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Group Therapy Waterfront Keys Home – Pool, Tiki Hut, Dockage, & Monthly Rentals

Summerland Key vacation home in Cutthroat Harbor Estates area

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Pool
Microwave, oven, stovetop, dishwasher
3 bedrooms, iron/ironing board, WiFi, bed sheets
Outdoor dining
Interior

Entire home

3 bedrooms2 bathrooms

Popular amenities

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

Explore the area

View in a map
Summerland Key, FL
  • Place, Venture Out Keys
  • Place, Upper Sugarloaf Key
    ‪8 min drive‬
  • Place, Florida Keys Beaches
    ‪10 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪44 min drive‬

Room options

About the neighborhood

Summerland Key

Cutthroat Harbor Estates stay.Your stay at this Cutthroat Harbor Estates vacation home places you within 6 miles (10 km) of Upper Sugarloaf Key and Florida Keys Beaches. Also within 9 miles (15 km) are Lower Sugarloaf Sound and Big Pine Key Flea Market.

What's nearby

  • Upper Sugarloaf Key - 8 min drive - 3.9 miles
  • Florida Keys Beaches - 10 min drive - 4.4 miles
  • Sugarloaf Beach - 20 min drive - 10.8 miles
  • Bahia Honda State Park - 37 min drive - 19.8 miles
  • Boca Chica Nude Beach - 39 min drive - 19.0 miles

Getting around

  • Key West Intl. Airport (EYW) - 31 min drive

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬8 min drive
  • ‪Kiki's Sandbar - ‬11 min drive
  • ‪5 Brothers Two - ‬8 min drive
  • ‪Morning Joint - ‬11 min walk
  • ‪Broil - ‬3 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.

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

Similar properties

Property amenities

Pool/Spa

  • Pool

Internet

  • Available in the house: WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Dishwasher
  • Microwave
  • Oven
  • Stovetop

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total (up to 50 lbs per pet)

Suitability/Accessibility

  • 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

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

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 2 (weight limit: 50 lbs per pet)
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

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
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. 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. Parties and events (including family gatherings) are allowed on site. Maximum attendees: 10. Long-term renters welcome. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation.

Frequently asked questions

How close is Group Therapy Waterfront Keys Home – Pool, Tiki Hut, Dockage, & Monthly Rentals to the airport?

This vacation home is 20.9 mi (31-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does Group Therapy Waterfront Keys Home – Pool, Tiki Hut, Dockage, & Monthly Rentals have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Group Therapy Waterfront Keys Home – Pool, Tiki Hut, Dockage, & Monthly Rentals to the beach?

This vacation home is 4.1 mi (8-min drive) from Florida Keys Beaches and 10.6 mi (19-min drive) from Sugarloaf Beach. Don't forget your sunscreen!

Does Group Therapy Waterfront Keys Home – Pool, Tiki Hut, Dockage, & Monthly Rentals offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Group Therapy Waterfront Keys Home – Pool, Tiki Hut, Dockage, & Monthly Rentals?

No, there is no casino at this vacation home.

What time is check-in at Group Therapy Waterfront Keys Home – Pool, Tiki Hut, Dockage, & Monthly Rentals?

Check-in begins at 4:00 PM.

Is there free parking at Group Therapy Waterfront Keys Home – Pool, Tiki Hut, Dockage, & Monthly Rentals?

Free parking is not available at this vacation home.

Does Group Therapy Waterfront Keys Home – Pool, Tiki Hut, Dockage, & Monthly Rentals have a pool?

Yes, there's a pool.

Does Group Therapy Waterfront Keys Home – Pool, Tiki Hut, Dockage, & Monthly Rentals have a spa?

There are no spa services available at this vacation home.

How close is Group Therapy Waterfront Keys Home – Pool, Tiki Hut, Dockage, & Monthly Rentals to downtown Summerland Key?

This vacation home is 2 mi away from Summerland Key.