Located in Cutthroat Harbor Estates, this vacation home is within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key. The vacation home includes a kitchen, a balcony, and a microwave.
You'll have the entire home to yourself and will only share it with other guests in your party.
Group Therapy Waterfront Keys Home – Pool, Tiki Hut, Dockage, & Monthly Rentals
Welcome to Group Therapy, your ultimate Florida Keys escape! This updated 3-bedroom, 2-bath waterfront home in Cudjoe Key offers a brand-new pool with sun shelf, shaded tiki hut, and 40 feet of concrete dockage — everything you need for extended island living. Just 30 minutes from Key West, it’s the perfect retreat for monthly renters seeking boating, fishing, and a laid-back lifestyle in a quiet residential neighborhood.
Outdoor Living & Amenities Lounge on the pool’s sun shelf, enjoy waterside dining in the screened porch for six, or unwind beneath the tiki hut. The fenced yard adds privacy and makes the home pet-friendly. Boaters will love the deep-water dockage — bring your own boat or rent one nearby to explore reefs, sandbars, and fishing grounds right off Cudjoe Key. An enclosed storage area and chest freezer make it easy to store gear and keep your catch fresh.
Spacious Interiors & Comfort Inside, the home is bright and airy with modern updates throughout. The fully equipped kitchen with island seating flows into a dining space for six and a comfortable living room with a large cozy (reclining) sectional and smart TV equipped with DirectTV. The top-floor master suite boasts double balconies with sweeping views and unforgettable stargazing at night. Each bedroom has its own balcony; two of three include wall-mounted smart TVs. . A brand-new in-unit washer and dryer makes extended stays easy. • Bedroom 1: King master suite, en-suite bath, double balconies • Bedroom 2: Queen bedroom • Bedroom 3: Twin bedroom with 2 beds
Neighborhood & Location Highlights Located at MM22 in Cudjoe Key, Group Therapy sits in a quiet, bike-friendly neighborhood with four bicycles provided.
Walk to local favorites: • Square Grouper – among the very best dining experiences in the Keys • My New Joint / 420 Lounge – cocktails, apps, and live music • My Morning Joint Café – the go-to for coffee, smoothies, + breakfast/lunch sandwiches
Cudjoe Key itself offers abundant opportunities for outdoor adventure and relaxation. Some of the best sandbars, reefs, and fishing grounds in the Florida Keys are right in your backyard. This island provides a relaxing escape from the busier tourist areas, with locally sourced seafood and authentic island experiences, while still being conveniently close to Key West’s attractions. Perfectly located between Key West and Marathon, it offers easy access to the vibrant cultural scene of Key West while giving you a tranquil base to return to at the end of the day.
Key Features at a Glance • Waterfront canalfront home with 40 ft dockage (bring your boat or rent nearby) • Brand-new pool with sun shelf • Tiki hut and outdoor lounging areas • Screened dining area for six, overlooking the water • 4 bicycles + nearby bike paths • Glass sliding door open to balconies off the living room, dining room, and every bedroom + master suite with double balconies & stunning views • Three smart TVs with DirectTV • Fenced yard + pet friendly • Covered off-street parking for 2 vehicles, with driveway space for 2 more or a trailer (4 total) • Brand-new washer/dryer in unit • Chest freezer + enclosed storage for boating/fishing gear • Quiet neighborhood, walking distance to dining, bars & coffee • Easy access to sandbars, reefs, kayaking, snorkeling & world-class fishing
The vacation home is air-conditioned and features a kitchen, 2 bathrooms, and a balcony, and there's space to spread out with 3 bedrooms. Other standard amenities include a washing machine and an ironing board.
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If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
Upper floors accessible by stairs only
Designated smoking areas
Services and conveniences
Iron/ironing board
Things to do
Gym
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
Fire extinguisher
General
Garden
Policies
Check-in
Check-in time starts at 4:00 PM
Minimum check-in age: 25
Check-out
Check-out before 11:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
Check-in must start on the 1st of the month. This home is available only for monthly stays (28+ nights).
Pool temp control is optional for $400/month; please request in advance.
Lift not for guest use; 40 ft dock with fenders available for your boat.
Pets
This property welcomes pets
Dogs only
2 total (50 lbs is the maximum weight per pet)
Service animals exempt from fees
Children and extra beds
Children allowed: ages 0-17
Events
Events allowed: family gatherings
Smoking
Smoking allowed: in designated areas
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
Parties and events (including family gatherings) are allowed on site; maximum attendees: 10
Long-term renters welcome
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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
Check-in: 4:00 PM
Check-out: 11:00 AM
Minimum check-in age: 25
We should mention
Details about charges, deposits, or other important information:
This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
Charges for extra guests may apply and vary depending on the property's policy.
A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
Parties and events (including family gatherings) are allowed on site. Maximum attendees: 10.
Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.
Additional information about polices, regulations, and more:
Long-term renters welcome.
There are no elevators.
Frequently asked questions
What is there to do near this vacation home?
This vacation home is situated in Cutthroat Harbor Estates, close to Florida Keys Beaches, Upper Sugarloaf Key, and Upper Sugarloaf Sound. You'll also find Venture Out Keys and Newfound Harbor Keys nearby.
Will I be able to park at this vacation home?
No, this vacation home doesn't offer parking.
Is this vacation home associated with a casino?
No, this vacation home is not connected to a casino.
Is there an indoor pool at this vacation home?
No, there is no indoor pool at this vacation home.
What amenities will couples enjoy at Group Therapy Waterfront Keys Home – Pool, Tiki Hut, Dockage, & Monthly Rentals?
Couples staying at this vacation home will value amenities like a kitchen, kitchens in some accommodations, as well as a garden.
Does Group Therapy Waterfront Keys Home – Pool, Tiki Hut, Dockage, & Monthly Rentals have a hot tub?
No, this vacation home doesn't have a spa tub.
Does this vacation home provide breakfast?
No, this vacation home doesn't offer breakfast.
Does this vacation home allow pets to stay free of charge?
Although dogs can't stay for free, they are welcome at this vacation home.
Does this vacation home have connecting rooms?
No, there aren't connecting rooms at this vacation home.
What is the closest airport to this vacation home?
The closest major airport to this vacation home is Key West Intl. Airport (EYW), which is 20.9 mi away (31 minutes by car). Another top airport is Marathon, FL (MTH-Florida Keys Marathon), which is located 29.3 mi away (39-minute drive).
Can I book a room with a balcony at Group Therapy Waterfront Keys Home – Pool, Tiki Hut, Dockage, & Monthly Rentals?
Yes, every accommodation at Group Therapy Waterfront Keys Home – Pool, Tiki Hut, Dockage, & Monthly Rentals comes with a balcony with some featuring water views.