Upstairs Awhile | Old Town Key West Monthly Rental (3BR)

A Second-Floor Home Base in the Heart of Old Town

Come Up, Settle In, Stay Awhile

Upstairs Awhile is a three-bedroom Old Town Key West monthly rental on Simonton Street, one block from Duval in the Heart of Old Town. It comes with two off-street parking spaces, something very few places this close to Duval can offer, along with a full kitchen, an upstairs kitchenette, and an in-unit washer and dryer. Everything here is set up for staying long enough to keep a routine.

The name comes from the way the place is laid out. An exterior stair brings you up from the parking area, and a white spiral staircase carries you the rest of the way to a top floor of wood-paneled gables. Below, Old Town keeps its pace. Up here, you set your own.

Unpack the suitcase. Learn which café you like. Stay awhile.

The Home

Bright Rooms Below, Wood-Paneled Gables Above

The main level is bright and simple, with light plank floors, recessed lighting, and a display ledge that runs along the walls just below the ceiling. The living room has leather sofas, a recliner, and a TV, with the spiral staircase rising from one corner.

The kitchen is fully equipped, with gray shaker cabinets, butcher-block counters, and stainless appliances. A wood dining table with bench seating sits along the windows.

Upstairs has a different character. Ceilings slope under white-painted rafters, the gable walls are paneled in warm wood with plank shelves, and the floors turn to rich, warm-toned hardwood. A kitchenette with a sink, microwave, and refrigerator means the morning coffee does not require a trip downstairs.

The Spiral

A Staircase at the Center of the Home

The white spiral staircase is the first thing you notice and the way you reach the two upstairs bedrooms. It rises from the living room to a landing ringed in turned wood balusters, where a small sitting area looks down over the stair opening.

It is a true spiral, so it takes a little care. Luggage goes up more easily one piece at a time, and guests who would rather avoid stairs should plan on the main-level bedroom.

Neighborhood – Heart of Old Town

A Block from Duval, a Walk from Everything

Upstairs Awhile sits on Simonton Street in the Heart of Old Town, one block from Duval. Most of what you will want during a month in Key West is within walking distance or a short bike ride. All distances are walking routes from the front door:

Beaches:

• Dog Beach (0.5 miles, 11-minute walk)
• Simonton Street Beach and Lagerheads Beach Bar (0.9 miles, 21-minute walk)
• Fort Zachary Taylor State Park beach (1.0 mile, 22-minute walk)

Restaurants:

• Duffy’s Steak & Lobster House (200 feet, 1-minute walk)
• Better Than Sex, a dessert restaurant (305 feet, 2-minute walk)
• Nine One Five (0.2 miles, 4-minute walk)
• Banana Café (0.3 miles, 6-minute walk)
• Moondog Café (0.3 miles, 7-minute walk)
• El Siboney (0.4 miles, 9-minute walk)
• Blue Heaven (0.4 miles, 10-minute walk)
• Louie’s Backyard (0.5 miles, 11-minute walk)

Attractions:

• Key West Lighthouse & Keeper’s Quarters (0.3 miles, 6-minute walk)
• Ernest Hemingway Home & Museum (0.3 miles, 7-minute walk)
• Key West Butterfly & Nature Conservatory (0.4 miles, 9-minute walk)
• Key West Firehouse Museum (0.5 miles, 10-minute walk)
• The Southernmost Point (0.5 miles, 11-minute walk)

Parking is the hard part of living in Old Town, and here it is already solved. Two off-street spaces come with the apartment, so bringing a car for the month is easy. Most days you can leave it parked and walk, or have our concierge (305 294-1129) arrange your own golf cart to get around the island and park it in the additional space.

The Accommodations

Two Levels, Three Queen Bedrooms

Upstairs Awhile sleeps six across two levels, with three queen bedrooms and a full bathroom on each level. The upper level works almost as its own suite, which gives two couples, or a family with older kids, some separation.

Main Level

• Bedroom 1: Queen bed
• Full bathroom with walk-in glass shower
• Full kitchen, living room, and dining area
• Full-size stacked washer and dryer

Upper Level (via the spiral staircase)

• Bedroom 2: Queen bed, wood-paneled gable walls
• Bedroom 3: Queen bed, wood-paneled gable walls
• Full bathroom with tub/shower combination; the sloped ceiling limits headroom, so taller guests may prefer the main-level bathroom
• Kitchenette with sink, microwave, and refrigerator

PARKING: Two uncovered off-street parking spaces, rare in Old Town and especially rare a block from Duval.

Good to Know

• Licensed for monthly stays only
• Two uncovered off-street parking spaces, rare a block from Duval
• Second-floor apartment reached by an exterior staircase; no elevator
• Spiral staircase to the two upper-level bedrooms
• Upstairs bathroom has a sloped ceiling with limited headroom; taller guests may prefer the main-level bathroom
• No private outdoor space or pool
• Full-size washer and dryer in the unit
• Full kitchen plus an upstairs kitchenette
• One block from Duval Street; expect some evening activity nearby
• Ideal for monthly stays, small families, and friends traveling together

Restrictions

• Smoke-free house
• Pets permitted with approval, please contact us
• No loud parties
• We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.