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

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

Entire home

3 bedrooms2 bathrooms

Popular amenities

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

Explore the area

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

Room options

Similar properties

About the neighborhood

Summerland Key

With a stay at this vacation home in Summerland Key (Cutthroat Harbor Estates), you'll be within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key. .This vacation home is 15.5 mi (25 km) from Bahia Honda State Park and 7.7 mi (12.3 km) from Lower Sugarloaf Sound.

What's nearby

  • Upper Sugarloaf Key - 8 min drive - 3.9 miles
  • Upper Sugarloaf Sound - 9 min drive - 4.7 miles
  • Florida Keys Beaches - 9 min drive - 3.8 miles
  • Lower Sugarloaf Sound - 13 min drive - 7.1 miles
  • Sugarloaf Beach - 20 min drive - 10.8 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
  • ‪Morning Joint - ‬11 min walk
  • ‪5 Brothers Two - ‬8 min drive
  • ‪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
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with an oven and a stovetop. There's a private balcony. Conveniences include a microwave and a washing machine.
Enjoy recreation amenities such as a fitness center or take in the view from a garden.
Guests will find features like internet access and onsite parking.

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
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

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total (up to 50 lbs per pet)

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

We should mention

This property does not have elevators

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