*CAREFREE ON CUDJOE* Waterfront Home & Pool + Last Key White Glove Service. | House in Cudjoe Key

8.8 (3 Reviews) |   Pet Friendly   3 Bedrooms  3 Bathrooms  9 Guests
Cutthroat Harbor Estates House | *CAREFREE ON CUDJOE* Waterfront Home & Pool + Last Key White Glove Service.

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* Waterfront Home & Pool + Last Key White Glove Service is located in Cutthroat Harbor Estates. *CAREFREE ON CUDJOE* Waterfront Home & Pool + Last Key White Glove Service provides accommodation, featuring Security/Safety, Sports/Activities, Barbecue/Outdoor Cooking, among other amenities. This House features Air Conditioner, Parking and Pet Friendly to make your stay a comfortable one.

*CAREFREE ON CUDJOE* Waterfront Home & Pool + Last Key White Glove Service 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
Guest Services
Barbecue/Outdoor Cooking
Child Friendly
Hot Tub
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Air conditioning
Bathrooms
  • 3 bathrooms
  • Hair dryer
  • Towels provided
Bedroom
  • 3 bedrooms
  • Bed sheets provided
  • Dining table
  • Living room
Kitchen
  • Toaster
  • Refrigerator
  • Ice maker
  • Coffee/tea maker
  • Oven
  • Dishwasher
  • Cookware/dishes/utensils
  • Stovetop
  • Microwave
Laundry
  • Laundry facilities
  • Near laundromat
  • Washing machine and dryer
Parking
  • Onsite parking
  • Car recommended
Pet Friendly
  • Service animals exempt from fees
  • Pet friendly
Accessibility
  • Smoke-free property
Activities
  • Basketball nearby
  • Swimming nearby
  • Windsurfing nearby
  • Water tubing nearby
  • Parasailing nearby
  • Tennis on site
  • Sailing nearby
  • Golf nearby
  • Fishing nearby
  • Ecotours nearby
Entertainment
  • Smart TV with cable/satellite service
General
  • Unit size: 2227 sq ft (207 sq m)
  • French
  • Spanish
  • English
  • Near the sea
  • Near a hospital
  • Near a health or beauty spa
  • Desk
  • Desk chair
Guest Services
  • Concierge services
  • Iron/ironing board
Internet
  • Free WiFi
Outdoors
  • Barbecue grill
  • Firepit
  • Balcony
Security/Safety
  • Fire extinguisher
  • First aid kit
  • 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)
Spa
  • Private pool
  • Hot tub
  • Heated 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

David K.
Mar 15, 2026 10:42:05 PM
Review Score:   6
Summary: 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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FAQ's

Is this property pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the property 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 property?

Best-rates for the Cutthroat Harbor Estates house starts from $443 per night with includes TV, Private Pool, Ocean View, Balcony/Terrace, Kitchen, Laundry, Parking, Pet Friendly, Child Friendly, Internet, Bedding/Linens, Pool, Oceanfront, Security/Safety, Sports/Activities, Barbecue/Outdoor Cooking, Hot Tub, Air Conditioner, View, Wellness Facilities, Guest Services with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

Is property 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 property 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 property?

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 property?

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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