Ananda - Discover Your Blissful Getaway, Steps from Smathers Beach, Shared Pool & Dog-Friendly Vibe!

2 BR
2 Baths
Sleeps 6


Welcome to "Ananda," your gateway to the ultimate tropical retreat, nestled just a short stroll away from the pristine shores of Smathers Beach. This exquisite condo offers the ideal setting for immersing yourself in relaxation and creating unforgettable memories in Key West. Start your day with a refreshing dip in the shared pool, or unwind in the bubbling hot tub, all while enjoying the lush tropical surroundings. Sip on your favorite cocktails as you take in breathtaking views from your private balcony, where the beauty of Key West unfolds before your eyes. Immerse yourself in the local culture as you embark on culinary adventures, sampling the finest local cuisine and experiencing the vibrant nightlife of Duval Street. Capture these moments with selfies at iconic landmarks such as the Southernmost Point and the historic Mile 0 sign, marking the beginning of an unforgettable Key West journey. Ananda invites you to embrace the tropical serenity and vibrant charm of Key West. Book your stay today and make cherished memories in this island paradise. Your Ananda experience awaits!

At Ananda, we're pleased to offer the option of bringing along your canine companions, allowing you to share your vacation with your four-legged family members. Up to two dogs weighing 30 lbs or less will be considered with the payment of a pet fee of $10 per night per pet, and registration through our third-party pet screening site (a $20 fee). Please take a moment to review our pet policy before booking and complete the registration process via the provided link after confirming your reservation.

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

Minimum Rental Period: The Homeowners' Association (HOA) mandates a minimum rental period of 30 nights, with no exceptions.

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 to maintain a smoke-free environment.

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

Sleeps Maximum of 6 Guests:

Bedroom 1: King Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV)

Bedroom 2: King Bed, Smart TV (no cable/satellite TV)

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

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


- Elevator

- Shared Pool/Spa

- Balcony with Outdoor Seating

- Tennis Court

- BBQ Grills and Picnic Tables

- Electric Car Charging

- One Covered Parking Space Included

- Linens and towels provided

- 1.5 miles to Duval Street

- 2.7 miles to Mallory Square

- 3.0 miles to Fort Zachary Taylor State Park & Beach

1901 S Roosevelt Blvd, 106W Key West, FL 33040

To purchase a vacation condo like this one, Dawn McComish with LoKation Real Estate Brokerage

Sleeping Arrangements

Bedroom 1 King
Bedroom 2 King
Living Room Sofa Queen

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
Car Wash Station
Clothes Dryer
Coffee Maker
Communal Pool
Electric Car Charging
Enhanced Cleaning
Hot Tub
Pets Considered
Private Entrance
Self Check-In
Smoke Alarm
Smoke Detectors
Washing Machine
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 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 Ananda, 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.



Great accommodations in Key West, FL
5/5 stars
Ananda Key was the perfect place to spend out families summer vacation. The location was fantastic, right across the street from Smathers Beach. Complex was very well maintained, clean, and safe. We rented a golf cart for the week which was a fun ride around town. Lindsay was an incredible host and made sure that her condo has everything needed for a comfortable stay. We spent a lot of time outside in the heat and water so having the washer/dryer was fantastic. We hope to visit again soon.
- Nicole
Ananda Stay
5/5 stars
When I first came upon this condo, it seemed almost too good to be true. We thought there had to be a catch! However everything was as perfect as it seemed online. Lindsay is the most thoughtful, detailed, available, personable and gracious host. She provided us with all the comforts of home as well as information we needed. She suggested places to shop, eat and see. This condo is just perfect! The amenities are new and well researched brands. Her kitchen was stocked with supplies we needed to enjoy meals in, bathroom was stocked with towels, mats, wash clothes, toilet tissue, and even shampoo. The walk in closets were stocked with bedding supplies. She has computers for working remotely. Ananda has a washer and dryer, beach towels and tennis racquets! The beds are comfy and overall decor is warm and beachy. There is a porch overlooking a large pond. It is a private, quiet area. The neighbors are friendly, grounds are immaculate and landscape is gorgeous. The location is incredible. You are far enough from the crowds to get work done or just relax, but a bike ride away. You are across the street from Smathers Beach. There is a salt water pool, hot tub and sauna. Lindsay had excellent restaurant recommendations and was of great help in anything we needed. She went way beyond to make our stay comfortable and memorable. Thank you Lindsay and Anana Key West for a wonderful stay! We will be back!
- Debbie

Debbie thank you for your awesome review! It is very nice of you to share the experience of your stay at Ananda in Key West. We agree that there are so many great things to mention about this condo along with everything that is offered. Thanks again and we hope to host you again soon.

- Manager Response

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