Key West Happy Hideaway Gated Key West Golf Club: 2 Bedrooms, Pool Steps Away, 28 Night Stays

$126-370/night
2 Bedrooms • 2 Baths (1 full, 1 half) • Sleeps 3-6
Allows pets Internet Near Ocean Pool (more...)

A two bedroom townhome inside the gated Key West Golf Club, with a community pool a few steps from the door, a free gym in the clubhouse, and a Rees Jones golf course on the other side of the landscaping. Stays here start at 28 nights, so this is somewhere to settle into rather than pass through.

2 bedrooms  ·  1.5 bathrooms  ·  Sleeps up to 6  ·  780 sq ft

Inside

Living space downstairs, both bedrooms up

Renovated in the fall of 2024. You walk in at ground level to one bright open room holding the kitchen, the dining table and the living area, with sliding doors out to the screened porch. All linens and towels are provided, and there is a stacked washer and dryer in the unit.

  • Master bedroom, upstairs  Queen bed, ample closet space, and a private screened balcony with two chairs with pull out leg rests
  • Guest bedroom, upstairs  Full bed, some closet space, its own balcony with seating, and the stacked washer and dryer
  • Living room, downstairs  Full size sleeper sofa with bedding included, two comfortable chairs, one with a leg rest, and a flat screen TV
  • Hall bathroom, upstairs  Large shower, toilet and vanity. This is the only full bathroom in the house
  • Half bath, downstairs  Toilet and sink, off the living and dining area
  • Kitchen  New appliances, a dishwasher, an ice maker and a dining table for four, stocked for cooking real meals rather than reheating them

Outside

Four outdoor spaces, and a pool a few steps away

  • Screened porch, downstairs  Through the sliding doors, with a plush couch and a table for two. The landscaping closes it in, so golfers are not looking at you and golf balls are not coming at the house
  • Fenced back yard  Small and private, with a new Weber grill
  • Two balconies, upstairs  One off each bedroom, both with seating. The master balcony is screened
  • Community pool  One of the two pools in Key West Golf Club, a few steps from the door, fenced and run by the HOA
  • Clubhouse gym  Free to guests. The access card for the pool and gym is on the key rack by the front door
  • The pond  Just behind the property, past the landscaping, with a bench and a water fountain
  • Beach gear  Two beach chairs, a beach bag, a small cooler, and pool and beach towels
  • Parking  Free, with no designated space, and ample room around the property

Location

Key West Golf Club, Key West

This is the quiet end of Key West, off College Road, behind a guard gate with 24 hour security. The golf course is a Rees Jones design and you can walk to the first tee. Old Town is a drive rather than a stroll, and that is the trade this address makes: you get the gate, the quiet, somewhere to park and a pool you can see from the door, and you drive in when you want Duval Street.

  • Walking distance  The golf course, the clubhouse gym and both community pools
  • Less than 10 minutes  The beaches, and two places in town to play tennis
  • A short drive  Old Town Key West, the marinas, Publix at Key Plaza and the pharmacies
  • Just across US1  Stock Island, with Hog Fish Grill, The Docks, Hurricane Hole, Matt's Stock Island Kitchen, Roostica and El Siboney
  • In the neighborhood  The Tennessee Williams Fine Art Center, the Key West Tropical Forest and Botanical Garden, and Lower Keys Medical Center

Good to know

Sleeps up to 6. This is a City of Key West occupancy limit rather than our preference, and it counts everyone staying, including infants and children. The city sets it by bedrooms, two per bedroom plus two, however the beds happen to add up.

28 night minimum, required by the City of Key West. Exceptions are not possible, so please do not ask us to make one. It is the reason this home suits people coming down for a month or a season rather than a long weekend.

There are stairs inside. This is a two floor townhome rather than a house up on stilts, so you walk in at ground level with no exterior flight to climb. What is upstairs is both bedrooms and the only full bathroom. Downstairs there is a half bath with a toilet and sink, but no shower and no bed. Anyone who cannot manage a staircase cannot sleep or shower on the ground floor here, and that is worth knowing before you book rather than after.

Pets are considered, one at a time, case by case. Tell us before you book that you are bringing one so we can approve it. Deposits and fees apply and depend on the pet, so we will quote you once we know what we are approving.

The primary renter must be 30 or older, and we ask for the names and ages of everyone in your party.

The guard gate has your name. They give you a temporary pass on arrival, and the HOA office by the pool issues your mirror hanger, open Monday to Friday 9:30 to 5. Arrive at a weekend and the temporary pass covers you until the office opens.

Two things carry a replacement charge. The pool and gym access card is $100 if it is lost, and the mailbox key is $50. Both live on the key rack by the front door, which is the easiest place to put them back.

Check in is from 4pm and check out is by 10am.

Cancellation is a full refund if you cancel more than 60 days before arrival. Inside 60 days there is no refund.

No smoking anywhere in the house, and cigarette butts need disposing of properly.

Booking direct

You are talking to Meredith, not a call center

You are booking straight with Pineapple Properties of the Florida Keys rather than through a platform, so there is no booking fee on top and you can simply call. Meredith is reachable by phone seven days a week. Three days before you arrive she emails the Welcome Letter with the address, the directions and a door code generated just for your stay, so you let yourself in at the keypad whatever time you land.

Cancellation Policy: One hundred percent (100.00%) of the total booking charges will be refunded if the cancellation is made more than 60 days prior to the arrival date of the reservation. For cancellations made within 60 days prior to the arrival date, no refund will be issued.

Key West Happy Hideaway is managed by Meredith Tracy, Pineapple Properties of the Florida Keys. 407.733.2128. Direct Books welcome. Meredith is a Property Manager who owns Pineapple Properties of the Florida Keys. She is thrilled to represent the owners. Meredith is a fifth-generation native Floridian, Meredith's first visit to the Florida Keys was 35 years ago when she was 18 years old. She went sport fishing with the legendary Captain Skip Bradeen in Islamorada, explored the islands from Key Largo to Key West, and was hooked! Meredith, her husband Barry, a realtor, and their children enjoyed vacationing in the keys for many years and after raising their family in Winter Park, Florida, Barry and Meredith moved here full time! She loves helping guests with personal recommendations of all her favorite spots to help make their vacation better than they ever imagined!

Key West, Florida

Property Type Townhome
Accommodation Entire Home
Check-In A keypad is available 24 hours a day to provide entry for guests
House Rules
  • Maximum occupancy: 6
  • Children welcome
  • Infants welcome
  • Smoking not allowed
  • Wheelchair inaccessible
  • Minimum age of primary renter: 30
  • Pets welcome
Setting & View
  • Near Ocean
  • Garden View
General
  • Internet / Wifi
  • Air Conditioning
  • Central Heating
  • Linens Provided
  • Towels Provided
  • Washing Machine
  • Clothes Dryer
  • Hot Water
  • Private Living Room
  • Fitness Room/Equipment
  • Hair Dryer
  • Iron & Board
  • Ceiling Fans
  • Laptop Friendly Workspace
  • Basic Soaps
  • Paper Towels
  • Toilet Paper
  • Hangers
  • Private Entrance
  • Lock On Bedroom Door
  • Extra Pillows & Blankets
  • Body Soap
  • Clothing Storage (closet or wardrobe)
  • Portable Fans
Kitchen
  • Kitchen
  • Refrigerator
  • Stove
  • Oven
  • Microwave
  • Dishwasher
  • Dishes & Utensils
  • Coffee Maker
  • Toaster
  • Ice Maker
  • Freezer
  • Blender
  • Kettle
  • Pots & Pans
  • Dining Table
  • Baking Sheet
  • Barbeque/Grill Utensils
  • Wine Glasses
Bathrooms 2 Baths (1 full, 1 half)
  • Hall Bath, Upstairs – Shower, Toilet
  • Half Bath, Downstairs – Toilet
The upstairs hall bathroom has a large shower, toilet, vanity. Towels provided. The guest bathroom downstairs has toilet and sink.
Sleeping Arrangements 2 Bedrooms, sleeps 3-6
  • Master Bedroom – 1 Queen Bed
  • Guest Bedroom – 1 Double Bed
  • Living Room – 1 Sleeper Sofa
The master bedroom has a screened porch attached and ample closet spaces. The guest bedroom has a balcony attached. The stacked washer/dryer is located in the guest bedroom.
Entertainment
  • Television
  • Satellite/Cable
  • Games/Board Games
  • Books
  • Smart TV
  • Exercise Equipment
Outdoor
  • Outdoor Grill
  • Deck/Patio (uncovered)
  • Lanai/Gazebo (covered)
  • Balcony/Terrace
  • Lawn/Garden
  • Tennis
  • Walkable to Golf
  • Fenced Yard
  • Outdoor Dining
  • Outdoor Seating
Pool/Spa
  • Communal Pool
Vehicles
  • Free Parking
  • Street Parking
Theme
  • Adventure
  • Historic
  • Romantic
  • Tourist Attractions
Attractions
  • Bay/Sound
  • Health/Beauty Spa
  • Marina
  • Museums
Leisure
  • Bird Watching
  • Eco Tourism
  • Outlet Shopping
  • Boating
  • Shopping
  • Wildlife Viewing
  • Water Sports
Sports & Adventure
  • Cycling
  • Deepsea Fishing
  • Bay/Sound Fishing
  • Fly Fishing
  • Golf
  • Jet Skiing
  • Kayaking
  • Parasailing
  • Pier Fishing
  • Sailing
  • Scuba Diving/Snorkeling
  • Snorkeling
  • Snorkeling/Diving
  • Swimming
  • Wind Surfing
  • Mini Golf
Safety
  • Deadbolt Lock
  • Emergency Exit Route
  • Fire Emergency Contact
  • Fire Extinguisher
  • First Aid Kit
  • Medical Emergency Contact
  • Exterior Lighting
  • Police Emergency Contact
  • Smoke Detector
  • Enhanced Cleaning Practices
  • Cleaning Disinfection
  • Common Surface Disinfectant Cleaned
  • Linens High Temp Wash
  • Cleaning Products
Expectations
  • Requires Stairs