Vacation Villa Rentals By Owner In Key West, FL

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

Sleeps

$288.44

FRESH! FRESH! FRESH! Everything in this house is brand NEW and clean from linens, bed spreads, furniture, and the paint to name a few!brbr Looking for a vacation get away A home away from home This 1400 square foot, gorgeous water front stilt house gives you plenty of room to relax, have fun and most importantly right now social distance. Newly renovated this year, from furniture and paint, to linens and mattresses, it is clean and beautiful inside and out. There are 3 bedrooms and 2½ bathrooms, a full kitchen, dinning room, and living room. The waterfront access and beach themed interior give you the vacation vibes that you are looking for. brbrA deck off of every floor and a widow’s watch above allows you to enjoy sunrises, moon rises & beautiful night skies. Outback there is a floating dock where you can sit out and relax, tan, fish or tie off your boat. Ramp access is available access to both Gulf of Mexico and Atlantic Ocean. No boat No problem! You can still cool off from the hot Florida sun in our luxurious 13 person swim spa that overlooks the canal. Lounge on the spacious rear covered deck facing the water where there is a tiki hut and a private outdoor shower. We also have new Kayaks and Bikes to cruise around and explore both the land and sea.brbrOnly 15 miles from downtown Key West and Big Pine Key, makes it an easy ride to a beautiful location. Well attended by locals and visitors alike Baby's Coffee, Fish Restaurant and Bay Point Deli & Market are places you won’t want to miss during your visit. Bay Point County Park has a Kiddie Park, and basket, tennis, and volley ball courts plus a wide open field to let your dogs run and a place to play Bocce ball all within walking distance from the house. Experience the relaxation provided by this home and the unique location for yourself.brbrSmall dogs under 50 pounds are allowed. A $300 non refundable pet fee will be charged if you wish to have your pooch accompany you. No cats, birds, hamsters or other animals aloud. If you have any questions regarding your pet feel free to reach out.

Summer get away desination- at the newly renovated three story fun house!

Key West, Florida, United States

3

Bed

Bath

9

Sleeps

$904.52

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

Seaside Retreat: Waterfront Home with private heated pool & lush landscaping

Key West, Florida, United States

Bed

3

Bath

8

Sleeps

$359.25

Escape to paradise in this spacious 4-bedroom, 2-bath waterfront home (2,600 sq ft) on Saddlebunch Key. Enjoy a private pool, tiki hut, kayaks, and a custom play structure — all just steps from a park and local coffee spot. Your perfect monthly Keys retreat!

Waterfront Pool Oasis: Tiki Hut, Kayaks & Family Fun!

Key West, Florida, United States

Bed

3

Bath

8

Sleeps

$292.16

Tucked away in the exclusive Gardens of Key West community, this elegant single-family home offers the perfect blend of tranquility and central Old Town living. Beautifully appointed and thoughtfully updated, the recently renovated kitchen features stunning marble countertops and opens to a soothing, tranquil, and inviting living area adorned with beautiful coastal furnishings. Attractive composite flooring and soaring ceilings enhance the bright, open first-floor design.brbrImpact doors lead to a private, heated pool area surrounded by lush, beautiful landscaping — creating a peaceful tropical retreat ideal for extended stays. The outdoor space features comfortable poolside seating perfect for relaxing afternoons, along with a dining table for four, ideal for al fresco meals in the warm island breeze.brbrUpstairs, the spacious primary suite and guest bedroom both feature vaulted cathedral ceilings, hardwood flooring, and en suite bathrooms, offering comfort and privacy for residents and guests alike.brbrQuietly secluded yet just moments from the energy of Duval Street, this refined tropical oasis offers the best of both worlds — privacy and proximity — making it the perfect monthly escape in the heart of Key West.brbrMonthly Rental Only: Due to a local city ordinance, the property is not licensed to be rented for less than 29 daysbrImportant 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. brbrMonthly rentals onlybrPets considered, 50lbs or less with a $200 non refundable pet feebrVirtual Tour Url: https://my.matterport.com/show/ m=jgNY7b67ALw

Pretty In Pink- Modern Comfort, Prime Location-2BD/2Bath- May-August 10% off!

Key West, Florida, United States

Bed

Bath

Sleeps

$476.79

Located on stock Island inside of Coral Hammock Townhomes. This community features a resort style pool, gym and is just 8 minutes from Duval Street. Make your holiday one for the books with a stay at our place.brbrBedroom 1 KingbrBedroom 2 QueenbrBedroom 3 Two twinsbrLarge pullout sofabrbrThis home is located next to Gone Coastal and Another Day in Paradise.

Slice of Paradise

Key West, Florida, United States

Bed

Bath

Sleeps

$806.58

Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach, pool, jacuzzi, with a restaurant and bar. Relax in the jacuzzi or sauna during your stay or workout in the onsite fitness center. Enjoy fishing off the dock, or rent bicycles and take in all that Old Town Key West has to offer.brbrKey West Shipwreck Museum and Mallory Square are just a 5 minute walk from this conveniently located resort. The Ernest Hemingway Home & Museum is 1 mile away.br.brWelcome to the heart of Old Town Key West. The resort overlooks the Gulf of Mexico with a private marina, private beach, pool, jacuzzi, restaurant and tiki bar. This two bedroom condo sleeps six, and features a fully equipped kitchen. The primary bedroom has a king size bed, jetted tub, as well as a full bathroom. The guest bedroom features either two twin beds or one queen, and has access to the full guest bathroom. The living room has a TV with cable, dining area for six, and a sleeper sofa. Off the living room is a balcony to enjoy the Key West ocean breezes. brbrResort fee is due at check-in, along with a refundable security deposit. Refundable security deposit is released, as long as no damages occur during your stay.brbrPlease note, guest bedroom may feature 2 twin beds or 1 queen bed. Please let us know your preference before booking. We will do our best to fulfill it, but it is not guaranteed.brbrUnits are assigned after booking, in seven night increments. Multiple week stays may be booked, room moves may be required.brbrHousekeeping changes linens and towels on Wednesday only. If daily housekeeping is desired, there is an additional fee imposed by the resort.brbrParking for one vehicle, per unit only. No oversized vehicles, RV's or trailers are allowed to park on property. Parking is extremely limited and multiple vehicles are not able to be accommodated.brbrMinimum Age: 25 years oldbrPet Policy: No PetsbrAn ID and credit card for a refundable security deposit will be required.brCheck-in is after 4 pm; brCheck-out by 10 am.brNo Smoking. Penalties will apply.brNon-Refundable Cancellation and Refund PolicybrbrWe 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.brbrPictures are representative of the unit, layout and decor may vary. Units assigned at time of booking, please inquire prior to booking about specific unit and bedding configurations. All units have a King Bed in the master bedroom and the second bedroom will either have two twin beds or one queen bed.brbrUnits are assigned in 7 night increments, multiple week stays may be booked, room moves may be required.

Heart of Key West - 2BR Waterfront at the Galleon Resort

Key West, Florida, United States

Bed

Bath

Sleeps

$561.38

Summary:brPoolside Suite is the PERFECT vacation home for family and friends looking for a fun-filled getaway in the heart of Key West. The tropical themed home shares a pool and sun deck with Poolside Retreat which is located directly next door, ideal for groups looking to make new friends! Not to be left out, this property has a designated off street parking spot - a luxury in Key West!brbrThe Space:brPoolside Suite offers 2 bedrooms and 1 bathroom, as well as an updated kitchen and a living room with plenty of seating. There is 1 king bed, 1 queen bed, and a queen sized pull-out couch located in the living room, allowing a max occupancy of up to 6 adults. brbrEnjoy the free WiFi, 3 flat screen TVs, and the comfy furnishings throughout the home. Just outside of the living room's French Doors, you'll find a tropical oasis complete with a shared heated pool, and plenty of pool chairs ready for you to lounge in. Gone Fishin Well when you get back, cook up the day's catch on the outdoor shared gas grill. There is so much to love about this Key West gem!brbrGuest Access:brOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival.brbrShared Features: Pool, grill, back deck, washer/dryer and driveway.brbrThe Neighborhood:brPoolside Suite is located in the heart of Old Town Key West and is just half a block from world famous Duval St. You are well within walking distance to some of the most popular spots in Key West such as the Earnest Hemingway Museum, the Southernmost Point, Key West Lighthouse, The Butterfly Conservatory and much more. There is a CVS about a block away in case you need to stock up on drinks and snacks. There are also amazing restaurants nearby such as Blue Heaven, Seven Fish, Santiago's Bodega, and the Better Than Sex Dessert Restaurant.brbrGetting Around:brThere is one off street parking spot for this property which is to the left of the front door on Olivia St. Please park in the correct spot which will be labeled Poolside Suite. The other spot belongs to the home next door which is Poolside Retreat.brbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance. Feel free to ask us for recommendations!brbrOther Things to Note:br- Shared washer/dryer in the back of the home.br- Pets Policy: Pets are welcome!brOur requirements are as follows: br•40lb maximum per petbr•$25/per nightbr•2 pet maximumbrPlease let us know if you plan on bringing your pet.br- This unit is apart of a small compound Poolside Paradise - combined with this unit and Poolside Retreat next door, allowing for larger groups of up to 10 guests!

Apartment

Parking, Pool, Near Duval St - Poolside Suite

Key West, Florida, United States

Bed

Bath

Sleeps

$462.76

OLD TOWN CLASSIC...brThis beautifully redesigned Conch house is in the heart of Key West. Located in the outstanding location of Southard and Ashe Streets, this upscale abode is just minutes from Duval's many restaurants and bars. You are within walking and biking distance to museums, shopping, and Fort Zachary Taylor beach. Come inside this bright and sunny retreat that boasts fully renovated baths and kitchen, wood floors, high ceilings, and Dade County Pine walls. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brStep into a generous and bright living area that begs you to stay a while. Tropical sunshine floods this space with promises of paradise perfection as you sink into your plush couch in relaxation. Enjoy your favorite shows on the large tv or nap before venturing out on our magical island. Adjacent to the living area is a dine-in kitchen with custom cabinetry and top-end appliances. Craft the perfect meal in this modern and fully stocked cooking space that overlooks the gazebo and small rear garden. Wash your stress away in the exercise studio on the bottom floor that includes an elliptical, peloton bike, free weights and full bath with steam shower for your enjoyment. Travel upstairs where you are greeted by a cozy living area that includes a wet bar with refrigerator drawers and a desk.brbrSLEEPING ARRANGEMENTS…brThere is a bright and sunny main level queen bedroom with an ensuite shower bathroom which also opens through glass doors to the gazebo and garden. A hanging closet and clothing dresser will hold all of your vacation gear. Upstairs offers two spacious ensuite bedrooms. The king bedroom offers a shower/soaking tub combination, tv, clothing dresser and a wall of glass that opens to a private balcony, painting the room with natural light. The second queen bedroom includes a tv, hanging closet, clothing dresser and glass-door shower bathroom.brbrOUTDOOR LIVING…brEnjoy your morning cup of java on the front porch of this lovely tree-lined street, perfect for people watching. In the rear of the home there is a gazebo and lush tropical garden with a sitting space that offers ample seating and a small dining table for eating al fresco. Fire up the grill for your fresh catch or juicy steaks under the sultry stars. The property is surrounded by gorgeous landscaped gardens and a solar heated pool & spa. 4 bikes are available so you can stroll downtown until your heart's content.brbrPARKING...brThis home has 1 parking spot available for a golf cart however there is plenty of on street parking in the neighborhood. Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily / monthly rates.brbrPETS...brSmall dogs are considered and a pet fee is required. Please inquire prior to booking or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in the comment. 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 this service to assist you with planning activities for your trip. They can also have your fridge stocked with all the necessities in advance of your arrival!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.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).

BRIGHT SUNSHINY DAY ~ Renovated 3 BR, 4 Ba Home w/ Pool, Spa & Exercise Room!

Key West, Florida, United States

Bed

Bath

Sleeps

$462.61

MONTH STAYS ONLY Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no cookie cutter small rental condo but a private townhome (one of only seven available for rent) in the Shipyard section of the Truman Annex with its gated entrance and 24 hour security. Our Bermuda-style cottage is steps away from sunning yourself on the beach, at the pool or enjoying the excitement of Duval Street with its many award winning restaurants, unique shops, creative art galleries, lively bars and bawdy night clubs. The famed Mallory Square and the water activities are also a short walk away. And value How about free reserved and secure parking behind my cottage High speed internet connection and cable TV in both bedrooms .brbrWe also offer themed getaways for your honeymoon; anniversary; birthday or a week of romance. brNOTE: I HAVE NICE OPENINGS IN THE SUMMER AND FALL. IT WOULD BE MY PLEASURE TO GIVE YOU A GIFT CERTIFICATE TO ONE OF KEY WEST'S BEST RESTAURANTS.brWe know you will enjoy building memories in our home as well as Key West. On my living room walls are paintings I have purchased in Cuba from my humanitarian and education trips to the island. The colorful and yet relaxing paint hues on the wall are from my visits to Bermuda which is why I call my vacation home 'A Touch of Bermuda in Key West'.brbrThe bedroom configuration is the best. The master bedroom suite is upstairs and separate from the downstairs bedroom and bathroom. Both parties have great privacy by not sharing a bathroom between two bedrooms.brbrYou will want to be outside much of the time so relax on my front porch facing picturesque Southard St. and say hello to your neighbors. Or for privacy, the very large back deck with comfortable chairs for reading and a dining table for six to enjoy a private dinner under the stars. brbrPets by special permission. No short weekend stays. It's not permitted by home owner association rules.brbrThe Truman Annex is a former Naval base in the heart of Old Town in Key West. President Harry Truman used to vacation here so this residential complex is named after him. There is a wonderful tour available in the home he used as his summer residence. Duval Street is two blocks away. The pool is 100+ steps out my back garden gate down a pebble path. The best beach in Key West, Ft. Zachary Taylor State Park is within walking distance and if you have little ones, the Splash Pad at the end of the street is a joy. The famed sunsets at Mallory Square are short walk away as are the many tourist attractions such as Hemingway House; the Aquarium and Mel Fisher's Treasure Museum. And if water sports are your thing, the snorkel, scuba and fishing trips all start at the local pier within walking distance of my cottage. brbrGolf: There is an 18 hole golf course in Key West which is open to the public. It's not Pebble Beach or Augusta National but you can keep your game up to snuff by playing course the only one on the Keys. The links are within a short drive from my cottage but alas, this is one attraction not in walking distance. Good luck in breaking par. brbrOther Activities: Some really fine dining at award winning restaurants. On the walls of my living room, I have a painting of the Blue Heaven restaurant, one of my very favorites. It is quintessential Key West. brbrCome on down. Minimum stay is 29 days/28 nights and all bookings are Saturday to Saturday except for special events such as the boat races and Fantasy Fest. brbrPS If your party is small and you want another nice option for good value, check out my casita (condo) here in the Truman Annex # 1049465 on VRBO. I will let the amenities speak for themselves in my listing. It is located six doors away from my Touch of Bermuda cottage.brKeywords: Cottage; Townhome, vacation home

Cottage

A Touch of Bermuda at Truman Annex

Key West, Florida, United States

Bed

Bath

Sleeps

$163.06

Relax at Villa Nomade in luxurious surroundings. Featuring a fully equipped kitchen with bar seating and dining area. The living room is furnished with comfy furniture and a 50TV. The bedrooms have queen beds. Enjoy outdoor dining on the deck surrounded by a tropical landscape. brVilla Nomade is located in the Shipyard Condominiums at the Truman Annex. The Shipyard is in the heart of Old Town Key West on the former U.S. Navy property of Truman's Little White house. Just steps from Duval St. and located near the Ft. Zach beach and Hemingway's house, all of Old Key West's sites are within easy walking distance. Our private oasis can be your tropical retreat.

Villa Nomade at Shipyard Condominiums

Key West, Florida, United States

Bed

Bath

Sleeps

$289.65

Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throughout the house to open up and let in the Key West sun. Relax in the living with a large screen TV or sit on the front porch to read a book and relax with the breezes or if needed, the porch fan. The kitchen is perfect to cook your fresh caught fish with enough room to seat four at the countertop.brThe master has a queen bed with its own ensuite that has a shower with multiple heads for a very luxurious shower. The guest room has two twins (that can be converted to a king) and it's own ensuite bathroom. This bathroom does have a shower/bath combination. Both bedrooms have walk in closets.brThe backyard has its own private pool and can be heated during our Winter months if needed. There is a table for 4 to eat al dente if preferred and two lounge chairs to get your tan on.brThis home does come with off street parking and a driveway for a medium sized vehicle.brCome, enjoy a month in this beautiful Key West Home!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.

Shady Palms - Stay In Comfort- May - Aug 10% OFF - 2BD/2.5Bath - Private Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$381.07

Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. The one bedroom Villa Porta is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway. Please email us even if the availability calendar looks full.brbrThe number one reason why people choose the Rose Lane Villas is our fabulous location and proximity to all things worth doing in Key West. br1/2 block to Hard Rock Cafebr2 blocks to Margaritavillebr2 blocks to Sloppy Joe’sbr3 blocks to the Historic Seaportbr4 blocks to Mallory Squarebr4.5 blocks to Schooner Wharfbr6 blocks to Hemingway’s HousebrbrPlease be aware of scams asking for wire transfers or offers from Craigslist. If you have any questions, please call our reservations desk.

Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$250.21

Welcome to “Bahama Palms” Key West! Newly renovated and full of Key West charm, this 2 bedroom 1 bath condo with washer and dryer is the perfect home base for your month-long stay in Old Town. Located in historic Bahama Village just a block and a half from Duval Street and 3 blocks to the famous Southernmost Point Buoy, everything you need is right out of your front door. Community pool and park located just across the street. 1/2 mile bike ride to Fort Zachary Beach. Includes 1 parking spot.brbrNewly renovated in summer 2022, Bahama Palms is ready to welcome guests. 2 bedrooms, 1 full bath with step in shower, large kitchen with a coffee bar, high top dining table and comfortable living area. In unit stackable washer and dryer. Working from home Enjoy our blazing fast 2Gbps WiFi at the expandable desk, while you look outside at the swaying palm trees.brTraveling nurse We offer discounts for our health care providers! Just ask!brParking for 1 car directly out front of the condo. Park it and walk or bike the island!brbrGuests will have access to the entire condo.

Bahama Palms

Key West, Florida, United States

Bed

1

Bath

Sleeps

$450.0

A Stay You’ll Never ForgetbrbrWelcome aboard Dolce Vita, a beautifully refitted luxury motor yacht offering a one-of-a-kind stay in Key West. Perfect for couples, families, friends — and even your dog — this unique floating retreat combines waterfront charm with full resort access.brbrWake up to marina views, enjoy coffee on the aft deck, and walk just steps to the pool. In the evening, take the complimentary shuttle into downtown and return to your peaceful marina setting.brThe boat has been newly renovated, boasts a brand new AC system and the interior refitted to a high standard. there is a spacious saloon with a smart TV and then a few steps steps down into the galley dining area. The galley is equipped with an induction stove top, microwave oven ,coffee perculator, air fryer and fridge freezer.brThe master cabin has a walk around queen bed and on suite bathroom with shower and another smart TV, while the forward cabin has a cozy double berth with adjoining bathroom.brUp on the aft deck there is a dining table and 4 chairs for alfresco dining or just chilling with cocktails.

tUnique Waterfront Yacht in 5 star resort. Pools, Gym & Downtown Shuttle

Key West, Florida, United States

Bed

1

Bath

Sleeps

$609.24

Searching for the perfect vacation home away from it all Your hunt ends in here! A Wave from it All is a remodeled and tastefully decorated 2-story townhome with its own private pool that epitomizes island living at its finest while offering all the comforts of home. Best of all, this home is nestled in the Truman Annex, a palm tree lined residential community with many historic buildings including the Truman Little Whitehouse, walking distance to many of Key West’s finest dining establishments, two blocks from the world-famous Duval Street, two blocks from the nightly sunset celebration at Mallory Square, and less than a half mile from the beach at Fort Zachary Taylor State Park. Break away from the ‘high seas’ of everyday life while you settle into for what’s sure to be a memorable Key West vacation!brbrThe double set of sliding glass doors on the back of the home open up to provide a private spacious tropical oasis of indoor/outdoor living space with a private pool. A large flat screen HD SMART TV hangs on the wall in front of comfortable seating options. The fully equipped kitchen has all the appliances and tools needed to prepare meals at home, on those nights that you chose to dine home with your pick of indoor or outdoor dining.brbrTruman Annex is the most exclusive private residence community in Old Town Key West. Located just off the main drag of Duval Street, The Truman Annex is an oasis of calm, quiet palm tree lined streets with many historic homes, 24-hour staff and restricted access in the evenings where you can use the entry gate keys to come and go on foot.brbrProperty includes..brCentral Heat and A/C, Ceiling Fans, Flat Screen TVs in Living Room & All Bedrooms, Fully Equipped Kitchen, Laundry Room with full size Washer and Dryer, Starter supply of paper products & cleaning supplies, Linens and Towels provided, Wireless high-speed Internet access & full cable included.brbr** Fully Fenced & Lushly Landscaped Private Yard with Pool. Pool can be heated for an additional charge.brbr** Designated Covered Off-Street Parking (one space)brbr** This property will accommodate up to 4 adultsbrbr** No Pets Allowedbrbr**The entire property is NON smoking or vaping

Tropical Oasis in the Truman Annex with a private pool

Key West, Florida, United States

Bed

Bath

Sleeps

$467.59

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrWhen you think of Key West, you think of spending relaxing days with your toes in the sand under the palm trees, and fun-filled nights walking through the Streets of Old Town on your way to catch the sunset at Mallory Square. Experience these kinds of days (and nights) at SOUTHERNMOST PALMS, a beautifully renovated villa, located at The Foundry in Truman Annex, Key West's most exclusive gated community. From this location, you'll be within walking distance to all that Key West has to offer. SOUTHERNMOST PALMS combined with Last Key Realty's unrivaled Guest Services is sure to make your stay in Key West a memorable one. Smoking is not permitted in any Last Key Realty home. In addition, the Foundry does not permit smoking in the front garden patio areas or balconies. Therefore, this home is not a good fit for vacationers needing smoking accommodations.brbrTHE LOCATION...brbrYou'll be just a few blocks from Mallory Square, Duval Street and all the restaurants, shopping, and attractions of Old Town Key West, yet you'll benefit from the peace and quiet that Truman Annex is known for. Although you won't need a car to get around from this excellent location, there is a reserved off-street parking space.brbrCompliance with Truman Annex Community Rules & Regulations is expected of all Last Key guests. This includes “Quiet Time” in all outdoor areas, public and private, after 10PM.brbrTHE LIVING AREA...brbrSOUTHERNMOST PALMS has been furnished and decorated in a lush tropical style that can be found throughout the home. The living area is the entire first floor and has an open plan, with 11-foot ceilings and double French doors that provide plenty of natural light to enter. There's a large flat screen TV and multiple comfortable seating options, including a plush sleeper sofa to accommodate extra guests. There's also a convenient powder room located on the first floor. The kitchen has top-of-the-line stainless steel appliances, with granite counter tops and all the tools needed to prepare a meal from home. The indoor dining table seats six comfortably or enjoy an outdoor meal at your own private courtyard out front, with an outdoor dining set and a gas BBQ grill.brbrTHE COMMUNITY POOL and FORT ZACHARY TAYLOR STATE PARK...brbrThe landscaped community pool is located just around the corner and across the street, with chaises and a cabana with restrooms. Or you can walk to Fort Zachary Taylor State Park, with the prettiest beach in Key West, just a half mile away from your front door.brbrTHE ACCOMMODATIONS...brbr• Master Suite: Located on the Second Floor with a King bed, a large flat screen TV, a private balcony, a large closet, and an en-suite bathroom with a walk-in shower.brbr• Second Bedroom: Located on the Third Floor with Two Twins OR One King bed, a flat screen TV, a closet, and an en-suite bathroom with a walk-in shower.brbrEach floor closes off with its own separate door as well for extra privacy.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• Community Pool Accessbr• Propane BBQ Grillbr• Assigned Off-street Parking for 1 CarbrbrOther notes:brbr• Interim housekeeping provided upon requestbr• This property will accommodate up to 6 adultsbr• 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.

**SOUTHERNMOST PALMS @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES.

Key West, Florida, United States

Bed

Bath

Sleeps

$593.22

bPLEASE NOTE THE POOL AND JACUZZI WILL BE CLOSED FOR RENOVATIONS FROM JULY 6, 2026 TO AUGUST 30, 2026/bbrbrIf you`re craving a Key West beach front accommodation with a bone fide front-line view to the sea, you know that Key West beach front rentals not easy to come by. But in this pretty vacation rental condominium, By The Beautiful Sea, you can instantly gratify this need for sensational vistas from your own vacation rental terrace right across the street from the beach. Make your first order of the day to breathe in the fresh ocean breezes with a walk along the beach and fulfill the desire to dig those toes into warm white sand . . . for after all your front yard isKey West by the sea on the the Atlantic Ocean side of the island. Your `back yard` view is not bad either. The entrance for this property connects with a second level walkway of the building, and offers views of beautiful tropical park-like landscaping. A short stroll from the condominium through the landscaped setting, leads to the large free form swimming pool and Jacuzzi. A major decision each day could be whether to enjoy the sun at the beach or pool side. And when it`s time to go dining, shopping, or enjoying the nightlife, Old Town is close by and an easy bike ride away. Ahhhh . . . life in paradise is good.brbrThe interior layout of this property was designed to maximize the opportunity to take in the ocean view from the living room and dining area, as well as the master bedroom. Sliding glass doors off the living room, lead to a private ocean view terrace. The kitchen adjoins the dining room through a pass through door, creating a floor plan that makes it easy for entertaining the family or a group of friends.brbrThe layout of the bedrooms is ideal for a family or three couples. You`ll need to flip a coin for the enviable master suite that has the ocean view, plus a door that leads directly to the sea-side balcony. Furnishings are tropical elegant with a honey-colored wood-and-wicker king size bed and romantic free-standing grandfather clock to remind you that it`s 5 o`clock somewhere. Another nice feature of the master bedroom is a walk-in closet. Next to this closet, the master bath provides a long vanity with two sinks, tiled floor, and bath-tub with in-tub shower.brbrThe other two bedrooms and second bathroom, are on the opposite side of the condominium, down a short hallway, just off the great-room. Immediately off the hall to the right is a bedroom with two twin beds, which can be made up as a king size bed upon request. Nicely decorated with white cottage furnishings, there is also plenty of daylight that streams in through a nice size window. Directly at the end of the hallway is the third bedroom with king size bed. Handsome honey-colored wooden furnishings fill the room in nice contrast with the coral colored walls. A window on one wall invites in the natural light.brbrThe second full bathroom, with standing shower and glass door, is situated off the hallway, easily accessed by both the second and third bedrooms. This bathroom also conveniently houses the washer/dryer, a welcome feature for a beach house, where you can come in and drop your towels and wet bathing suits.brbrA notable layout feature of this property is that it`s an end unit in the condominium building, making it one of the more desirable locations in the complex as you only have neighbors on one side. It is located on the first floor, but elevated second level, since the covered parking is directly below. This design provides a wonderful view of the ocean, the perfect Key West by the sea experience. The entrance to the unit can be reached by stairs or elevator. There is designated covered parking, and the condominium complex is gated and secured with an electronic key entrance.brbrBedding Summary:brbrMaster Bedroom 1 – King size bedbrbrBedroom 2 – 2 Twin Beds (can be made as a king size bed)brbrBedroom 3 – King size bedbrbrbrAmenities: Located in a beach condominium complex across the street from Key West Smathers` Beach. Private balcony with front-line view to the sea. Balcony access from great-room and master suite. Resort style heated swimming pool, hot tub, separate men and women saunas and changing rooms near pool for guest use only. Tennis courts, propane BBQ grills on the grounds. Fully equipped kitchen, central A/C, Wi-Fi, cable TV and DVD, stereo, washer / dryer. Linens and towels are provided.brbrActivities: This property is Key West by the sea! Everything beach! Sunning, swimming, catamaran rentals, volleyball, beach food trucks. Easy walk to the White Street Pier, Salute Restaurant for dining on the beach, ocean front children`s playground, historic garden club, nature preserve, much more. A bike / walking path winds along the ocean and leads you to the heart of Old Town Key West where you find restaurants, nightlife, museums, everything Key West has to offer.brbrArea: This area of Key West is often referred to as the beachside neighborhood due to the close proximity to the southern shore of the island. This part of the island feels like a beach town neighborhood with light ocean breezes, and it`s not unusual to see folks walking or biking on the bike path in their bathing suits with towel and cooler under arm. A paved biking and walking path stretches along the southern shore dotted with parks and food and water sport concessions making it easy and interesting to stroll or bike. There is a pre-Civil War Fort along the waterfront, West Martello near Higgs Beach that now houses the Key West Garden Club.brbrParking: Designated covered parking for one vehicle. One additional vehicle may park in the adjoining lot. All vehicles parked must display parking passes issued by the condominium. Scooter parking allowed. Bicycle racks near elevator. No boats, RV`s, Jet ski`s or trailers of any kind are allowed in the parking area.brbrRestrictions: No smoking. This condominium is offered as a vacation rental in a preferred beachfront condominium in Key West. Pets are not allowed. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian. No boat, trailer (bike or boat), jet ski, or RV parking. Guests must agree to abide by condominium regulations.brbrPAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.brThere is designated parking for one (1) car at ‘By The Beautiful Sea.’ Drive in the gate and turn left. See the second parking space under the building marked #2. This is your parking space. You are also allowed 1 additional parking space anywhere in the general parking area.

By the Beautiful Sea - Key West Beach Front Condo - w Pool Access

Key West, Florida, United States

Bed

Bath

Sleeps

$262.56

*BRAND NEW LISTING* 28 Day Minimum!!! 'Summer Breeze' will make you and your family feel fine! This is a gorgeous, clean, upgraded, top floor, 2/2 condo, sleeps 4, with a spectacular view! Common pool, grill area, tennis court and a nice friendly atmosphere will make you and your family happy to have chosen this great property. Smathers Beach is across the street, Higgs Beach is a short walk, Duval Street a short bike ride or walk. Literally anything on the island is within your reach! 28 day minimum stay - set up for 4 adults only. Bring your bikes or rent them here and be anywhere in Key West within minutes! Maybe you want to rent a golf cart and do the same!

Summer Breeze: Spectacular View, the Beach, Pool and all the Amenities. 2BR/2BA

Key West, Florida, United States

Bed