House in Cudjoe Key, FL
9 guests · 3 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this house rental
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 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.
THE LOCATION…
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.
THE PRIVATE POOL, BOAT LIFT & GROUNDS...
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.
THE LIVING AREA...
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.
THE ACCOMMODATIONS...
** 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.
ALL LAST KEY VACATION HOMES INCLUDE:
** 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 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
** Jacuzzi Spa
** Propane BBQ Grill
** 100’ Seawall and Floating Dock
** 14k lb Boat Lift
** Fish Cleaning Station
** Double Kayak w/ Paddles
** Snorkel Gear
** Bikes
** 2 Sets of Golf Clubs
** Outdoor TV
** 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
** Max of 2 Pets Allowed with Additional Fee of $200 per pet
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.
THE LOCATION…
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.
THE PRIVATE POOL, BOAT LIFT & GROUNDS...
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.
THE LIVING AREA...
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.
THE ACCOMMODATIONS...
** 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.
ALL LAST KEY VACATION HOMES INCLUDE:
** 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 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
** Jacuzzi Spa
** Propane BBQ Grill
** 100’ Seawall and Floating Dock
** 14k lb Boat Lift
** Fish Cleaning Station
** Double Kayak w/ Paddles
** Snorkel Gear
** Bikes
** 2 Sets of Golf Clubs
** Outdoor TV
** 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
** Max of 2 Pets Allowed with Additional Fee of $200 per pet
Amenities
Non-smoking
Pets allowed
Family friendly
Map of Cudjoe Key, FL
Ratings and reviews
10 / 10Outstanding·May 2025
We had an incredible month-long stay at this beautiful home in the Florida Keys! The house was spotless, well-equipped, and perfectly located right on the water. Having access to the boat lift made our time on the water even more enjoyable and convenient.The pool was a great bonus, and the outdoor space—including a nice screened-in porch that kept the bugs away—was perfect for relaxing after a day out boating or exploring. The incredible sunsets each evening were a highlight, and it was such a treat to be able to walk right out the door and go paddleboarding anytime we wanted.One of the best parts was that they allow dogs, so our pup Finn had a great time too!The management team was top-notch—very responsive and attentive, with a concierge service that went above and beyond by delivering packages and checking in to ensure we had everything we needed.Everything about this property made our stay easy, comfortable, memorable, and a short drive to Key West. We would absolutely stay here again and highly recommend it to anyone looking for a great spot in the Keys!
10 / 10Outstanding·Apr 2023
1st I would like to say Nadia went above and beyond to make our trip.. Outstanding. It was peaceful it was comfortable it was everything it said it was and we loved it
6 / 10Average·Mar 2026
The property was fantastic. Beautiful sunsets and an awesome swimming pool. The cottage was nice. The main house was OK. I wouldn’t say it was commiserate with the cost however. The furniture was a mish mash of stuff from what I would call garage sale level. There were stains on all the upholstery and the carpet. The pool was 65 degrees when I checked in. I was told the pool temperature was set to 90 degrees and the hot tub was set to 104. I had to manually go in and adjust the temperature so we could use them. The master bath is plumbed backwards so hot is cold and cold is hot. I had to call the property manager to figure this out. There were people constantly coming and going without us being notified. This was beyond the maintenance people that were scheduled to be there. The cleaning people never showed up for the mid stay cleaning. I had gotten up early and tidied the house and left for the day so as not to be in their way.they were supposed to be there at 10 AM. I returned after 3 PM and no one had come to clean. It was a big inconvenience. The house smells musty and the cottage has an over powering perfume smell that even after leaving all the doors and windows open for an afternoon could not be cleared. Not sure what they are trying to cover up. The home should be furnished like a 3m house not a college frat house. The outdoor furniture was dirty and stained as well. The chairs for the table on the balcony don’t go with the table so they are the wrong height.
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Top rated by guests
8.8Excellent
(3 Ratings)
"We had an incredible month-long stay at this beautiful home in the Florida Keys! The house was spotless, well-equipped, and perfectly located right on the water. Having access to the boat lift made ou..."
Kim S.Don't miss out! Price and availability may change
