33040, Florida, United States Vacation Rental Private-vacation-homes By Owner - Page 38

This property is a rare find! Sleeping 6 and located over 2 floors, its located in the beautiful resort of Santa Maria. The condo itself is overlooking the pool, enjoys 2 stunning balconies with its own outdoor furniture. Fully equipped kitchen, 2 1/2 bathrooms, TVs and wifi throughout. The property is located in one of the best destinations within the historic old town. Just 2 blocks from Duval Street, and also just 2 blocks from the beach. You really can have it all! brbrWe are proud to bring this property to the community. We have been looking at the key west market for the past 3 years and truly believe this property is the one we have been waiting for! Sleeping 6, its located in the premier resort in Key West. Santa Maria resort is Number 1 on TripAdvisor and regularly obtains awards as one of the best boutique hotels in the US. The property is over the top two levels of a stunning corner townhouse. Overlooking the pool and located on the side walkway which leads directly from the car park into the resort. brbrAs an owners unit, you do not pay the daily resort fee of $35 a day. This economic alternative means you wont receive daily cleaning (although you are welcome to upgrade to daily cleaning for an additional fee). You still get full enjoyment of the pool and we provide you with a parking permit which allowed one car to park within the car park by the hotel (this is on a first come first serve basis) brbrAs you are not paying this fee to the hotel you do not get access to the reception, happy hour, hotel pool towels. You do get access to the gym (although the water bottles are only provided for hotel guests)brbrTHE PROPERTY LEVEL 2 The unit itself has been perfectly designed with 4 balconies. 2 of which have fantastic views overlooking the pool!brbr We give you access by remote codes for the duration of your stay. The entrance up a flight of stairs provides a very private experience. You enter into a beautifully appointed living room which consists of a sofa bed which sleeps 2. The kitchen at the rear has been fully equipped and includes all eating and cooking utensils. On the same level you can also enjoy a half bathroom, and the unit enjoys its own washer/dryer. There is a balcony directly from the living room with outdoor furniture. brbrLEVEL 3 The upper level has two bedrooms with their own bathrooms and plenty of closet space. Each room has its own tv. The master bedroom has its own balcony overlooking the pool. We provide linen, towels and towels for the pool area

Key West dream townhouse -Sleeps 6 Like new! Old Town - Perfect location

Key West, Florida, United States

Bed

Bath

Sleeps

$531.46

Everyone enjoys time in Key West, and staying at The Orchid Oasis take it to a new level. We are a family of Conchs that have been born and raised in Key West for seven generations, and we look forward to welcoming you to stay in our home. brbrThis home is located just minutes from everything that's great about Key West. You can walk or ride a bike to both Smather's Beach or Higgs Beach in under five minutes, and you're just two minutes from White Street pier where you can watch the most amazing sunsets you'll ever see!brbrOur pictures show you all the great aspects of this home so be sure to look through them to get a good feel for the house and the layout. brbrWe offer all the comforts you need for your stay in paradise including WiFi, flat screen TVs, laundry, lovely and inviting pool with waterfalls and ample parking space. There is a 4 person maximum limit to this home (NO EXCEPTIONS). brbrThis home is in a quiet area of Key West and is not recommended for parties or group celebrations. We ask you to please be respectful of the neighbors and keep the noise level to a minimum.brbrWe can also provide home cooked meals for an additional fee! Want authentic Cuban roast pork with rice and black beans and the best Key Lime Pie on the island Or maybe a custom made batch of Key Lime Fudge made by the woman who invented it Or Key West Pink Shrimp & Cheese Grits WE CAN DO THEM ALL! brbrThis property has a ONE MONTH minimum stay requirement.brbrNOTE: We are VERY selective about who we rent to! This home is right next to our primary residence so we only rent to couples or groups of four or less. If you are coming to party, be loud and make a mess please don't even inquire. We want tenants who are going to treat this home like they're own.

Orchid Oasis - Only Minutes from Smather's and Rest Beaches!

Key West, Florida, United States

Bed

Bath

Sleeps

$914.51

Summary:brbrLuxury 2BD/ 2BA Suite with Two Oasis Pools, Pergola, Outdoor Bar and Grill and Private Porch with Amazing ViewsbrbrbrbrThe Space:brbrEscape the Ordinary....brbrbrbrThe Carysfort Lighthouse Suite is a luxury 2 BD/ 2BA stand-alone house located directly in front of one of our two brand new oasis pools with direct access to the pool deck and brand-new property amenities that sleeps up to 6 guests. Completely renovated in 2024, the suite is our premier unit and offers breathtaking pool views through the rear glass folding doors with Key West Lighthouse and partial Duval Street views from the private front porch located on a quiet Key West Lane. The suite also comes with an exclusive off-street parking spot for your stay.brbrbrbrSuite Amenities:brbrbrbr• Luxury king master bedroom with premium linensbrbr• Luxury queen bedroom with premium linensbrbr• Queen sleeper sofabrbr• Fully equipped brand new kitchen with bar seatingbrbr• Spa quality glass master en-suite bathroombrbr• Second bathroom with showerbrbr• Hardwood flooring throughout the suitebrbr• Spacious front porch with lighthouse and partial Duval St. viewsbrbr• Smart TVs with the latest Roku device for apps and streamingbrbr• High-speed Fiber Wi-Fibrbr• Washer and dryerbrbr• Luxury well-appointed furnishing and artworkbrbr• Reserved and exclusive off-street parking space for one vehiclebrbr• Accordian door access to one of the property's two oasis pools directly behind the unitbrbr• Our largest suite at more than 800 square feetbrbr• Luggage hut to store luggage and belongings in before check in or after check outbrbrbrbrLocation:brbrThe Carysfort Reef Lighthouse Suite offers the perfect blend of convenience and tranquility, located just a half-block from world-famous Duval Street. While you’re steps away from the vibrant energy of Key West’s best shops, restaurants, and nightlife, the resort is tucked away on a peaceful, picturesque lane, providing a quiet retreat. The iconic Hemingway House Museum, just behind the property, is only a 2-minute walk away, and Fort Zachary Taylor Park and Beach are also within easy walking distance. Experience the best of both worlds—close to the action, yet an oasis of peace and quiet.brbrbrbrAbout the Property:brbrWelcome to The Lighthouse Suites Collection, an exclusive six-unit luxury vacation rental resort offering in the heart of historic Old Town Key West. Just steps from Duval Street and a short walk to Fort Zachary Taylor Park beach, our location places you at the center of Key West’s most iconic attractions and vibrant nightlife.brbrbrbrThe Lighthouse Suites Collection is truly one of a kind. This mini resort is defined by its luxurious suites, on-site parking, and exceptional location. Our immaculate 5-star accommodations are enhanced by a unique outdoor experience featuring two tropical oasis pools with spacious pool decks, a pergola with a cozy seating area and fire pit, and a fully equipped outdoor kitchen and BBQ grill with a Brio filtered water and ice maker station.brbrbrbrWhether you’re planning a romantic escape, a memorable family vacation, or an unforgettable group retreat, the Lighthouse Suites Collection offers the ultimate Key West experience, blending luxury, comfort, and first-class amenities.brbrbrbrIn March 2025, we completed a full renovation of our outdoor common areas, exclusively accessible to guests of our six suites.brbrbrbrThe property now features two brand-new oasis plunge pools, each with its own sundeck, offering the perfect spot to sunbathe or unwind by the pool. Guests can relax on our teak chaise loungers or indulge in one of our two luxury double chaise cabanas. We also added a 200-square-foot pergola, separated into two areas: one half features a cozy seating area with a swing and fire pit, perfect for enjoying an elegant evening cocktail. The other half houses a fully equipped outdoor kitchen, complete with a BBQ, sink and two refrigerators. To top it off, the kitchen includes a Brio filtered water and ice maker system to keep you hydrated on warm Key West days.brbrbrbrProperty Amenities:brbrbrbr• Two brand-new heated oasis plunge pools, each with waterfalls and pool showerbrbr• Brand-new spacious pool decks around each poolbrbr• Six luxury teak chaise loungers with umbrellas and pillowsbrbr• Two brand-new double chaise luxury resort cabanas seating two guests eachbrbr• Two in-pool chaise ledge loungers to sunbathe and cool off simultaneouslybrbr• A brand-new 200 SF teak pergola with a louvered open or closed ceilingbrbr• Luxury couch and daybed swing under the pergola with an elegant fire pitbrbr• Fully equipped outdoor bar, BBQ grill with a sink and fridge under the pergolabrbr• Covered bar kiosk for enjoying a cocktailbrbr• Key West tropical foliage throughout the property with lighted step-stone pathsbrbr• Exclusive on-street parking spaces with room for six vehicles and 1 per suitebrbr• Schlage smart lock security on all Suites and gate access to the propertybrbrbrbrGroup Accommodation:brbrIf you need more room for your party, contact us about renting one or more suites for your stay. We have 3, two-bedroom suites, 2, one-bedroom suites, 1, one-bedroom bungalow accommodating a maximum of 30 guests. The property is perfect for weddings, other large gatherings, and events.brbrbrbrFrequently Asked Questions:brbr1. Are the pools and amenities shared brbrYes, the 6 Suites share all the amenities above which are exclusive to only guests staying with us on property and is secured with smart locks on the gate access to the property common areas.brbrbrbr2. What is the parking situation Can I bring more than one vehicle brbrParking in Key West can be challenging, but we’ve made it easier for our guests. Our property includes five reserved parking spaces and one exclusive off-street parking space for the Carysfort Light Suite, all conveniently located on Eanes Lane, right next to the Suites. Each space is clearly marked with signage along the buildings.brbrbrbrWe can accommodate one vehicle per suite. If you rent multiple suites, you’ll be assigned the corresponding number of parking spaces. For your convenience, a property map showing the location of all six parking spaces is included in the photos. Additionally, we will send the property and parking map in your welcome packet for easy reference.brbrbrbr3. Where is my Suite located brbrPlease refer to the property map in the pictures, which will show you the location of your Suite on the property. All three properties are adjacent to each other and the property is fenced in with smart lock gates.brbrbrbr• The Alligator Reef (2BD, 1BA), American Shoal (2BD/1BA), Sombrero Reef (1BD/ 1BA), and Tortugas Harbor Suites (1BD/ 1BA) are located at 419 Truman Avenue in the same historic building, with Sombrero Reef and Tortugas Harbor Suite located upstairs.brbrbrbr• The Key West Lighthouse Suite is a separate individual queen bungalow with a loft featuring a queen bed, located at 215 Eanes Lane.brbrbrbr• The Carysfort Light Suite is a separate individual 2BD/ 2BA with its own exclusive off-street parking space, located at 217 Eanes Lane.brbrbrbr4. Do I need a vehicle or transportation brbrIf you have a vehicle, we have rare parking available that most lodging on the island cannot offer but you do not need a vehicle to enjoy your stay with us. The property is located one-half block off Duval Street on quaint and quiet Eanes Lane delivering one of the best lodging locations on the Island close to everything but in a peaceful and quiet location. Here are the distances to some Key West Landmarks:brbrbrbr• Key West Lighthouse Museum, 2-minute walkbrbr• Ernest Hemingway Home and Museum, 2-minute walkbrbr• Blue Heaven Restaurant, 5-minute walkbrbr• Southernmost Point Buoy, 8-minute walkbrbr• Key West Butterfly Conservatory, 8-minute walkbrbr• Sloppy Joe’s Bar, 12-minute walkbrbr• Key West Amphitheater and Park, 12-minute walkbrbr• Mallory Square Sunset, 12-minute walkbrbr• Fort Zachary Taylor State Park & Beach, 12-minute walkbrbrbrbrWe look forward to welcoming you to paradise!

Carysfort Reef Light Suite

Key West, Florida, United States

Bed

Bath

Sleeps

$523.51

Welcome to Old Key West. Our Classic Old Town style duplex, with two independent fully renovated homes in the same property, ideal for families with kids, big groups, business travelers, couples get away, and friends vacation. This elegant homes are very well located in the middle of all the fun, but with the privacy and the peace of this paradise island; fully equipped for your convenience and at walking distance to great views, parks, beach and excellent restaurants.brThe spacebr*Please note that this home only allows minimum stays of 28 nights or longer.brbrCome and live a real Old Town experience in Key West. Our home from 1929, is located in a quiet, residential area near the Historic Seaport, beaches, sport activities, the Southernmost Buoy and the iconic Duval street, where food, wine, art and music are fused magically.

Two fully independent units in a Duplex, with independent entrances. One Rent!

Key West, Florida, United States

Bed

Bath

12

Sleeps

$1538.98

THE PROPERTY: Villa Josine not only has curb appeal but also is a stunning example of a Key West eyebrow house. This architectural style was popular in the 1800’s and helped keep the second story cool, prior to the advent of air conditioning. Unlike those of the 1800’s, this home has been completely renovated with modern amenities and high-end designer finishes. It’s large enough for your entire family to enjoy. brbrThere are 4 spacious bedrooms with 4 ensuite baths. Located on the first floor are two of the bedrooms, one with a king bed and the other with two twin beds. This sleeping area would be ideal for a young family or older family members. Two additional bedrooms are located on the second floor, one with a king bed and the other with a queen bed. All bedrooms include TVs and ceiling fans and are brilliantly furnished, such that you may not want to leave your room. There is also a convenient half bath on the first floor. brbrThe main area on the first floor includes a grand, vaulted ceiling and a large, open concept living room/dining room and kitchen. Top of the line stainless steel appliances, white quartz counter tops and open shelving will allure your family’s chef to create sumptuous meals, even while on vacation. The kitchen is adorned with a large island with seating for four and is cleverly trimmed in historic Dade County pine. An additional dining area overlooks the back of the home and private pool via a wall of glass doors. brStep outside onto the spacious, comfortably furnished covered deck. You can spend time reading, relaxing, or chilling in the pool. Surrounded by lush landscaping, you will feel as if you are in a private wonderland. brBeautiful furnishings and natural light abound throughout this home. Nooks and crannies, eclectic art and Key West charm are elegantly highlighted in this unique and exquisite home. Come stay a while in Villa Josine!brbrBED CONFIGURATION: The home offers 4 bedrooms each with their own ensuite bathroom. The 2 first floor bedrooms offer a king bed and 2 twin beds, while the 2 second floor bedrooms offer a king bed and a queen bed. **The twin beds cannot be joined to form a king.**brbrOUTDOOR AMENITIES: Enjoy your morning coffee or tea on Villa Josine’s welcoming front porch. Relax at the back of the home by the large sparkling pool with friends and family or enjoy a respite from the sun on the covered deck. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. Outdoor dining on the deck is a wonderful option with seating for eight and a gas grill. Whatever you choose, this private, tropical outdoor area is exactly what you think of when you think of Key West. brbrPARKING: This home offers the convenience of off-street parking for one vehicle. brbrLOCATION: Villa Josine sits in a quiet neighborhood on Elizabeth Street - one of the most sought-after streets in Key West! Relax in the heart of the Old Town North of Truman” district, which is conveniently located within walking distance to all the fun activities and fine dining that Key West has to offer. You are just a few steps from the historic Key West Cemetery and only two blocks from world famous Duval Street. William Butler Park is nearby, as are several Key West Conch homes. brbrPETS: This home is NOT pet friendly. (If you have pets, please browse through our many homes that are pet-friendly).brbrSMOKING: This is a non-smoking home and property. brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Managed by Historic Key West Vacation Rentals***

~ VILLA JOSINE ~ 4 B/4.5 BA large designer home with pool in a great location

Key West, Florida, United States

Bed

Bath

Sleeps

$246.92

Garden of Roses | Private Hot Tub, Prime Key West Location!brbrExperience the essence of Key West living at Garden of Roses, a beautifully restored conch-style home in a fantastic location. Just a block away from Duval Street, this monthly rental offers the perfect retreat for those looking to enjoy both comfort and convenience. With a private hot tub, lush gardens, and secure off-street parking, it's the ideal setting for a tropical escape.brbrThe Ambiance:brBlending historic charm with modern upgrades, this cozy Key West home comfortably sleeps up to 8 guests. The thoughtful layout provides privacy and space for everyone:br- Bedroom 1: King Bedbr- Bedroom 2: Queen Bedbr- Bedroom 3: Two Twin Bedsbr- Living Room: Sofa Bed for additional sleeping optionsbrbrThe open-concept living area is filled with natural light, creating a bright and airy atmosphere. Whether you're here to relax or work remotely, you'll appreciate the high-speed WiFi and multiple smart TVs with cable and streaming services. The modern kitchen, with granite countertops and stainless steel appliances, is fully equipped for meal prep, and the adjoining patio area offers a gas grill and outdoor dining space, perfect for enjoying a meal in the fresh air.brAfter a day exploring the island, unwind in the private hot tub or relax in one of the three serene outdoor seating areas, surrounded by lush greenery and sunshine.brbrGuest Access:brOur simple, contactless check-in process ensures a smooth arrival. You'll receive a personal access code ahead of time for quick entry.brbrThe Neighborhood:brLocated at the corner of Whitehead and Louisa Streets, this home puts you right in the heart of Key West. You're just steps away from the lively Duval Street, home to popular dining, shopping, and entertainment venues. Visit iconic landmarks like the Southernmost Point, the Ernest Hemingway Home, and the famous Blue Heaven restaurant. For beach lovers and history buffs, Fort Zachary Taylor Historic State Park is also nearby, offering both sandy shores and a historic fort to explore.brbrGetting Around:brKey West is easy to navigate by foot, but if you prefer to explore on wheels, there are many bike and scooter rental options close by. Fury and Island Bicycles offer convenient pick-up and drop-off services, and Minty's provides scooters and golf carts to get you into the island spirit. Alternatively, rideshare options like Uber and Lyft, or local taxis, such as Pink Taxi, are readily available. The home includes a spacious off-street parking area for those traveling by car.brbrOther Things to Note:br- The home is equipped with a private washer and dryer for your conveniencebr- Pets are welcome—just reach out for additional details. br- You'll also benefit from off-street parking, which is perfect for larger vehicles. br- Central air conditioning to keep you comfortable throughout your stay.br- Mid-stay cleaning services are available upon request.br- Relax and unwind in your very own private hot tub.br- Guests must be 25 years of age or older to reserve this property.br- A minimum stay of 30 days is required, in accordance with local regulations.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrTo 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, pool, and common outdoor areas. No cameras are placed in private or interior spaces.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.

Garden of Roses | Private Hot Tub, Prime Key West Location!

Key West, Florida, United States

Bed

Bath

Sleeps

$508.84

MODERN TROPICAL JEWEL WITH STUNNING OCEAN VIEWS…brThis contemporary and spacious custom-built gated home will beguile your senses, luring you inside with the finest of amenities and stunning design. Just a stone's throw away from the infamous Southernmost Buoy, you are truly seated in the heart of paradise in this small gated community. Designer finishes and top-of-the-line fixtures can be found throughout and will soothe and spoil your inner pleasure-seeker. This vibrant and bustling area is ideal for those looking for all the excitement and frivolity of Key West and may not be ideal for those guests who are particularly sensitive to outdoor noises. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brLush landscaping beckons you onto the front porch where you can sit and sip your morning java while marveling over the exquisite view of the Atlantic Ocean. Enter your retreat and pass by a powder room before entering the Great Room. The crisp white-out kitchen comes complete with quartz waterfall-counter island, stainless steel appliances, walls of impact-resistant windows with loads of island sunshine spilling in to brighten your spirits. There is a desk area with a window view that adjoins the kitchen. Enjoy your fresh catch at the dining table with for 4, then scoot across the room to collapse on the roomy sectional and binge on your favorite shows with a nearby Sonos speaker system (also in all bedrooms).brbrSLEEPING ARRANGEMENTS:brOne downstairs bedroom is just off the living area and has two cozy twin beds (can be converted to a king), with matching bedside tables and reading lamps, large tv, clothing dresser, and hanging closet. The private bathroom features custom floor-to-ceiling tile, glass-door shower with single sink vanity. Travel up the stairs to access two more bedrooms. The first offers a plush queen bed, large TV and a bathroom with floor-to-ceiling tile shower/tub. The third bedroom has a luxurious king bed and sitting area. Two large TVs offer viewing in bed and sitting area. Enjoy another ocean view from your room! A huge walk-in closet stores your clothing and the bathroom offers a double sink vanity, floor-to-ceiling tile and a large glass-door shower with rain shower head. A laundry closet with stacked washer/dryer is included.brbrOUTDOOR LIVING…brLush foliage surrounds the home exterior and lures you outside to your private dipping pool (heated in the winter months), outdoor shower, gas grill and sun lounging chairs. A rooftop terrace and two levels of front porches with seating look out to unobstructed views of the glorious Atlantic vista.brbrPARKING...brThere is one designated parking space for this home.brbrBOOKING DATES:brThis home is only available as a monthly rental (28 night min). 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.brbrPETS...brDogs that are 30 lbs and under are permitted and a pet fee is required.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)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).

SEA FOREVER ~ Downtown Ocean View Home w/ 3 BR, 3.5 Ba w/ Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$418.26

****This property requires a minimum stay of 28 nights in the same calendar month****brbr***Brand New Pool with waterfall, saltwater, heater, and a chiller to maximize comfort! brbrbrTropical Properties Vacation Rentals invites you to our beautiful historic home located in Historic Old Town Key West. This home is located just two blocks from Duval Street and in the center of all things Key West. This home was originally built in 1929 and has been painstakingly restored to include every modern amenity.brbrbrThe spacebrLOCATION: This tropical destination is a two block walk from Duval Street where you will be dazzled with boutiques, restaurants, nightlife, gallery viewing, shopping and an abundance of other activities, yet the neighborhood is quiet and serene. The homes is located 5 blocks from South Beach, 8 blocks from the North Harbor, a comfortable walk or bike ride to everything Key West.brbrHOUSE LAYOUT: The home is boasts a gorgeous brand new front porch and new pool, with an abundance of patio furniture an outdoors oasis. This home has hard wood floors and modern tile throughout, a spacious family room, central air, washer/dryer located inside the home, a dishwasher all rarities in Key West rentals and makes this a truly enjoyable space.brbrBEDROOMS: This home offers 3 beautiful bedrooms with 2 full bathrooms. Every bedroom on the first floor has a TV, all have tropical décor, new linens and comforters.brThe first floor features 2 bedrooms. The first bedroom boasts a queen bed, dresser, two night tables and a large closet. The second bedroom also has a queen bed, two night tables and large closet. The living room included a brand new sofa queen sleeperbrThe second floor is a loft accessed by stairs as shown in the photographs with a ceiling height of 5'2 and has two twin beds, 2 dressers, night stands, and a clothes rack.brbrCOMMON AREAS: The kitchen contains all brand new top of the line appliances, a refrigerator with an ice-maker, microwave and dishwasher. The dining area contains a comfortable configuration.brbrPETS: No pets are allowed in this home, this is NOT pet friendly.brbrPARKING: There is designated parking space on property for two FULL SIZE vehicles, an absolute rarity in Key West.brbrOUTDOOR AMENITIES: The tropical outdoor space is furnished with several seating areas both in the sunshine and shade. The back of the home offers a quiet respite from the hustle and bustle of nearby Duval Street.brSecurity cameras are installed on the exterior of the house. Front door, side alley, and facing backyard/pool. brbrOTHER AMENITIES: Iron & Ironing Board, 2 x Hair Dryers, Bed Linens, Towels, Beach Towels, Washing Machine, 3 x TV's, Washer dryer, Dryer, Garden (Private), Ceiling Fans, 2 x showers, high speed internet connection, air conditioning, 2x Fire ExtinguishersbrKitchen stove, Refrigerator ,Cookware & Kitchen Utensils, Dishwasher, Microwave, Toaster, Keurig, Blender and BBQ grill and utensils.brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr****This property requires a minimum stay of 28 nights in the same calendar month****

TROPICAL PROPERTIES VACATION RENTAL - KEY WEST

Key West, Florida, United States

Bed

Bath

Sleeps

$781.93

Charming Key West Oasis – Your Private Slice of Paradise!brbrEmbark on a month-long journey of relaxation and exploration at Seacret Paradise, a hidden gem tucked away in the heart of Old Town Key West. Located just two blocks from the Key West Express and Dry Tortugas ferry terminal, and mere steps from Old Town Bakery, Dive Bar, and Eaton Good, this private retreat blends peace, comfort, and unbeatable access to all the island’s magic.brbrThis charming four-bedroom, three-and-a-half-bath home comfortably accommodates up to nine guests and is ideal for couples, families, or anyone looking to immerse themselves in the Key West lifestyle. Enjoy bright indoor-outdoor living, a sunny balcony, a fully equipped kitchen, and a quiet lane location just minutes from the best dining, music, and waterfront sights in Old Town.brbrBooking Requirements: To ensure a smooth stay, all reservations require a signed rental agreement and a refundable security deposit hold. The deposit hold is $500 for and will be placed on a credit card 2–3 days prior to arrival and released within 5–7 days after check-out, provided no damage or policy violations occur. A Guest Service Fee is included in all reservations and varies based on length of stay.brbrPlease note: In accordance with City of Key West regulations, this property requires a minimum 28-day stay. This allows you to settle in, unwind fully, and explore the island at your own pace.brbrPet Policy: One dog under 30 lbs allowed with owner approval and pet depositbrbrCleaning Fee Breakdown:brTo ensure cleanliness and comfort during your extended stay, the $650 cleaning fee includes a Mid-Stay Clean (A full refresh halfway through your 28-day visit) and a Post-Departure Clean (A deep clean to prepare the space for future guests)brbrSome Additional Amenities (see amenities for full list):brPack-n-play and portable high chair available in upstairs bedroom closetbrFast Wi-FibrSmart TVsbrStrong A/CbrWasher/dryerbrDishwasherbrIce Maker in FreezerbrOne off-street parking spot (compact fit)brbrbrWhether you're here to write your next chapter, chase sunsets, or enjoy fresh croissants every morning, Seacret Paradise offers everything you need to live like a local—luxuriously.

Old Town Seacret Paradise! 4 BR with Pool!

Key West, Florida, United States

Bed

Bath

9

Sleeps

$605.09

Welcome to Your Tropical Escape at Duval Square brbrDiscover the perfect Key West getaway in this beautiful 2-bedroom, 2.5-bathroom retreat located in the exclusive gated community of Duval Square. Nestled on upper Duval Street—just steps from restaurants, cafés, and island conveniences - this property offers the ideal blend of privacy, luxury, and unbeatable location.brbrProperty Highlights:br~ Spacious & Stylish LivingbrRelax in the bright, comfortable living room featuring a sofa bed, convenient powder room, and easy access to your private balcony.brbr~ Master Bedroom SuitebrUnwind in the serene master suite with a king-size bed and a newly renovated private bathroom.brbr~ Second Bedroom SuitebrPerfect for guests or family, the second bedroom offers a queen bed and its own private bathroom for total comfort and privacy.brbr~ In-Unit Washer & DryerbrPack light and enjoy the convenience of doing laundry right at home.brbr~ ParkingbrA rare luxury on Duval Street—this rental includes one reserved parking space.brbr~ Private Outdoor OasisbrStep onto your private balcony and soak in the tropical breezes while you relax in your personal hot tub - the perfect spot for morning coffee, sunset cocktails, or unwinding after a day of exploring Key West.brbr~ Unbeatable Location - 1075 Duval Street brWalk to galleries, dining, boutique shops, and nightlife… yet return home to a private, peaceful retreat above it all.brbrCommunity Amenities:br• Sparkling swimming poolbr• Lush tropical landscapingbr• On-site restaurants, shops, bank, and convenience storebrEverything you need is right at your doorstep.br________________________________________brReady to indulge in the perfect Key West experience brThis luxurious and ideally located home books quickly—secure your stay today and experience island living at its finest!

Duval Square Retreat w/ Private Hot Tub, Pool, Parking & Walkable Location!

Key West, Florida, United States

Bed

Bath

6

Sleeps

$605.13

Island Dreaming – Your Luxury Key West Getaway - MONTHLY RENTALbrWelcome to Paradisebrbr*** Please note for 2027 High Season rentals Jan- February - Arrival after the 5th of January for 6 week minimum is required in order to get accurate pricing***brbrDiscover the ultimate island retreat at Island Dreaming, a spectacular Key West vacation home nestled between the charm of Old Town and the tranquility of the Meadows District. Whether you're traveling with family or friends, this private oasis blends upscale amenities with the laid-back lifestyle of the Keys.brbr Property Highlightsbrbr Location: Quiet yet central – walk to downtown, yet enjoy serene privacybr Bedrooms: 4 spacious bedrooms including two primary suitesbr Bathrooms: 3.5 modern bathroomsbr Parking: Off-street parking for 1 vehiclebr Size: Comfortably sleeps 8+ guestsbrbr Outdoor Oasisbrbr Private Saltwater Pool: 12’ x 18’, heated (by request), custom-tiled with waterfall & in-pool loungersbr Outdoor Kitchen: BBQ grill, sink, and ice-maker – perfect for entertainingbr Multiple Outdoor Living Spaces:brbr Expansive front porch for morning coffeebr Back deck for cocktails under the starsbr Shaded & sunny lounging areasbrbr Lush Landscaping: Tropical flora, paver walkways, irrigation, and outdoor lightingbrbr Interior Featuresbrbr Seamless Indoor-Outdoor Living: 9-ft ceilings & 16-ft glass doors connect the living area to the poolside deckbr Gourmet Kitchen: Fully equipped for all your culinary needsbr Wine Lovers’ Dream: 600-bottle, walk-in, climate-controlled wine roombr Two Primary Suites:brbr First-floor suite with private bathbr Second-floor suite with vaulted pine ceiling & private balconybrbr Bright Living Room: Natural light and pool views with wall-to-wall glass doorsbrbrAdditional Amenitiesbrbr Whole-house water filtration systembr Custom-designed staircasebr Pool heat available (fee applies; must be requested in advance)br High-speed WiFi & smart TVsbr Washer & dryerbrbrPerfect LocationbrbrLocated in a diverse, upbeat neighborhood, Island Dreaming puts you close to:brbr Duval Street nightlifebr Local restaurants & barsbr Art galleries, shops, and attractionsbr Beaches & marinasbrbrIdeal Forbrbr Familiesbr Groups of friendsbr Extended staysbr Guests seeking a luxury, peaceful vacation with easy access to the actionbrbrAdditional fees may be added after booking:br Pool heating fee of $300 per month for the months of November-March(optional)br Reservations of more than a month require a mid stay cleaning feebr brBook Your Stay Today and Start Living the Island Dream!

Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$284.21

Located in the heart of Key West's historic district on a quiet lane with parking directly in front of the private gated entrance to the home. 3 blocks from Historic Seaport and Duval Street.This is one of Key West's most coveted locations.brPrivate, perfect distance for walking or biking to local shops, bars or restaurants.brSurrounded by beautiful historic homes and mature Key West landscapes. This is a location you will want to visit more than once. Find your Key West home away frobrbrbrLocated in the heart of Key West's historic district on a quiet lane with parking directly in front of the private gated entrance to the home. Close to the beautiful seaport and downtown Duval Street.

Beautiful Old Town 2 bedroom Cottage on a Private Lane

Key West, Florida, United States

Bed

Bath

Sleeps

$1596.38

Key West is waiting for you at this superb 4-bedroom resort. Fresh and new inside and out, With 2 king beds, 1 queen bed, 2 twin XL beds, and 1 futon, guests will have plenty of space to relax. The 4 bathrooms feature a large pool and private back deck tub, 4 showers, and jetted bathtubs for a terrific stay. It's easy to see why you'll be able to unwind at our place. Excellent location just a couple blocks from Southern buoy and Duval. Play pickle ball and lounge on the beach just 2 blocks. Includes 4 bikes

4-bedroom resort style home in awesome Key West with large pool and private deck

Key West, Florida, United States

5

Bed

Bath

10

Sleeps

$599.06

SOUTHERN CROSS:brWelcome to this charming home in Bahama Village - Old Town Key West. This modern and elegant home was constructed in 2021 and features 3 bedrooms, 3.5 baths, off-street parking, and your own private pool! Available for rental stays of 28 days or longer, this home is perfectly situated in the heart of Old Town Key West. Guests are just 1.5 blocks to iconic Duval Street which features some of the best shopping, restaurants, and live music in the country. You're 2 blocks to the historic Key West Lighthouse and Hemingway House Museum, and 3.5 blocks to Southernmost Point or Key West's best restaurant...Blue Heaven!brbrDETAILS & AMENITIES:brEnjoy the enchanting atmosphere of this home which features the perfect blend of luxury, comfort, and island living! The home is complete with modern amenities like a private swimming pool, air conditioning, WiFi, a gas grill, two sets of washers & dryers, tankless hot water heaters for long & relaxing showers, ceiling fans in each bedroom, an EV charging station, and off-street parking, The bright, open layout also features impact-rated doors and windows, solid wood cabinetry, Dade County pine floors, quartz countertops, and professional-grade Viking appliances in a chef's dream kitchen. Each bedroom is spacious and filled with natural light, while the bathrooms are elegantly appointed and strategically placed for convenience--including a half bath with outdoor access, perfect for poolside guests.brbrSLEEPING ARRANGEMENTS:brThis home features a king bedroom suite on the main level with its own private bathroom. The master bedroom suite is upstairs and features a king bed with a large tiled shower with glass surround. The third bedroom suite is also on the second level and contains a full bed and a twin bed...also with its own private bathroom. A half bath is located on the main level and is perfect for pool guests or simple convenience. brbrOUTDOOR LIVING:brEnjoy the best of island outdoor living with a private concrete swimming pool, covered front and rear porches with composite decking, and a gas grill for delicious cookouts.brbrPARKINGbrThis home has two designated off-street parking spots in the front driveway. There is also ample on-street parking in the neighborhood if you have extra guests.brbrPETS:brThis home allows small dogs only.brbrBOOKING DATES:brThe home is only available as a monthly rental (28 night minimum).brbrCANCELLATION:brBookings canceled at least 60 days before the start of the reservation will receive a 100% refund. Cancellations inside of 60 days are non-refundable.

SOUTHERN CROSS: 3 BR, 3.5 BA home in Old Town Key West with Private Pool & AC!

Key West, Florida, United States

Bed

Bath

7

Sleeps

$1329.13

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrIf the rhythm of the islands has been calling and you're ready for a taste of the good life, then a stay at HALFWAY TO HAVANA is just what your soul is craving! Situated between the calm waters of the Florida Bay and the vibrant nightlife of Cuba's capital City, this unique vacation home blends the laid-back island vibes with all of the modern conveniences you’ve come to expect.brbrThis 4-bedroom, 4-bathroom property is the combination of 2 side-by-side private homes, reminiscent of the simple cigar-maker cottages that once lined the streets of Key West. The cigar-makers would be quite envious of the modern amenities and thoughtful touches these homes feature, such as the fully fenced backyard with spacious pool and parking for two vehicles. Located ON Duval Street, you'll be steps away from all that Key West has to offer. Paired with Last Key’s exceptional Guest Services & Complimentary In-House Concierge, you’ll be feeling the rhythm of the island in no time.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, HALFWAY TO 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 two off-street parking spaces available.brbrTHE LIVING AREA & KITCHEN...brbrEach home features a living and dining space, complete with a dining table and a flat screen TV. Each living area features a comfortable couch to lounge on. The kitchens feature modern appliances and all of the tools you'll need to prepare meals at home.brbrTHE PRIVATE POOL & GROUNDS...brbrThe property really shines when you get out to the private pool behind the units. Plenty of space to lay out and soak up some sun. Enjoy a swim or sit by the heat-optional private pool in the chaise lounges. Enjoy a poolside meal at the outdoor dining set while using the deluxe BBQ grill. You'll have everything you need for a cookout with the whole gang. The hot tub is a perfect place to end your day with a relaxing soak under the stars.brbrTHE ACCOMMODATIONS...brbr** Master Suite 1: Located in the First House with a King bed and an en-suite bathroom with a walk-in shower..brbr** 2nd Bedroom: Located in the First House with Two Twins OR One King and an en-suite bathroom with a shower and tub combo.brbr** Master Suite 2: Located in the Second House with a King bed and an en-suite bathroom with a walk-in shower.brbr** 4th Bedroom: Located in the Second House with a King bed 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 TVs in Living Room & All Bedroomsbr** 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 & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced Private Yardbr** Private Pool with available Pool Heatbr** Hot Tubbr** Two Off-Street Parking Spacesbr** Propane BBQ GrillbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 8 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.

**HALFWAY TO HAVANA @ DUVAL** Two Cottages w/ Pool + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

Sleeps

$249.31

Escape to the laid-back charm of Key West with The Gumbo Limbo Cottage, a beautiful and beachy vacation rental. Nestled in the heart of the island, this charming 1933 shotgun house has been impeccably restored and uniquely decorated, creating a tranquil and inviting atmosphere for your month-long getaway.brbrAs soon as you step inside, you'll be greeted by hardwood floors and vaulted ceilings that flow throughout the home. The front reading room, complete with a small refrigerator and desk, is the perfect spot for an early morning coffee or an afternoon nap, while the foyer doubles as a dining room with seating for four.brbrThe master bedroom is just inside French doors that lead to a king-size bed and a separate bathroom, including a private outdoor shower that can be accessed via a side door off of the bathroom. brbrThe guest room features a comfortable queen size bed, and both rooms are located off the main dining area, along with a guest bathroom with a large soaker tub and shower combo.brbrThe open living room and kitchen provide the perfect space for entertaining and cooking for your family and guests. The kitchen is complete with dishware and cookware, ready for you to create your own delicious items. There is countertop seating for two and a gas grill on the lower deck for BBQs. When the living room becomes too warm, you can lower the solar screens to let in natural light without the heat. The sliding glass doors open to the sundeck, complete with a table for six and lounging furniture, making it easy to enjoy indoor-outdoor living.brbrThe backyard is a true oasis, with lush Florida foliage and a large Florida almond tree, and Gumbo Limbo, which are native to Key West. Spend your days lounging on the sundeck or exploring all that this vibrant island has to offer. And, when it's time to wind down, retire to the comfort of your cozy home-away-from-home, complete with linens included and free WiFi. Please inquire about our pet policy. Don't miss out on the opportunity to experience the laid-back charm of Key West this winter - book your stay at this beautiful vacation rental today!brbrImportant Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. brbrGuests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check. brbr-------------brFree WiFibrCookware, Dishware, linens, & towels are provided.brMonthly Rental Only: Due to a local city ordinance, the property is not licensed to be rented for less than 29 days

The Gumbo Limbo Cottage - Your Happy Place - 2BD/2.5 Bath

Key West, Florida, United States

Bed

Bath

Sleeps

$606.36

Welcome to your private slice of paradise in the Keys! This exquisite waterfront home offers an unparalleled opportunity to immerse yourself in coastal luxury. Nestled on a sprawling 1/3-acre property, our retreat boasts breathtaking grounds and a mesmerizing ambiance that promises an unforgettable stay.brbrHighlights of Your Stay:brbr Spectacular Indoor-Outdoor Living: Soak in stunning bay views from our spacious patio deck, perfect for al fresco dining or simply admiring the gorgeous Key West sunsets. Lush greenery provides a serene sense of privacy, creating your own secluded oasis.brbr ️ Resort-Style Amenities: Bury your toes in the sand of your private beach-like backyard lounge, or take a stroll through our zen garden, illuminated by captivating bistro lights in the evening. Lounge by the large outdoor saltwater pool or unwind in the resort-style tiki hut overlooking the pool, complete with charming chandelier lighting and a comfortable dining area.brbr ‍♀️ Complimentary Adventure Gear: Explore the bay with our complimentary bikes, paddleboards, and kayaks. brbr ️ Spacious & Luxurious Interiors: Enjoy a generous open floor plan featuring a gourmet kitchen equipped with gas appliances. The dining room comfortably seats up to eight guests, making it ideal for family gatherings or entertaining friends.brbr Elegant Accommodations: The master bedroom features a king-size bed and offers direct access to the patio deck overlooking the channel—wake up to serene water views and start your day in tranquility. Additional bedrooms include one with a queen bed and ample closet space, and another featuring bunk beds and a cozy sofa.brbr Entertainment Galore: Unwind in our bar/game room, complete with a tiki bar and convertible sectional sofa, providing extra space for relaxation and fun.brbr Bring Your Boat & Jet Skis: With a 50ft dock and nearby access to both the Atlantic Ocean and the Gulf of Mexico, you're set for aquatic adventures. Explore nearby sandbars and private islands, enjoy breakfast at Geiger Key, or let us connect you with the best local guides for unforgettable excursions.brbr Ample Parking: Plenty of parking space is available, including room for your trailer or RV.brbrLocal Delights Within Walking/Biking Distance:brbr☕ Famous Baby’s Coffee: Start your day with artisanal coffee and delicious bagels, croissants, and pastries at this local favorite.brbr Baby's Food Truck: Mouth-watering burgers and sandwiches from Baby's Food Truck.brbr Family Park: Enjoy a nearby park equipped with basketball, volleyball, and tennis/pickleball courts and more—perfect for some fun and exercise during your stay.brbrBook Your Dream Getaway Today!brbrIndulge in the ultimate coastal experience—whether it's lounging by the pool, kayaking the bay, or unwinding in our resort-style tiki hut. Just 15 minutes from the vibrant Duval Street, you can enjoy the excitement of Key West while retreating to your peaceful sanctuary.brbrEscape to this luxurious retreat and create unforgettable memories in the Keys.brbrReserve Now and Start Your Adventure!brbr**HOUSE RULES**brbr-No Parties/Eventsbr-No loud outdoor noise after 9pm / before 9am, please be respectful of our neighborsbr-No Diving into Pool or off of Dock, there is no lifeguard on dutybr-No sand in the pool. This could cause expensive damage to the filter. Please use wash bin for feet before entering the pool when coming from beachbr-Please do not leave doors to outside open to avoid letting in insects and to preserve A/Cbr-Additional house rules may apply and will be provided prior to booking check-in date or by requestbrbrbrIt is important to note that water depths and tides may vary in the area surrounding the property. Prior to booking, please consider and verify whether water depths are suitable for your needs. While we are happy to provide answers based on our knowledge of the area, please use extreme caution when boating and use the dock at your own risk. We only allow one docked boat per booking. We can also arrange for an offsite dock for additional boats with access to deeper waters in conjunction with this booking, subject to availability and appropriate fees.brbrPets allowed (smaller dogs and cats) with prior approval of breed and a pet fee (per pet).

Your own Private Resort! 50ft Dock on Canal w/ Pool, Tiki and RV Hookup!

Key West, Florida, United States

Bed

Bath

Sleeps

$670.15

Only one block to the Hemingway House and two blocks to the Green Parrot bar! Restaurants, beaches, bars, entertainment all within incredibly short walking distance. Walk the town on a warm evening and return to cool off in the back yard pool.brbrThis impeccably renovated property makes the perfect vacation getaway. At first glance, you'll confirm its aesthetic appeal and secluded location half a block from Key West's celebrated Duval Street. If two bedrooms, two-and-a-half baths, an outstanding pool and deck area, and dedicated off-street parking meet your needs, you can't find a better residence anywhere on the island. See our other VRBO properties listing number 3023197 and 2232811 !br

FunSeeker 1/2 block off Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$270.87

Available for monthly, or longer, rentals this three-story townhouse is located on a picturesque street in the beautiful, gated Truman Annex community. It’s close to all the major attractions yet just far enough away to be quiet and relaxing. Duval Street, the center of it all, is just two blocks way. The nightly Sunset Celebration at Mallory Square, a must see, is just four blocks away. The recently opened Truman Waterfront Park, including a free waterpark for the kids, is just a short walk / two-minute drive from our townhouse. There’s bound to be something for everyone in Key West - restaurants, nightlife, Fort Zachary Taylor State Park and Beach, Little White House, Key West Aquarium, Butterfly Conservatory, parasailing, snorkeling, diving, fishing, fine dining - the list goes on and on. brbrThe first floor, complete with living room, dining area, and kitchen features vaulted ceilings providing a bright and airy feeling. There’s also a half bath on the first floor. The master suite with en suite bath is located on the second level. It has French doors opening onto a private balcony. The laundry center is also on the second floor. The third-floor guest suite, with its own full bath, has many windows overlooking the tropical garden below. The shared, heated swimming pool is close by and is complete with lounge chairs for sunning. brbrThe unit includes free high-speed wireless internet so you can keep up with all those e-mails or just let everyone know what a wonderful time you’re having. brbrThe living room also has a high-def LED SMART TV with surround sound. Therefore, watch HD programming or access your Netflix account and stream a movie. brbrCome enjoy one of the many local festivals - Fantasy Fest, Hemingway Days, Powerboat Races, Lobster Fest or just relax in the townhouse enjoying the tropical Caribbean Island.br brYOU MUST BE 25 OR OLDER TO RENT THIS UNIT. NOT AVAILABLE TO SPRING BREAK STUDENTS (SORRY). PLEASE INDICATE THE NUMBER OF ADULTS AND CHILDREN IN YOUR INQUIRY AND GIVE THE AGES OF THE CHILDREN. THIS UNIT IS DESIGNED TO ONLY ACCOMMODATE 4 PEOPLE.brbrKeywords: Townhouse

Truman Annex, two blocks from Duval

Key West, Florida, United States

Bed

Bath