Tipsy Turtle

Tipsy Turtle: Luxurious Waterfront Villa on Duck Key with Stunning Views and Modern Upgrades!

2 BR
2.5 Baths
Sleeps 4


Welcome to Tipsy Turtle, where luxury meets the Florida Keys lifestyle. This tastefully updated villa, perched on the picturesque Duck Key, offers a waterfront retreat that will enchant you from the moment you arrive. Begin your day with the serene water views as you sip your morning coffee, letting the tranquility wash over you. In the evening, the breathtaking views will captivate your senses as you unwind on the back porch, savoring your preferred cocktail. Duck Key itself is a haven of activities, ensuring there's always something to do. But if you're inclined to explore more of the fabulous Florida Keys, you'll find that you're only a little over an hour's drive from the vibrant scenes of Key West or the enchanting allure of Key Largo. At Tipsy Turtle, you have the perfect balance of relaxation and adventure right at your doorstep. It's time to dive into your unforgettable getaway and experience the allure of the Florida Keys like never before.

Please be aware of the following essential policies for your stay at Tipsy Turtle:

No Resort Amenities: This property does not participate in the Resort Rental Program. As a result, amenities provided by the Resort, including swimming pools, the lagoon, child care center, boat/trailer storage, and similar services, are not available with this rental. If you have any questions or need further information, please don't hesitate to ask.

No Onsite Boat Dockage/Trailer Parking: Boat dockage and/or trailer parking is not available on-site. Duck Key Marina offers rental options for slips and trailer parking, making it convenient for those looking to explore the surrounding waters.

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 to maintain a smoke-free environment for all guests.

No Pets: Per the HOA, pets are strictly prohibited on the resort property or within the property to maintain a pet-free environment for all guests.

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

Sleeps Maximum of 4 Guests:

Bedroom 1 (2nd Floor): Queen Bed, En-Suite Bathroom, Smart TV

Bedroom 2 (2nd Floor): Queen Bed, En-Suite Bathroom, Smart TV

Living Room: Sofa, Chair, Smart TV

Kitchen: Nicely equipped (all things necessary to prepare and serve a meal)



- Private Upper/Lower Balconies

- Outdoor Seating

- Linen's and towels provided

- There are 2 exterior cameras at the property, 1 at front door facing the front stairs and 1 at the back door facing the back stairs.

5069 Sunset Village Dr Duck Key, FL 33050

Sleeping Arrangements

Bedroom 1 Queen
Bedroom 2 Queen

Bathroom Configuration

Bathroom 1: Combo Tub Shower, Toilet
Bathroom 2: Combo Tub Shower, Toilet
Bathroom 3: Toilet

Property Rules

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


Air Conditioning
Clothes Dryer
Covered Patio
Enhanced Cleaning
Hair Dryer
Private Entrance
Satellite or Cable
Self Check-In
Smoke Alarm
Smoke Detectors
Washing Machine
Basketbal Court
Beach Front
Beach View
Car Necessary
Car Not Necessary
Car Recommended
Cleaning Disinfection
Coffee Maker
Coin Laundry
Communal Pool
Computer Monitor
Deepsea Fishing
Desk Chair
Dining Table
Dishes Utensils
Eco Tourism
Enhanced Cleaning Practices
Fire Pit
Fishing Bay
Fitness Center
Golf Course Front
Golf Course View
Heated Pool
Hot Tub
Jet Skiing
Kitchen Island
Linens High Temp Wash
Minimum Age Limit
Near Ocean
Ocean Front
Ocean View
Pets Not Allowed
Pool Table
Private Pool
Scuba Or Snorkeling
Self Checkin Checkout
Smart Tv
Water View



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 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 Tipsy Turtle, 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.



Tipsy Turtle in Duck Key is Awesome
5/5 stars
Tipsy Turtle in Duck Key is the nicest VRBO I have ever stayed in ! The attention to detail is outstanding. It has a beautiful water view and is within walking distance of anything you could possibly want. I can't wait to return.

Thank you for your glowing review! We're thrilled to hear that Tipsy Turtle in Duck Key is the nicest VRBO you've ever stayed in and that you appreciated the outstanding attention to detail. We're delighted that you enjoyed the beautiful water view and the convenient location within walking distance of everything you could possibly want. We can't wait to welcome you back for another wonderful stay!

- Manager Response
Should Be Call Terrific Tipsy Turtle!
5/5 stars
I live in Naples and for the last 20 years have been going to The Keys for a "staycation" and I encourage other FL local to do the same. The Tipsy Turtle is by far my favorite find. Based on the pictures, I knew it would be special but the accommodations exceeded my high expectations. I felt pampered my entire stay in the clean and plush surrounding while still enjoying the awesomeness of the middle-key vibe with central access to great fishing and a reasonable drive to Key West for the day. I was torn between enjoying the views from my upper deck patio or going out locally for great food, so no bad choice either way. My son especially enjoyed the quick walk to the marina with more tarpon than the infamous Robbies, both he and my husband fished from the banks daily. While there are plenty of great local food option, I enjoy breakfast and sometimes a late night snack and the kitchen had everything I needed. Staying at the Tipsy Turtle was a special family getaway that allowed me the luxury to RELAX but my guys to have an equally good time fishing/playing.
- Missy

Missy, Thank you for sharing your experience at The Tipsy Turtle! We're thrilled to hear that you had such a wonderful stay and that our accommodations exceeded your high expectations. It's fantastic to know that you felt pampered in the clean and plush surroundings while still enjoying the vibrant Middle Keys atmosphere. We're glad you appreciated the central access to great fishing and the convenience of a reasonable drive to Key West for the day. It sounds like you had some amazing family moments, whether enjoying the views from the upper deck patio or exploring the local area for food and fishing. We're delighted that our kitchen had everything you needed for your meals, and we're thrilled to have provided you with a special family getaway where you could relax while your guys had an equally good time fishing and playing. Thank you for choosing The Tipsy Turtle, and we hope to welcome you back for another fantastic stay in the future!

- Manager Response
3/5 stars
The house is beautiful kitchen wonderful full of everything you need Beds and bathroom adequate. Double standard in this key no pets aloud but they are everywhere there is no beach to access only in private areas . Definitely a double standard here no sunset views from house only view of large metal building and very noisy from bridge traffic!
- Sandra
5/5 stars
My family enjoyed our stay at Tipsy Turtle. It was my wife and my first time at a Air B&B. It was exactly as shown in the photos. When we arrived the place was very clean. If you are going to visit the Florida Keys and want a very nice place to stay I would totally recommend Tipsy Turtle.
- Joseph

Joe, thank you so much for choosing Tipsy Turtle for your first AirBnB experience! We're thrilled to hear that you and your family enjoyed your stay, and that the cleanliness and accuracy met your expectations. We appreciate your recommendation and hope to welcome you back to the Florida Keys in the future!

- Manager Response
Amazing villa
5/5 stars
This amazing up to date villa did not disappoint. The owner took great care in furnishing the villa with high end furniture and state of the art kitchen and bathroom fixtures. In the morning you can sip your coffee on the porch and watch the iguanas play on the grass! We will surely come back to the Tipsy Turtle next year!
- Robert & Barbara

Robert, Thank you for your wonderful feedback! Delighted to hear you enjoyed the high-end amenities and the playful iguanas at Tipsy Turtle Villa. We look forward to welcoming you back next year for another memorable stay.

- Manager Response
Tipsy Turtle
4/5 stars
Tipsy Turtle is beautifully appointed! When we arrived, it was perfectly clean. The towels, extra blankets and tissues were folded into designs. It was like entering a cabin on a cruise ship. The view from the unit is obstructed a little by the marina, but it is still lovely. I notified the property agent about a couple of insignificant details and received an immediate response. The only thing that we did not like was that the lights and fans in the upstairs bathrooms turn on automatically when you enter the room. Even if you turn them off quickly, they turn back on in a few seconds. Therefore, if you go to the restroom in the middle of the night, the light and fan comes on which will likely fully wake up the person going to the bathroom and his/her roommate. We figured out a way to bypass the system. Just for information - the coffee maker is a new Keurig which will accommodate pods and a 12 cup coffee pot for ground coffee. However, you will need coffee filters (cup shaped, not cone-shaped) for the coffee pot. These small details did not take away from how terrific this unit is and the excellent customer service that accompanied our stay.
- Beth

Beth thank you for the review! We are glad you enjoyed Tipsy Turtle and all the little details that made your stay nicer. We hope to host you again soon.

- Manager Response
Beautiful Villa
5/5 stars
Our stay was very pleasant. The villa was beautiful and just as listed. We would definitely stay there again.
- Susan Vetter

Susan thank you for the review! We are glad you found Tipsy Turtle to be beautiful and pleasant during your stay in the Keys. We hope to host you again soon.

- Manager Response

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