Vacation Rentals By Owner In Key West, FL

THE PROPERTIES: With plenty of space in an ideal location, Maisons de Luxe combines a large two-story home with a stylish two-story cottage. Family, friends, or wedding guests will appreciate being together yet apart in this smart setting. If you need less space than Maisons de Luxe offers, each property may be rented separately. brbrGRAND MAISON (The Main House): Just beyond the staircase, an open concept living room and kitchen will excite you. Equipped with everything you need to prepare meals in a comfortably furnished home, you will enjoy entertaining guests at Grand Maison. An indoor-outdoor living space spills onto the covered porch and saline pool. Swim in the sunshine, lounge by the pool, or keep an eye on the kiddos from the shaded lanai…the options are endless. brbrThe first floor of Grand Maison also includes an ensuite king bedroom and a convenient half bath. The second floor includes three ensuite bedrooms. The twin bedroom with ensuite bath and vaulted ceiling is a charming space for your children. The other two bedrooms have ensuite baths with walk in showers, bedside tables, lamps, and natural light. This is the Key West lifestyle you have dreamed about. brbrPETITE MAISON (The Cottage): Your vacation begins on the second floor of this cottage with an inverted floorplan. A second-floor open concept living room peers into the petite yet mighty kitchen. The living room’s French doors open out to a comfortably furnished covered veranda. Enjoy outdoor dining or relaxing with a cocktail in the tropical breezes. On the first floor you will find two beautiful king ensuite bedrooms as well as a stackable washer and dryer. This unique home’s mix of white walls, wood accents and stylish art, will help you appreciate the Key West vibe. brbrBED CONFIGURATION: Grand Maison has four bedrooms, each with its own ensuite bathroom and TV. The first-floor king bedroom is perfect for family members who prefer single floor accommodations. There are 3 equally beautiful bedrooms on the second floor. One bedroom has two twin beds (cannot be joined together) and the other two bedrooms have king beds. Petite Maison has two king bedrooms with ensuite baths on the first floor. When rented together, Maisons de Luxe has a total of 6 bedrooms. brbrOUTDOOR AMENITIES: Grand Maison offers a private saline pool with water feature surrounded by sunshine, palm trees and lounge chairs. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. A comfortably furnished outdoor porch and gas grill are available just steps outside the double sliding glass doors. Enjoy the covered front porch and second floor balcony. Petite Maison offers a second floor comfortably furnished covered veranda. When rented together, you can enjoy all the amenities at Maisons de Luxe!brbrPARKING: There is parking for two cars however, from this convenient location, you may find yourself touring Key West on foot. brbrLOCATION: The homes of Maisons de Luxe are located on Duval Street and an adjacent Lane. Both homes are on the southern end of Duval Street near cafes and night clubs. You can walk to many attractions including the Southernmost Point and the Key West Butterfly and Nature Conservatory. brbrPETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry- no cats.brbrSMOKING: This is a non-smoking home. brbr**Guests must be 25 years of age or older unless accompanied by an adult.brbr**Managed by Historic Key West Vacation Rentals.

~ MAISONS de LUXE ~ 2 Stunning Homes w/ Private Pool ON DUVAL.

Key West, Florida, United States

Bed

Bath

Sleeps

$360.28

THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished second-floor duplex home comes with Key West charm and contemporary touches. To explore the first-floor home, search for “Poinciana Garden” or book “Poinciana Paradise” to reserve the entire home for family or friends. brbrWalkable to many shops and attractions, you will feel like a local in no time. Enjoy coffee or cocktails on your covered porch with a treetop view. Prepare meals in the bright and sunny kitchen with built in corner hutch, open shelving, and gas range. With so many local dining options, you won’t even mind being without a dishwasher. An open concept living area with vaulted ceilings provides natural light and adds to the airy ambiance of your vacation home. This area is cooled by a brand new mini-split AC and ceiling fan. The primary bedroom includes an ensuite bath, TV, nightstands, brand new mini-split AC, and ceiling fan. Stroll through its French doors onto the private porch and enjoy the Florida breeze with a delightful book. Sun yourself in the shared yard or take a jaunt to the beach. When the day is over, you may find yourself relaxing under the stars and enjoying conversation with newfound friends. brbrBED CONFIGURATION: The king bedroom has an ensuite bathroom with a tub/shower combination and a mini-split AC. There is a sleeper sofa in the living room for a child or guest. brbrOUTDOOR AMENITIES: Open the French doors from your bedroom and step out onto the second-floor covered porch. The backyard features a shared gas grill, washer and dryer, lush garden, chaise lounge chairs, and outdoor dining set.brbrPARKING: There is on-site parking for one small car as well as a bicycle rack for your convenience. Please note this home is on a tiny, one-way lane. brbrLOCATION: Historic Old Town, North of Truman and 2 blocks from the excitement of Duval Street. A majority of the best Key West attractions are located here as well as numerous restaurants, shops, and galleries. The neighborhood boasts historic homes, shotgun, and conch style homes. You will enjoy being right in the middle of everything!brbrPETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry, cats are not allowed.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***

~ POINCIANA TREETOP ~ Casual second floor duplex 2 blocks from Duval Street!

Key West, Florida, United States

Bed

Bath

3

Sleeps

$1108.0

THE PROPERTY: Nancy & Carl invite you to share their love of the island in their enchanted 3-bedroom home. Live like a local in this unique Key West property. Designed for relaxation and indoor-outdoor living, this home exudes local architecture, art, and joie de vivre. From its welcoming front porch to its private back yard, you will know from the start, that you are in a special place. brbrThe living room is comfortably furnished with plenty of seating for family and friends. From here you can open the expansive French doors and enjoy the patio area or take a dip in the cocktail pool. The kitchen is nearby and equipped with a gas range, stainless steel refrigerator, granite island and grey and white custom cabinets. You will find all that you need to entertain family and friends. If you are not dining at a local restaurant, you can opt for a meal at the handsome dining room table or dine al fresco, just outside the kitchen door; the choice is yours. A convenient half bath with stone vessel sink, washer and dryer and a folding counter, round out the first floor. The beautiful staircase at the front of the home will lead you to the bedrooms. If you are looking for the epitome of Key West, look no further than Southard Comfort! brbrBED CONFIGURATION: All three bedrooms are located on the second floor, have vaulted ceilings and are characteristically Key West. The primary bedroom with king bed includes a TV, dresser, ceiling fan, closet, and skylight as well as an ensuite bath with tiled shower and vessel sink. The second bedroom has a queen bed, nightstands, a dresser, closet, TV, and plenty of natural light. The third bedroom is also bright and includes a queen bed, dresser, closet, and TV. A shared Jack and Jill bath with access from the second and third bedrooms is adorned with louvered pocket doors, a tiled, walk-in glass shower as well as two separate vanities with granite countertops. brbrOUTDOOR AMENITIES: The cocktail pool with figurine water feature is located right off the living room to provide you with easy indoor-outdoor living. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. Rinse off in the outdoor shower after a dip in the pool or a day at the beach. Enjoy outdoor dining on the patio area with umbrella table and chairs and gas grill.brbrPARKING: This home comes with your own private driveway with space to park one vehicle-a real Key West treat!brbrLOCATION: Old Town, North of Truman Ave, just 4 blocks to the Historic Seaport area and 6 blocks to the excitement of Duval Street. brbrPETS: This home is NOT pet-friendly. (If you have pets, please browse through our many homes that are pet-friendly).brSMOKING: 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***

~ SOUTHARD COMFORT ~ Feel the Key West vibe in Old Town with a private pool.

Key West, Florida, United States

Bed

Bath

Sleeps

$985.51

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!brbrTHE PROPERTY: Dreaming of putting your toes in the sand or sipping coffee on your dock Then this is the vacation home for you! The lush backyard is gated and leads out to the warm Gulf of Mexico. Just steps from the water’s edge, this unique paradise has a dock for your shallow-draft fishing boat. There are several outdoor areas of enjoyment including a dining table, loungers, and covered porch with comfortable furnishings. brbrIndoors, you will find a large living room with plentiful seating and a TV. Via large French doors, this room has views of the covered porch, pool area and sea. A bonus room/study with pocket doors and NEW twin beds is located near the living room. The dining area has ample table seating for 6. In the kitchen you will find everything you need to prepare meals or cook up your catch of the day. Stainless steel appliances, a slide-in range and solid surface countertops provide the conveniences of home. Peninsula seating allows you to socialize with your guests. The open-concept first floor is perfect for entertaining and embodies the indoor-outdoor Florida lifestyle. brbrThree bedrooms are located on the second floor and have their own TVs and ceiling fans. A primary king ensuite with soaking tub and walk-in shower offers a wide balcony and commanding water views. A queen bedroom and a full/double bedroom share a hall bath with a tub/shower combination as well as direct access to the treetop balcony.br brThis private paradise is a boater’s dream. Not a boater Then enjoy the pool, direct water access and breathtaking sunsets right from your backyard. Gulf Pointe’s Sea Vista embodies life on the turquoise waters of Key West. brbrBED CONFIGURATION: The primary ensuite bedroom has a king bed and balcony. Two additional bedrooms, one with a queen bed and one with a full/double bed, share a full bath and balcony. There are twin beds in the first-floor bonus room/study.brbrOUTDOOR AMENITIES: Just beyond the property’s fence and rarely available in rentals, there is dock access for a shallow draft, 21-foot maximum boat. Enjoy your private deck, outdoor shower, and stunning gulf views. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. A gas grill, outdoor dining table with umbrella and comfortable loungers complete your outdoor experience. brbrPARKING: There is a dedicated, covered parking spot for one car. brbrLOCATION: Midtown East in the gated community of Gulfview Pointe. Close to restaurants, retail shopping, and amenities. The energy of Duval Street, the magic of the Historic Seaport, and the beauty of the Atlantic Beaches are short bike rides away.brbrPETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry, cats are not allowed.brbrSMOKING: This is a non-smoking home and property.brbr***Please note that the cleaning fee includes a full mid-stay clean***brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Managed by Historic Key West Vacation Rentals.***

~ SEA VISTA ~ A waterfront dream with private heated pool and boat launch.

Key West, Florida, United States

Bed

Bath

Sleeps

$567.39

**This home is available in August only as a monthly rental (28 nights in the same month).** Come and live like a local! brbrTHE PROPERTY: Enjoy fresh air and sunshine from your front porch or backyard hot tub at Casablanca Too. This unpretentious home has been beautifully updated and is ready to welcome you. The living room looks out to the covered front porch and has lots of natural light, large screen, TV, cool wall AC and a comfy slip-covered sofa. The room is adorned with new lighting and two gorgeous swivel club chairs that allow you to converse with family and friends or turn to watch TV. If you need to work from home, the new fold-down console has plenty of room for your laptop and when done, you can fold it back to its original size. New hardwood floors adorn the home, making it easy to keep clean. brThe cozy updated kitchen has outdoor access and is complete with all that you need to prepare meals or snacks. New appliances include a stainless-steel refrigerator and range. Just outside the kitchen you will find the new dining area furniture with seating for four and boho lighting. brThe spacious king bedroom with wall mounted TV, wall AC and new furniture includes dual night stands with storage, bedside lamps, and a beautiful white headboard. French doors lead out to your private hot tub. The ensuite bath includes a pedestal sink, open storage shelves and tiled stall shower with glass door. New patio furniture and a sun shade adorn your backyard oasis. Start your day with coffee on the covered front porch. Take your bike or walk to Duval Street and enjoy all the excitement that make Key West unique. When you are done for the day, come home and enjoy dinner on the grill and a hot tub massage in a peaceful part of town!brIf you are vacationing with another couple or family, you may rent the other side of this duplex which sleeps four and has a private pool. Look up Casablanca to do this individually or look up Casablanca Grande” to rent both sides of this duplex home simultaneously.brbrBED CONFIGURATION: Enjoy your spacious king size bed and ensuite bath, with wall AC. brbrOUTDOOR AMENITIES: From your bedroom, you can open the French doors and step out to the backyard’s lush foliage and private hot tub. You will also enjoy the new outdoor dining set, umbrella, and gas grill. Your own washer and dryer may be found in the outdoor area near the hot tub.br brPARKING: This home includes off street parking for one car. brbrLOCATION: Historic Old Town, North of Truman Avenue and close to The Meadows, a residential district. Walk to Duval Street in 15 minutes or take a 5-minute bike ride to Higgs Beach or the Southernmost Point. Fausto’s Food Palace, The Best Coffee in Town, Bayview Park, and the Key West Cemetery are also just a short walk away.brbrPETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry, cats are not allowed.brbrSMOKING: This is a non-smoking home and property.brbr***Staying for a month or longer Request a quote for a minimum of 28 nights to see our discounted monthly rates.brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Managed by Historic Key West Vacation Rentals***

~ CASABLANCA TOO ~Chicly updated home with hot tub in a quiet location.

Key West, Florida, United States

Bed

Bath

Sleeps

$869.27

THE PROPERTY: Enjoy the walkable location of this charming property. As you enter the home from its covered rocking chair front porch, you are in the open concept living room and kitchen. The compact kitchen with peninsula seating is equipped with everything you need to prepare meals or snacks. The living room is comfortably furnished, including a TV and ceiling fan. The room’s large French doors open onto the partially covered deck where you can enjoy dining poolside. The fresh ‘catch of the day’ will taste great when cooked on the gas grill. The outdoor dining table is partially covered and provides a respite from the sun. After a day exploring Key West, cool off in your private pool or enjoy cocktails in the covered lounge area. brbrIdeal for a small family or two couples, this home provides a bedroom and full bath on each level. The primary open loft bedroom is located on the second floor and includes an ensuite bath with walk-in shower. The TV and seating area are a bonus in addition to the vanity/desk for primping or working in your home away from home. The secondary bedroom and hall bath with walk-in shower are located on the first floor. The built-in shelves, window seat, ceiling fan and TV add to this comfortable sleeping area. brbrThis home includes a small bonus space with a built-in bookcase and a love seat. No matter which room you choose as yours, this distinctive Key West cottage is sure to delight! A washer and dryer are located outside for your use.brbrBED CONFIGURATION: The primary king loft bedroom, ensuite bath with louvered door, and seating area are on the second floor, accessible via an open riser staircase. Please note upstairs shower may be tight for taller people due to sloped ceiling. The loft area is open to the area below as seen in the photos. The second queen bedroom with hall bath is on the first floor. brbrOUTDOOR AMENITIES: Private, refreshing cocktail pool with outdoor shower, gas grill, loungers, and Adirondack chairs. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. The deck also includes a dining table and chairs as well as a comfortably furnished covered lounge area. brbrPARKING: No designated parking. On-street parking available in the neighborhood. brbrLOCATION: Old Town, South of Truman Ave. Known as Uptown Key West, this area features beautiful Victorian homes, historic cottages, and quiet tree lined streets. Potter’s Cottage is conveniently located minutes from Key West’s major attractions – including sun kissed beaches, restaurants, museums, galleries, and shopping. Just one block from the famous Duval Street, this location offers limitless opportunities to explore the city by foot. 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***

~POTTER'S COTTAGE~ Key West charmer in great location with private pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$357.57

CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 AtlanticbrStart Date: May 2025-Estimated Completion: Spring 2026brPlease be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026.brImportant Notes:br-Units available for booking will not be under construction.br-All amenities, including the pool, spa, and sunning beach, will remain open and fully operational throughout the project.brbrBeautifully Renovated 2nd Floor Condo with Ocean & Preserve Views – 28-Day Minimum StaybrbrWelcome to your home away from home! This beautifully renovated 2nd-floor unit features luxurious finishes throughout and offers the perfect blend of comfort and style. Step out onto the expansive 40-foot private balcony, where both bedrooms and the living room open to stunning views of a serene nature preserve and the Atlantic Ocean.brbrThe condo is fully equipped with all the modern conveniences needed for a relaxing and enjoyable vacation, including high-speed Wi-Fi. Each of the two spacious bedrooms is outfitted with a King bed, and for added flexibility, the guest bedroom can be arranged with two Twin beds upon request.brbrThis is a non-smoking unit designed for your comfort and peace of mind.brbrLocated just a short walk or bike ride from the island’s top amenities, you’ll also be less than 1.5 miles from the historic district—home to renowned restaurants, charming shops, and vibrant nightlife. Whether you’re seeking adventure or tranquility, this location has something for everyone.brbrFeel free to call us or stop by for local tips and recommendations—we’re happy to share our favorite spots with you.brbrWe’re confident that once you stay here, you’ll want to return year after year.brbrPlease note: This property requires a minimum stay of 28 days.

Sea La Vie, Elegant Key West 2BR/2BA | Renovated Condo at 1800 Atlantic

Key West, Florida, United States

Bed

Bath

6

Sleeps

$1433.25

The Galleon Resort in Key West is a Perfect Resort for you, your Guests and your Family. The unit is spacious and very beautiful. The decor is everything you would desire in a Key West accommodation: tropical, clean lines and filled with every need possible.brbrThis Unit was built for the Developer and is unique with many extra features which includes a private sun-deck. It is a Penthouse Unit with 3 private bedrooms, an additional King bed in the loft and a queen pull-out sleeper sofa in the living room. brbrA full kitchen in the main unit and a small efficiency kitchen in the lock-out unit. The over sized balcony which streches the width of the entire unit gives you a panoramic view of the yachts, ocean and tarpon swimming among the floating docks below. The amenities are varied making family needs ideal from fishing off the dock to catch dinner, sunbathing by the pool, treasure hunting on the beach, jet skiing to a near by island, taking a short 5 minute drive to Play Key West Goldf Club (A Reese Jones Design) or chartering a boat for a day of fishing.brbrbrThe Resort: The Galleon Resort has it all ! Whether you just need to rent the efficiency (see our other add) or the two or three bedroom this is much cheaper than going to any of the 5 Hotels in the Marina/Malory Sq Area.. Go for the Resort Lifestyle!

Very Rare-The Galleon 3 King Bd, 3 Bath w/ 4th king bd in loft + sleeper sofa

Key West, Florida, United States

Bed

Bath

Sleeps

$187.72

CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through the Spring of 2026. This construction WILL impact your stay if you are staying during the week days. Please contact All Florida Keys Property Management for more detailed information. brbrSpacious 2-Bedroom Condo with Ocean Views & Island ComfortsbrbrThis beautiful 2-bedroom, 2-bath condo offers a lovely view of the Atlantic Ocean and an extra-large floor plan with a slightly oversized private balcony—accessible from both bedrooms and the living room. It’s the perfect island retreat with all the comforts of home.brbrEnjoy a full-size, fully equipped eat-in kitchen and a full-size washer and dryer for added convenience. Whether you're here for a short stay or an extended escape, this condo provides the space and comfort you need to truly relax.brbrKey West offers something for everyone:brFrom its rich literary and artistic history to live theatre, museums, and exciting water sports. For thrill-seekers, even skydiving adventures await. Enjoy world-class restaurants, a laid-back atmosphere, vibrant live music, and a welcoming, safe environment—all with perfect winter temperatures in the only frost-free city in the continental U.S.brbrCome visit paradise. We promise you won’t regret it.

Charming 2 Bdrm Oceanfront Oasis Key West Beach access Old Town Bike ride.

Key West, Florida, United States

Bed

Bath

Sleeps

$404.36

Located just two miles from picturesque Smathers Beach, this well appointed two bedroom, two bath condo is ideally situated in Key West. Explore all Key West has to offer, located just three miles from vibrant Duval Street, and four miles from historic and majestic Mallory Square.brbrThe property features two pools, a hot tub, park-style grills, picnic tables, onsite bar, and much more.brThis spacious two bedroom condo features a king primary suite with hardwood flooring, a connecting ensuite full bathroom with shower and bath tub. The guest bedroom features a queen bed with wood flooring. The condo also features a full kitchen, with a full refrigerator, microwave, stove, oven, dishwasher, coffee maker (drip style), toaster, blender, dishes and utensils. The living room features a queen-size sleeper sofa, HD TV, a dining area and access to a private patio. This is a two-story condo and the bedrooms are upstairs.brbr*Must climb stairs — Stairs required to access the unit, Stairs may be required to access bedroomsbrbrGuest must be 25 yrs old to rent and check-in to this unit.brbrUnits are assigned in seven night increments, multiple week stays may be booked, room moves may be required.brOccupancy limits are strictly enforced.brbrNo RVs, campers or mobile homes may be parked on the premises. Parking is limited to two (2) vehicles per unit.brbrWelcome Center hours of operation are: Sunday to Thursday 9am – 5pm and Friday/Saturday 8am – 10pm. Late arrivals must call the welcome center for arrangements.brbrAn ID and a credit card is required upon arrival for a refundable security deposit.brbrWe do not accept liability for any inconveniences beyond our control including but not limited to temporary defects or outage of utilities, closures of resort amenities, or limitation of any other service. We will not provide refunds, reimbursements, or compensation for inconvenience or interruption of utilities, resort amenities, or any other service.brbrGumbos is not currently operating as a bar or restaurant.brbrLaundry facilities located on top floor of buildings for a fee. Towel Exchange is not available.brbrPictures are representative of units on property. All feature similar layouts, decor and amenities. Property features most 2 story units. There exists a chance you may be assigned a single story unit. Specific unit is assigned at check-in by the front desk.

Waterfront Property - Marina Access - Spacious - Excellent Key West Condo

Key West, Florida, United States

Bed

Bath

6

Sleeps

$1577.63

Welcome to Bottom’s Up Bungalow — Your Private Tropical Escape in Old Town Key WestbrbrStep into a world of comfort and island charm at Bottom’s Up Bungalow, perfectly situated in the serene Meadows subdivision, just minutes from the vibrant heart of Key West. This immaculate 2-bedroom, 2-bathroom single-family home combines classic Florida bungalow appeal with modern amenities to create an inviting retreat that has earned over 100 glowing five-star reviews from delighted guests.brbrHome Highlights & FeaturesbrbrSpacious & Inviting Living RoombrBright and airy, the living room is designed for relaxation and socializing. Sink into the plush sectional sofa that easily converts into a sleeper for additional guests, or unwind in the comfortable sitting chair while enjoying your favorite shows on the large flatscreen TV. Natural light floods the room through large windows, creating a warm and welcoming atmosphere.brbrElegant Formal DiningbrJust off the living room, the formal dining area comfortably seats four — perfect for intimate dinners or leisurely breakfasts. The classic design complements the polished hardwood floors that flow throughout the home.brbrChef’s Dream KitchenbrThe heart of the home is a spacious, open-concept kitchen featuring generous counter space, high-quality appliances, and all the essential cookware and utensils to prepare anything from casual snacks to gourmet meals. A breakfast bar with stools offers a casual dining option, while the adjacent informal dining nook provides a cozy spot for family meals. Double French doors open onto the poolside patio, inviting fresh air and natural beauty inside.brbrTranquil Primary SuitebrThe primary bedroom is a serene sanctuary, outfitted with a luxurious king-size bed, a sturdy chest of drawers, and a large closet with a full-size washer and dryer tucked inside for your convenience. Step through elegant French doors to the pool and garden, perfect for early morning coffee or evening relaxation under the stars.brbrSpa-Like Primary BathroombrLocated just outside the primary suite, the hallway bathroom boasts a spacious custom shower with sleek tilework, a large vanity with ample storage, and a linen closet to keep all your essentials neatly organized.brbrFlexible Guest BedroombrThe second bedroom features two twin beds that can easily be converted into a king bed upon request, ideal for couples or friends traveling together. This room also includes a chest of drawers, a roomy closet, and a private en-suite bathroom complete with a shower, vanity, and toilet — providing comfort and privacy for your guests.brbrResort-Style Pool & Outdoor LivingbrStep outside to your private tropical paradise. The oversized pool, heated from December through May, is perfect for a refreshing swim any time of year. The attached whirlpool spa (note: not a hot tub) offers soothing bubbles to relax tired muscles. Surrounding the pool is an elevated deck with two sun loungers — ideal for soaking up the Florida sun. Enjoy meals or drinks at the outdoor dining table shaded by an umbrella, or retreat to the custom-built gazebo featuring a wet bar and bespoke seating, making it the ultimate space for entertaining or unwinding.brbrLush Tropical Gardens & PrivacybrThe beautifully landscaped gardens are enhanced by tasteful lighting and privacy fencing, creating a secluded oasis that feels worlds away from the bustle of downtown Key West. The tranquil greenery invites you to savor quiet moments with family and friends in any season.brbrParking & ConveniencebrOne assigned parking space is available in the driveway for your ease and security. Additional vehicles can be parked roadside, subject to availability, allowing you to bring along extra guests or rental cars with peace of mind.brbrPrime Location Near the Best of Key WestbrTucked away on a quiet one-way street within a peaceful community, Bottom’s Up Bungalow offers the perfect balance of tranquility and accessibility. You’re less than one mile from the excitement of Duval Street, famous beaches, and the marina. Enjoy the vibrant nightlife, eclectic dining, and unique shops of Old Town, then retreat to your calm, private sanctuary at day’s end.brbrWhy Choose Bottom’s Up Bungalow brbrWhether you’re here for a romantic getaway, a family vacation, or a fun trip with friends, Bottom’s Up Bungalow provides the perfect home base. With its spacious layout, thoughtful amenities, lush outdoor spaces, and unbeatable location, this bungalow promises a memorable Key West experience filled with relaxation, adventure, and island charm.brbrWe invite you to be our guest and experience the magic of Bottom’s Up Bungalow on your next trip to Key West!

BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL

Key West, Florida, United States

Bed

Bath

Sleeps

$969.75

Location, location, location. Our spacious1800 Atlantic 3 bedroom condo offers a fabulous view of the ocean from all three bedrooms, the kitchen and the living room. Birds of various types, boating activities, lush oasis gardens are just a few reasons why people keep returning to our paradise property. Click on 'more information' also click on 'More info on Brad & Dee' to learn more about island. brbr1800 Atlantic is located in the middle of the Island on the Atlantic side. Two miles up is the Key West Airport and 2 miles south is the famous Mallory Square where the cruise ships dock. Off of Mallory Square is Duval Street where so many shops, bars, restaurants, and museums are located.brbrKey West is a small island but we still recommend you renting a car, scooters, or even rent bicycles to get around to see it all. There are so many unique and great places to eat at or visit for entertainment. brbrEvery evening down at Mallory Square they have a Sunset Celebration. This is where people with unique talented skills perform. Also down here are many fun vendors who set up shop. Everyone watches and waits to see the sun dip into the ocean. Now for the nightlife to wakeup and begin. brbrMallory Square and Duval Street.is the Center of where it all happens. There are lots of tourist shops available and in the evening many live bands play at the bars. Some people like to do the Duval Crawl where they go from bar to bar. Jimmy Buffet's first Margaritaville is located down here to remind all you Parrotheads that it's 5 O'clock somewhere. There are many historic museums to explore. Never a dull moment. There is so much Happening on this little Island that is only about 4 miles long and 2 miles wide. Grab your favorite drink and enjoy the SUN, SAND, SEA AND FIREBALL SUNSETSbrbrPLEASE NOTE: THERE WILL BE ONGOING CONSTRUCTION WORK AT THIS COMPLEX MAY 2025 UNTIL MARCH 2026 REPAIRING BALCONIES. THERE WILL BE NOISE AND DUST DURING THE WEEKDAYS

Panoramic 3BR/3BA Condo - Direct Beach Ocean Front

Key West, Florida, United States

3

Bed

3

Bath

Sleeps

$268.16

The Simonton Studio is neat, sweet and complete. This pet friendly accommodation is the perfect location for exploring Key West. So, get out there and live it up in Key West and come home to a king size bed and everthing you need to fix your own cocktails.brbrLocated in a 6 unit compound this tiny Association is located in the heart of Old Town on Simonton St. Walk to the Hemmingway House, the Butterfly Conservatory and stroll Duval street with it's shops, restaurants, galleries and museums. brbrPeople ask me about parking more than anything and this condo does not come with assigned parking but the spaces in our block, on the street out front available on a first come basis. I provide additional tips for finding parking with my instructions but I encourage you to not bring a car into Old Town as it is an historic district and over 100 years ago it was not anticipated that tens of thousands of visitors would come to enjoy it's beauty so there simply is not enough parking in Old Town for all who come and changing that would affect the historical value. A car is not a practical way to tour Old Town because parking is scarce and expensive all over town. Locals have adapted and have taken to bicycles to travel the Town. The City of Key West has implemented a bus service around Old Town called the Duval Loop and it stops a half block from this rental. brbrShould you book this property I strongly recommend you purchase the cancellation insurance offered by VRBO, particularly during hurricane season. Flights are frequently canceled by the airlines and while they may be willing to rebook new flights I do not have the flexibility to give you new dates and you will be expected to pay for the dates you booked. Cancellation insurance will cover this in most cases. brbrThere is no pool at this property but there are small beaches all around the island and several are within walking distance of this property; Southernmost Beach would be closest at 6 blocks away. Fort Zachary Taylor State Park has the beach that locals like best, it is a State Park so there is a fee but the facilities are excellent: picnic tables, grills, outdoor shower, indoor shower, change rooms, restaurant, chaise lounges for rent and a water view that is the best in Key West. brIf you prefer a pool there is an excellent public pool at 300 Catherine St. The MLK Community Pool is an 11 minute walk from the condo and this roof-top, outdoor pool offers excellent sunbathing and views of Key West. brThere are also hotels that welcome patrons of their restauant to use their pools and I provide info on those locations in the condo. brbrThank you,brPam MacKenzie

Apartment

Simonton Studio, an Old Town get-away for 2

Key West, Florida, United States

Bed

Bath

Sleeps

$300.53

The Jungle Breeze condo at LaBrisa Condominiums.br*Ocean Viewbr*Free WiFibr* Free Covered Parkingbr* Final cleaning included in pricebr* KING size bed.br* Accommodates 2 adultsbr* Recently renovated this condo features all new flooring and a brand new kitchenbr* Full size washer and dryer. brbrThis is not a hotel; it is a privately owned condo facing the ocean with a view of swaying palms and turquoise waters. The Jungle Breeze condo is the perfect getaway for a romantic couple or a small family. The Jungle Breeze condo features a fabulous view of the ocean and the beach.brbrThe road construction around the condominium property mentioned in reviews has been completed as of February 2022, there are still road construction projects happening around the island but none that affect this property. brActivities and Attractions : At Smathers beach you will find available such activities as windsurfing, sail boarding, snorkeling and kayak or Jet Ski tours. Old Town, Key West and Duval St are about 1mile away and there you will find dozens of restaurants, famous bars, art galleries, museums, live theater, boutique shopping and tours available on both land and sea. Key West is a bicycle friendly town and this is a great option for touring our small island of 2 miles by 4 miles.brbrCovid 19 : the mask order in Key West has been rescinded but you will find some businesses do require a mask to enter their premises so please always carry a mask with you. Residents of LaBrisa Condominiums may be required to wear a mask on the elevator if there have been reported cases of Covid on the property. brThank you,brPam MacKenzie

Your Condo by the Beach with Ocean View

Key West, Florida, United States

Bed

Bath

Sleeps

$681.49

DETAILS AND AMENITIES...brEnter this inviting open floor plan with incredible natural lighting throughout. Three sets of French doors take you from the living/kitchen space out to the outdoor entertainment area, consisting of a private heated lap pool all to yourself, propane gas grill, swing set, outdoor dining for 4, additional outdoor seating and pool loungers. Wood flooring, high ceilings and breezy ceiling fans in each room will keep you cool and refreshed on a sultry summer's day. Whip up your favorite family meals together in the gourmet kitchen that comes with gorgeous granite countertops, custom cabinetry, updated stainless steel appliances and dining for 6. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrSLEEPING ARRANGEMENTS...brThe downstairs guest room comes with a queen size bed and a private porch. There is a full bathroom just outside of this bedroom with a walk in shower. Upstairs you will find the king master bedroom with an en suite full bathroom that comes with a desirable claw tub, walk in glass shower and washer/dryer set. Adjacent to the master bedroom is an enclosed, air-conditioned Florida room with cozy seating which then leads you out to an additional outdoor, covered balcony with incredible views of the lush tropical pool area. Steps down the hall is another guest room with a queen size bed, an en suite full bathroom with a shower/tub combination and a private, covered balcony area. The colorful, teal-tiled poolside cottage comes with a queen size bed and an en suite full bath with a shower/tub combination, and it is air-conditioned. All bedrooms are equipped with a flat screen TV and ample closet space including the guest cottage.brbrOUTDOOR LIVING...brCool your senses and quench your island craving with this magnificent outdoor space that offers your own exceptional private poolside lounging space. THIS POOL IS ALL YOURS--YOU DO NOT SHARE IT WITH ANYONE ELSE! Take advantage of the additional outdoor dining space for being able to enjoy your fresh catch of the day in the evening hours followed by swimming under the stars. This community’s quaint pathways are just a few steps away from all the island's main attractions. brbrPARKING...brThis home comes with one covered parking space. No trailers, boats, jet skis or motor homes are allowed. No vehicle length over 18’ long, including trailer hitches, or 80” wide is allowed on property. Additional vehicles may park in the Opal Key Resort parking garage just a five minute walk/drive away.brbrPETS...brPets are permitted with a required pet fee. Please provide pet size, breed and age upon booking. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool Heat 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. Cancellations 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.

BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!

Key West, Florida, United States

4

Bed

4

Bath

Sleeps

$4734.49

Summary:brbrTwo 4 BDR/4BA SuitesbrbrbrbrThe Space:brbrWelcome to Old Harbor House, an exquisite vacation rental combining two spacious 4-bedroom suites in the heart of Key West. Perfectly situated on Front Street, you're just steps away from the vibrant Mallory Square, where you can enjoy the daily sunset celebration. This luxurious penthouse retreat accommodates up to 20 guests, making it ideal for weddings, family reunions, or group getaways. Recently remodeled, our property beautifully blends modern luxury with the historic charm of over 200 years of Key West heritage, featuring restored brick walls and soaring 12-foot ceilings. Each oversized bedroom boasts a private bathroom, ensuring comfort and privacy for all guests. The chef's kitchen is fully equipped for culinary enthusiasts, perfect for preparing meals to share together. With separate entrances for each suite and a prime downtown location, there’s no need for a car—you can easily walk to all the best attractions in the area. Experience the unique charm and elegance of Old Harbor House; a one-of-a-kind stay awaits you!brbrbrbrGuest Access:brbrThere are two separate 4 bedroom/4 bathroom suites located in the same building. Both have private entrance.brbrbrbrThe Neighborhood:brbrDowntown Key WestbrbrbrbrGetting Around:brbrWalkable distance to all.

Apartment

Harbor Luxe Celebration Suites

Key West, Florida, United States

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