Entire home
**CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…
Holiday home in Summerland Key with private pool and kitchen
Photo gallery for **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…





Reviews
10 out of 10
Exceptional
3 bedrooms3 bathroomsSleeps 9206.9 sq m
Popular amenities
Explore the area

Cudjoe Key, FL
- Place, Upper Sugarloaf Key9 min drive
- Place, Upper Sugarloaf Sound10 min drive
- Place, Florida Keys Beaches11 min drive
- Airport, Key West, FL (EYW-Key West Intl.)46 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 @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…
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
Add dates for prices
Amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Pet-friendly
Have a question?
Get instant answers with AI powered search of property information and reviews.
Similar properties

BLUE PEARL - 5 Bedroom/ 4 Bathroom Pool, Kayak, Bike, Canal Front w/ Boat Lift
BLUE PEARL - 5 Bedroom/ 4 Bathroom Pool, Kayak, Bike, Canal Front w/ Boat Lift
- Pool
- Kitchen
- Washer
- Dryer
9.4 out of 10, (3 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
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
We should mention
A car is recommended for transport to and from this property
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 Bahia Honda State Park 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 cycling and ecotours.

Cudjoe Key, FL
What's nearby
- Upper Sugarloaf Key - 9 min drive - 7.3 km
- Upper Sugarloaf Sound - 10 min drive - 8.5 km
- Florida Keys Beaches - 11 min drive - 7.0 km
- Lower Sugarloaf Sound - 14 min drive - 12.5 km
- Sugarloaf Beach - 21 min drive - 18.4 km
Getting around
Restaurants
- Boondock's Grille & Drafthouse - 9 min drive
- Kiki's Sandbar - 11 min drive
- 5 Brothers Two - 9 min drive
- Morning Joint - 17 min walk
- Broil - 5 min drive
Frequently asked questions
About the host
Hosted by Last Key Realty
Languages:
English, French, Spanish
Premier Host
They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback




























