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

10.0 (2 Reviews) |   Pet Friendly   3 Bedrooms  3 Bathrooms  9 Guests
Cutthroat Harbor Estates House | *CAREFREE ON CUDJOE @ THE BAY* Waterfront Home & Pool + LAST KEY SERVICES…

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
** 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

*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 Pet Friendly, Pool, Private Pool, among other amenities. This House features Pet Friendly, Pool, Private Pool, 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.

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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
Hot Tub
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Air conditioning
  • Heating
Bathrooms
  • Towels provided
  • 3 bathrooms
  • Hair dryer
Bedroom
  • Bed sheets provided
  • 3 bedrooms
  • Dining table
  • Living room
Kitchen
  • Toaster
  • Coffee/tea maker
  • Ice maker
  • Oven
  • Refrigerator
  • Dishwasher
  • Spices
  • Microwave
  • Stovetop
Laundry
  • Washing machine and dryer
  • Laundry facilities
  • Near laundromat
Parking
  • Onsite parking
  • Car recommended
Pet Friendly
  • Pet friendly
Accessibility
  • Smoke-free property
Activities
  • Marina nearby
  • Power boating nearby
  • Scuba diving nearby
  • Golf nearby
  • Sailing nearby
  • Fishing nearby
  • Tennis on site
  • Swimming nearby
  • Parasailing nearby
  • Ecotours nearby
Entertainment
  • Smart TV with cable/satellite service
General
  • Unit size: 2227 sq ft (207 sq m)
  • English
  • French
  • Spanish
  • Near a hospital
  • Near a health or beauty spa
  • Near the sea
  • Desk chair
  • Desk
Guest Services
  • Iron/ironing board
  • Concierge services
Internet
  • Free WiFi
Outdoors
  • Balcony
  • Firepit
  • Barbecue grill
Security/Safety
  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
Spa
  • Hot tub
  • Heated pool
  • Private pool

Policies

Check-in
Check-in time starts at 4:00 pm minimum check-in age: 25
Check-out
Check-out before 10:00 am
Child Policy
Children are welcome.
Event Policy
No events allowed
Pet Policy
Pets allowed service animals are welcome, and are exempt from fees
Smoking Policy
Smoking is not permitted

Extra-person charges may apply and vary depending on property policy government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges host has indicated there is a smoke detector on the property host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher and a first aid kit special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

Reviews

Kim S.
May 22, 2025 07:07:56 PM
Review Score:   10
Summary: 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!
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