Vacation Home Rentals By Owner In Key West, FL

Oasis getaway, 3 bedroom, 3 bath, including chefs kitchen. This home has all the amenities on the water, located in a quiet, safe neighborhood. Lush gardens surround this property with all the privacy one needs, heated pool, spa jacuzzi, outdoor shower, bar and grill.br42' of marble dock to accommodate your boat, with fish station for your convenience. Minutes from the Gulf or Atlantic Ocean as well as Old Historic Key West and all it has to offer.

Luxurious, Elegant Home, Waterfront With Dockage

Key West, Florida, United States

Bed

Bath

Sleeps

$1960.88

pJust a short distance from the sea, this pet-friendly vacation home lets you experience it all. Jump into your car and make short work of the 2-minute drive to Key West Golf Club or the 3-minute drive to Key West Tropical Forest and Botanical Garden (and enjoy the property's convenient onsite parking in the meantime). /ppRelax by the communal pool or sip a drink on the deck or patio of this 5000-sq-ft vacation home, which also features a fitness center and a BBQ grill. For a change of scenery, come inside and enjoy the WiFi and cable/satellite TV. /ppAir conditioning and an office are featured at this 8-bedroom, 8.5-bathroom rental. Bathroom amenities include a hair dryer and towels. The kitchen is equipped with an oven, a stovetop, and a refrigerator, as well as a coffee maker, an ice maker, and a microwave. And you won't have to pack extra clothes, because you'll have a washer and dryer, too. /p

The Starboard House at Solaire Lunara Bay

Key West, Florida, United States

Bed

Bath

Sleeps

$876.38

Summary:brThis 3 bed 2 bath home with an amazing HEATED pool is located right off the quieter end of Duval St. The home consists of 2 separate units Poolside Suite and Poolside Retreat which are side-by-side and have their own living rooms and kitchens. This property is perfect for larger groups looking for a memorable time in Key West and is walking distance to popular restaurants, attractions, shops and bars!brbrThe Space:brBring the whole family together for a reunion or holiday celebration at this spacious, Key West home located just a block from the non-stop fun of Duval Street. This rental, with space for up to 10 guests, features an enclosed yard, a private pool, a furnished patio, two full kitchens, and off-street parking for two vehicles (a real rarity in Key West). And dogs up to 40 pounds are welcome for a small nightly fee.brbrPoolside Retreat Bed Layout: brBedroom 1: Queen brLiving Room: Queen pullout couchbrPoolside Suite Bed Layout:brBedroom 1: KingbrBedroom 2: QueenbrLiving Room: Queen pullout couchbrbrIdeal for an extended family or a few couples traveling together, this home offers free WiFi, four cable TVs, two full kitchens, and a gas grill for a family cookout on the furnished patio.brbrGuest Access:brOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival.brbrThe Neighborhood:brThis home is located one block from Duval Street, the most popular street in all of Key West, where you'll find fantastic restaurants, unique local shops, and year-round special events and festivals. Play on the sand and people-watch at Southernmost Beach, just a half-mile away. Visit the many historic sites including the Ernest Hemingway Home & Museum and the Key West Lighthouse, both only a couple blocks from your front door, as well as the Truman Little White House and the Mel Fisher Maritime Museum, just under a mile away over on Front Street.brbrGetting Around:brParking Information: There are 2 private off street parking spots on the Olivia St side of the property. They are labeled Poolside Retreat & Poolside Suite.brbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance. Feel free to ask us for recommendations!brbrOther Things to Note:br- Private washer/dryer located outside.br- This unit is pet friendly. Our requirements are as follows: br•40lb maximum per petbr•$25/per nightbr•2 pet maximumbrPlease let us know if you plan on bringing your pet.br- Are you within 90 days of your check in date a & have a smaller group Rent just Poolside Retreat or Poolside Suite!

Heated Pool, Steps to Duval St - Poolside Paradise

Key West, Florida, United States

Bed

Bath

Sleeps

$821.26

Enjoy a luxurious tropical stay at this first floor 2-bedroom 2 bath 1,100 sqft townhome in Key West Florida. It features a king and two queen beds, ensuring a serene night's sleep for all guests. With amenities like AC, heating, and full ensuite bathrooms, your comfort is our top priority. The living room offers additional space with a cozy sofa bed for additional guests. The private outdoor grilling area and complete gourmet kitchen with a full size refrigerator with ice maker, electric oven and many gourmet appliances allows for full meal preparations for everyday and special occasions. Our heated private pool, outdoor shower and sundeck along with a smaller cocktail pool are one of a kind. You can even connect additional rooms and suites to sleep up to 12 guests. We also offer room service, bike rental, grocery and beverage shopping and full concierge services. We are just a 3 minute stroll from the public beach at Higgs, city park, children's playgrounds, tennis, pickleball, professional bocee courts, great restaurants, beach volleyball, a dog park, a dog beach and a fishing pier, all located in the peaceful high-end Casa Marina residential neighborhood, perfect for leisurely walks with someone special. The Key West Garden Club's landscaping display and orchid showings are also located on the beach. Art galleries, museums, live music venues, theaters and the world famous Duval Street are all within walking distance. You are sure to make many treasured memories with a stay at our townhome in paradise. We are located in the heart of historic Old Town. For your security and peaceful enjoyment, this property is surrounded by a bamboo privacy fence. This desirable property is highly recommended and reasonably priced. No resort or parking fees.brbrLocationbrYour Hemingway Caribbean Townhome is situated in a prime island location on the southern side of Key West in the prestigious residential Casa Marina neighborhood surrounded by majestic and luxurious homes with beautiful tropical gardens, perfect for pleasant walks any time of day. We are only a 3 minute stroll to Higgs Beach, Salute's Restaurant and West Martelo Tower, a Civil War Fort which is now home to the Key West Garden Club and walkable tropical gardens. We are a 13 minute walk to the Southernmost Point and a 12 minute walk to the Butterfly House. We are also close to several excellent restaurants and only a 9 minute drive from the airport.brbrOther Nearby Restaurants and AttractionsbrNearby access to the free Duval Loop Bus, provides access to the Historic Seaport, aquarium, Sloppy Joes, Truman Waterfront Park, Southernmost Point, Butterfly House and Nature Conservatory, Mel Fisher and Sails to Rails museums, art galleries and other attractions. Walking minutes to several nearby restaurants include: Durato's (2min), Ana's Cafe and Southernmost Grocery Store (8min), El Siboney Cuban (8min), Oasis Mediterranean (7min), White Street Pizza (7min) and famous Sandy's Cafe for authentic Cuban coffee and sandwiches (5min).brbrBeach, Pool and Outdoor LivingbrJust steps from the beach, your townhome is surrounded by lush gardens and palm trees. You can lounge on your private sundeck, next to your private heated lagoon-style pool, amidst lush palm trees in your private garden setting. There is also a private grilling area next to your pool. The common area is complete with hammock swings and a dining table under our mango tree and a putting green. Higgs Beach, which is just down the street, is also ideal for romantic evening walks for stargazers.brbrFurnishingsbrOur decor reflects a true Key West vibe. The gourmet kitchen is complete with an electric range, full size refrigerator with ice and water in the door, microwave, double sink, a george/forman, Keurig and a drip coffee maker, toaster, silverware, pots/pans, cookie sheets, roasting pans, grilling tools, a large and a mini blender to make your tropical drinks, an electric griddle, a dishwasher and many other speciality appliances. Your livingroom includes a lounging and sleeping area in front of a smart TV as well as a seating area with a reading library and a coffee table suitable for playing board games (which are also provided). brbrSleeping ArrangementsbrYour townhome sleeps up to six guests and includes a king and a queen bedroom. Each bedroom has an ensuite bathroom. Bodywash, shampoo, conditioner, extra toilet paper, large bath sheet towels and a hair dryer are provided. The king bedroom also has a large double sink vanity with drawers and shelves for your toiletries. Our bedrooms are equipped with cozy Tommy Bahama comforters. Each bedroom has a television complete with cable channels and free WiFi for your entertainment and convenience. Your livingroom includes a queen sofa bed and a separate couch suitable for a restful night's sleep, perfectly arranged for families or couples with friends. brbrDetails and AmenitiesbrYour first-floor Carribbean Townhome is 1,100sqft. Your private lagoon style pool is heated and sunrounded by a raised sundeck. For your convenience bike rentals, an iron and ironing board and washer/dryer service are all available on our property. We are family and pet friendly. Wrapped breakfast bars, nuts, fruit snacks, gourmet meatsticks, cheese and crackers, mini muffins, coffee/teas are provided in the condo along with fresh Florida oranges and grapefruits in our common area. Higgs Beach city park is nearby, complete with tennis, pickleball, sand volleyball, professional bocce courts, two playgrounds for children, White St. fishing and observation piers, an oceanside restaurant and a dog park. The White Street Pier is a quarter mile over the ocean with spectacular views of sunrise and sunset and excellent fishing.brbrConcierge ServicesbrEnjoy our concierge service to assist you before or during your stay with planning activities with the very best of Key West. From bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset sails, sandbar excursions, scuba diving, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. We can also arrange licensed massage therapy for you and your party, in our gardens or in your suite and have your condo stocked with groceries, adult beverages and all the necessities in advance of your arrival.brbrParkingbrFree off-street parking in front of and around the townhome compound.brbrYou Need To KnowbrOur property is equipped with fire extinguishers and smoke detectors.brOnsite parties, weddings and other events can be scheduled with prior approval by property owner.brGovernment issued photo ID and a credit or debit card or cash deposit may be required at check-in for incidential chargesbrExtra person charges may apply per the property's policies.brReport any damages prior to check out.brKey West Quiet Time may apply after 10pm on weekdays and 11pm on weekends through 8am in the morning. Thank you for supporting our efforts to be a good neighbor. Please note that your condo is located in a noise sensitive area. When you return from the parties, celebrations and live music on Duval street you will have a quiet, tranquil and restful sleep.brbrMake special memories that will last for a lifetime while relaxing at our paradise townhouse.

Hemingway Caribbean Townhome/Private Pool by Beach,Key West charm,free parking

Key West, Florida, United States

Bed

Bath

Sleeps

$1949.37

Thinking about getting your extended family or friends together for a Key West family reunion vacation This one-of-kind gated Key West vacation rental compound, with large shared swimming pool in spacious landscaped tropical garden setting, could be the perfect place.brbrFamily Reunion Key West vacation rental includes: The Flower Power House, a 2-story house with attached cottage suite, plus a 3-story town home - Coco`s Poolside Retreat . Gated together in an authentic Old Town Key West compound, this layout lends itself ideally to being combined and rented together. The compound is shared with one additional townhouse within the gates.brbrA special feature of this `mini-compound` property is the large 40’ x 16’ swimming pool that is edged with irregular flag-stone rocks which gracefully `grow` into the landscaped garden. The garden has ample lounging areas. Just a few short blocks from the beach, this unique private complex is located in Old Town Key West conveniently close to shopping, art galleries and restaurants. There is one covered parking space, some off-street parking, and street parking is not metered.brbrBedding Summary:brbr1st Floor 1 King size bed, 1 Queen size bed, 2 Twin size bedsbr2nd Floor - 1 King size bed, 4 Twin size beds.brAttached Cottage Suite - Floor Planbrbr 2nd Floor – 1 King size bedbr1st Floor – Built in Twin bed with trundle bed (2 twin beds)brCoco`s Poolside RetreatbrbrSecond Floor - 1 Queen size bed, 1 Queen size sleeper sofabrThird Floor - 1 king, 2 twin beds (can be make into a King size bed)brbrAmenities: Spacious tropical garden. Large 40` X 16` feet swimming pool (heated, shared), smart TV`s, a/c, stereo, telephone, washer dryer, linens and towels provided, fenced yard, large porches, kitchens.brbrActivities: Close to Higgs Beach (a short walk), and 2 parks. Ride your bike to Duval Street and the southernmost point of the U.S. in fewer than five minutes. Walk to Duval Street in 20 minutes.brbrArea: This property is ideally located in the White Street Gallery District of Old Town Key West in a historic neighborhood just a few streets from White Street and Higgs Beach. From this location you can quickly walk to Fausto`s Fine Food Palace (fine wine, cheeses, and gourmet foods), Sandy`s Cafe of Cuban coffee, numerous art galleries (White Street Gallery area), and yoga and exercise studios. Duval Street shops, attractions, and the Historic Seaport District is about twenty minute walk.brbrRestrictions: Smoking permitted only outside please. No pets. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.brbrPAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.

Family Reunion Compound - Great for Groups! Large pool.

Key West, Florida, United States

Bed

Bath

Sleeps

$161.65

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to Tropical Tee-Time – your serene island escape nestled in the lush, gated Key West Golf Club community on Stock Island! brbr brbrThis charming 2-bedroom, 1.5-bath townhome offers a peaceful retreat just minutes from the excitement of downtown Key West. Step inside to find a bright, open-concept living space with tropical décor and all the comforts of home. The fully equipped kitchen makes it easy to whip up meals, while the private back deck is perfect for morning coffee or evening cocktails surrounded by swaying palms. As a guest at Tropical Tee-Time, you’ll have access to two resort-style community pools, including a beautiful lagoon-style pool, as well as a well-equipped fitness center for staying active during your stay. This home is also dog-friendly, so your furry companion can enjoy the island vibes right alongside you. Ideally located just five miles from the energy and excitement of Duval Street, you’ll be close to world-class dining, shopping, and nightlife. Smathers Beach is only four miles away for sun-soaked days by the sea, and Marathon is just an hour’s drive, making this the perfect home base for exploring the Lower Keys. Whether you're hitting the greens, lounging poolside, or discovering the charm of Key West, Tropical Tee-Time offers the perfect blend of comfort, convenience, and island adventure. brbr brbrSLEEPS MAXIMUM OF 4 GUESTS: brbr brbrBedroom 1 (2nd Floor): Queen Bed, Smart TV (no cable/satellite available) brbr brbrBedroom 2 (2nd Floor): Queen Bed, Smart TV (no cable/satellite available) brbr brbrLiving Room: Sofa w/ Two Recliners, Chair, Smart TV (no cable/satellite available) brbr brbrKitchen: Nicely equipped (everything needed to prepare and serve meals) brbr brbrAMENITIES: brbr brbr- Two Shared Pools (chlorine & not heated) brbr brbr- Private Patio brbr brbr- Propane BBQ Grill brbr brbr- Single Serve & Drip Coffee Maker, Toaster, Blender brbr brbr- Parking for up to 2 Vehicles brbr brbr- Linens and towels provided brbr brbr- 3.6 miles to Smathers Beach brbr brbr- 4.6 miles to Duval Street brbr brbr- 4.7 miles to Southernmost Point brbr brbr- 4.7 miles to Key West Historic Seaport brbr brbr- 5.2 miles to Mallory Square Sunset Pier brbr brbr- 5.3 miles to Forty Zachary Taylor State Park Beach brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. brbr brbrPet Policy: Up to one friendly and well-behaved dog 25 LBS or less will be considered with a $10/night pet fee. To help maintain a safe and welcoming environment for all, we require every guest to submit pet or assistance animal information through BetterPet Passport. Guests will simply submit household pet information, request an accommodation for an assistance animal, or confirm they are not bringing a pet/animal. It's free, and only requires creating an account if you're bringing a pet or animal. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time. brbr brbrSecurity Cameras: For the safety and security of our guests and property, two exterior security cameras monitor the front and back porches. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.

Tropical Tee-Time: 2BR Townhome in Key West Golf Club with Two Shared Pools, Fitness Center, Dogs OK

Key West, Florida, United States

Bed

Bath

Sleeps

$1564.28

Summary:brbrDiscover your dream Key West vacation at Lunara Bay - a collection of 26 Luxury homes in a gated community!! Altair House is a 6BR, 6.5BA pet-friendly estate blending island charm with modern elegance, just minutes from downtown. Dock boats up to 40’ at private slips, relax in your private pool, enjoy free access to FYT gym, and curated itineraries from our local guest experience team.brbrbrbrExtend your stay 7+ nights for 10% off your entire stay!brbrbrbrThe Space:brbrIndulge in luxury with our private boat excursions and chauffeur services. Sail away on tailored aquatic adventures or arrive in style with our elite transportation solutions. Experience excellence, tailored just for your stay. Please reach out for more information!brbrbrbrThe Altair House is everything you’re looking for, both modern and laid-back. This residence fully embraces its oceanic surroundings, inviting you to experience complete tranquility.brbrbrbrThe sleeping arrangements of the home are as follows:brbrBedroom 1: King bed with a walk-in closet, double vanity en-suite bathroom & balcony accessbrbrBedroom 2: King bed with a walk-in closet, double vanity en-suite bathroom & balcony accessbrbrBedroom 3: King bed with en-suite bathroombrbrBedroom 4: King bed with en-suite bathroom and balcony brbrBedroom 5: Two twin over twin bunk beds, this room does not have a doorbrbrBedroom 6: Double bed with en-suite bathroom brbrbrbrThe open-concept floor plan seamlessly connects the indoor and outdoor areas, making it perfect for entertaining and spending quality family time. Whether you're relaxing by the pool, playing a game of pool, grilling delicious meals, or simply relaxing in one of the multiple dining and seating areas, this home has everything you need to create lasting memories.brbrbrbrThe fully equipped kitchen is ready to cater to your culinary desires, whether you prefer to cook your own meals or hire a private chef. Stay connected with high-speed internet access and enjoy the convenience of keyless entry, making your vacation experience even more seamless and hassle-free.brbrbrbrOutside, the spacious fenced-in turf yard provides a safe space for children to play, as well as a perfect area for your furry friends to roam around.brbrbrbrGuest Access:brbrGuests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay.brbrbrbrBoating & Private Dock Slip:brbrWe encourage boating. Here's what you need to know in order to do so safely:brbr- Dock in our exclusive marina which accommodate boats up to 40’ in length. Maximum one boat per slip.brbr- There is no power or pump out service to the slips.brbr- The Florida Keys are a notoriously difficult place to navigate.brbrbrbrHow to Access: Stair access only the home is elevated above sea level.brbrbrbrThe Neighborhood:brbrWelcome to Lunara Bay!brbrNestled in a gated community less than a mile from Key West, Lunara Bay offers a family-friendly atmosphere with a local park just a short walk away—perfect for spending time with loved ones.brbrbrbrExplore & Dine Nearby:brbrEnjoy fresh seafood and local flavors at Hogfish Grill, Roostica, or Chico’s Cantina. Visit Hurricane Hole for happy hour and scenic waterfront views. Rent a boat for a day at Stock Rock Café or embark on a kayak tour with Lazy Dog.brbrbrbrBoating & Marina Access:brbrMany homes offer private boat docking or slips available at the onsite marina. A public boat ramp is conveniently located across the highway - Key Haven Boat Ramp.brbrbrbrNeed personalized recommendations Ask your GEM for their top things to do and places to go!brbrbrbrGetting Around:brbrTravel by car, boat, or plane to our luxury estate. The driveway allows parking for up to 3 vehicles and your boat trailer. brbrIf you didn’t travel by water, you can also drop your boat at one of the public boat ramps in Key Haven or Stock Island. brbrRent a golf cart, scooter, moke or bike for the day to explore the area. Feel free to ask us for recommendations!brbrbrbrOther Things to Note:brbr- Elevate your visit with our Private Chauffeur Service for effortless luxury transportation.brbr- Private washer/dryerbrbr- Located in gated communitybrbr- Free gym access at FYTbrbr- Pets are welcome! Our requirements are as follows: brbr•40lb maximum per petbrbr•$250/staybrbr•2 pet maximumbrbrbrbrInteraction with Guests:brbrYour dedicated GEM is at your service to answer any questions or curate unforgettable experiences tailored to your dreams in the Keys.

Altair House at Lunara Bay

Key West, Florida, United States

Bed

Bath

14

Sleeps

$964.9

4 Bedroom, 3 Bathroom, Sleeps 8brLuxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be at Mother Ocean. This home is located in the private community of Key Cove Landings, on an exclusive lane of waterfront residential homes. The perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. This home includes plenty of off-street parking in the private garages, as well as on private driveways leading to the house.brThis home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with a sectional leather couch around a large HD flat screen Smart TV. There is a dining table with seating for up to 6 diners, with additional seating for 4 at the kitchen bar. brThe master bedroom has a King sized bed, a large flat-screen HD TV, and an en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony. The second bedroom has two twin beds that can be converted to a king with ample notice, a flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The third bedroom is also on the 2nd floor with a full size bed, flat screen TV, and also with balcony access. On the main floor there is a fourth bedroom with twins bed. There is a full bath down the hall for convenience.brOut back is one of the highlights of this home: the covered lanai and pool area. The covered outdoor dining area comfortably seats six for a poolside meal. The pool is heavenly, with views of the open water and visiting heron on the tropical greenery that surrounds the back yard. There is also a pool lounge area with comfortable chaises in a piece of deck that gets equal sunshine and shade. brAMENITIES: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. Pets Considered. This property will accommodate 8 adults.brbrDockage is not available at this home's development.brbrRATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).brbrDOG FRIENDLY. Please contact us to confirm specific pet policies.

Oceanfront 4-Bed 3-Bath home with pool

Key West, Florida, United States

4

Bed

Bath

8

Sleeps

$686.92

NEW LISTING! brbrDREAMY OLD TOWN RETREAT…brThis Upper Duval classic abode exudes historic charm in quintessential Key West flair, yet offers the sleek comforts of modern island vibes. Cradled in an exceptional location, enjoy an ideal walkable lifestyle to the excitement of Duval Street, the white sands of the Atlantic Ocean, eclectic galleries and fine dining. Unwind and exhale in this southernmost gem that will exceed your expectations!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brFind your island zen as you enter a sun-dappled open concept layout, brimming with tropical sunshine flooding through French Doors and oversized windows, soaring ceilings, rich hardwood floors and iconic Dade County Pine walls. A state-of-the-art kitchen is your inner chef's dream, stocked with all the tools for creating a sumptuous feast for friends and loved ones. This exquisite interior is fashioned to soothe your senses and ease you into blissful serenity. Enjoy Youtube TV live streaming for binge-watching all your favorite shows. You will find the washer/dryer on the back deck in a shed just beyond the fence off the driveway. brbrSLEEPING ARRANGEMENTS:brEach of the 3 bedrooms offers ensuite privacy and plush king beds for the ultimate restorative slumber. The spacious primary suite boasts a gleaming walk-in shower and double vanity. The adjacent guest room has a shower/tub combination, perfect for soaking after a day of adventures. The private poolside cottage features a full bath with a walk in shower and a full refrigerator for added comfort and convenience.brbrOUTDOOR LIVING…brThe interior of the home flows seamlessly to a grand outdoor tropical oasis, designed for relaxing or entertaining. Sink into the sparkling pool (comes heated during the cooler months) surrounded by a spacious deck that is embraced by lush greenery and foliage. Dine under the splendor of sultry stars and nautical breezes.brbrPARKING...brThis home offers an off street parking space.brbrPETS...brThis is a DOG friendly home, NO CATS. Please include the size and breed when inquiring.brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrTRANQUILITY RESIDES HERE...brVirtual Tour Url: https://my.matterport.com/show/ m=2PhrccNBKwu

SANDY CHIC ~ NEW LISTING! Upscale 3 BR/3.5 Ba Home w/ Pool and Parking!

Key West, Florida, United States

Bed

Bath

Sleeps

$1245.79

Charmayne's Cottages | Your Private Group Oasis in the Heart of Key WestbrbrExperience the ultimate Key West getaway at Charmayne's Cottages—a private collection of six vibrant and charming units located just steps from iconic Duval Street. Perfect for family gatherings, group retreats, or multiple couples traveling together, this unique property offers the ideal blend of shared space, privacy, and unbeatable access to everything the island has to offer.brbrThe Ambiance:brCharmayne's Cottages features six individually styled units, each bursting with personality and island charm. With a mix of cozy studios, a spacious two-bedroom suite, and comfortable one-bedrooms, this property can accommodate up to 14 guests. Some units include full kitchens with stainless steel appliances, others offer convenient kitchenettes or mini-fridges—ideal for everything from quick bites to group meals. Enjoy inviting living spaces, air conditioning, cable TV, and free WiFi across all units, along with cozy outdoor areas to sip coffee or soak up the spectacular Key West sun!brbrGuest Perks:brEnjoy stress-free, contactless check-in with personalized entry codes for each unit—perfect for larger groups arriving at different times. Unit D includes a private on-site parking space, and all other units have access to nearby paid parking options. Beach towels are included for easy beach days, and pet-friendly accommodations mean your furry companions can join the fun too!brbrNeighborhood Highlights:brLocated just off Truman Avenue, you'll find Charmayne's Cottages at the center of it all. Explore Key West on foot from this unbeatable location—walk to the Southernmost Point, Hemingway Home and Museum, Key West Lighthouse, and the Butterfly and Nature Conservatory. Duval Street's legendary nightlife, vibrant dining scene, and quirky boutiques are just a stone's throw away.brbrTransportation Tips:brPlease note that this property includes one designated parking space. Paid parking is available nearby for additional vehicles. We also offer other creative parking solutions, just ask! Key West is a pedestrian- and bike-friendly island, so feel free to explore on foot or rent bicycles, scooters, or golf carts for maximum flexibility. We're happy to offer local tips and transportation recommendations!brbrOther Things to Note:br- We welcome dogs with a $20/per dog per night fee.br- All units include air conditioning, cable TV, and WiFi.br- Two exterior security cameras are in place for added safety.br- Guests must be 25 years of age or older to reserve the property.br- Units are located on both the first and second floors.br- There is one dedicated off-street parking space available for use.brbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, driveway, walkways, and common outdoor areas. No cameras are placed in private or interior spaces.brbrWhether you're gathering with loved ones, reuniting with friends, or planning a group escape, Charmayne's Cottages is your dream destination for an unforgettable stay in paradise. Book the entire property today and enjoy the perfect blend of comfort, style, and location in the heart of Key West!brbrAt Colocada Vacation Rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Charmayne's Cottages | Private Group Oasis!

Key West, Florida, United States

7

Bed

Bath

20

Sleeps

$260.21

City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to Vahevala, your charming Mid Town Key West retreat! brbr brbrThis private home is your oasis, boasting a refreshing pool and an ideal proximity to both pristine beaches and the vibrant Duval Street. At Vahevala, you'll find the perfect blend of relaxation and excitement. Unwind and savor the moment by the pool, cocktail in hand, as you soak up the sun and tranquility of your ultimate relaxation retreat. Indulge in relaxation on the nearby Smathers Beach, embrace the charm of a leisurely stroll along Duval Street, and capture memories with a selfie at the iconic Southernmost Point. Your Key West getaway at Vahevala is ready to make your dreams of sun, fun, and relaxation a reality. brbr brbrSLEEPS MAXIMUM OF 6 GUESTS: brbr brbrBedroom 1: Queen Bed brbr brbrBedroom 2: Queen Bed brbr brbrBedroom 3: Murphy Wall Bed (Full Size) brbr brbrFamily Room: Sofa, Smart TV brbr brbrLiving Room: Sofa, Chair brbr brbrKitchen: Nicely Equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- Private Pool (heated to ~85 degrees Nov-Apr) brbr brbr- Outdoor Seating brbr brbr- Propane BBQ Grill brbr brbr- Off Street Driveway Parking for 1 Vehicle brbr brbr- Linens and towels provided brbr brbr- 0.5 miles to Higgs Beach/White Street Pier brbr brbr- 1.0 miles to Smathers Beach brbr brbr- 1.2 miles to Upper Duval Street brbr brbr- 1.3 miles to Southernmost Point brbr brbr- 1.9 miles to Key West Historic Seaport brbr brbr- 2.2 miles to Lower Duval Street brbr brbr- 2.3 miles to Fort Zachary Taylor State Park Beach brbr brbr- 2.4 miles to Mallory Square Sunset Pier brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. brbr brbrNo Pets: Pets are strictly prohibited. To help maintain a pet-free environment for all, we require every guest to confirm they are not bringing a pet/animal. It's free, and does not require creating an account. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited on premises to maintain a smoke-free environment. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time. brbr brbrSecurity Cameras: For the safety and security of our guests and property, two exterior security cameras monitor the front door and carport. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.

Vahevala: Your Tranquil Mid-Town Key West Oasis, 3BR Home, Pool & Close to Beaches & Duval Street!

Key West, Florida, United States

Bed

Bath

Sleeps

$432.73

Welcome to Your Private Tropical Waterfront RetreatbrbrLive like a local in this peaceful, private Key West hideaway tucked along the Riviera Canal. This home blends tropical charm with comfort, offering everything you need for an extended stay in paradise. Thoughtfully designed and newly remodeled, it’s perfect for couples, small families, or friends seeking a serene, authentic Key West experience.brbrWith a large private pool, lush native landscaping, and a beautiful outdoor shower, this property embodies the relaxed island lifestyle. It’s a pet-friendly waterfront home ideal for those who want privacy and comfort while being just minutes from Key West’s beaches, restaurants, and attractions.brbrThe SpacebrbrThis cozy home offers three bedrooms, 1.5 baths, and bright, open living spaces that flow easily from indoors to outdoors. You’ll find everything you need for a comfortable long-term stay, including high-speed Wi-Fi, a fully equipped kitchen, and a washer/dryer.brbrLiving Room:brBright and cheerful with beautiful windows that let in plenty of natural light, the living room is furnished with two soft leather sofas, a Stress-less leather recliner, and a large Samsung Frame TV. A bookshelf holds books and games for relaxing evenings, and the open floor plan connects seamlessly to the kitchen and dining area.brbrKitchen & Dining:brThe open kitchen is fully equipped for long stays, with quality cookware, utensils, a coffee maker, blender, and full-size appliances. A large dining table comfortably seats six — perfect for shared meals, morning coffee, or a friendly board game.brbrPrimary Bedroom:brYour private retreat features a king bed, a comfortable mattress, and soft linens for a restful night’s sleep. The room is filled with natural light, cooled by a ceiling fan, and offers plenty of storage for extended stays. Local art and simple coastal décor create a peaceful atmosphere, and a smart TV adds modern comfort.brbrSecond Bedroom:brA cozy queen bedroom with a comfortable mattress, soft bedding, and a desk for a private workspace — ideal for remote work. Includes a small closet, dresser, and a smart TV.brbrThird Bedroom:brBright and welcoming with a queen bed, large closet, small dresser, vanity, natural light, and a smart TV — the perfect spot to unwind after a day of exploring the island.brbrBathrooms:brThe home has 1.5 baths — a full bathroom with a spacious shower and modern fixtures, plus a convenient half bath. Outside, enjoy a private outdoor shower surrounded by tropical greenery — a true Key West delight.brbrOutdoor LivingbrbrThe outdoor space is the star of this property. Step into your own private oasis with a large pool, surrounded by lush, native landscaping for total privacy. There’s plenty of seating for lounging, dining, or reading in the shade.brbrEnjoy the grill for outdoor cooking, the fire pit for cozy evenings under the stars, and the outdoor shower for rinsing off after a swim. This peaceful setting is perfect for morning coffee, afternoon sunbathing, or sunset cocktails.brbrThe home sits on a quiet canal that can accommodate a boat up to 50 feet, giving easy access to both the Atlantic Ocean and the Gulf of Mexico — a prime location for boaters, fishermen, and island hoppers.brbrAmenities at a GlancebrbrTropical, private, and pet-friendly waterfront homebrbrLarge private pool surrounded by native landscapingbrbrOutdoor shower, grill, and fire pitbrbrCanal access for boats up to 50 ftbrbrThree bedrooms (1 king, 2 queens)brbr1.5 bathroomsbrbrFully equipped kitchen and dining for sixbrbrHigh-speed Wi-Fi and Samsung Frame TVbrbrSmart TVs in every bedroombrbrWasher and dryerbrbrAmple storage and workspacebrbrBright natural light and terrazzo flooringbrbrPeaceful residential neighborhood, close to everythingbrbrLocationbrbrLocated on the Riviera Canal, the home offers a peaceful residential setting with quick access to everything Key West has to offer. You can bike anywhere — the beaches, local cafés, waterfront restaurants, and Old Town are just a short ride away.brbrIt’s the perfect location for those who love boating, fishing, or simply soaking up the tropical lifestyle. Whether you spend your days out on the water, exploring local shops, or lounging by the pool, you’ll return to your own quiet retreat each evening.brbrPet FriendlybrbrWe know pets are family! This home is pet friendly for well-behaved dogs (with a small additional fee). The fenced outdoor area and shaded spaces make it a comfortable spot for furry companions to enjoy, too.brbrRates & StaysbrbrDiscounts available for longer staysbrbrMinimum 28-day rentalbrbrUtilities and maintenance includedbrbrProfessionally managed with local supportbrbrGuest AccessbrbrYou’ll have exclusive use of the entire home, pool, and outdoor areas — everything is completely private. Parking is available for one car in the driveway and free parking in street.brbrAdditional NotesbrbrThis home is best suited for small families or groups of friends seeking a quiet, comfortable, and authentic stay. It’s not suitable for parties or large gatherings.brbrWhether you’re escaping winter, working remotely, or simply craving sunshine and calm, this tropical private waterfront home offers the perfect base for a month in paradise.brbrRelax, recharge, and experience Key West like a local.

Key West Lush Tropical Canal front Retreat 3BR Private Pool, Bring Boat & Pet

Key West, Florida, United States

Bed

Bath

Sleeps

$682.8

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrExperience the blend of historic charm and modern conveniences at TASTE OF HAVANA. This 2-bedroom, 2-bathroom cottage located ON world-famous Duval Street offers a front-row seat to the vibrant energy of Key West while providing a private pool and off-street parking for those who appreciate the finer things that come with island living. From the prime location and desirable amenities to having Last Key Realty’s unrivaled Guest Services & In-house Concierge, every detail of TASTE OF HAVANA is curated for an unforgettable island escape.brbrTHE LOCATION...brbrIf you've heard of Key West, you undoubtedly know of the famous 'Duval Street' with its selection of fabulous restaurants, shops, and nightlife. With a prime Duval Street address, TASTE OF HAVANA is truly the choice location for a group that wants to be in the heart of it all. You can enjoy unrivaled people watching from your porch or hop down your steps to any of the attractions within walking distance, including the Southernmost Point, Hemingway House, and famous spots like Sloppy Joe's, and any number of delicious restaurants. Should you decide to venture off the island, you do have one off-street parking space available. brbrTHE LIVING AREA...brbrStep inside to the cozy living space defined by eclectic Cuban décor. The plush sofa sits in front of the flat screen TV for those nights your group stays in. The living room flows into the fully equipped kitchen and dining nook.brbrTHE POOL & BACKYARD...brbrThe true TASTE OF HAVANA lifestyle is found outdoors. Out front, the private patio overlooking Duval Street is the ultimate vantage point for people-watching or enjoying a sunset cocktail as the town comes to life. When you are ready to escape the bustle, retreat to your backyard oasis. Tucked behind lush, tropical landscaping, you’ll find the saltwater pool, heat-optional for year-round enjoyment. This fully fenced sanctuary includes comfortable poolside loungers and a large propane grill, perfect for an al fresco BBQ.brbrTHE ACCOMMODATIONS...brbr** Master Bedroom - with a King bed, flat-screen TV, full closet, and an en-suite bathroom with a walk-in shower.brbr** Guest Bedroom - with a King bed, flat-screen TV, full closet, and an en-suite bathroom with a walk-in shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TV in Living Roombr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & Cable TV includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked condo also includes, but is not limited to the amenities on this list:brbr** Private Pool with Available Pool Heatbr** Designated Off-street Parking Space for 1 Vehiclebr** Propane BBQ GrillbrbrOther notes:br** Interim housekeeping provided upon requestbr** This property will accommodate up to 4 adultsbr** Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**TASTE OF HAVANA @ DUVAL STREET** Cozy Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

Bed

Bath

4

Sleeps

$589.46

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrHAVANA ESPECIAL is a charming, single-level 2-bedroom cottage located directly on the world-famous Duval Street in Old Town Key West. This inviting retreat features two private suites and a fully equipped kitchen, ensuring a comfortable stay just steps away from the island's best dining, shopping, and entertainment. Guests can enjoy the quintessential Key West experience from the classic front porch, an ideal spot for people-watching, while the inclusion of a rare private parking space provides ultimate convenience in this vibrant historic district. Combined with Last Key Realty’s Five-Stra Guest Services & In-house Concierge, your trip to the tropics is sure to be one you treasure for a lifetime.brbrTHE LOCATION...brbrIf you've heard of Key West, you undoubtedly know of the famous 'Duval Street' with its selection of fabulous restaurants, shops, and nightlife. With a prime Duval Street address, HAVANA ESPECIAL is truly the choice location for a group that wants to be in the heart of it all. You can enjoy unrivaled people watching from your porch or hop down your steps to any of the attractions within walking distance, including the Southernmost Point, Hemingway House, and famous spots like Sloppy Joe's, and any number of delicious restaurants. Should you decide to venture off the island, you do have one off-street parking space available. brbrTHE LIVING AREA...brbrInside, the home opens into an inviting living area with vibrant Cuban-inspired accents and a unique island flair. The plush sofa faces the flat-screen TV, providing the perfect space for relaxing on quiet evenings at home. The living area connects seamlessly to the home's fully-equipped kitchen and a quaint dining nook.brbrTHE HOT TUB & OUTDOOR SPACE...brbrThe exterior spaces of HAVANA ESPECIAL offer distinct ways to enjoy the island lifestyle. The front porch serves as a premier lookout over Duval Street, providing a front-row seat to the local parade of characters and the perfect backdrop for an evening drink as the night's energy builds. For a more secluded experience, the rear courtyard transforms into an open-air dining room, complete with a propane grill and patio seating ideal for sharing a fresh seafood dinner. The hot tub is a perfect place to end your day with a relaxing soak under the stars.brbrTHE ACCOMMODATIONS...brbr** Master Bedroom - with a King bed, flat-screen TV, full closet, and an en-suite bathroom with a walk-in shower.brbr** Guest Bedroom - with a Two Tin Beds OR One King bed, flat-screen TV, full closet, and an en-suite bathroom with a walk-in shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TV in Living Roombr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & Cable TV includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked condo also includes, but is not limited to the amenities on this list:brbr** Designated Off-street Parking Space for 1 Vehiclebr** Propane BBQ Grillbr** Hot TubbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 4 adultsbr** Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

**HAVANA ESPECIAL @ DUVAL STREET** Cottage & Pool + LAST KEY SERVICES…

Key West, Florida, United States

Bed

Bath

Sleeps

$572.39

Welcome to our stunning 4-bedroom vacation home in the heart 15 minutes from Key West! Nestled in the beautiful mangroves, this property offers the perfect escape for your next getaway.brbrAs you step inside, you'll be greeted by a fully stocked kitchen, complete with a stove, oven, refrigerator, grill, and all the necessary appliances and utensils to whip up delicious meals. Gather around the dining table or enjoy a barbecue on the outdoor patio, surrounded by the lush tropical landscape.brbrWhen it's time to unwind, cozy up by the outdoor firepit or enjoy a movie night on the smart TV with satellite/cable channels. For the fitness-minded, you'll have access to the on-site fitness room and equipment. And don't forget to take advantage of the free WiFi, washing machine, and dryer for a hassle-free stay.brbrJust a short 20-minute drive away, you'll find the vibrant Duval Street, where you can explore the local shops, restaurants, and the famous Florida Keys Beaches. For a round of golf, the Key West Golf Club is just an 11-minute drive from your doorstep.brbrProperty features ample parking for your RV and 30 Amp service via external outlet. Waste removal services available nearby.brbrWhether you're seeking a relaxing retreat or an adventure-filled vacation, our 4-bedroom vacation home is the perfect destination. Book your stay today and experience the beauty and charm of the Florida Keys!

Private Paradise, Waterfront Home - 15 minutes from Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$188.05

Summary:brConveniently situated in the picturesque Truman Annex gated Community, Gulf Getaway is a charming 2 bedroom 2.5 bath perfect for your next island getaway. brbrIn addition to its prime location, this storybook corner unit features 2 private balconies off of each bedroom and a back deck equipped with all of your outdoor dining necessities. Close enough to everything, but just far enough away Gulf Getaway allows you to enjoy the peaceful serenity of Key West.brbrThe Space:brOn the second floor you will find the 2 bedrooms, each featuring a queen size bed, attached full bathroom and balcony. Perfect for accommodating 4-6 guests, additional sleeping arrangements can be found in the queen pullout couch on the first floor.brbrThe open first floor plan with a half bath is perfect for relaxing after a long day. Equipped with an LG cable tv, complimentary Wifi and French doors leading out to the back deck, the natural sunlight in Gulf Getaway keeps the space bright and airy. From an espresso maker, to a Keurig and smoothie maker, the rooster-themed kitchen is stocked with all of your cooking and drink necessities. There is also a hose outside for washing off sand from the beach and a private back entrance to make accessing the back patio a breeze.brbrGuest Access:brOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to check-in to enter the unit. brShared Community Features: This home also includes access to the neighborhood pool- exclusive to Truman Annex homes and has lounge chairs perfect for sunbathing. brHow to Access: the bedrooms are located on the second floor with stair access only.brbrThe Neighborhood:brExplore all that Key West has to offer including Truman Annex’s brand new Waterfront park and pier overlooking the Gulf. On Thursdays catch the sunset farmers market at the park or bring the kids to the splash pad for a fun-filled waterpark adventure. Just a 2 block stroll from the world-famous Duval Street, Gulf Getaway is walking distance to endless shopping and dining options.brbrGetting Around:brParking Information: There is assigned parking provided for 1 vehicle. We can provide you with recommendations for parking additional vehicles upon request.brbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance.brbrOther Things to Note:br- In the upstairs hall closet, you will find a stackable washer and dryer.br- Pets Policy: Pets are welcome!brOur requirements are as follows: br•40lb maximum per petbr•$250/per staybr•2 pet maximumbr- This home has a 28-night minimumbr- Mid-stay cleans are available upon request.

Gulf Getaway | Condo w/Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$190.18

Full renovation completed in November 2024. This beautiful townhouse has a perfect location in Truman Annex. Truman Annex is an exclusive gated community within Old Town Key West. Coastal Soul is within walking distance to anything you will want to do...dining, music, bars , shopping, art galleries and more. brCoastal Soul is two story townhouse. The entrance to the main level contains a covered front porch with table and chairs for two. The front door from this porch provides access to the main level which is the living area. The living area contains a fully equipped kitchen with ceiling fan, coffee maker, pots, pans, plates, glasses and silverware. This level also includes a half bathroom, a dining area and living room (with a ceiling fan) and an entertainment center with a 55” flatscreen television. Double French doors from the living room open to the tropical rear yard containing a spacious deck with a table and seating for four. The community pool is just steps from the rear yard gate. The second floor level has two bedrooms and a 2 full bathrooms. The master bedroom is furnished with a queen size bed, has a vaulted ceiling with a ceiling fan, an over sized closet as well as a television. French doors from the master bedroom lead to your own private balcony. The en suite bathroom contains a shower, a vanity complete with amenities such as a blow dryer, soap and towels. The washer and dryer are located in the hallway & is a great amenity for guests. The second bedroom has a full size bed and a closet as well as its own entrance to a private full bathroom. The townhouse has central air conditioning. There are also 2 beach chairs for your use. This unit also has a dedicated off street private parking space.(please see added information for maximum size vehicle in parking info)The townhouse is also a short walk to Fort Zachary Taylor State Park (best beach in Key West) and Waterfront Park. Thank you for your interest in our tropical retreat, the perfect vacation place. brbr**Front door exterior RING doorbell added for security purposes

Truman Annex 2 bedroom 2.5 bath Townhouse- Newly renovated. Steps to pool

Key West, Florida, United States

Bed

Bath

4

Sleeps

$1028.58

Family friendly, secluded retreat within Key West Truman Annex gated community. Our lanai is a destination in of itself and makes this home extra special. We have some of the most comfortable bedding in Key West prepping you well for each day’s adventures. The fully-equipped kitchen is superb. Location Location Location. There is one vehicle carport, Duval is a block away, yet there is no clatter. This single-family home has three bedrooms and three full bathrooms. Private lanai area great for outdoor living and family dining and relaxing in the tropical atmosphere of Key West. Bring your emotional support or service animals so nobody is left at home, diminishing the experience for all. The entire home is available for your use and enjoyment. Just text if you need anything from dining advice to experience suggestions. We hope that you can stay with us.

Casa Cristol- Family and Pet Friendly - Classic KW Charm Superb Location!

Key West, Florida, United States

Bed

Bath

Sleeps

$340.81

SOUTHERN HOSPITALITY...brFind your luxurious, island retreat nestled in the heart of Old Town, just blocks from the beautiful beaches and minutes from town. An upscale refuge designed to surpass all of your expectations boasting an ideal entertaining space within an enchanting tropical setting. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES...brAlthough conveniently located, this home comes with the perk of one off street parking spot so you can come and go as you please. Pull up to this attractive abode with swaying palms greeting you in the island breeze. Step inside to find an open concept layout boasting cathedral ceilings, hardwood flooring and cheery natural lighting throughout bringing the outdoors inside. Find an updated and fully equipped kitchen with stainless steel appliance, granite counters, a wine chiller and bar seating for 2. The living space is filled with comfortable furnishings and a flat screen TV. All the TVs in this house are smart TVs available for your log in information. This property is equipped with security cameras located on the front of the home facing the yard.brbrSLEEPING ARRANGEMENTS...brThe main house offers two guest rooms beginning with a queen bedroom with a flat screen TV and an en suite full bathroom with a walk in glass shower that can also be accessed by the main hallway. A king master suite is located off the Great Room and comes with a flat screen TV, French doors to your private backyard and an en suite full bathroom with a walk in glass shower. A poolside cottage comes furnished with a queen bed, half bath and an adjoining room with a twin sofa sleeper and writing desk. brbrOUTDOOR LIVING...brAn awe inspiring, sparkling pool greets you in this incredibly lush backyard area - a heat option is available during winter months. Savor your surroundings in a lounge chair and dine al fresco together in the evenings. Rinse off in the outdoor shower which can also be accessed from the cottage and head into town for all the fun! Serviced every Friday. brbrPARKING...brEnjoy an off street parking space inside the gates. brbrPETS...brThis is NOT a pet friendly home.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). brbrSIMPLY HEAVENLY...

SOUTHERN CROSS ~ Conveniently Located 3 Bedroom, 2.5 Bathroom Gem w/ Pool

Key West, Florida, United States

Bed