Beach

- 2.6 miles to Smathers Beach

620 Thomas St, #278 Key West, FL 33040

Sleeping Arrangements

Bedroom 1 Queen
Bedroom 2 Twin (2)

Bathroom Configuration

Bathroom: Combo Tub Shower, Toilet

Property Rules

Check In: After 4pm
Check Out: Before 10am
Smoking: Not Allowed


Air Conditioning
Clothes Dryer
Coffee Maker
Communal Pool
Enhanced Cleaning
Hair Dryer
Iron and Board
Private Entrance
Satellite or Cable
Smoke Alarm
Smoke Detectors
Washing Machine



Frequently Asked Questions

  • Reservations cancelled 60 days or more prior to the scheduled check-in date, will receive a refund of 100% minus a $250 cancellation fee
  • Reservations cancelled less than 60 days prior to the scheduled check-in date, will not receive a refund
  • Refunds will not be issued for weather events (including hurricanes), pandemic's, flight cancellation, mandatory evacuation orders, etc
    • It is the guests responsibility to protect themselves in these sceanrio's
    • We STRONGLY encourage guests to purchase trip insurance to protect themselves in these scenario's
      • Rental Guardian offers two types of trip insurance at the time of booking
        • Regular Trip Insurance
        • Cancel For Any Reason Trip Insurance



Terms of Waiver: As an enrolled, Covered Guest, staying at an iTrip Franchisee property, under this plan, you will not be obligated to pay for Covered Damage (defined below) to real or personal property of the owner of the rental unit located within the rental unit occupied by the Covered Guest. When the Covered Guest purchases this plan, the property manager waives the right to charge the Covered Guest for Covered Damage to the unit as a result of your inadvertent acts or omissions during the duration of the Stay. Maximum limit of this waiver of liability varies between $1,475.00 - $2,500.00 aggregate per stay.
Conditions: The Limited Damage Waiver Program has certain conditions. Covered Damage does not include, and the Covered Guest remains liable for, the following:
·      Damages caused by Intentional Acts of a Covered Guest.
·      Damages caused by gross negligence or willful and wanton conduct.
·      Any damage that the Covered Guest does not report to iTrip staff in writing by the time the Covered Guest checks out of the unit.
·      Damage from theft without a valid police report.
·      Damage caused by any pet or other animals brought onto the premises by any Guests, whether or not the property is "pet friendly".
·      Damage or loss of any property owned by or brought onto the premises by a Covered Guests or invitee of Covered Guest.
·      Property Damage resulting from any motorized vehicle or watercraft operated by a Covered Guest.
·      Damaged Caused by any forbidden items or property usage including but not limited to BBQ Grills, Candles, Cigarettes, etc.
·      "Covered Damage": All damages to property of the unit's owner, up to $2,500.00 in the aggregate for each Stay, that occurs during the Covered Guest's stay and that is the result of the inadvertent acts or omissions of the Covered Guest or the Covered Guest's invitee, excluding the damages listed in the conditions section above.
·      "Covered Guest": All registered guests and all persons booked to share the same unit of accommodations and have paid the required plan cost.
·      "Stay": The stay at an iTrip unit, from the date of a Covered Guest's check-in to the date of check-out.
Administrative Procedure: iTrip staff will administer and determine whether a damage qualifies as Covered Damage. Such staff will have the sole authority to determine the nature and extent of damages, necessary repairs and eligibility for the waiver of liability described herein. The Covered Guest must report any theft or damage to the unit or its contents to iTrip staff by the time of check-out or any otherwise applicable damage waiver for such Covered Guest will be void. The iTrip Franchisee has ultimate claim administration authority. Arbitration is required prior to litigation.
Terms of Coverage: The plan takes effect upon check-in on the booked arrival date to an iTrip unit. All coverage shall terminate upon normal check-out time of the iTrip unit or the departure of the Covered Guest, whichever occurs first.
Fee: Varies from $59.00 - $100.00 for your covered stay. This fee is non-refundable.
IMPORTANT NOTE: Violation of any condition of the terms of iTrip voids the Damage Waiver Program without refund of any portion of booking/damage waiver fee. Guest Agrees that damages not covered by the Damage Waiver Program or in excess of the Damage Waiver Program limit of $1,473.00 - $2,500.00 shall be paid by guest immediately. Guest authorizes iTrip to charge the cost of damages to guest's credit card in accordance with this agreement and the terms and conditions of the rental agreement. By submitting payment for this reservation, you authorize iTrip to include the costs of this Damage Waiver Program in your reservation. Please contact iTrip directly if you do not wish to participate in this plan or assignment.
Unless Tenant elects the Limited Damage Waiver Program, Tenant agrees to pay for damage to the Unit or property within the Unit, except normal wear and tear, that occurs during the Tenant's stay in the Unit. Tenant authorizes iTrip to charge the amount of damages, as determined solely by iTrip, to guest's credit card in accordance with this agreement.
  • Pets are welcome at some of our properties on a limited basis and only as arranged in advance
  • ​Addition of any other pet is prohibited, without prior approval, and subject to immediate eviction and loss of security deposit and rent
  • All guests bringing a pet agree to abide by all terms of the Pet Addendum to Rental Agreement listed below
  • Additionally, we reserve the right to restrict the weight of dog(s), number of dogs and/or certain breeds of dogs
  • You must have prior approval for each dog that you bring and your dog(s) must be housebroken and well-behaved
  • You will be responsible for any damages as well as additional cleaning or treatment needs due to fleas or “accidents."
  • You take fully responsibility for your pet and hold iTrip Vacations Key West and owner harmless and will defend any lawsuits resulting from the actions of your pet
  • Also, the pet is considered personal property for the purposes of this agreement 
  • Please bring your pet’s bedding as they are not permitted on the furniture or bedding. Pet bedding is not permitted in the washer or dryer
  • You are responsible for notifying us if your dog is aggressive or has a bite history and you may be required to purchase Dog Owner Liability Insurance
  • To bring your pet(s), guest(s) must agree to the following terms:
    • ​​Guests must register their dog(s) with our third party pet screening site.
    • Guests must pay the Pet Fee + Tax for each dog.
    • Guests agree to keep their dog(s) under control at all times.
    • Guests agree to keep their dog(s) in a crate when the dog is left home alone.
    • Guests agree to promptly report any damage caused by dog(s).
    • Guests agree to pay any costs for damage done by dog(s). Pet damage is not covered under the limited damage waiver.
    • If damages are not reported, but are found by owners/agent after check-out, it will be documented and necessary replacement or repair costs will be charged to guest(s) credit card on file.
    • Guests agree that their dog(s) is housebroken.
    • All dogs must be up to date on rabies vaccinations and all other vaccinations. Heartworm preventative is highly recommended.
    • All dogs are to be treated with Advantage or similar topical flea and tick repellent three (3) days prior to arrival. Fleas are very rampant in this area and can cause harmful/fatal illness to humans and pets. All items above are the sole responsibility of the dog owner.
    • Guests agree that the dog will not get on the furniture or bedding.
    • Guests agree that dog(s) will be rinsed of sand & dried thoroughly before entering the unit. Guest linens & towels should never be used on your dog!
    • Guests agree that dog(s) will not be washed in the bathtubs or showers inside the unit. This must be done outside with the hose.
    • Guests agree to adhere to local ordinances, leash laws and licensing requirements.
    • Guests agree to clean up after their dog(s) & dispose of their dog(s) waste promptly. Additional fees will be charged if dog waste is left on property.
    • Guests agree to keep dog(s) from being noisy, barking or aggressive, and from causing any annoyance or discomfort to others. Guests will remedy any complaints immediately.
    • iTrip Vacations Key West, and/or the Owners are not responsible for guests’ dog(s). Guests agree to pay agents promptly for any damage, loss or expense caused by their dog(s) and will defend any lawsuits resulting from the actions of their dog(s).
    • No personal dog beds or other such items should be put in the washer or dryer!
    • Repairs to screening on the porch will be assessed at labor charges for rescreening if your dog(s) break through the screen for any reason.
    • All excess dog hair will be swept, vacuumed or otherwise picked up and removed from the inside of the unit prior to departure.
    • “Vicious or Dangerous Dogs” trained for dog fighting or with any tendency or disposition to attack any dog other domestic animals or humans without provocation, are not permitted at any time. Any dog with a recorded history of biting is strictly prohibited.

Rental Agreement


iTrip Key West, the Agent of the Owners, and Tenant agree as follows: Above Tenant is at least twenty-five (25) years of age (an "adult") and will be an occupant of the unit Cocktails & Dreams, during the entire reserved dates. In addition to Tenant, other authorized occupants may be family members or friends of Tenant. Use of the premises will be denied to persons not falling within the foregoing categories. Should any unauthorized persons occupy or use the Premises, Tenant shall vacate the premises immediately without any refund. No key will be issued to anyone who is not an adult.


The undersigned Tenant, for himself/herself, his/her heirs, assignors, executors, and administrators, fully releases and discharges Owner from any and all liabilities, claims, demands, and causes of action by reason of any injury, loss of damage by whatever nature which has or have occurred, or may occur to the undersigned, or any of his/her guests as a result, or in connection with the occupancy of the premises and agrees to hold Owner free and harmless of any claim or suit arising there from. In any action concerning the rights, duties or liabilities of the parties to this agreement, their principals, agents, successors or assignees the prevailing party shall be entitled to recover any reasonable attorney’s fees and costs. Owner reserves the right to terminate this Agreement upon their discretion at any time.
The undersigned Tenant will comply with the provisions set forth in this Agreement and acknowledge responsibility for all occupants during the rental term to comply with such provisions of this Agreement.


Reservations may be placed up to one (1) year in advance, but are subject to the rates in effect for the year said reservations are placed. All times are Eastern Standard Time and currency is USD unless otherwise noted. While every effort will be made to have the unit available for check in at 3:00 pm, during high season cleaning crew may require additional cleaning time and check in may be delayed up to 5 pm.



Cocktails & Dreams
5/5 stars
Cocktails & Dreams is the perfect location in Old Town Key West. It is close to everything but still very quiet. It is an updated 2 bedroom and one bath condo with two porches so you can enjoy the sun or find some shade. We enjoyed it so much that we rebooked it for next year. You won't go wrong by choosing this location.
- Keith

Keith thank you for sharing your experience with us. We are happy you enjoyed your stay at Cocktails and Dreams. We always enjoy having returning guests so thank you for booking with us again. We shall see you next year.

- Manager Response
Cocktails & Dreams
5/5 stars
This condo was in a great, safe and walkable location to everything happening in Key West. Clean and nicely updated inside with all the appliances you need, plus two balconies. The hosts were very responsive from booking until checkout. I’d stay here again!
- Michael
Another Day In Paradise
5/5 stars
Our family of 4 had an amazing stay at Cocktails & Dreams! Truly Paradise! The condo complex is quiet and secure. The condo has many modern amenities and updates. The location is perfect for walking and biking- we loved the 2 bikes available and easily rented 2 more bikes for the week. The condo is close to beach, sunset, restaurants and shopping! The pool is great too! Scott and Tina answered all of our questions quickly and are very accommodating! We highly recommend Cocktails & Dreams and are looking forward to our next stay!
- JoMarie

JoMarie Thank you for the review! We are happy that you enjoyed your stay and all the amenities at Cocktails and Dreams. We agree, it is a great location to all of the attractions of Key West. We hope to host you and your family again soon.

- Manager Response
Perfect Vacation
5/5 stars
Cocktails & Dreams exceeded our expectations. The location is perfect for walking to restaurants and attractions. The bikes came in handy for grocery store runs. The condo was nicely decorated and very clean. We look forward to our next visit and stay at Cocktail & Dreams! Thank you for sharing your home-away-from-home with us.
- Joyce

Joyce thank you for your review! We are very happy that you enjoyed Cocktails and Dreams. Yes a bike is the best way to get around downtown Key West. We hope to host you again soon.

- Manager Response
A great condo for Key West!
5/5 stars
Everything about a recent stay at cocktails and dreams was great. The check-in process went smoothly. The check-in process went smoothly. The condo is well appointed and offers easy access to all of Key West’s major attractions. I would highly recommend this upstairs unit as I have heard that noise can be an issue with downstairs condos. We had no problems whatsoever with noise from other units. Would stay here again!
- Jeffrey

Jeffery thank you for the great review! We are very happy that you enjoyed your stay at Cocktails and Dreams. We look forward to hosting you again soon.

- Manager Response
Great place!
5/5 stars
This is in a fantastic location in Key West! The bikes make it very easy to get around and are included in the price! We loved staying here and would definitely recommend.
- Amanda

Thanks for the great review Amanda! We are very happy that you enjoyed your stay! Hope to host you again soon.

- Manager Response
Amazing time at Cocktails and Dreams
5/5 stars
We just spent an amazing week at Cocktails and Dreams. It was impeccably clean and very spacious. We enjoyed the location of being just far enough away from Duval, but close enough to walk. We enjoyed having 2 bikes to use and able to bike everywhere in Key West. Great location to Ft Zachary park and Truman Waterfront. A great place to walk in the morning. A safe neighborhood and very welcoming We had 2 teenage girls with and enjoyed walking to everything and having some freedom. It is also a a great place for any kids. It does have stairs that weren’t specified in the description but wasn’t an issue for us but be aware of you have problems with stairs. The management company/Scott and Tina were amazing hosts. We had a couple minor issues and they were resolved very quickly and around our schedules. The unit had everything you need to enjoy your vacation for a week or if your able to longer. Thank you again to the owners to opening up your place for us to use and the management company for your hospitality. Someday we will be back.
- Kim

Thank you Kim. It was great meeting you and your family and we're so glad you had an amazing week at Cocktails & Dreams. We hope to see you again soon.

- Manager Response

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Toll Free (888) 413-7911