*CAREFREE ON CUDJOE @ THE BAY* Waterfront Home & Pool + LAST KEY SERVICES… | House in Cudjoe Key
House


Available rates:
3 Bedroom House in Cutthroat Harbor Estates, Cudjoe Key
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
** 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
** Max of 2 Pets Allowed with Additional Fee of $200 per pet
*CAREFREE ON CUDJOE @ THE BAY* Waterfront Home & Pool + LAST KEY SERVICES… is located in Cutthroat Harbor Estates. *CAREFREE ON CUDJOE @ THE BAY* Waterfront Home & Pool + LAST KEY SERVICES… provides accommodation, featuring Balcony/Terrace, Security/Safety, Sports/Activities, among other amenities. This House features Balcony/Terrace, Security/Safety, Sports/Activities, to make your stay a comfortable one.
*CAREFREE ON CUDJOE @ THE BAY* Waterfront Home & Pool + LAST KEY SERVICES… has 3 Bedrooms , 3 Bathrooms, and max occupancy of 9 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Cutthroat Harbor Estates has interesting places to visit. If you want to learn more about the House in Cutthroat Harbor Estates, such as places to visit and things to do nearby, you can check below to learn more.

This Property is OneKey Eligible
Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.
Unique Amenities
- Air Conditioner
- Parking
- Pet Friendly
- Pool
- TV
- View
- Private Pool
- Ocean View
- Balcony/Terrace
- Oceanfront
- Security/Safety
- Sports/Activities
- Bedding/Linens
- Wellness Facilities
- Fireplace/Heating
- Guest Services
- Barbecue/Outdoor Cooking
- Child Friendly
- Internet
- Kitchen
- Laundry
Policies
What Our Guests say 500 + Reviews

FAQ's
Is this Cutthroat Harbor Estates house pet-friendly for guests?
Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.
Does the Cutthroat Harbor Estates house have a swimming pool?
Yes, this Cutthroat Harbor Estates house has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.
How much does it cost per night to stay in Cutthroat Harbor Estates house?
Best-rates for the Cutthroat Harbor Estates house starts from $643 per night with includes Air Conditioner, Parking, TV, Oceanfront, Fireplace/Heating, Laundry, View, Private Pool, Ocean View, Wellness Facilities, Guest Services, Child Friendly, Kitchen, Pet Friendly, Balcony/Terrace, Security/Safety, Sports/Activities, Internet, Pool, Bedding/Linens, Barbecue/Outdoor Cooking StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.
Is Cutthroat Harbor Estates house a family-friendly place to stay?
Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.
Is the Cutthroat Harbor Estates house wheelchair accessible or offer services for disabled guests?
Based on the information received from our partner, the Cutthroat Harbor Estates house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.
What is the minimum night stay policy for the Cutthroat Harbor Estates house?
Based on the information reported by the owner or manager, the Cutthroat Harbor Estates house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.
What cancellation policy is in place for Cutthroat Harbor Estates house?
Based on the information reported by the owner or manager, details for the cancellation policy for the Cutthroat Harbor Estates house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.
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