Top-rated for creating memorable stays with your pets.
Firepit available
One of the few properties with a dedicated outdoor firepit.
Centrally-located
You're never far from where you need to be with this convenient location.
3 bedrooms3 bathroomsSleeps 9
Popular amenities
Private pool
Hot tub on site
Onsite parking available
Pet-friendly
Kitchen
Washing machine
Explore the area
Cudjoe Key, FL
Upper Sugarloaf Key
Place, Upper Sugarloaf Key
7 min drive
Florida Keys Beaches
Place, Florida Keys Beaches
8 min drive
Upper Sugarloaf Sound
Place, Upper Sugarloaf Sound
8 min drive
Key West, FL (EYW-Key West Intl.)
Airport, Key West, FL (EYW-Key West Intl.)
38 min drive
Rooms & beds
3 bedrooms (sleeps 9)
Bonus Room
1 Single Bed
Guest House
2 Queen Beds and 2 Double Sofa Beds
Master Suite
1 King Bed
Second Bedroom
1 Queen Bed
3 bathrooms
Bathroom 2
Guest House Bathroom
Master Bathroom
Spaces
Kitchen
Balcony
About this property
**CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service...
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
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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
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
About the area
Summerland Key
Located by the sea, this holiday home is in Cutthroat Harbor Estates, a neighbourhood in Summerland Key. Florida Keys Beaches and Coupon Bight Aquatic Preserve reflect the area's natural beauty and area attractions include Blue Hole and Wilhelmina Harvey Park. Big Munson Island and Looe Key National Marine Sanctuary are also worth visiting. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with ecotours and cycling.
National Key Deer Refuge Visitor Center - 16 min drive - 19.2 km
Getting around
Key West, FL (EYW-Key West Intl.) - 32 min drive
Restaurants
Boondock's Grille & Drafthouse - 9 min drive
Morning Joint - 17 min walk
Kiki's Sandbar - 11 min drive
The Bent Prop - 7 min drive
Looe Key Tiki Bar & Restaurant - 9 min drive
Frequently asked questions
Does **CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service... have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at **CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service...?
As of 18 Aug, 2026, prices found for a 1-night stay for 2 adults at **CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service... on 1 Oct, 2026 start from S$15,919, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is **CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service... pet-friendly?
Yes, pets are allowed at this property.
How much is parking at **CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service...?
On-site parking is available at the property.
What time is check-in at **CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service...?
Check-in begins at 4:00 PM.
What time is check-out at **CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service...?
Checkout is at 10:00 AM.
Where is **CAREFREE ON CUDJOE** Waterfront Home & Pool + Last Key White Glove Service... located?
Located in Cutthroat Harbor Estates, this holiday home is 0.4 mi (0.7 km) from Venture Out Keys and 2.4 mi (3.9 km) from Florida Keys Beaches. Venture Key and Out Key are also within 10 minutes.
About the host
Hosted by Last Key Realty
Languages:
English, French, Spanish
Premier Host
They consistently provide great experiences for their guests