Prime Time

Prime Time: A Tropical Paradise on Big Pine Key, Canal Front Duplex, Swift Access to Atlantic & Gulf

2 BR
2 Baths
Sleeps 6


Discover Prime Time – Your Tropical Canal Front Retreat on Big Pine Key! This delightful canal front duplex brings the essence of the Florida Keys to life, offering a vibrant tropical ambiance and direct access to open waters. Dock your boat along the seawall and set off on fantastic fishing adventures just minutes away. Start your day on the screened porch, where you can savor your morning coffee or unwind with your favorite cocktail while watching boats cruise by. The serene setting is perfect for soaking in the laid-back Keys lifestyle. There's an abundance of activities to enjoy in the Florida Keys, with Key West a mere 40 minutes away and Marathon just 20 minutes from your doorstep. Explore the local attractions, restaurants, and the natural beauty of the region. Should you require additional space, consider our listing for 'Prime Time 2,' as both sides of this duplex may be available, making it ideal for accommodating larger family gatherings. Your tropical paradise in the Keys awaits at Prime Time!

Please be aware of the following essential policies for your stay at Prime Time:

Minimum Rental Period: County zoning requires a minimum rental period of 28 nights, and no exceptions can be made.

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.

Peak Season Rentals: If you're interested in renting December through March, all bookings must be for the entire month, starting the beginning of the month and ending the end of the month. Consecutive months may be booked, as long as they follow this requirement. If you're interested in booking other dates, please contact us for approval prior to booking. Bookings made during these months that do not adhere to these requirements are subject to cancellation by the host.

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

No Pets: Pets are strictly prohibited within the property to maintain a clean and allergen-free environment for all guests.

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

Boating Safety: Due to bridges and varying water depths, it is your responsibility to verify that your boat can safely navigate the local waters, access the canal, and fit the listed dockage before booking this property. Please ensure that your boating activities are conducted safely and in compliance with local regulations.

Sleeps Maximum of 6 Guests:

Bedroom 1: King Bed, En-Suite Bathroom, Flat Screen TV with FireStick (no cable/satellite TV)

Bedroom 2: Two Twin Beds

Living Room: Sofa with Pull-Out Full Bed, Smart TV (no cable/satellite TV)

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



- Private Dock (30 feet of seawall)

- Fish Cleaning Station with Water

- Outdoor Seating

- Propane BBQ Grill

- There is parking for a maximum of 2 vehicles (including boat trailers) on the property. Recreational Vehicles may not be parked on the property.

- Linen's and towels provided

29643 Constitution Ave Big Pine Key, FL 33043

Sleeping Arrangements

Master King
Guest Twin (2)
Living Room Sofa Full

Bathroom Configuration

Bathroom 1: Shower, Toilet
Bathroom 2: Shower, Toilet

Property Rules

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


Air Conditioning
BBQ Grill
Clothes Dryer
Coffee Maker
Covered Patio
Enhanced Cleaning
Hair Dryer
Iron and Board
Private Entrance
Screened Patio
Self Check-In
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 Prime Time, 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.



Constitution Ave property
5/5 stars
Liked the house. Great kitchen, big, new appliances. We struggled with the fire tv. The screened in porch was a disappointment. Old, uncomfortable, paint peeling furniture. Tina was great. She respond to us quickly. She was very helpful
- Mike

Thank you for your review Mike! We are glad you liked Prime Time! We hope to host you again soon.

- Manager Response
Good Times On Big Pine.
5/5 stars
Me and my wife had a really great time at prime time. Great location, we ran are inflatable all over the place. Ran to Sea Camp ,picnic Island and the furthest we ran to content key. Only a half hour to Key West by car went there three times during the windy days. We went to Islamorada and met friends one day also. Primetime was clean and a great place to stay for the month. This was our first big trip in retirement and thoroughly enjoyed it. Would love to do it again.!!!
- Dave Whitty

Thank you Dave for your review. It was great meeting you and your wife and we're glad you had a great time at Prime Time. We hope to see you again soon.

- Manager Response
Big Pine Key Adventure
2/5 stars
We enjoyed our month stay in Big Pine Key. We were five days into the rental when the refrigerator/freezer died. Fortunately, there was a commercial ice maker on the porch and a small dorm style refrigerator. The property manager brought another small unit. The property owner came the following Wednesday with a used appliance. The ice maker in the freezer did not function. The broken appliance was placed on the porch. This created a traffic jam of furniture on the porch. My husband called the property manager with this news and requested a financial credit toward a future rental. The property manger indicated he would check with the owner and get back with us. The day we checked out we made an additional call. It has been 10 days since the last call with no response. We own rental properties and understand that "things happen". However, communication is extremely important. We would prefer a negative response rather than silence.
- Mary

Thank you for your review and we're glad you enjoyed your stay at Prime Time. We are sorry that the refrigerator/freezer died during your stay. Fortunately, as you mentioned, there was a small dorm style refrigerator and commercial ice maker on the porch, as well as an additional small dorm style refrigerator we delivered the same day. The refrigerator was under warranty and the owner immediately called the warranty company and was able to schedule a service call for that Wednesday. In the meantime, the owner purchased a used refrigerator just in case the current refrigerator could not be fixed. The owner drove 7 hours each way to deliver the used refrigerator that Wednesday, as well as meet the service tech. As you’re aware, the service tech did not show up and when the owner called the warranty company, he was informed there was a mistake and the service tech won’t be out until the day you were scheduled to check out. We installed the used refrigerator and moved the broken refrigerator to the back porch where it was out of the way and the tech would still be able to access electricity to inspect the refrigerator. There was no mention of any issues with the placement of the broken refrigerator that day or afterwards. After installing the used refrigerator, you discovered and notified us that the ice maker on it wasn’t working, but stated that was ok because you had the commercial ice maker on the porch. You did call us a couple days later and asked for a discount for a future booking for the “inconvenience”. We did reach out to the owner and unfortunately it took longer than anticipated, we apologize for that. The refrigerator could not be repaired and will be replaced under warranty with a new refrigerator. We feel strongly that our communication during your stay was timely, effective and we (and the owner) did our best to rectify the situation as quickly as possible to the best of our ability.

- Manager Response

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