Home Vacation Rentals By Owner In Key West, FL

Showing 160 Of 2059 Vacation Rentals
Slider Thumb
Exceptional(2)

$395.5

/ Nightly
Condo

Poolside Hide-Away @ Palm Gardens offered by Rent Key West Vacations

Key West, Florida, United States

Poolside Hide-Away is a first floor one bedroom, one bath historic condo, that can accommodate up to 4 people, with wrap around porch, private hot tub along with the shared amenities of Palm Gardens. The condo sits in the back of the building next to the pool. As you enter through the french doors from the wraparound porch, you are welcomed into the living area, with its warm wood walls and furnished with a teal colored sofa (sleeper) to bring in the Caribbean touches Key West is known for.brbrA full kitchen with its granite counters will allow you to cook up a feast or simply make your morning first cup of coffee. The galley style kitchen is complete with refrigerator, stove, microwave and dishwasher for your convenience.brbrThe principal bedroom has a king bed. The adjacent bath has shower stall and stacked washer/dryer.brbrPalm Garden is a small 5 unit compound in two buildings, with a seasonally heated pool and common BBQ area to make the most of your Key West getaway. Located just six blocks from Duval St or the Historic Seaport, you can be in the heart of the action in just minutes by strolling or riding bicycles to get there even faster. Parking is on street parking in the neighborhood, should you be arriving by car in spaces not marked as residential parking.brbrPoolside Hide-Away's location on White Street is close proximity to Sandy's Cafe for your Cuban cheese toast and bucci, just two blocks away. You have to pass Key West Cupcakes to get your Cuban coffee! Fausto's Food palace grocery is just kitty corner from Sandy's to grab anything you need.
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(42)

$645.62

/ Nightly
Private Vacation Home

Coco's Poolside Retreat

Key West, Florida, United States

Coco’s Poolside Retreat is a cheerful three-story townhome tucked inside a private, gated mini-compound in Old Town Key West. Designed as a creative complement to its neighbor, the Flower Power House, this laid-back retreat is situated in a tropical wonderland of a yard and walks right out to a huge, sparkling 40’ swimming pool shared with only two other homes—making it feel both social yet private. With porches on the first and second floors looking right out over the gardens, there’s always a sunny spot to sip morning coffee or evening cocktails after exploring the best of Key West.brbrInside, bright island colors, handmade art, and whimsical details create a fun, welcoming vibe across all three levels. The main floor’s open living area is nice for gathering, with a fully equipped kitchen and half bath. Upstairs, the second floor has a queen bedroom and a separate sitting room with a queen sleeper sofa, both opening onto a wide porch with views of the pool and yard. The top floor has two more bedrooms—one with a king bed and another with two twins (convertible to a king)—plus a Jack and Jill bathroom, making it easy for families or friends to spread out.brbrCoco’s Poolside Retreat feels like a perfect hideaway set off the street and hidden behind the big white gate and lush trees, yet you’re right in the White Street Gallery District. Most of your neighbors are local, full time residents making for a peaceful vibe, but a short walk or quick bike ride gets you to the beaches, art galleries, cafés, and local favorites like Salute on the Beach. It’s a perfect home base for guests who love a tropical, local feel, a bit of whimsy and a great pool. Book Coco’s Poolside Retreat to soak up Key West’s colorful, laid-back spirit, and look into booking the Flower Power House as well, for the complete Family Reunion Compound if the whole crew is coming along!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.
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(38)

$1251.93

/ Nightly
Private Vacation Home

The Flower Power House - Boho Beautiful

Key West, Florida, United States

When you enter the gate next to the painted 1306 sign, you’ll find yourself immersed in this one-of-a-kind tropical wonderland. Welcome to the Flower Power House, where Key West’s free spirit lives on in every colorful corner. Built in 1938 and reinvented over decades by its owner-artists, this isn’t your average vacation rental—it’s an ever-evolving, artful hideaway with handmade details and a playful maze-like layout that invites discovery. Each door leads somewhere fun: a cozy sleeping porch, a pastel pink seashell carriage house, or a sunlit loft tucked under open-beam ceilings. Forget hotel perfection; here, charm comes from bespoke creativity and the joy of offbeat island treasures.brbrInside, you’ll find six bedrooms spread across three interconnected spaces. French doors open nearly every room to breezy porches, and no two rooms are alike—think tropical colors, original art, funky shapes and textures, and vintage finds that harken back to the “good ol‘ days” of quite a “hippy” Key West. Play games in the spacious living area under soaring cathedral ceilings, cook together in two kitchens plus a kitchenette, or sneak off to a private nook with a book to unwind. The vibe is eclectic, colorful, and quirky—perfect for guests who appreciate artful character over a predictable, commercialized feel. brbrOutside, you’ll waltz through the thriving foliage crafted by the owner’s own hands—an enchanting backyard full of winding walkways, darting lizards, and layers of tropical plants that feel part garden, part storybook. Covered porches wrap around the home on both levels, inviting long conversations and slow mornings. Just beyond, a massive 40’ swimming pool glimmers in the sun ready for splashing and cooling off. Please note the pool is shared with only the two neighboring townhomes. If you are interested in renting one of the townhomes as well, please inquire about renting our Family Reunion Compound property! This includes both Flower Power House and the Coco’s Poolside Retreat townhome for hosting even more friends and family!brbrThe Flower Power House is truly unique. Tucked in the heart of the White Street Gallery District, you’re a short walk or bike ride to local cafés, art galleries, the beach. Coming back to the Flower Power House after a night out adventuring on Duval Street and beyond is a blast. If you love places that are soulful, creative, and a little askew, the Flower Power House is your perfect home base for making awesome vacation Key West vacation memories!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.brbrRestrictions: Smoking permitted only outside please. No pets. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.
Bed 5

Bed

Bath 4

Bath

Sleep 13

Sleeps

Slider Thumb
Exceptional(1)

$235.0

/ Nightly
Private Vacation Home

Caribbean Cottage - 2BR/2BA Sleeps 6, Heated Pools

Key West, Florida, United States

28 DAY MINIMUM RENTAL! brRENTALS START ON 1ST DAY OF MONTH!brbrHistoric unit - RENTALS START ON THE 1ST DAY OF MONTH!brHistoric Caribbean Cottage is an Historic Bahamian house that has been completely renovated December, 2018. Located on a 2 block long lane situated between Duval Street and Simonton Streets, just off U.S. 1 (Truman Avenue).brbrSit on the front porch with 2 rocking chairs and a porch swing and watch people strolling down the street and listen to the soothing sounds of the blue water fountain in the front garden. There is a bicycle lock up in the front, too. brbrWalk inside the living room and be greeted with “Caribbean” blue walls with a custom made sleeper sofa (5” memory foam mattress) with an under water critter motif. Relax in the blue swivel bucket chair with foot stool while watching the 56” Smart TV to watch sports or your favorite channels. Bring your Sling, Netflix and Prime passwords to watch TV/movies on our newly provided 5G fiber optic WiFi. A small chest with pull out shelf for computer work is also provided as well as office chair. Local art completes the “relaxed” attitude of this living space.brbrThe front bedroom off the hall features a king deluxe memory foam bed, Pottery Barn furniture with pull out baskets under the bed for extra storage. Custom sea glass art by Robin Renee Hix adorns the walls and another 56” Smart TV is on the wall facing the bed. There is a makeup vanity/desk, Pottery Barn closet and storage for your convenience. USB ports are on the bedside lamps and wall. brbrWalk down the hall to the colorful bathroom on the right. Tiled in a rainbow of muted colors, a 17” high toilet for your comfort, shower with magnetic shower head to wash your furry friends if you bring them, Tommy Bahamian body wash, shampoo, conditioner and body lotion is also provided for your total comfort. Beach towels, bath towels in a lovely shade of blue complete this bath.brbrThe custom kitchen with beautiful quartz counter tops will dazzle you! Appliances included are refrigerator/ice maker, garbage disposal, glass top stove and microwave. Everything needed to cook/bake a gourmet meal are provided including blender, food processor, Vita Mix, pots, pans, drink glasses, sharp knives, cutting boards, drip coffee maker, toaster, etc. Sit at the custom 2 person bar for coffee with swivel bar stools and charge phones/pads in the USB ports. There is a Bluetooth speaker there if you want to listen to news or a podcast while enjoying waking up.brbrThe second bedroom/bath is at the rear of the cottage. Walk out the kitchen door under awnings and you will find the second king bedroom which is built over the historic cistern used for water collection in the past. More Pottery Barn furniture features a king deluxe memory foam mattress, bedside tables with USB connections and a large walk-in closet with a barn door covering the opening. On the wall facing the bed is another 56” Smart TV. The bathroom here also has a 17” high toilet with unique turquoise and navy blue glass on the floor. Ever taken an outdoor shower Well here you can in our tropical paradise! Totally private with hot/cold water and Tommy Bahama toiletries, enjoy watching the clouds float by or look at the nighttime stars! The shower also has another door that opens to the pool for your convenience.brbrIn the rear, tropical plants, including many different types of orchids, surround the heated pool which is private for your use from 5pm till 9am. From 9a-5p the Adults only pool is shared with my other guests and the gate is open for their use during this time. A locked gate at the side of the cottage provides privacy in the evenings. There is a second heated pool across the street for your use as well. On the rear deck is a table/6 chairs with a large rectangular umbrella to enjoy a meal outside as well as two outdoor lounge sofas to enjoy drinks and conversations. Washer/dryers are for your use, as well. A gas BBQ grill is on the deck outside the kitchen. brbrOther extras provided are free WiFi, Amazon Alexa’s in each room, central AC/heat, ceiling fans throughout, Dyson cordless vacuum and all cleaning/soap supplies. brbrBook this unit today to insure you have the best location to spend your month of vacation time on the perfect tropical Island getaway. Don’t forget Key West has bus transportation all around Old Town that runs every 15 minutes and we have a stop just a block away!brbrWe look forward to hosting you and making your vacation PERFECT!brbrTwo heated pools, the pool behind Caribbean Cottage is shared with my other guests daily from 9-5p. Your pool is private for your use from 5p-9a. The 4 washers/dryers are for your use. Weber Gas Grill. Bike lockup. The entire home is yours to enjoy.brbrI am always available by text and there are staff available 24/7 to assist you in any way.brbrIn the heart of Historic Old Town, yet quiet and secluded, there is a bike/moped rental at the corner of Center and Truman, a CVS, Drs. Office, Subway and dry cleaners across Truman at the entrance to Center Street. There are multiple restaurants, bars and attractions all around us. The sandy beach on the Atlantic side of the island is a short 5 block walk away with a restaurant/bar on the beach.brbrBike, moped, electric car or FREE bus will get you wherever you might want to go in Old Town plus we are within walking distance of most places you might want to visit.brbrFree wi-fi through out the property!brRental MUST begin on first day of month during Season (Jan-May) for a minimum of 28 days. During other times if the year checkin can be other times of the month.
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(42)

$181.89

/ Nightly
Condo

THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!

Key West, Florida, United States

PLEASE BE ADVISED IF BOOKING THIS UNIT FOR AUGUST 2026: The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. The HOA expects the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. There is no other pool available at the Shipyard, so we have adjusted our rates to offset the inconvenience.brbrCOZY VALUE IN TRUMAN ANNEX…brThis 2nd Floor one bedroom, one bath condo is located in The Shipyard, a neighborhood of the coveted Truman Annex in the heart of Old Town Key West! You will be in walking distance from Fort Zachary’s gorgeous beach and picnic area, Duval Street, Mallory Square and more! Throw your cares to the wind as you unwind in this charming, tree-shrouded neighborhood with walking paths and lanes. This small but sensational gem is an upstairs unit with all of the creature comforts you will need in paradise! br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brEasy breezy comfort greets you as you enter this charming home. Travel up the carpeted stairs to a bright and cheerful open living room and kitchen/dining space. Unwind on the plush furnishings as cheerful sunlight floods the living room and creates a happy and carefree environment. A smart TV offers a wide array of programming for your viewing indulgence. The dining/kitchen area is adjacent to the living room, with a dining table nearby. The kitchen is fully equipped with a dishwasher, stove, microwave, refrigerator and both a Keurig and drip coffee maker. The cabinets are stocked with every kitchen tool you will need to craft delicious meals. brbrSLEEPING ARRANGEMENTS…brUnwind from your day of island fun in the king bedroom. A wall-mounted smart tv is available for lazy days when it just feels right to linger in your cozy bedding and binge on your favorite shows. The storage closet houses a fold-up twin bed and extra bath linens for your enjoyment. The bathroom is next door with a glass-door shower and a washer/dryer closet is adjacent to it for your convenience.brbrOUTDOOR LIVING…brThe Shipyard offers a beautiful community pool lined with lounge chairs perfect for soaking up the sun. Open the French door to the roomy private terrace, inviting sultry breezes and Key West sunshine inside. This wonderful extension to the living space has a table for 2 where you can have your morning coffee or enjoy a cocktail after a long day of exploring. There are also 2 more cushioned wicker chairs for lounging outdoors.brbrPARKING...brThis home does offer parking for one vehicle (vehicle cannot exceed 18 ft), but oversized trucks and extra large SUVs are not permitted and will have to park outside of this community.brbrPETS...brThis is a pet friendly home with a required pet fee. Please include the size and breed when inquiring. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPet feebrbrBOOKING 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.brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.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!brbrCOME STAY A WHILE...
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

Slider Thumb
Exceptional(2)

$179.62

/ Nightly
Apartment

Moongate, a Stylish Studio Retreat near Duval, Pet-Friendly, Gated and Private

Key West, Florida, United States

Welcome to our newly remodeled studio apartment, a hidden gem just two blocks from the iconic Duval Street! Nestled within a private gated compound, this chic and cozy space offers the perfect blend of comfort and convenience for your Key West getaway.brbrStep inside and be greeted by a thoughtfully designed studio that seamlessly combines style and functionality. The fully equipped kitchen boasts modern appliances, including a full-sized refrigerator, icemaker, dishwasher, and stove. Prepare your favorite meals with ease, and enjoy them at the dining area or al fresco.brbrThe bathroom is brand new, featuring contemporary fixtures and a refreshing ambiance. A washer and dryer are conveniently tucked away in the unit, making longer stays a breeze. The walk-in closet provides ample storage space for your belongings, keeping the living area clutter-free.brbrFor a restful night's sleep, choose between the comfortable Murphy queen bed on the main floor or ascend to the queen loft bed for a cozy elevated retreat. The flexibility of these sleeping arrangements makes the studio perfect for solo travelers, couples, or hosting friends.brbrMurphy queen bed and loft queen bedbrFully equipped kitchenbrFull-sized refrigerator, icemaker, dishwasher, and stovebrNew bathroom with modern fixturesbrWasher and dryer in-unitbrWalk-in closetbrTwo TVs for entertainmentbrDedicated work spacebrHigh-speed internet includedbrbrWe know your furry friends are a part of the family, so feel free to bring them along! Our studio is pet-friendly, and we've created a welcoming environment for your four-legged companions.brbrSituated just two blocks from the vibrant Duval Street, you're in the heart of the action. Explore the lively atmosphere, world-class dining, and vibrant nightlife that Key West is renowned for. With a private gated compound, you can enjoy tranquility while being moments away from the city's energy.brbrBook your stay now and experience the best of Key West living in our recently remodeled studio – your home away from home!brbrOutdoor camera monitors walkway.
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb

$415.0

/ Nightly
Condo

~LA MAISONNETTE~ Gated condominium 1 block from the allure of Duval Street.

Key West, Florida, United States

THE PROPERTY: Location, location, location, is what this chic condominium is all about! From here you can walk 1 block to the many attractions of Duval Street, including restaurants, cafes, bars, and shops. Or you can bike or drive about one mile to Higgs Beach and relax in the sunshine. This quiet residential oasis is in the middle of everything Key West. Vacationing in this gated community, surrounded by lush foliage, will give you a taste of what it might be like to live here. brbrBegin your stay with coffee or tea on your shared, covered front porch. Take a dip in the community's cocktail pool or have lunch in the garden patio area before heading out to sight-see. The home’s first floor includes a living room, TV, ceiling fan, powder room, dining area and kitchen, where you can prepare a quick meal or snack. This bright and sunny area was completely refurbished with gorgeous furniture, a brand-new kitchen with white cabinets, counters, and stainless steel appliances.brbrThe redesigned, stylish bedroom with nightstands, bedside lamps, and updated ensuite bath with walk-in shower are located on the second floor. The spacious King bed, dreamy linens, and ceiling fan make for easy sleeping. Hardwood, tile floors and bedroom area rug help keep this home clean and comfortable. A shared, coin-operated washer and dryer are located on the grounds of the property. If you are ready to explore Duval Street, walk to dinner at a fabulous restaurant and relax in the privacy of your gated condominium, then La Maisonnette is the vacation spot for you! brbrBED CONFIGURATION: The second-floor bedroom has a King bed, TV, ceiling fan and ensuite bath with glass walk-in shower. There is a queen size sleeper sofa on the first floor.br brOUTDOOR AMENITIES: Shared cocktail pool with water feature. The pool is heated seasonally (November through April). Several outdoor dining areas, lush gardens and a shared grill are available for your enjoyment. brbrPARKING: No designated parking. On-street parking in the neighborhood may be available. brbrLOCATION: Old Town, 1 block from Duval Street and just off Truman Avenue. You can easily walk to many restaurants, bars, and shops from La Maisonnette. The Ernest Hemingway Home and Museum is also nearby. 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***
Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(18)

$438.15

/ Nightly
Private Vacation Home

MONTHLY RENTAL, 1 block to Duval, POOL, personal resort, 3/3, pets OK

Key West, Florida, United States

Welcome to Shipwrecked in Paradise! Historic Key West Eyebrow House with private pool..... ONE block to Duval, the Hemingway House, and the Lighthouse. Four blocks to the Southernmost Point. Our home is full of Key West charm. It was built by shipbuilders in the Classical Revival style called an Eyebrow House that created an awning to block the harsh sun in the late 1800's. Dade County Pine was used throughout, giving it a boat and Key Westy feel.... or shiplap as we call it today!brbrNewly purchased and newly renovated in August 2020. New furniture, new bedding, new linens, fresh paint, new bathroom in master, new outdoor furniture. brbrLive like a local in this renovated, private, historic Key West home located in the heart of Old Town near the corner of Truman and Whitehead, one block off Duval. We are at the quiet end of Truman where it turns into a one-way street. Some of the best restaurants in town are within 2 blocks: Santiago's Bodega, Blue Heaven, Moondog Cafe, Nine One Five, The Green Parrot. The beach at Ft. Zachary Taylor is a quick bike ride away. brbrThis private home offers 3 bedrooms, all with queen beds, and 3 en suite bathrooms. There is a bedroom on the main level and 2 bedrooms upstairs, each with their own staircase leading up to it on opposite ends of the home for complete privacy. There is a large eat-in kitchen with seating for 6... or enjoy your meal outdoors by the pool. The living area has plenty of seating with all new furniture and a pull-out sectional sofa with a queen bed. There are TV's mounted in the living room and each of the 3 bedrooms. Cable and internet are provided. brbrThe outdoor area is a true paradise. Enjoy the heated pool with waterfall and jets, 2 chaise lounges for sunning, and a dining table for 8. There is a private balcony off the upstairs bedroom and an inviting front porch for watching the comings and goings of Key West.brbrWant to get out on the beautiful waters surrounding Key West The Florida Keys are home to the only living coral reef system in the United States and the third largest in the world. Sea Monkey Ocean Adventures offers private trips to snorkel at the reef, cruise around Key West, visit a sandbar, or enjoy a sunset cruise.... or any combination of these activities... See our website at seamonkeyoceanadventures.com or inquire for questions. We offer $150 off a half day charter with your booking.brbrThe house is rented monthly beginning the first of the month. Please inquire if you have questions about Key West Monthly Vacation rentals. City ordinance requires monthly stays on most homes. It is often more economical to rent a house for a month than a hotel for a week or two. You have more space, a private pool, the ability to cook in, and space for family and friends to visit during your stay and share the cost.brbrAdd Florida Sales Tax and Accommodations Tax at 12.5%brAdd a one time cleaning fee of $225brbrREVIEWS AND EXPERIENCE: I have been managing my own properties for 15 years. Although this is a new property for me, please see my other vrbo listings: 2333364 and 2331506 for my 5 star reviews and rating as an owner and manager.brbrCOVID 19: If Highway 1 to Key West becomes closed or if rentals become disallowed during your scheduled stay, you will be refunded 100% if you must cancel.br
Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(11)

$351.03

/ Nightly
Private Vacation Home

Tropical oasis in a former author’s retreat. Sleeps 4.

Key West, Florida, United States

Former residence of an author and decorated accordingly, this cute cottage is quintessential Key West. Perfect monthly rental has two bedrooms, one full bath plus outdoor shower, is an authentic Old Town Cigar Maker's Cottage and the location of the actual writing of Laurence Shames' famous book FLORIDA STRAITS. Key West is a former home of many other authors including Ernest Hemingway and Tennessee Williams and this lovely getaway reflects that heritage in its decor and lending library! Lush foliage and brick meandering walkways surround the swimming and wading pools. Brand new living room furniture and decor in 2019. All new memory foam mattresses. Brand new shower head with features, brand new sink faucet, new ceiling fans as of 1/21, newly finished bar area, brand new hot water heater. WiFi and access to your smart network on roku.Other features of this charming home include hardwood and tile floors, ceiling fans and central a/c in every room, a large eat in kitchen with all appliances and kitchen items/utensils including dishwasher, high ceilings, sun room, and an expansive deck with gas grill perfect for entertaining. In home washer and dryer. This monthly rental property is within walking distance to Truman and Duval streets, Higgs beach pier, local grocery stores, restaurants, shopping, St. Mary's Star of the Sea basilica and the beach! This cottage is perfect for a couple's retreat or a group getaway to remember! Professionally cleaned by a third party service after each guest's stay. Book your dream Southernmost vacation today!
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(5)

$370.61

/ Nightly
Private Vacation Home

Beautiful quiet neighborhood. Sunsets! Huge pool! 10 min to Key West

Key West, Florida, United States

Beautiful 3 Bedroom 2 full bath home directly on the water with a full wraparound deck and fully fenced!Get away from it all in this beautiful hidden gem in a quiet neighborhood 10 minutes from the excitement of Key West! Enjoy a drink or have an entire meal with seating for 8 under the spacious tiki hut. Swim in one of the largest and deepest HEATED OR COOLED in-ground salt water pools in the area or stretch out on the sandy beach right by the waters edge! Sit out on the dock and see your own personal sunset every night! Take your boat out! Catch fresh fish for dinner!Take the kayaks out and cruise the bay! Walking distance to world renowned Baby's Coffee or to the local market and the local restaurant with fresh fish caught daily! Tennis courts and a playground within walking distance. All new furniture and appliances. 2 50+ Smart tvs. 2 King Bedrooms, 1 room with 2 twins, 1 queen pullout. Mother in Law suite downstairs features a King bed, full bath and queen pullout along with a full size refrigerator and freezer that has its own separate entrance right by the pool and is completely separate from the upstairs living area. There is also a bait freezer on the property as well. Property is fully fenced with automatic gates and lush foliage all around! Book now for the vacation you will never want to leave. I know I didn't! Inquire today!brbr**Per Monroe County Law, Rentals must be a minimum of 28 days**brbrbrFloors, windows and exterior paint has recently been redone !
Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(59)

$615.29

/ Nightly
Condo

Exclusive Key West Beach Front - 2BR Luxury Condo w/Gym and Pool Access (Newly Refurnished!)

Key West, Florida, United States

Rare, one-of-a kind designer condominium located in an exclusive gated Key West beachfront property. The Exclusive Key West Beachfront vacation rental has breath taking views overlooking the ocean and natural aquatic bird sanctuary. A spacious ocean front balcony provides the perfect setting for gazing and relaxing. Luxurious amenities include large heated swimming pool and immaculate tennis court overlooking the ocean, plus a second free form heated swimming pool.brbrA Miami South-Beach based architect designed the interior space of this property by setting a dramatic loft-like ladder that leads to spacious second floor. Metal railing creates a long hallway that offers a full birds-eye view of the ocean and beautiful perspective of the living and dining rooms below. Mahogany pocket doors open to the large second floor bedroom suite with queen size wicker sleigh bed and private bath.brbrDownstairs the spacious open floor plan for the living and dining and kitchen area is made to feel extraordinarily grand with roof-high open ceilings and ocean views. This open floor plan creates a spacious feeling and makes it ideal for entertaining the family or a group of friends. At the face of the downstairs hall you will find a private bath and at the end of the hall is the second bedroom with king bed and an ensuite bathroom. For extra sleeping the living room offers a queen sleeper sofa. The layout of the bedrooms is ideal for two couples or a family.brbrLocated where the Casa Marina District meets the Beachside neighborhood, this Miami `South-Beach` style condo property is located on the prestigious fourth floor location right on the ocean with an enviable view of the ocean and the White Street Pier. And yet it is within walking distance to dining on the beach, charming ocean front park with strolling piers, playground, historic garden club, nature preserve, much more. Right outside the gate a bike path winds along the ocean and leads you to the heart of Old Town and downtown Key West. This bike path exclusive location gives you everything Key West has to offer with incredible convenience and island style.brbrBedding Summary:brbrUpstairs - Large bedroom with queen wicker sleigh bed, private bath, and ocean view.brDownstairs - Bedroom with king bed, private bath, covered outdoor sitting porch.brLiving Room - Queen sleeper sofa brAmenities: The condominium complex for this property is small, exclusive, gated, and secured with an electronic numeric entrance. Elevators to your floor. It offers a large heated swimming pool and tennis court that overlook the ocean on one side of the building, and on the other there is free-form heated swimming pool. Tropical landscaping is immaculately maintained in this prestigious complex. A large covered private balcony for this property overlooks the ocean with a fantastic view of the White Street Pier. Central A/C, washer dryer, parking. Fully equipped kitchen, Wi-Fi Internet Access, Roku-Smart TV. Linens and towels provided.brbrActivities: Exclusive beachfront overlooks natural bird sanctuary adjacent to tropical nature preserve. Just down the street, Higgs Beach offers dining at Salute on the Beach, charming ocean front children`s park with strolling piers, playground, historic garden club, nature preserve, tennis and pickleball courts and much more. Right outside the gate a bike path winds along the ocean and leads you to the heart of Old Town. A bike path exclusive location gives you everything Key West has to offer with incredible convenience and style.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 to Higgs or Smathers Beach 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, the West Martello, that is now home to the Key West Garden Club.brbrParking: There is designated parking in gated parking lot for this property. A second car may be permitted. Guests will be given a parking permit for their vehicle. Absolutely no boat, trailer (bike or boat), or RV parking in this parking lot.brbrRestrictions: Smoke Free Home. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian. This home is offered as an exclusive vacation rental in the most requested beachfront condominium locations in Key West. Pets are not allowed. No boat, trailer (bike or boat), 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.brPARKING: Parking pass must be dispayed at all times. There is gated off-street parling for one (1) car at Exclusive Key West Beach Front. To enter the gate, use the secure gate code provided. Drive in the gate and turn right. See the elevator and park in any of the parking places near the elevator. Please avoid parking in a reserved parking space or the covered garage, as these are reserved for long-term residents. Notice: Condominium association rules forbid parking trailers or motorcycles at this property - this rule is strictly enforced.
Bed 2

Bed

Bath 3

Bath

Sleep 6

Sleeps

Slider Thumb

$879.47

/ Nightly
Private Vacation Home

A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!

Key West, Florida, United States

KEY WEST IN STYLE...brImagine carefree days in the tropics, spent in the comfort of this exceptionally located retreat with every conceivable amenity, pairing luxury with island bliss. Just blocks to the action on Duval St. and some of the island's favorite bars and restaurants, this abode offers convenience for your every whim. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES...brStep up to this picture perfect setting surrounded by lush vegetation drawing you into your island dwelling. Find yourself greeted inside with a tastefully decorated and sun-filled Great Room perfect for bringing the family together. Cozy and inviting furnishings surround a flat screen TV for movie and game nights. A fully equipped and updated kitchen allows you to whip up your meals seamlessly for everyone to enjoy around the dining table for 6 or casually at the bar top for 3. brbrSLEEPING ARRANGEMENTS...brHead up to the second level to a king guest room with a flat screen TV, en suite bathroom with a shower and jet tub with an adjoining balcony off the suite. On the 3rd floor you will find a room with two twins that can convert to a king upon request, and another queen guest room across the hall. A shared bathroom lies steps away with a shower. A sofa sleeper occupies the Great Room with the convenience of a powder room nearby.brbrOUTDOOR LIVING...brSoak up sultry sunshine and revel in the island breezes out on the back deck with a sparkling private pool (heated in the winter!) gas grill and seating to dine al fresco with a cocktail in hand. Enjoy swinging on the front porch as you savor your sweet surroundings. This charming Key West townhome ensures a memorable escape as you bask in lazy days indoor or tool around town without any agenda but fun! brbrPARKING...brOne parking space is provided, making coming and going a breeze.brbrPETS...brDogs are permitted and a pet fee is required.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 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrA SOUTHERNMOST SOLACE...
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(2)

$815.63

/ Nightly
Condo

Beautiful Key West Resort! Hyatt Windward Pointe two bedroom. Book now!

Key West, Florida, United States

Concierge Realty is proud to present luxury villas at Hyatt Windward Pointe!brbr**Reservations are available in weekly (7 night) increments with arrivals and departures on Fridays, Saturdays, and Sundays only.brbr**All bookings are time sensitive and availability can change at any time. Send us a message to confirm exact availability prior to making a booking request. brbrSet along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the laid-back Key West style with a modern, upscale resort ambiance. Here is a retreat where you can slow down and forget the rush and stress of your day-to-day life.brbrThis ultra-spacious, ultra-plush two bedroom at Hyatt Windward Pointe features a master bedroom with a king bed and master bath outfitted with a walk-in shower and spa tub, and the guest bedroom with a queen bed. Enjoy the convenience of having a full kitchen, dining area, living room, TV, fully-furnished balcony and complimentary Wi-Fi access!brbrBask beside the lushly landscaped pool that gives you the illusion that you’re softly floating on the open sea, grab a snack at Abbey Road poolside sandwich and snack bar or get your blood pumping at the fitness center at site resort Hyatt Key West Resort & Spa.brbrComplimentary self-parking is available at the resort. No recreational vehicle parking is permitted. No valet parking is available. Tesla and electric car charging stations are available. Boat and trailer parking is available at $25 plus tax per night and must be booked in advance by calling the front desk.brbrbrThe Vrbo calendar helps provide availability and estimated price quote. Always inquire with the agent and do not reserve airfare until your confirmation has been received.brbrAny issues with resort service, accommodations, physical plant, amenities, etc. are the direct responsibility of the developer and must be handled through the resort, not Concierge Realty.  Photos are thought to be truly representative of the resort and accommodations.  Any variation from the photo and actual property are unintentional, so guests are encouraged to do their own due diligence prior to reserving. Any variance or disruption including but not limited to renovation, unavailable amenity, change in decor, etc. during the stay, whether announced prior to reservation, occurring during the stay or announced after confirmation, is a matter strictly between the guest and resort, are not deceptive advertising, breach of contract or the responsibility of Concierge Realty.brbrNote that the images are representative of this villa and that a specific view type is not implied nor promised by virtue of the images. A specific view category must be addressed with rental agent. Concierge Realty reserved the right to reserve any view category unless one has been agreed upon in writing.  The resort confirmation will show the view designation and the villa will be placed within that view category unless, in a rare instance the view will be noted as not guaranteed in which case the resort reserves the right to place the guest anywhere within the property.  Issues regarding view within the guaranteed view category are to be addressed with the resort management as Concierge Realty is not responsible for villa placement.brbrPlease be advised that if a non-domestic credit card is used to reserve a vacation rental, additional fees may be incurred.brbrAll details are accurate to the best of our knowledge.  Any questions with regard to view, amenities, bedding configuration, decor or other details should be addressed with Concierge Realty, Winter Garden, FL.brbrGuests are encouraged to do their own due diligence to assure that the resort and villa will meet their expectations.
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(37)

$351.76

/ Nightly
Condo

**THE OSPREY'S NEST @ SUNRISE SUITES** Condo & Pool + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrWant to be in Key West, have access to all the fun, but not be in the middle of the crowd at the end of the day Then step away from the hustle and bustle and come roost at… THE OSPREY’S NEST. Boasting views from your private balcony on the top floor of Sunrise Suites, 2-Bedrooms, 2-Bathrooms, and a full kitchen; THE OSPREY’s NEST has all the necessary ingredients for a great vacation. Conveniently located near the entrance to Key West and close to the airport, THE OSPREY’S NEST is an ideal jump off point for exploring Key West and the Florida Keys. Pair this home with Last Key Realty’s Five Star Guest Services and in-house concierge, and your vacation in paradise will be truly unforgettable.brbrTHE LIVING AREA & KITCHEN...brbrTHE OSPREY’S NEST is a great place for those ready to escape and fly south! The living area is ideal for relaxing after a day of exploring the Keys by land, air, or sea. Relax and enjoy the flat-screen TV from the comfort of your couch or any of your four bar stools. The kitchen has all the goods you’ll need should you decide to put your culinary skills to work while on vacation. Four chairs are at the dining table on the balcony if you and your friends want to sip coffee with the sunrise or toast to the sunset.brbrTHE ACCOMMODATIONS...brbr** First Bedroom: King bed, flat screen TV, closet, and en suite bathroom. brbr** Second Bedroom: Two Twins OR One King bed, flat screen TV, closet, and en suite bathroom.brbr** Living room has a queen size sleeper sofa.brbrTHE COMMUNITY POOL & GROUNDS...brbrSunrise Suites is about 3 miles from Duval Street and provides a community pool, hot tub, tennis courts, and free parking. Smathers Beach, Key West's largest public beach, is just 2 miles away. Need to get to the airport for your flight home or to hop on the seaplane to the Dry Tortugas National Park The Key West International Airport is only half a mile away!brbrWhen you’re ready to take a dip, Sunrise Suites offers a large community pool and a hot tub. Work on your tan using the chaise lounges that sit poolside. There’s also an outdoor shower and public restrooms next to the pool. Guests have access to the on-site gym and tennis court, as well as the charcoal grill and picnic tables if you are looking to BBQ. If you need to break a sweat, there is a fitness center on site. Conveniently, this unit has its own designated covered parking spot, plus first-come visitor parking in the lot.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** In-home Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen Smart 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** Designated covered parkingbr** Community Poolbr** Community Hot Tubbr** Grilling Area w/ Picnic Tablesbr** Gymbr** Tennis CourtbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** Max of 2 Pets Allowed with Additional Fee of $200 per petbr** 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.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(40)

$721.82

/ Nightly
Private Vacation Home

Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool

Key West, Florida, United States

Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you`re just 1/2 block off Duval Street in Old Town Key West. It is indeed rare to find a cottage property in this downtown island location situated on two full private lots with such lush mature tropical landscaping.brbrA focal point of this unique property is the Key West quintessential indoor / outdoor living that makes island life so wonderful. Even though you are located in the down town Key West area, the entire large back garden is made private with high fences and unless you`ve been back in this yard you would never know this spacious garden is here. A redesign of the garden features an adorable tropical living area complete with lounging hammock stretched between a giant gumbo-limbo and grand palm tree. A round stone garden table set amidst a stage of soft river stones and variety of fanciful foliage, makes a relaxing setting to enjoy a garden lunch that you can buy right across the street at Fausto`s Fine Food Palace. At the front part of the garden, next to the cottage, is a wooden pool deck which is joined by sliding glass doors to the interior living room and pool-side bedroom. The wooden deck surrounds the graceful lounge pool which you enter down a graduated underwater stair case.brbrIn contrast to the expansive back garden, the interior sitting room area of the Down Island Digs vacation cottage is made cozy and charming. Colorful walls of Caribbean blue and sage green create the back drop for whimsically framed mirrors that offset the comfy coral colored sofette, fan-back `queen chair` and home spun dining table that command the space between the indoors and outdoors. Then over-sized sliding glass doors open up the back of the cottage by connecting the deck on both sides of the living room to draw guests onto the deck to the outdoors. Chocolate colored wicker outdoor living room furniture provides plenty of pool side seating under a forest green awning to create an irresistible tropical indoor / outdoor living room comfortable for lounging.brbrThe U-shaped kitchen is traditional cottage-style with bright white tiles and light wood cabinets. Adjoining the small dining and living room area, the kitchen is fully equipped, offers a full size electric range, dishwasher, and refrigerator with ice maker and has a nice view of the pool and garden so the cook can be part of the party. The Cottage wooden floors throughout the living room, kitchen, and bedrooms feel nice to bare feet.brbrThe bedrooms have a tropical flare and are comfortable and inviting. The coral colored spacious master suite is toward the front of the cottage and offers a luxurious king size, cottage-style white 4-poster bed, with pillow top mattress, full size sofa sitting area, and wall mounted flat screen TV. The master suite offers an en-suite bath and has direct outdoor access to the front porch of the cottage for sitting and watching the world go by.brbrThe sage-colored pool side bedroom is toward the back of the cottage and offers a queen size bed and bedside TV and DVD player. This bedroom has a view of the pool and sliding glass doors that open out directly onto the pool deck for that quick dip in the morning.brbrInterior Layout: The floor plan of this vintage cottage has been re-worked to focus the main living area toward the back of the cottage so that indoor / outdoor pool garden living is maximized. The cottage is not entered through the front door, but instead is accessed through an extra tall locked green garden gate situated immediately to the left of the front of the cottage. Once through the gate a deck leads to the back of the cottage where you enter to the interior. As you enter the cottage you step into the sitting / dining / kitchen area which also has sliding glass doors on the back wall that lead to the pool deck and garden.brbrProceeding forward, past the dining area, you find the sage colored pool-side bedroom which also has a sliding glass doors leading to the pool. Immediately to the right of this bedroom is a full bathroom just off the open hall. At the end of the hall just past the kitchen, is door to the coral colored master bedroom. Located towards the front of the cottage, the master suite was the original living room space, before the cottage was reconfigured to meet modern requirements of linking the interior to the outdoor pool garden area. An en-suit bathroom joins the master bedroom to the right of the bedroom door.brbrThe front sitting porch, and front door entrance, is visible to the street but has been railed off to block street access and has been re-designed to become a private sitting porch for the master bedroom.brbrNotes: The layout of this cottage makes it ideal for 2 couples or it is a wonderful space for 1 couple or single who want to spread out. The sleeper sofa in the master suite works great for one couple with a child, or for guests who need extra space and do not mind sharing a bedroom.brbrIf you love this cottage but need to sleep more people, you can rent it with the four bedroom Pavilion Villa. You can combine a rental of both properties and sleep up to 12 by renting the Island Rendezvous vacation compound.brbrBedding Summary:brbrMaster bedroom Four Poster king (pillow top mattress) size bed.brQueen Sleeper sofabrSecond Bedroom - queen size bed.brLiving room - twin sleeper sofa.brAmenities: Swimming pool, pool deck, large tropical gardens. New fully equipped kitchen, a/c, telephone, Internet, cable TV and DVD, stereo, washer / dryer. Linens and towels are provided. brbrParking: Private off - Street Parking in lot across the street for one car. If you arrive by car plan to park it in your designated private parking space and enjoy walking or biking around the island.brbrActivities: This property is located right next door to our Pavilion Villa and is just a few blocks from Mallory Square Sunset Celebration, steps from Fausto`s Food Palace for grocery shopping, excellent downtown restaurants, popular clubs, the Historic Seaport, and tropical shops makes this one of the most requested and convenient accommodations in Key West. With the size of the garden in this downtown location we are pleased to offer it as one of our more unique properties available in Old Town.brbrArea: Downtown Old Town Historic Key West. Just one-half block off Duval Street. Walk to all Old Town Key West features. Great restaurants, shops, galleries, clubs, Hemingway House Museum, Light House Museum, Custom House Museum, Key West Aquarium, Ship Wreck Museum. 10 minute stroll from the famous Sunset Celebration at Mallory Square.brbrRestrictions: Smoke free house. Smoking permitted outside only. Absolutely no pets. (Please don`t ask!) This home is offered as an exclusive vacation rental in the most requested location in Key West. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.brbrPAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.brPARKING: There is one (1) parking space only for Down Island Digs, but please note it is NOT the driveway to the left of the house. The parking space is kiddy corner, and across the street from the house. With your back to the house, look across the street and to your right, to see the lot.brbrPark in the space in the lot marked with the parking sign on the fence that reads ‘508 Bahama St.’ DO NOT park in ‘Fausto’s Fine Foods’ parking lot directly across Bahama St. There is a parking attendant who watches nearly 24 hours a day, and if you park there you will be ticketed or towed.brbrShort Driveway in front of the House: There is a short driveway in the front to the left side of the cottage, between this property at 508 Bahama St., and the cottage next door at 510 Bahama St. Notice: This space is for loading and unloading only. This space is too short to park a car in, and if your car hangs out even slightly over the sidewalk, you will most certainly be given a ticket by the diligent parking officers that patrol downtown Old Town Key West. Do not block the gates, or you will be in violation of fire safety regulations.
Bed 1

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(3)

$608.97

/ Nightly
Private Vacation Home

Atlantis House Suites

Key West, Florida, United States

Summary:brbrWelcome to your private Key West retreat featuring two beautifully appointed suites surrounded by a lush tropical garden in one of the island’s most desirable locations. Just a short stroll from White Street Pier and Higgs Beach, this charming property offers the perfect balance of relaxation, comfort, and convenience.brbrbrbrThe home consists of two separate suites, each with its own private entrance, making it ideal for couples traveling together, small families, or friends who appreciate both privacy and shared outdoor space.brbrbrbrThe Palm Suite is the larger of the two and features a comfortable king-size bed and a queen sleeper sofa, providing ample space to relax after a day exploring the island. The suite includes a convenient kitchenette equipped with a mini refrigerator, coffee maker, and toaster, perfect for light meals and morning coffee. The spacious bathroom offers a spa-like feel with a walk-in shower, jetted soaking tub, dual his-and-hers vanities, and a private enclosed toilet room.brbrbrbrThe Banyan Suite offers a similar design in a slightly more intimate setting. This suite features a king-size bed, kitchenette, and a bathroom with a shower, jetted tub, and private enclosed toilet room, along with its own private entrance for added comfort and independence.brbrbrbrBoth suites include assigned off-street parking, a valuable amenity in Key West, and share access to a beautiful tropical garden where guests can relax and enjoy the island breeze.brbrbrbrThe location truly sets this property apart. Just steps away, the iconic White Street Pier offers breathtaking sunrise views and a favorite local spot for fishing and morning walks. Nearby Higgs Beach features sandy shores, waterfront dining, volleyball courts, and historic landmarks. From here you can easily explore the charm of Old Town Key West by foot or bike while still enjoying a peaceful residential setting.brbrbrbrWhether you're visiting for a relaxing beach getaway, a romantic escape, or an island adventure, this property provides the perfect Key West experience with comfort, privacy, and an unbeatable location.brbrbrbrThe Space:brbrThe property offers two separate suites, each with its own private entrance.brbrbrbrPalm Suite is the larger of the two and features a king bed and a queen sleeper sofa, along with a convenient kitchenette equipped with a mini refrigerator, coffee maker, and toaster. The spacious bathroom includes a walk-in shower, jetted soaking tub, dual his-and-hers vanities, and a private enclosed toilet room.brbrbrbrBanyan Suite offers a similar layout in a slightly more intimate setting. It features a king bed, kitchenette, and a bathroom with a shower, jetted tub, and private enclosed toilet room, along with its own private entrance.brbrbrbrBoth suites include assigned parking and share access to a lush tropical garden, creating a peaceful island retreat.brbrbrbrGuest Access:brbrPrivate entrancebrbrbrbrThe Neighborhood:brbrThe property is located in the charming Casa Marina neighborhood, one of the most desirable and peaceful areas of Key West. This historic residential district is known for its beautiful conch-style homes, quiet tree-lined streets, and relaxed island atmosphere while still being close to everything.brbrbrbrJust a short walk away is White Street Pier, a favorite local spot for morning walks, fishing, and watching the sunrise over the Atlantic. Nearby Higgs Beach offers sandy beaches, shaded picnic areas, volleyball courts, and waterfront cafés, making it a perfect place to spend a relaxing afternoon by the ocean.brbrbrbrThe neighborhood also features several parks, tennis courts, and the historic West Martello Tower botanical gardens, all within walking distance. While the area feels tranquil and residential, it is only a short bike or golf cart ride to the vibrant energy of Duval Street, where you will find world-class restaurants, lively bars, galleries, and boutique shopping.brbrbrbrGuests love this location because it offers the best of both worlds—a quiet island neighborhood close to the beach, yet only minutes from the heart of Old Town Key West.brbrbrbrGetting Around:brbrThe best way to get around Key West is by walking, biking, or using a golf cart, as most of the island’s attractions are close together. From the property, guests can easily walk to nearby beaches, parks, and the historic White Street Pier and Higgs Beach.brbrbrbrBicycles are one of the most popular ways to explore the island, allowing visitors to comfortably reach Old Town and Duval Street in just a few minutes. Golf carts, scooters, taxis, and rideshare services are also widely available for convenient transportation around the island.brbrbrbrOther Things to Note:brbrBanyan Jacuzzi button is on the vanity side. Give a door a little push to line up the door when openingbrbrbrbrInteraction with Guests:brbrSelf check in but manager is available for assistance.
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(4)

$637.52

/ Nightly
House Boat

Ocean views!
No regrets

Key West, Florida, United States

Your Ocean front vacation house on water awaits you! Experience Key West staying above it's beautiful clear water. There is a little something for everyone from adventure seekers, to people who just want to get away and enjoy island life, wildlife, sunsets and water activities. From under the boat at any given time you might see many types of fish, stingrays, various crabs, starfish, octopus, lobsters, nurse sharks and even manatee from time to time! From above; view gorgeous sunsets, various sea birds catching their meals and even a military jet formation on occasion. Many great areas to kayak/paddleboard all starting from right off the boat. There are several miles of mangrove trails to view wildlife and fish or just simply get lost in nature. Kayak or paddle board up to Cow Key Marina restaurant as well as Hurricane Hole’s restaurant and grab some lunch.brbrThis houseboat is a 2 bed, 1 - bath with full kitchen/bar high-end appliances including an induction cooktop, and spacious relaxing living room. You can also bring your work here and work in peace in this very spacious home office. Also Off the front you have a covered patio with a ceiling fan and the spacious roof top deck with a complete bar top with great views of the bay.brbrThe master bedroom has a king size bed. brbrThe kitchen is A full size with standard size appliances you have the usual comforts of home.brbrThis unit also includes a washer and dryer.brbrNOTE # The houseboat is NOT to be moved from its slip. brIt is a stationary floating cottage.
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(79)

$2064.38

/ Nightly
Villa

Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking

Key West, Florida, United States

Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theaters and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a huge, fabulous decks that overlooks the action on Duval St. br brComprised of two buildings—a luxurious Duval St. penthouse with 3 bedrooms and 2.5 baths, and a lovely 3 bedroom, 3.5 bath guest house. The two-story penthouse is designed after a chic urban flat with an island twist. The spacious, open floor plan is complemented by beautiful island-style furnishings and art work. French doors open onto terraces from every room, and there is a covered dining terrace off the gourmet kitchen. A private heated pool or hot tub with waterfall is the perfect finishing touch. brbrThe guest house has three bedrooms, all with private baths, graciously spread out over three floors. The ground floor features a fabulous gourmet kitchen, dining area, half bath, and sitting room with a wall of French doors that open onto the deck and private heated pool with waterfall. brbrThe master bedroom is located on the second floor and has a balcony and marble bathroom. Down the hall is a cozy den with a sleeper sofa. The two third-floor guest suites are spacious and private with beautiful tree-top views of Old Town. brbrAmenities include 2 off-street parking spaces, two private heated pools, gourmet Viking kitchens, HD flat screen TVs, Ipod docks, WiFi, laundry, and central heat & air conditioning. brbrbrKeywords: Key West Vacation Rental, Walk to everything.
Bed 6

Bed

Bath 6

Bath

Sleep 16

Sleeps

Slider Thumb
Exceptional(56)

$295.56

/ Nightly
Private Vacation Home

Mojitoville: 3 bedroom pet-friendly, Old Town, Private Pool, Historic Seaport

Key West, Florida, United States

Mojitoville is perfect for the discriminating guest who wants to enjoy close proximity to Key West's Historic Seaport with its fine fishing, restaurants and activities and also to Duval Street. brbrThe perfect location, 1 block to the Eaton Street Seafood Market and Old Town Bakery or 2 blocks to the Conch Republic Seafood Company, Cole's Peace Artisan Breads, Half-Shell Raw Bar, the Boathouse Restaurant, Schooner Wharf Bar and a stroll around the Seaport or just 4 blocks to Duval Street, completely renovated Mojitoville will amaze you with the detailing (beautifully refinished original wooden floors and Dade County pine walls), decorating and attention to detail! On the Historic Register and also sporting an Old Island Restoration Foundation designation, sit on the front porch and watch the world go by or enjoy the totally private landscaped rear deck, heated pool and gas BBQ grill! brbrThe historic cottage features two bedrooms, one with king pillow top bed, 42' wall flat screen TV the other with queen pillow top bed, 42' flat screen TV. Also, the wonderful loft has two twin beds and a private sitting area for relaxing. *We find that the size and layout of the house is best suited for 2 to 4 adults, or 2 to 4 adults + 2 children (that can use the spiral staircase to the loft; there is not a bathroom in the loft). brbrThe master king bedroom features an ensuite bath with shower and hair dryer, the second bath off the hallway and close to the circular stairs to the loft includes a tub/shower, hair dryer and W/D. brbrThe great room at the rear of the cottage has a vaulted ceiling and double French doors across the wall that open to a private deck surrounded for privacy with fencing and tropical foliage, heated pool with table and chairs. The great room consists of a living room and kitchen. The living room features a 32' Phillips flat screen (which is adjustable for sweeping movement and viewing), and comfortable, intimate seating. brbrThe elegant and fully equipped kitchen has a dishwasher, microwave, refrigerator, stove, garbage disposal, glass top stove, stainless steel appliances, quartz counter tops and everything you could desire to prepare a gourmet feast! There is a high pub/dining table in the kitchen area that seats four, as well as a table with 6 dining chairs just through the French doors on the deck.brbrSince Hurricane Irma (2017) we have: replaced all rear area fencing and most rear area plantings; had the pool refinished; replaced the pool filter; had new composite decking installed and repaired the air conditioning. We have also installed a new Bosch refrigerator/freezer, a new dishwasher, new ADA height toilets and a new on demand hot water heater. The living area has a new sofa and leatherette chair and all mattresses were replaced recently. brbrPlease note that we do not rent by the night, only longer term, minimum 28 nights.brbrPets are welcome with pre-approval; they must be at least one year of age, well behaved and house-trained. The pet fee is $200 per pet per stay (i.e. one dog = $200, two dogs = $400). If you have a pet in the house, you will be required to to have a $500 security deposit to cover any excessive cleaning or damage. This will be returned to you (or the balance if fees are incurred) once the house has been checked after you depart. brbrAnd a final note: due to the COVID-19 event we will refund in full all monies paid if the Keys are closed to entry by vacation renters and you are unable to reach our home due to government-imposed travel restrictions.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Home Most popular vacation rentals in Key West