Carefree on Cudjoe

Monthly Rentals Only - Choose 29 Nights for a Full Quote

Address: 22927 Drake Lane Location: Cudjoe Key Type: Private Home
3 Beds 3 Baths Sleeps 8 Pets Allowed
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!
From the moment you arrive to this spectacular Florida Keys home, you will feel all your stresses and worries simply melt away. CAREFREE ON CUDJOE is an expansive waterfront property that evokes the easy-going nature of Keys living and provides an ideal setting for those looking to enjoy a ‘carefree’ vacation. There will certainly not be a shortage of fun to be had at CAREFREE ON CUDJOE; spend your days floating in the heated pool under the sun with beverage in hand or hop in your boat docked right outside to explore the beautiful waters of the Lower Keys. Included with your rental is Last Key Realty’s Five-Star Guest Services and Complimentary Concierge, known for providing memorable vacations. So leave the worries to us and prepare to experience the laidback lifestyle of the Florida Keys at CAREFREE ON CUDJOE.


CAREFREE ON CUDJOE is located at Mile Marker 23 on Cudjoe Key. You'll be only a 30-minute drive or Uber ride from downtown Key West, and the commute is beautiful: sapphire blue waters on either side of the road. Best of all, you won't even have to go far to find restaurant and entertainment options within minutes of your front door. Take a leisurely stroll or bike ride to Keys' favorite, Square Grouper, for fresh seafood and live music. You’ll also be within a few minutes of Broil Small Island Steakhouse and Tonio’s Seafood Shack and Tiki Bar.


CAREFREE ON CUDJOE has every coveted outdoor amenity one could ask for. Situated on an oversized corner lot, there is over 100 feet of boat dockage and the 14,000 lb lift allows for you to take your boat out of the water when needed. The floating dock is perfect for jet skis or smaller water crafts. There’s a convenient fish cleaning station next to the boat dock so you can clean your fresh catch before throwing it on the grill. Launch the tandem kayak right from your back yard to enjoy the abundance of marine life in this area. The heated pool gets plenty of sun all day long and there are multiple seating and lounging options in both the sun and shade. Gather the group under the covered patio for a poolside BBQ using the propane grill and outdoor dining table that seats 6. The grounds also include ample parking for multiple vehicles, an RV, boat trailer, and more. Guests can also use the snorkel gear and 2 sets of golf clubs on property.


This elevated Keys home offers a homey, comfortable interior that complements the sunny, beachy exterior. The gorgeous ocean views can be appreciated from every angle of the living area. There are plenty of seating options for everyone in your group to gather in front of the large flat screen TV. The fully equipped gourmet kitchen includes stainless steel appliances and every tool you’ll need to prepare meals at home. The dining area inside has seating for 6 and the dining area on the screened in porch also has seating for 6.


** Master Suite - Located on the Second Floor with a King bed, a flat screen TV, a private balcony, and an en-suite bathroom with a walk-in shower and a soaker tub.

** Second Bedroom - Located on the First Floor with a Queen bed, a flat screen TV, a private balcony, and direct access to the hall bathroom with a shower and tub combo.

** Bonus Room – Located on the First Floor with a Twin trundle bed and access to the shared hall bathroom with a shower and tub combo.

** Guest House Suite - Located in the private Guest House with a Queen bed, a flat screen TV, and an en-suite bathroom with a walk-in shower. The guest house has a full kitchen, dining area, and living room with a Queen sleeper sofa.


** Washer & Dryer
** Central Heat and A/C
** Ceiling Fans
** Flat Screen Cable TVs in Living Room & All Bedrooms
** Fully Equipped Kitchen
** Basic stock of spices
** Starter supply of paper products
** Starter set of cleaning products
** Linens and Towels provided
** Wireless high-speed Internet access and HULU Live TV is included
** Full Time Concierge Service

In addition, this fully stocked home also includes, but is not limited to the amenities on this list:

** Fully Fenced & Landscaped Private Yard
** Private Heated Pool
** Propane BBQ Grill
** 100’ Seawall and Floating Dock
** 14k lb Boat Lift
** Fish Cleaning Station
** Double Kayak w/ Paddles
** Snorkel Gear
** 2 Sets of Golf Clubs
** Queen Sleeper Sofa
** Ample Off-Street Parking

Other notes:

** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.
** Additional interim cleanings available
** This property will accommodate up to 8 adults
** Pets Allowed

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  • Smoke Detector
  • Car Recommended
  • Bath & Pool Towels Provided
  • Balcony
  • Linens & Pillows Provided
  • Off-Street - Carport
  • Off-Street - Driveway
  • First Aid Kit
  • Fire Extinguigher
  • Hair Dryer
  • Cooking Spices
  • Refrigerator
  • Dishwasher
  • Dishes & Utensils
  • Keurig & Drip Coffee Makers
  • Toaster
  • Microwave
  • Blender
  • Cable
  • TV in Living Room
  • WiFi
Indoor Amenities
  • Washer
  • Dryer
  • Air Conditioning
  • Iron & Ironing Board
  • Heating
Outdoor Amenities
  • Pool Heat Available
  • Boat Slip
  • Propane Grill
  • Beach Essentials
  • Private Pool
  • Museums
  • Historic
  • Water View
  • Medical Services
  • Botanical Garden
  • Marina
  • Library
  • Hospital
  • Babysitting
  • Festivals
  • Ocean View
  • Cinemas
  • Restaurants
  • ATM/Bank
  • Playground
  • Shopping
  • Churches
  • Near Ocean
Nearby Activities
  • Roller Blading
  • Jet Skiing
  • Pier Fishing
  • Scenic Drives
  • Tennis
  • Wind Surfing
  • Fishing
  • Health Beauty Spa
  • Live Theater
  • Snorkeling
  • Walking
  • Beach Combing
  • Scuba or Snorkeling
  • Reef
  • Spa
  • Massage Therapist
  • Boating
  • Cycling
  • Swimming
  • Sailing
  • Golf
  • Deep Sea Fishing
  • Para-sailing
  • Basketball Court
  • Sight Seeing
  • Water Tubing
Perfect For
  • Family
  • Eco Tourism
  • Romantic
  • 1 King
  • 3 Queen
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