Find Bungalows in Key West

OVERVIEWThe Cigar House is a 100+ year old “Cigar maker’s house”. The recently completely renovated house is charming, spacious, secluded and private. The cottage has a raised vaulted wood ceiling, creating a rustic, Caribbean ambiance. The downstairs floor is the original Dade County Pine. All window, door, and floor trim is turn of the century style, and all windows are 6/6 double-hung sash. All linens and towels are furnished.The house has a Starlink secured high speed wi-fi network, streaming internet TV, and two (2) 32" Samsung SMART HDTVs. The house has central air conditioning, a ceiling fan, and a stacked LP washer and dryer. There is a Weber propane barbecue located on the pool deck.The cottage can comfortably accommodate a maximum of four (4) guests – who are comfortable sharing an open social living environment.FIRST FLOORThe kitchen, living, dining, sitting, and bathroom and a small bedroom are located on the first floor. The living room has a queen sleeper sofa/ day bed and a 32" Samsung SMART HDTV. The bathroom, located off the living room, has been recently completely renovated and has a vaulted ceiling and a new full size marble walk-in shower. There is a full bed in the small bedroom at the end of the living room.KITCHENThe kitchen is new and contemporary with mahogany cabinets, white Corian countertops, and integrated Corian sink, and serve thru access to the dining room. The ceiling is vaulted with architectural beams and LED lighting. The kitchen has a pantry, refrigerator, electric range, garbage disposal, microwave, and Braun coffee maker, Krupps toaster, dishes, flatware, glasses (service for 6), pots, pans, and all the basic cooking utensils. There is a French door providing access to the rear deck where the washer and dryer are located.LOFT SLEEPING AREAA ship's ladder is used to access the loft sleeping area. The loft has a queen bed, and a 32" Samsung SMART HDTV.COMMON ELEMENTSThe five (5) house compound is private and secure with a 25' x 10' heated pool including a 5' x 10' heated Jacuzzi. In addition, there is a 10' x 8' heated Jacuzzi. There are brick walkways, and a 40' x 10' sun deck, including a stainless steel propane barbecue, chaise lounges for sunbathing and relaxing; and tables and chairs for dining. Throughout the property there is secured wireless internet access, and CCTV security monitoring. The design of the property lends itself perfectly for small gatherings with friends and family.LANDSCAPINGThe landscaping is lush including various palm species, Poinciana, Spanish limes, avocado, bananas, hibiscus, bougainvillea, halliconias, bromeliads, and orchids, brick walkways. EXCELLENT LOCATIONThe house is located in Old Town Key West at the corner of Thomas and Angela Streets - (2) blocks west of the center of Duval Street in one of the oldest sections of Key West; (4) blocks east of Fort Zachary Taylor State Park/Beach, the best beach and picnic area in Key West. The gated compound is within easy walking or biking distance to everything in Old Town Key West, Duval Street, and the best entertainment and dining on the island.CHICKENS & ROOSTERSThe City of Key West protects chickens and roosters, and considers them as part of the history and charm of Key West. As a result, Key West and many of the islands throughout the Florida Keys have free-range chickens and roosters. You will definitely see and hear chickens and roosters during your stay in Key West. Some visitors to Key West love them, and some visitors hate them - personally, I enjoy them best roasted, with plantains, and black beans and rice!CRITTERSAlso, please remember that you are in the tropics and most life forms typically thrive in the tropics. Please don' t be surprised or alarmed if you see a lizard, or an insect.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:The house arrival and departure information, house and property rules, and guest registration will be emailed to the guest prior to arrival..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

Evoking the hypnotic beauty and storied history of the Florida Keys, the guest rooms within our meticulously restored Caroline Street inn are refined yet relaxed; six singular hideaways that might easily masquerade as private bedrooms in the elegant home of a fifth-generation Key West family.

Welcome to Banana Wind — Your Perfect Key West Retreat!Located in the charming Truman Annex Foundry Building, Banana Wind offers a spacious and stylish 2-bedroom, 2.5-bath townhome just steps away from the best of Old Town Key West.This beautifully maintained condo comfortably sleeps up to 6 guests with a king bed in the primary suite and two twin beds in the guest room (convertible to a king upon request). A cozy sofa bed in the living room provides extra sleeping space for your group.Prime Location:Just 3 blocks from bustling Duval Street, 2 blocks to the serene Truman Waterfront, and only half a mile from Fort Zachary Taylor Beach. Walk to restaurants, shops, nightlife, and historic sights — no car needed!Inside Your Home Away From Home:First Floor: Bright and inviting living room with oversized windows, a sleeper sofa, and plenty of seating. Enjoy meals around the formal dining table for six, and prepare your favorites in the fully equipped modern kitchen with full-size appliances and all the utensils you’ll need. A convenient powder room completes this level.Second Floor: Relax in the spacious primary suite featuring a king bed, flat-screen TV, work desk, ample storage, and a private balcony perfect for morning coffee. The ensuite bath includes a shower and bathtub. Laundry facilities are also located on this floor.Third Floor: The guest bedroom offers two twin beds (convertible to king), a workspace, generous storage, and a private ensuite bathroom.Outdoor Perks:Enjoy the fenced courtyard and front lanai with comfortable outdoor seating and a gas grill — ideal for unwinding after a day of exploring.Community Amenities:Take a refreshing dip in the shared pool, complete with lounge chairs and a restroom. Towels are provided inside the condo. One assigned parking space is included for your convenience.Need More Space?Traveling with a larger group? Check out our sister properties, Unit 18 and Unit 20 (Southern Escape), located right next door with identical layouts and amenities.Banana Wind is the ideal home base for your Key West getaway, combining comfort, convenience, and a prime location to help you experience all the island’s must-see spots.Book now and start your unforgettable Key West adventure!About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 28.About events:No events allowed.

Welcome to Casa Tranquila! This 2-bedroom townhome is perfect for your escape to Key West. Located in Old Town just five blocks off of Duval, it boasts 3 total queen beds, 2 fully renovated en-suite bathrooms with showers, huge new smart TV's, PRIVATE HOT TUB, grill, fire pit, laundry, and all-new finishes inside and out. This beautiful rental has everything you need for a comfortable stay in a super convenient location whether you're heading to Duval, the beaches or the marina. Tons of extras including a starter set of toiletries and paper products, a fully stocked kitchen with all of the essentials for cooking and grilling your own meals, an additional wine fridge and drink fridge in addition to all brand-new appliances in the kitchen, and multiple sets of bed and bath linens. You'll never want to leave!Parking for one vehicle or golf cart on street in front of townhome.This home is available for monthly rental (minimum of 28-days). Owners will consider dates other than an entire same-month booking - please feel free inquire before reserving your dates if you'd like.About pets:Pets allowed: dogs less than 50 lbs per pet (limit one pet total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.The home does NOT include crib, high chair, etc.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Welcome to Southern Escape — Your Perfect Key West Getaway!Nestled in the heart of the Truman Annex Foundry building, Southern Escape is a beautifully remodeled 2-bedroom, 2.5-bath townhome designed with your comfort and relaxation in mind. This stylish retreat comfortably sleeps up to 6 guests, featuring a king bed in the primary suite and two twin beds in the guest room — which can easily convert to a king upon request.Enjoy bright, sun-filled living spaces with light wood floors, quartz countertops, stainless steel appliances, and plush furnishings. The open floor plan includes a cozy living room with a sleeper sofa and a large 55” flat-screen TV, perfect for unwinding after a day of exploring.Location is everything: Just 3 blocks from the vibrant Duval Street, 2 blocks to the serene Truman Waterfront, and a short walk to Fort Zachary Taylor Beach, Southern Escape puts you right in the center of Old Town Key West’s best attractions — no car needed!Home highlights:First Floor: Open living and dining area with ample natural light, updated kitchen with full-size appliances, and a convenient half bath.Second Floor: Primary suite with king bed, workspace, flat-screen TV, ensuite bathroom, private balcony, and in-suite laundry (full-size LG washer/dryer).Third Floor: Guest bedroom with twin beds (convertible to king), ensuite bathroom, and plenty of storage.Outdoor Spaces: Fenced courtyard, front lanai with seating, gas grill, and a shared pool with lounge chairs and restrooms. Towels provided!Parking: One assigned parking spot included.Need more space? Book our sister property, Banana Wind (Unit 18), just steps away for your larger group.Whether you’re here to relax by the pool, stroll through Old Town, or explore Key West’s famous sights, Southern Escape offers the perfect home base for an unforgettable vacation.Book your stay today and experience the best of Key West living!About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 28.About events:No events allowed.

With a stay at this vacation home in Key West (Key West Historic District), you'll be steps from Duval Street and 5 minutes by foot from Florida Keys Beaches. This vacation home is 0.3 mi (0.5 km) from Mallory Square and 0.7 mi (1.2 km) from Ernest Hemingway Home and Museum. Take in the views from a garden and make use of amenities such as complimentary wireless internet access and barbecue grills. Free self parking is available onsite. Make yourself comfortable in your vacation home.

The 3 4 Time is an ideal spot for travelers wanting to discover the city. The 3 4 Time offers a pleasant stay in Key West for those traveling for business or leisure. The hotel is conveniently located a short 5km drive from Key West International Airport. There's plenty to do nearby, with Good Times Key West, Key West Conch Life Charters and Jennifer Fox Esthetician all within a short distance. At the end of a busy day, travelers can unwind and relax in the hotel or go out and enjoy the city. This Key West hotel offers parking on site. According to our trusted guests, the facilities at this hotel are first-rate.

Two bed room bath and a half townhouse located on a quiet street in Old Town Key West. Located two blocks east of Duval, in proximity to St. Mary's Star of the Sea Basillica, you are a close walk to all Old Town has to offer. Easy access to Duval, Historic Seaport, Key West Theatre, White Street Gallery,as well as Higgs and Smathers Beaches. Penny's Perfect Place is an end unit of a three unit building;. Conch Town Villas complex has two buildings comprised of full time residences as well as other owner occupied homes. HOA ensures all homes and common areas are maintained, Home has a modern, spacious, equipped, eat in kitchen, half bath and over-sized couch with smart TV on first floor. Small back deck with grill; Front porch with outdoor furniture and sun sail. Upstairs has two bedrooms each with a closet, one king and one queen size bed: plus an updated bathroom featuring a walk in shower and lighted fog free mirror. Entire house has LVP flooring for your comfort and convenience. Additionally house has a rare, reserved, off street parking space. However if you fly, private car rental service is available. Car will be delivered to the reserved parking spot. We don't do the car rental but it is through a trusted partner. **Due to city ordinance, this property has a 28 day minimum rental**About pets:Pets allowed: dogs less than 50 lbs per pet (limit 2 pets total).About checkOut:Check out before 11:00 AM.About children:Adults only.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Tortuga Hammock Townhouse Highlights:Location: Stock Island, within the gated Coral Hammock community, close to Key West and local marinas.Type: 2-bedroom, 2.5-bathroom end-unit townhouse.Renovation: Fully updated in 2020 with modern finishes.Interior Features:Granite countertopsStainless steel appliancesTile and bamboo floorsOpen main floor plan with French doors to a private balconyBedrooms:2 queen bedsEach with private en-suite bathroomsMaster bedroom has an additional private balconyLiving Space:Powder room on main floorDining area for up to 6 guestsComfortable tropical decor with custom artworkOutdoor & Community Amenities:Overlooks pool area and lush landscapingGated community for privacy and securityAssigned secure parkingNearby:2 blocks to marinas and boat rampsWalking distance to restaurants like Roostica, Hogfish Bar & Grill, and Matt’s Stock IslandRental Terms:Minimum 3 nights No early check-ins/late check-outs (check-in 4 PM, check-out 10 AM)About pets:No pets allowed, service animals permitted.1- Dog Upon Approval & Fee Applied.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 3-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About events:No events allowed.

With a stay at this vacation home in Key West, you'll be within a 10-minute drive of Florida Keys Beaches and Smathers Beach. This vacation home is 5.3 mi (8.5 km) from Duval Street and 5.2 mi (8.4 km) from Ernest Hemingway Home and Museum. Take in the views from a garden and make use of amenities such as complimentary wireless internet access and barbecue grills. Free self parking is available onsite. Make yourself comfortable in your vacation home.