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**CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…

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Property grounds
Property grounds
3 bedrooms, desk, iron/ironing board, free WiFi
Fridge, microwave, oven, stovetop
Fridge, microwave, oven, stovetop

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 82227 sq ft

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Pet friendly
  • Kitchen
  • Pool

Explore the area

Map
Cudjoe Key, FL
  • Venture Out Keys
  • Venture Key
  • Florida Keys Beaches
    ‪10 min drive‬
  • Key West, FL (EYW-Key West Intl.)
    ‪40 min drive‬

Room options

About the neighborhood

Summerland Key

Seaside stay .Within a 10-minute walk of this Cutthroat Harbor Estates vacation home, you'll find Venture Out Keys and Venture Key. Also, Out Key is within half a mile (1 km) and Florida Keys Beaches is within 3 miles (5 km).

What's nearby

  • Upper Sugarloaf Key - 9 min drive - 5.0 miles
  • Florida Keys Beaches - 10 min drive - 5.3 miles
  • Key West Visitors Center - 20 min drive - 12.4 miles
  • Sugarloaf Beach - 23 min drive - 11.9 miles
  • Bahia Honda State Park - 31 min drive - 20.8 miles

Getting around

  • Key West Intl. Airport (EYW) - 32 min drive

Restaurants

  • ‪Mangrove Mama's - ‬7 min drive
  • ‪Boondocks Grille & Draft House - ‬9 min drive
  • ‪Kiki's Sandbar - ‬11 min drive
  • ‪The Square Grouper Bar & Grill - ‬3 min drive
  • ‪Looe Key Tiki Bar & Grill - ‬9 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

**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
** 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

Property manager

Last Key Realty

Languages

English, French, Spanish

Similar properties

Property amenities

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Car recommended
  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Wheelchair accessibility
  • Smoking not allowed

Services and conveniences

  • Concierge services
  • Iron/ironing board

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near the marina
  • Near the sea

Things to do

  • Heated pool
  • Tennis
  • Basketball nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Water tubing nearby
  • Windsurfing nearby

Safety features

  • 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 (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Unit size: 2,227 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • Pets are welcome
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

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
Onsite 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 there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.

Property is also known as

208

Frequently asked questions

How close is **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… to the airport?

This vacation home is 21.4 mi (32-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… to the beach?

This vacation home is 4.1 mi (8-min drive) from Florida Keys Beaches and 11.2 mi (22-min drive) from Sugarloaf Beach. Don't forget your sunscreen!

Does **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…?

No, there is no casino at this vacation home.

What time is check-in at **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…?

Check-in begins at 4:00 PM.

Is there free parking at **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…?

Free parking is not available at this vacation home.

Does **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… have a pool?

Yes, there's a private pool.

Does **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… have a spa?

There are no spa services available at this vacation home.

How close is **CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… to downtown Summerland Key?

This vacation home is 2 mi away from Summerland Key.

**CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES… Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 2 out of 2 reviews
Rating 8 - Good. 0 out of 2 reviews
Rating 6 - Okay. 0 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Kim S.

Liked: Cleanliness

Perfect Waterfront Getaway in the Keys – Dog-Friendly with Top-Notch Amenities!

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!
Stayed 31 nights in Apr 2025

10/10 Excellent

Michael W.

Liked: Cleanliness

Comforts of. Home.

1st I would like to say Nadia went above and beyond to make our trip.. Outstanding. It was peaceful it was comfortable it was everything it said it was and we loved it
Stayed 29 nights in Mar 2023