Vacation Rentals By Owner In Key West, FL

Summary:brbrSet on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residences. Unwind in the perfect blend of adventure and relaxation in sunny Key West.brbrbrbrOn property, you can find access to our resort pool, ocean marina, and the ability to book a sandbar or sunset cruise.brbrbrbrDon’t miss out on fine dining at our award winning restaurant, Tavern N Town, or grab a delectable meal poolside at Chicken Walk.brbrbrbrThe Space:brbrExperience comfort and convenience in this expansive 2-bedroom condo, featuring a full kitchen, washer/dryer, and your own private balcony retreat. Steps to our onsite marina - at an added cost reserve a private boat slip, or explore ocean activities with our onsite watersports company - Brightwild Adventures.brbrbrbrSleeping arrangements include:brbrBedroom 1: King bed and en-suite bathroom with a double vanity and whirlpool tubbrbrBedroom 2: King bed with en-suite bathroom (separated via lock out door)brbrLiving Area: Queen sleeper sofabrbrbrbrThe fully-equipped kitchen features stainless-steel appliances and includes all cooking essentials. With its open-concept floor plan, the indoor living area seamlessly connects to the private balcony, creating the perfect space for quality time.brbrbrbrGuest Access:brbrPersonalized check in experience!brbrOur luxury resort offers a heated pool, hot tub, on-site marina, restaurant and waterview fitness center.brbrGuests have access to a local Guest Experience Manager (GEM) for recommendations such as on-site bike rentals, water excursions, and our favorite places to eat.brbrbrbrThe Neighborhood:brbrConveniently located on north Key West, Beachside Resort sits on an ideal seven acres of land situated just 10 minutes from Duval Street, ensuring you can be as close or as far from the ‘happenings’ as you’d like. Our hotel contains over 200 guest rooms and suites, two on-property restaurants, a 46,000 gallon pool and Key West’s largest ballroom.brbrbrbrGetting Around:brbrParking Information:brbrGarage parking available on property for $25/night; with electric charging stations.brbrbrbrOn-site Shuttle & Rentals:brbrWe provide a daily shuttle from 9am to 11pm for easy access to Key West and its famed Duval Street attractions or check out our on-site bike & watercraft rentals at Brightwild Adventures.brbrbrbrOther Things to Note:brbr- Host your wedding, corporate, or social events in one of Key West's largest ballrooms with full in-house catering services available.brbr- This property is not pet-friendly.brbr- Private stackable washer/dryer.brbr- Parking is $25 per night, per vehicle plus tax.brbr- All housekeeping services are by request, additional fees may apply. No daily service provided.brbr- Primary Guest must be at least 21 years of age or older in order to reserve this property.

Two Bedroom Residence

Key West, Florida, United States

2

Bed

2

Bath

6

Sleeps

$617.81

Summary:brbrSet on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residences. Unwind in the perfect blend of adventure and relaxation in sunny Key West.brbrbrbrOn property, you can find access to our resort pool, ocean marina, and the ability to book a sandbar or sunset cruise.brbrbrbrDon’t miss out on fine dining at our award winning restaurant, Tavern N Town, or grab a delectable meal poolside at Chicken Walk.brbrbrbrThe Space:brbrStart each morning overlooking the Gulf of Mexico from your private balcony of this 2-bedroom condo, complete with everything you need for your Beachside escape.brbrbrbrSleeping arrangements include:brbrBedroom 1: King bed and en-suite bathroom with a double vanity and whirlpool tubbrbrBedroom 2: King bed with en-suite bathroom (separated via lock out door)brbrLiving Area: Queen sleeper sofabrbrbrbrThe fully-equipped kitchen features stainless-steel appliances and includes all cooking essentials. With its open-concept floor plan, the indoor living area seamlessly connects to the private balcony, creating the perfect space for quality time.brbrbrbrGuest Access:brbrPersonalized check in experience!brbrOur luxury resort offers a heated pool, hot tub, on-site marina, restaurant and waterview fitness center.brbrGuests have access to a local Guest Experience Manager (GEM) for recommendations such as on-site bike rentals, water excursions, and our favorite places to eat.brbrbrbrThe Neighborhood:brbrConveniently located on north Key West, Beachside Resort sits on an ideal seven acres of land situated just 10 minutes from Duval Street, ensuring you can be as close or as far from the ‘happenings’ as you’d like. Our hotel contains over 200 guest rooms and suites, two on-property restaurants, a 46,000 gallon pool and Key West’s largest ballroom.brbrbrbrGetting Around:brbrParking Information:brbrGarage parking available on property for $25/night; with electric charging stations.brbrbrbrOn-site Shuttle & Rentals:brbrWe provide a daily shuttle from 9am to 11pm for easy access to Key West and its famed Duval Street attractions or check out our on-site bike & watercraft rentals at Brightwild Adventures.brbrbrbrOther Things to Note:brbr- Host your wedding, corporate, or social events in one of Key West's largest ballrooms with full in-house catering services available.brbr- This property is not pet-friendly.brbr- Private stackable washer/dryer.brbr- Parking is $25 per night, per vehicle plus tax.brbr- All housekeeping services are by request, additional fees may apply. No daily service provided.brbr- Primary Guest must be at least 21 years of age or older in order to reserve this property.

Ocean Front Two Bedroom Residence

Key West, Florida, United States

Bed

Bath

Sleeps

$499.13

Summary:brbrSet on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residences. Unwind in the perfect blend of adventure and relaxation in sunny Key West.brbrbrbrOn property, you can find access to our resort pool, ocean marina, and the ability to book a sandbar or sunset cruise.brbrbrbrDon’t miss out on fine dining at our award winning restaurant, Tavern N Town, or grab a delectable meal poolside at Chicken Walk.brbrbrbrThe Space:brbrEnjoy your morning coffee on your private balcony with views overlooking the resort and pool area.brbrOur two-bedroom, two-and-a-half-bathroom condo provides everything you need for your next getaway to Beachside Key West.brbrbrbrSleeping arrangements include:brbrBedroom 1: King bed and en-suite bathroom with a double vanity and whirlpool tubbrbrBedroom 2: King bed with en-suite bathroom (separated via lock out door)brbrLiving Area: Queen sleeper sofabrbrbrbrThe fully-equipped kitchen features stainless-steel appliances and includes all cooking essentials. With its open-concept floor plan, the indoor living area seamlessly connects to the private balcony, creating the perfect space for quality time.brbrbrbrGuest Access:brbrPersonalized check in experience!brbrOur luxury resort offers a heated pool, hot tub, on-site marina, restaurant and waterview fitness center.brbrGuests have access to a local Guest Experience Manager (GEM) for recommendations such as on-site bike rentals, water excursions, and our favorite places to eat.brbrbrbrThe Neighborhood:brbrConveniently located on north Key West, Beachside Resort sits on an ideal seven acres of land situated just 10 minutes from Duval Street, ensuring you can be as close or as far from the ‘happenings’ as you’d like. Our hotel contains over 200 guest rooms and suites, two on-property restaurants, a 46,000 gallon pool and Key West’s largest ballroom.brbrbrbrGetting Around:brbrParking Information:brbrGarage parking available on property for $25/night; with electric charging stations.brbrbrbrOn-site Shuttle & Rentals:brbrWe provide a daily shuttle from 9am to 11pm for easy access to Key West and its famed Duval Street attractions or check out our on-site bike & watercraft rentals at Brightwild Adventures.brbrbrbrOther Things to Note:brbr- Host your wedding, corporate, or social events in one of Key West's largest ballrooms with full in-house catering services available.brbr- This property is not pet-friendly.brbr- Private stackable washer/dryer.brbr- Parking is $25 per night, per vehicle plus tax.brbr- All housekeeping services are by request, additional fees may apply. No daily service provided.brbr- Primary Guest must be at least 21 years of age or older in order to reserve this property.

Pool View Two Bedroom Residence

Key West, Florida, United States

2

Bed

3

Bath

6

Sleeps

$378.5

Summary:brbrSet on seven acres of property overlooking the Gulf of Mexico, experience luxury at Beachside Resort & Residences. Unwind in the perfect blend of adventure and relaxation in sunny Key West.brbrbrbrOn property, you can find access to our resort pool, ocean marina, and the ability to book a sandbar or sunset cruise.brbrbrbrDon’t miss out on fine dining at our award winning restaurant, Tavern N Town, or grab a delectable meal poolside at Chicken Walk.brbrbrbrThe Space:brbrStart each morning overlooking the Gulf of Mexico from your private balcony of this 1-bedroom condo, complete with a full kitchen, washer/dryer, and 2 full bathroomsbrbrOur one-bedroom, two-bathroom condo provides everything you need for your next getaway to Beachside Key West.brbrSleeping arrangements include:brbrBedroom 1: King bed and en-suite bathroom with a double vanity and whirlpool tubbrbrLiving Area: Queen sleeper sofabrbrbrbrThe fully-equipped kitchen features stainless-steel appliances and includes all cooking essentials. With its open-concept floor plan, the indoor living area seamlessly connects to the private balcony, creating the perfect space for quality time.brbrbrbrGuest Access:brbrPersonalized check in experience!brbrOur luxury resort offers a heated pool, hot tub, on-site marina, restaurant and waterview fitness center.brbrGuests have access to a local Guest Experience Manager (GEM) for recommendations such as on-site bike rentals, water excursions, and our favorite places to eat.brbrbrbrThe Neighborhood:brbrConveniently located on north Key West, Beachside Resort sits on an ideal seven acres of land situated just 10 minutes from Duval Street, ensuring you can be as close or as far from the ‘happenings’ as you’d like. Our hotel contains over 200 guest rooms and suites, two on-property restaurants, a 46,000 gallon pool and Key West’s largest ballroom.brbrbrbrGetting Around:brbrParking Information:brbrGarage parking available on property for $25/night; with electric charging stations.brbrbrbrOn-site Shuttle & Rentals:brbrWe provide a daily shuttle from 9am to 11pm for easy access to Key West and its famed Duval Street attractions or check out our on-site bike & watercraft rentals at Brightwild Adventures.brbrbrbrOther Things to Note:brbr- Host your wedding, corporate, or social events in one of Key West's largest ballrooms with full in-house catering services available.brbr- This property is not pet-friendly.brbr- Private stackable washer/dryer.brbr- Parking is $25 per night, per vehicle plus tax.brbr- All housekeeping services are by request, additional fees may apply. No daily service provided.brbr- Primary guest must be 21 years old or older in order to reserve this property.

Ocean Front Suite | Beachside Resort

Key West, Florida, United States

Bed

Bath

Sleeps

$411.14

Welcome aboard Sentient, your own private 63’ boat in Key West! We're thrilled to have you & hope you enjoy every moment of your stay. Whether you're relaxing on deck, enjoying the sway of the water, or soaking in the sunset, we want you to experience the tropical island vibes with all the comforts of home mixed in. Aboard you will find 2 full beds & baths, a full pull out, a full kitchen & coffee bar, snorkel gear, comfortable seating & more! Step aboard & enjoy your own tropical paradise!brbrSleep & Comfort brbrCaptains suite with queen bed, 2 nightstands, storage & closet, window, & full private bathroombrbrCrew quarters with twin bunks, nightstand, storage & closet, window, & direct access to full bathroom brbrTwo full bathrooms with showers, storage, soaps, conditioner, lotion, towels and extra toilet paper brbrA cozy full sized pull out in the living room for extra guests - a memory foam topper is provided along with sheets, blankets, & pillowsbrbrAir conditioning throughout for your comfort brbrFull Kitchen & Living Space brbrFully equipped kitchen with stove, microwave, refrigerator, and cookwarebrbrOpen-concept living area with all around windows & bluetooth, perfect for relaxing or entertainingbrbrFully equipped coffee bar with barstools & suppliesbrbrOutdoor Bliss brbrSpacious sundeck with panoramic marina views—ideal for morning coffee or sunset cocktailsbrbrRelax on the partially shaded, large back deck, with comfortable seating & serene marina views (Seating can be rearranged to your liking) brbrStretch out on the sun-drenched bow—your private tanning havenbrbrTake in sweeping views from the elevated flybridge—complete with cushioned seating, ocean breezes, and the best vantage point on the yachtbrbrAmenities ☀️brbrFree parking on-sitebrbrFree shuttle that will take you around Key WestbrbrTwo sparkling poolsbrbrSnorkel gear, beach chairs, beach towels & morebrbrOn-site waterfront bars & restaurants with the best fresh seafood aroundbrbrOn-site fitness centerbrbrLounge area with fire placebrbrOn-site play area for your littles brbrLaundromat available at the marina for your use ($2.50 per cycle)brbrLocation Perks brbrSteps from Key West’s vibrant attractions, nightlife, and water adventuresbrbrPlenty of nearby restaurant to choose from with fresh seafood and live music brbrGolf cart, bike, and moped rentals nearbybrbrSecure dockage with easy access and ship store, as well as plenty of nearby conveniencesbrbrFishing, snorkel, & sandbar charters at a discounted rate brbrBoat rentals & sunset trips available at the marinabrbrTucked away in one of the most sought-after marinas near Key West, and just minutes from all the action, you not only get to experience private waterfront views, but you have direct access to world-class fishing and diving just steps from your dock. Spend your day paddling through the crystal clear waters, snorkeling the reefs, or hooking fish, then head down to Duval Street to enjoy the nightlife, fresh seafood, bars and unforgettable sunsets at Mallory Square. Then relax back at your quiet floating oasis, sip a sparkling cucumber water as you end your day swaying under the stars.brbrPlease note: brStaying on a boat has some added risks that a house does not. Decks get slippery and you must step from the dock to the boat, it is not a huge step but some guests may find it challenging. With that in mind we do require a signed waiver to stay. This will be sent to you after you book and you will need sign it and send it back to us to confirm your booking. Thank you for understanding. brbrDisclaimer:brTo ensure the best fit for your stay: this is an authentic boat experience so it will not be the same feeling as staying in a house or hotel, (which is kinda the point ). Water pressure may be lighter, there will be slight rocking, and although there is air conditioning, temperatures may not be as low as you would like (low to mid 70s are normal). If you’re expecting a hotel-like environment, this may feel different. This is not a hotel, you will have the full experience of staying on a boat, living the local Key West life.brPlease keep these things in mind when you book. brIf you have any questions or concerns please reach out to us before you book so we can make your vacation as enjoyable as possible!

House Boat

Sentient Waters: 63' Boat With Full Amenities & Sun Deck

Key West, Florida, United States

Bed

Bath

Sleeps

$2868.44

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrIn Key West, every day is a celebration of what makes Summer such a beloved season - warm weather, no agendas, and spending quality time with family and friends. SUMMER SOLSTICE provides the perfect setting for a large group looking to enjoy exactly that. As a combination of two side-by-side private homes located in the heart of Old Town, Summer Solstice offers an unbeatable location and plenty of comfortable accommodations for everyone, as well as numerous luxuries, including:brbr** Two fully equipped kitchensbr** Two spacious living areasbr** Nine Private Bedrooms, each with an en-suite bathroombr** Two private saltwater poolsbr** Two designated off-street parking spacesbrbrSUMMER SOLSTICE can be rented exclusively through Last Key Realty and includes our Five-Star In-home Guest Services - marking a vacation that's sure to give you the Summer feels any time of year!brbrTHE PRIVATE SALTWATER POOLS...brbrDown a tiny lane you'd have to be looking for is a row of homes tucked just a half block from Duval Street but without the hustle and bustle of the main drag. Summer Solstice is the combination of the first two homes on that row and can be accessed through one of two gates opening up to the private pool areas. The pool areas are connected via an open gate that allows your crew to pass through and mingle between the homes. Fully fenced for privacy, these pools will undoubtedly be the primary gathering places for your group. The saltwater pools can be heated in the cooler months to your liking and get equal amounts of sunshine and shade throughout the day. Comfortable chaises offer the perfect lounging options for relaxing outdoors. Each home has a full outdoor dining set and a propane grill to bring the group together for happy hour or a poolside BBQ.brbrTHE LIVING AREAS...brbrSUMMER SOLSTICE offers two spacious living areas designed to accommodate a large group. The living areas are equipped with huge SMART TVs and comfortable furnishings. In addition, the plush sofas, armchairs, and indoor dining tables provide plenty of seating options for your whole crew. Both living room sofas pull out to Queen sleepers to accommodate extra guests. brbrBoth kitchens are fully-equipped with every appliance and tool needed to prepare a meal at home, that is when you're not enjoying the fantastic array of Old Town restaurant options within walking distance.brbrTHE ACCOMMODATIONS...brbrThis compound of two homes will keep your whole group satisfied. Each bedroom has a flat screen TV, an overhead fan, and an en-suite bathroom.brbrBed Configuration Summary:brbrHouse 1 = 5 Bedrooms + Sleeper Sofabrbr** 2 Twins OR 1 King - First Floorbrbr** 2 Twins OR 1 King - Second Floorbrbr** King - Second Floorbrbr** Queen - Second Floorbrbr** 2 Twins OR 1 King - Second FloorbrbrHouse 2 = 4 Bedrooms + Sleeper Sofabrbr** 2 Twins OR 1 King - First Floorbrbr** 2 Twins OR 1 King - Second Floorbrbr** 2 Twins OR 1 King - Second Floorbrbr** King - Second FloorbrbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen HD TVs in Living Room and 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 and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** 2 Fenced and Lushly Landscaped Backyards br** 2 Private Saltwater Pools with available Pool Heatbr** Outdoor Showerbr** 2 Propane BBQ Grillsbr** 2 Queen Sleeper Sofasbr** 2 Off-Street Parking Spaces (with restrictions - NO LARGE VEHICLES)brbrOther notes:brbr** In person welcome br** Interim housekeeping provided upon requestbr** Max of 2 Pets Allowed with Additional Fee of $200 per petbr** This property will accommodate 22 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.

Private Vacation Home

**SUMMER SOLSTICE @ OLD TOWN** Unique 9BR/9.5BA Compound + LAST KEY SERVICES…

Key West, Florida, United States

Bed

Bath

Sleeps

$306.4

Welcome to Pilar Cottage, a charming studio located within the peaceful Harbor Walk Hideaways complex in Key West's Historic Seaport district. This cozy one-bedroom, one-bathroom retreat features upscale furnishings and offers a small shared dipping pool, making it a perfect spot to soak up the Florida sun.brbrComfort and Amenities:brPilar Cottage is thoughtfully designed to ensure a relaxing and enjoyable stay, offering a range of features that cater to your comfort and convenience.brbrSleeping Arrangements:brThe cozy bedroom features a plush Queen bed outfitted with a luxurious Tempur-Pedic mattress, guaranteeing a restful night's sleep. For additional guests, the living area includes a full-size sofa sleeper that easily converts into a bed, providing ample space for up to four guests to sleep comfortably.brbrEntertainment:brEnjoy large flat-screen Smart TVs available in both the living room and bedroom, equipped with streaming options so you can enjoy your favorite shows and movies. The complimentary high-speed Wi-Fi throughout the cottage ensures you stay connected, whether you're planning your next adventure or catching up on social media.brbrConvenience:brWhile it doesn't have a full kitchen, the cottage includes a mini fridge, microwave, and a Keurig coffee maker with complimentary coffee supplies. The elegantly appointed bathroom features a granite vanity and a walk-in shower.brbrRelaxation Spaces:brStep outside to discover the shared outdoor area, where you can unwind in the inviting small dipping pool, complete with a soothing waterfall feature. This tranquil space is ideal for lounging under the sun, enjoying a good book, or relaxing with friends. With comfortable outdoor seating available, you can sip your morning coffee or evening cocktails in a peaceful setting.brbrEasy Arrival:brExperience a seamless check-in process through our contactless system. You'll receive a personalized access code to enter the cottage before your arrival, ensuring a hassle-free experience.brbrExplore the Neighborhood:brAtocha Cottage is ideally located in the vibrant Historic Seaport District, surrounded by a delightful mix of bars and restaurants that embody the essence of Key West. Enjoy a variety of dining options, from casual seafood spots to more upscale eateries, all offering fresh local flavors and charming outdoor seating.brbrAs night falls, the area comes alive with a lively nightlife scene, perfect for enjoying cocktails and live music. Don't miss the enchanting sunset celebrations at Mallory Square, where you can experience street performances and the vibrant local arts scene. With so much to explore nearby, you'll immerse yourself in the unique culture and charm of Key West.brbrTransportation Tips:brParking: Please note that there is no designated parking on-site. However, paid parking is available across the street and at 300 Grinnell St. We can provide further recommendations for additional parking if needed.brbrExplore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the cottage. Feel free to ask for local recommendations!brbrOther Things to Note:br- Group Accommodations: Consider renting additional cottages within Harbor Walk Hideaways to host larger groups of up to 14 guests.br- Laundry Facilities: On-site laundry is not available.br- Pet-Friendly: We welcome pets (up to 40 lbs) with a $20/per pet per night fee.br- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Pilar Cottage | Spectacular Studio w/ Shared Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$327.41

Welcome to African Queen Cottage, a charming retreat within the serene Harbor Walk Hideaways complex in Key West's Historic Seaport district. This inviting one-bedroom, one-bathroom cottage combines modern comforts with a prime location, perfect for enjoying the local attractions and beautiful waterfront.brComfort and Amenities:brAfrican Queen Cottage is designed for your relaxation, featuring:brbrSleeping Arrangements:brA plush Tempur-Pedic queen mattress in the bedroom and a full-size sofa sleeper in the living room, accommodating up to 4 guests comfortably.brbrEntertainment:brLarge flat-screen Smart TVs are provided in both the living room and bedroom, ensuring you can stream your favorite shows and enjoy complimentary Wi-Fi.brbrConvenience:brThough it lacks a full kitchen, the cottage is equipped with a kitchenette featuring a mini fridge, microwave, and Keurig coffee maker for your convenience. The spacious bathroom is elegantly designed and is handicap accessible.brbrRelaxation Spaces:brTake a dip in the shared small dipping pool with a soothing waterfall feature, or unwind in the outdoor area, complete with lounge chairs and dining spaces perfect for soaking up the Florida sun.brbrEasy Arrival:brExperience a seamless check-in process with our contactless system. Before your arrival, you'll receive a personalized access code to enter the cottage, along with direct contact information for our local guest experience manager.brbrExplore the Neighborhood:brAtocha Cottage is ideally located in the vibrant Historic Seaport District, surrounded by a delightful mix of bars and restaurants that embody the essence of Key West. Enjoy a variety of dining options, from casual seafood spots to more upscale eateries, all offering fresh local flavors and charming outdoor seating.brbrAs night falls, the area comes alive with a lively nightlife scene, perfect for enjoying cocktails and live music. Don't miss the enchanting sunset celebrations at Mallory Square, where you can experience street performances and the vibrant local arts scene. With so much to explore nearby, you'll immerse yourself in the unique culture and charm of Key West.brbrTransportation Tips:brPlease note that there is no designated parking on-site. However, paid parking is available across the street and at 300 Grinnell St. We can provide further recommendations for additional parking if needed. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the cottage. Feel free to ask for local recommendations!brbrOther Things to Note:br- Group Accommodations: Consider renting additional cottages within Harbor Walk Hideaways to host larger groups of up to 14 guests.br- Laundry Facilities: On-site laundry is not available.br- Pet-Friendly: We welcome pets (up to 40 lbs) with a $20/per pet per night fee.br- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

African Queen | Perfect Suite Near Historic Seaport

Key West, Florida, United States

Bed

Bath

Sleeps

$438.86

Atocha Cottage at Harbor Walk HideawaysbrbrWelcome to Atocha Cottage, a serene getaway nestled within the charming Harbor Walk Hideaways complex in Key West's Historic Seaport district. This delightful 2-bedroom, 1-bathroom cottage combines modern comfort with a prime location, just steps away from local attractions and the beautiful waterfront.brbrComfort and Amenities:brAtocha Cottage is designed for relaxation, featuring:brbrSleeping Arrangements: brTwo cozy Queen beds with Tempur-Pedic mattresses and a full-size sofa sleeper in the living area, accommodating up to 6 guests comfortably.brbrEntertainment: Large flat-screen Smart TVs in both bedrooms and the living room, offering streaming options and free Wi-Fi.brConvenience: While it lacks a full kitchen, the cottage is equipped with a mini fridge, microwave, and Keurig coffee maker for your convenience.brRelaxation SpacesbrUnwind in the elegantly designed bathroom, complete with a walk-in shower and high-quality linens. Outside, enjoy the small shared dipping pool with a soothing waterfall feature, along with a spacious deck area for lounging in the sun.brbrEasy Arrival:brEnjoy a hassle-free check-in experience with our contactless procedure. Prior to your arrival, you will receive a personalized access code to enter your cottage.brbrExplore the Neighborhood:brAtocha Cottage is ideally located in the vibrant Historic Seaport District, surrounded by a delightful mix of bars and restaurants that embody the essence of Key West. Enjoy a variety of dining options, from casual seafood spots to more upscale eateries, all offering fresh local flavors and charming outdoor seating.brbrAs night falls, the area comes alive with a lively nightlife scene, perfect for enjoying cocktails and live music. Don't miss the enchanting sunset celebrations at Mallory Square, where you can experience street performances and the vibrant local arts scene. With so much to explore nearby, you'll immerse yourself in the unique culture and charm of Key West.brbrTransportation Tips:brParking: Please note that there is no designated parking on-site. However, paid parking is available across the street and at 300 Grinnell St. We can provide further recommendations for additional parking if needed.brbrExplore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the cottage. Feel free to ask for local recommendations!brbrOther Things to Note:br- Group Accommodations: Consider renting additional cottages within Harbor Walk Hideaways to host larger groups of up to 14 guests.br- Laundry Facilities: On-site laundry is not available.br- Pet-Friendly: We welcome pets (up to 40 lbs) with a $20/per pet per night fee.br- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval!

Key West, Florida, United States

Bed

Bath

Sleeps

$562.28

Summary:brbrDiscover a relaxed and thoughtfully designed island retreat at The Margaret Suite, a beautifully updated studio nightly vacation rental located at Bayview House, a lovingly restored historic property in the heart of Old Town Key West. Blending coastal charm with modern comfort, this inviting suite is ideal for couples or small families seeking a stylish and centrally located home base.brbrbrbrThe Margaret Suite features an open-concept studio layout with vaulted ceilings and soft coastal finishes that create a bright, airy feel throughout. The sleeping area includes a comfortable queen bed with crisp linens and bedside lighting, while the living space offers a cozy seating area with a convertible twin-sized sofa bed and a flat-screen TV — perfect for relaxing after a day in the sun.brbrbrbrThe bathroom offers a sleek walk-in glass shower, modern fixtures, and a contemporary vanity.brbrbrbrThe kitchenette is compact yet well-equipped for light meals and snacks, featuring a refrigerator, cooktop, microwave, coffee maker, sink, and essentials — ideal for easy breakfasts or casual evenings in.brbrbrbrThis studio comfortably sleeps up to three guests and includes access to the amenities at Bayview House:brbr- Shared swimming poolbrbr- Shared on-site laundrybrbr- Air conditioning, Wi-Fi, and flat-screen TVbrbr- First-come, first-serve off-street parking (2 spaces total for the property) plus nearby street parkingbrbr- Prime Old Town location near the waterfrontbrbrbrbrBayview House places you within walking distance of Key West’s iconic attractions, including Mallory Square, Key West Historic Seaport, the Ernest Hemingway Home and Museum, and Fort Zachary Taylor State Park for beach days and snorkeling.brbrbrbrWhether you’re visiting for a romantic getaway, a weekend escape, or a longer island stay, The Margaret Suite offers a calm, stylish retreat just steps from the dining, nightlife, and culture that make Key West unforgettable.brbrbrbrBook your stay at The Margaret Suite and enjoy the charm of a boutique historic property with the comfort and convenience of a modern vacation rental in the heart of Old Town.

The Margaret Suite

Key West, Florida, United States

Bed

Bath

Sleeps

$1400.34

Welcome to Harborwalk Hideaways!brbrOverview:brDiscover Harbor Walk Hideaways, a beautifully renovated vacation rental complex nestled in the Historic Seaport district of Old Town Key West. This sought-after destination features three charming cottages—Atocha, Pilar, and African Queen—each named after legendary vessels that frequented Key West. Ideal for relaxation, the property boasts a serene outdoor area complete with a plunge pool and inviting dining space.brbrThe Ideal Retreat:brPerfect for larger groups, Harborwalk Hideaways offers a private outdoor oasis. Enjoy the refreshing dipping pool, a tranquil water feature, and new outdoor furnishings. This tropical escape is perfect for gathering with family and friends, day or night.brbr- - Cottage Details - -brAtocha Cottage:brType: Two BedroomsbrBedroom 1: Queen BedbrBedroom 2: Queen BedbrAdditional Sleeping: Full-size sleeper sofa in living areabrbrAfrican Queen:brType: StudiobrBedroom: Queen BedbrAdditional Sleeping: Full-size sleeper sofabrbrPilar's Cottage:brType: StudiobrBedroom: Queen BedbrAdditional Sleeping: Full-size sleeper sofabrInterior FeaturesbrbrEvery cottage is designed with meticulous attention to detail. Each bedroom includes:br- Large flat-screen Smart TVsbr- Bedside lighting with charging stationsbr- Full-length mirrorsbr- Comfortable Queen beds with Tempur-Pedic mattressesbrbrThe living spaces feature:br- Barstool seatingbr- Kitchenettes equipped with mini-fridges and microwavesbr- Stylish bathrooms with granite vanities and newly tiled walk-in showersbr- Easy Check-Inbr- Enjoy a seamless arrival with our contactless check-in process. A personalized access code will be provided prior to your arrival.brbrLocal AttractionsbrSituated in the heart of the Historic Seaport District, you'll be within walking distance of popular dining and entertainment spots, including:br- Conch Republic Bar & Grillebr- Boat House Bar & Grillbr- Dante's Pool Barbr- A&B Lobster Housebr- Waterfront BrewerybrbrDon't miss the stunning sunsets at nearby Mallory Square or the vibrant nightlife on Duval Street, just a short stroll away!!brbrTransportation TipsbrParking: Please note there is no designated parking on-site, but paid parking is available across the street and at Grinnell St.brbrExplore Key West conveniently by bicycle, scooter, golf cart, rideshare, or on foot, as many attractions are easily accessible.brbrOther Things to Note:br- Kitchen Facilities: Each unit includes a mini-fridge, microwave, and Keurig coffee maker; there is no full kitchen.br- Laundry: On-site laundry facilities are not available.br- Pet-Friendly: We welcome pets (up to 40 lbs) with a $20/per pet per night fee.br- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrAt Colocada Vacation rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

Harbor Walk Hideaways | Group Compound In Old Town, Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$338.88

A FEAST FOR THE EYES…brThis exquisite 3 bedroom, 3 bath abode will delight your artistic senses with its gorgeous interior and lush outside spaces. Owned by a renowned London-based designer, this worldly and sophisticated showpiece home displays amazing attention to detail and has been fully renovated and restored for your pleasure. This is a fantastic Midtown location, near the Casa Marina and Atlantic beaches and just a short distance to the island's attractions.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brThis home features a beautifully designed interior that includes high ceilings, hardwood floors and an open floor plan. Step inside to the living area where East meets West with a whimsical modern flair. The large tv and beautiful furnishings invite you to relax and enjoy the artistry that surrounds you. A dining table for 6 inhabits the living area and there is also a kitchen bar with seating for 3. The immaculate kitchen is fully equipped with modern appliances and is stocked with everything you'll need. Sliding doors to the backyard oasis merge inside and outside spaces, giving you the authentic Key West living experience. Each bedroom has its own bathroom and there is a full-sized laundry room upstairs as well. brbrSLEEPING ARRANGEMENTS...brA queen bedroom resides downstairs that opens to the front porch. There is a TV and adjoining bathroom that offers a glass-door shower and has double entry doors to the pool area and downstairs. A storage closet is located in the bathroom. Travel upstairs to the other bedrooms. The primary suite offers a lovely office area that overlooks the backyard oasis. The king bedroom lulls you in with its promise of relaxation and the enjoyment of its unique design. A large tv and two closets ensure your comfort in this grand space. The bathroom features a shower/tub combination. The third bedroom houses two twin beds (can be converted to a king upon request), with a tv and small dresser. The third bathroom is adjacent to the twin bedroom and offers a shower/tub combination. brbrOUTDOOR LIVING...brThere is a front porch as you enter the home and an upper balcony that looks out over the backyard and heated pool. Enjoy your morning coffee and views from these lovely spaces, then venture out to your sparkling pool with teak deck. Your outdoor refuge is surrounded by tropical foliage, al fresco seating for dining under the stars, lounge chairs for sunbathing and a gas grill. You and your loved ones will enjoy many hours in this backyard slice of heaven.brbrPARKING...brThere is off street parking on the double driveway.brbrPETS...brDogs under 35 lbs are considered and a pet fee is required. Please leave the size / breed in the comments when inquiring. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is offered only 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).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!

Private Vacation Home

WALKING ON SUNSHINE ~ Exquisite 3 BR, 3 Ba Home w/ Heated Pool & Parking!

Key West, Florida, United States

Bed

Bath

Sleeps

$1197.59

`In-the-know` travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia`s Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval, and because it is all the way at the end of an unknown lane it is well hidden from public view. Unless you`ve stayed in this villa before, there`s no-way you`d ever know it`s just steps off Upper Duval Street in one of the prettiest parts of Old Town Key West..brbrThe property itself is authentic Key West and unique all-the-way. Pineapple carvings on the fence gracing this property just hint at the island-living charm you find inside. Art work by famous local Caribbean folk artist David Wegman perched above the gates welcomes you at the entrance. Enter the large wooden blue-green gate off the little private lane and you step into the beautiful courtyard with a crystal clear swimming pool. A statue of the happy Buddha graces the pool side and further welcomes you to your home in Key West and once inside the courtyard you are treated to even more art work; this time canvas art pieces painted by the late Key West artist Sanford Birdsey are uniquely incorporated into the courtyard walls.brbrThe layout of this vacation villa was re-worked in October 2008 by local designers to maximize comfort and sleeping options that now include four full bedrooms that all open to the private courtyard. The room layout features one spacious great-room with open kitchen / living room and a flat screen HD TV. The great-room opens directly to a covered lanai that has a dining table for `el fresco` dining.brbrThe best way to visualize the layout of this Amelia`s Hideaway is to consider each room as it is situated within the courtyard. The house is built as an `L-Shaped` villa with each room in the house opening to the courtyard, and then 3/4 of the roof of the villa is an expansive Mexican tiled roof-top deck. We begin our descriptive tour as you pass the rooms once inside the courtyard gates.brbrRoom One: Bedroom #1 (yellow room) is a large room and is set as a full suite offering 2 twin beds that can be put together to make a king size bed and a private full bath divided into two - shower room and powder room with commode and sink. There is also a table conveniently placed for your lap-top. This room also offers a full size sofa that can be made into a queen bed.brbrRoom Two: Bedroom #2 (blue room) has a king size bed. This bedroom connects to a full bathroom with bath tub. The design is decidedly unique and very tropical using tumbled marble in an unusual design.brbrRoom Three: Bedroom #3 (rose room) has a Queen bed and offers a writing desk. While this bedroom connects to the same full bathroom as bedroom #2, the door connecting this bedroom to the courtyard is just steps from the `pool bath` which can be used as a private bath for the `rose room`.brbrRoom Four: The great-room (living room / kitchen) is the fourth room down the line of the courtyard. The great-room has a beautiful retro-style blue and white kitchen that is open to the cream colored living room area on the other end of the room that provides a sofa and love seat. This combined living area has a flat screen HD TV. The sofa in this great-room is a queen sleeper sofa if you need another bed in a private sleeping area. The main dining area for this room is found in the covered lanai just out the French doors from the kitchen offering a Caribbean `el fresco` dining.brbrRoom Five: The `pool bath` is an artistically tiled full bathroom with a blue and white design created by a local Key West artist. This bathroom has entrances from the lanai as well as the `great room.`brbrRoom Six: The sixth room (green room) is Bedroom #4 and is considered the master suite for this villa as it is situated `off to itself` offering the most privacy. This bedroom offers a king size bed and a private full bathroom. The bathroom is tiled in tumbled marble tile of muted tones of golden brown.brbrRoof Top Deck: The next living space in this unique Key West villa is outdoors and upstairs on the large Mexican tiled roof top deck which expands over 3/4 of the roof. This upper deck is reached by a stair case just outside the master suite. The upper deck offers the perfect spot for private lounging, sunning, star gazing, catching the ocean breeze, or staging a roof top cocktail party or dinner. This deck is furnished with outdoor furniture, built-in side bench seating, and outdoor lighting.brbrLaundry: Finally, back towards the entrance gate is a separate building which serves as the laundry and utility area.brbrThe general design of this property lends itself perfectly to small gatherings of families and friends and should be considered an ideal spot for a gathering of family or friends.brbrBedding Summary:brbrbrBedroom #1 - 2 twin size beds (can be made as a king size bed); queen sleeper sofa.brbrBedroom #2 - king size bed.brbrBedroom #3 - queen size bed.brbrBedroom #4 - king size bed.brbrAmenities: Well hidden at the end of little known lane. Private swimming pool, large private gated courtyard, expansive private roof-top sun deck, privacy fences. Fully equipped kitchen, el fresco dining, a/c, telephone, color cable TVs, stereo. Laundry room with washer / dryer. Linens and towels are provided. Designated parking spot at a nearby lot.brbrActivities: Elegant Upper Duval St. - Close to the Southernmost Point of the United States. Cafe neighborhood features art galleries, wonderful eateries and internationally famous fine restaurants, coffee houses, fine gift and clothing stores, Grand Vin wine tasting, Flamingo Crossing home made ice cream. Here you start at the top of Duval St. near the Atlantic Ocean and can take the 20 min stroll to the Gulf of Mexico (remember it takes 3 to 4 Key West streets to equal the distance of a typical city block). Sailing, boating, diving, museums, nightlife.brbrArea: Walk out your gate and down the lane to everything you want to see in Historic Key West. Best restaurants, shops, galleries, clubs, Hemingway House Museum, Light House Museum, Custom House Museum, Key West Aquarium, Butterfly Conservatory, 4 blocks from Southernmost Point of the U.S., close to beaches. Walk everywhere from here.brbrRestrictions: Smoke free house. Smoking permitted outside only. No pets please. 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: Parking is NOT allowed on the lane, directly in front of Amelia’s Hideaway. Please understand that this is designated as a fire lane by the City of Key West. However, you are welcome to use this area for unloading and loading your vehicle when you arrive or bring in groceries.brbrOur company does provide one designated off-street parking spot for you. The lot is located at 600 Amelia St, about 5-minute walk from your property. Your spot is marked with a red sign that reads “521 Amelia.”brbrSince this part of the island was developed before there were cars, parking can be challenging and should be expected. It is best to park your car, remove your valuables, lock up, and forget about it when you are here. Enjoy your location and walk or bike everywhere if possible.

Private Vacation Home

Amelia`s Hideaway - Hidden Key West Courtyard - Steps off Duval w Private Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$283.73

PICTURESQUE LANDMARK GUESTHOUSE WITH CELEBRATED RUM BAR...brSteeped in the rich 19th century lore of treasure hunts, romantic rum-running adventures, daring bootleggers, and notorious moonshiners and racketeers, the Hideaway room within the Speakeasy Inn is nestled in true Key West magic. This unique conch-style adult-only retreat is brimming with authentic stories of derring-do during Prohibition days. The inn was the home of Raul Vasquez, a cigar selector at the local Gato cigar factory, whose true passion was rum running between Key West and Cuba. He cut a colorful swath in this southernmost community, smuggling rum and storing it in his secret cellar - one of the few basements in Key West! You are right on Duval Street, renowned for its proliferation of whimsical art galleries, stellar restaurants and relaxing bars. Nestled in the heart of Old Town, you are only a couple blocks from the beach and the Southernmost Point.br***All guests must be 21 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.brbrDETAILS AND AMENITIES...brOn the first floor of the Speakeasy Inn resides the Rum Bar, which boasts an impressive selection of delicious rums from all over the globe. Join us for our rum tastings of both vintage and popular rums. Each guest room offers outdoor seating for its occupants. Amenities in the rooms include flat screen TVs, individually operated ACs, coffee makers, refrigerators, microwaves, and all rooms have private bathrooms with showers.brbrSLEEPING ARRANGEMENTS...brThe Hideaway room is located upstairs and offers a king bed, a stocked kitchenette, a shower bathroom and a clothing wall hanging system for your convenience.brbrOUTDOOR LIVING...brTake in the island air and sip on your frosted cocktail just outside of your room, with cushioned seating for your enjoyment. Upstairs features our wraparound porch overlooking Duval Street, a favorite people-watching spot! It has been restored to perfection for the pleasure of our guests. brbrPARKING...brParking is limited and not guaranteed, offered on a first come first serve basis at an additional fee of $15 per night. There are also some free as well as metered on street parking spaces on the surrounding streets. Most guests walk or bike ride to all of the nearby attractions once they secure a parking space.brbrPETS...brThis is not a pet-friendly inn.brbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrJOIN THE ADVENTURE...

HIDEAWAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

Key West, Florida, United States

Bed

Bath

Sleeps

$285.31

PICTURESQUE LANDMARK GUESTHOUSE WITH CELEBRATED RUM BAR...brSteeped in the rich 19th century lore of treasure hunts, romantic rum-running adventures, daring bootleggers, and notorious moonshiners and racketeers, the After Hours room within the Speakeasy Inn is nestled in true Key West magic. This unique conch-style adult-only retreat is brimming with authentic stories of derring-do during Prohibition days. The inn was the home of Raul Vasquez, a cigar selector at the local Gato cigar factory, whose true passion was rum running between Key West and Cuba. He cut a colorful swath in this southernmost community, smuggling rum and storing it in his secret cellar - one of the few basements in Key West! The Inn's tropical decor features hand-crafted beds and tables made from original 1876 Dade County pine, reflecting a respectful nod to its most illustrious history. You are right on Duval Street, renowned for its proliferation of whimsical art galleries, stellar restaurants and relaxing bars. Nestled in the heart of Old Town, you are only a couple blocks from the beach and the Southernmost Point.br***All guests must be 21 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.brbrDETAILS AND AMENITIES...brOn the first floor of the Speakeasy Inn resides the Rum Bar, which boasts an impressive selection of delicious rums from all over the globe. Join us for our rum tastings of both vintage and popular rums. Each guest room offers outdoor seating for its occupants. Amenities in the rooms include flat screen TVs, individually operated ACs, coffee makers, refrigerators, microwaves, and all rooms have private bathrooms with showers.brbrSLEEPING ARRANGEMENTS...brThe After Hours room is located upstairs and offers a king bed. Enjoy a stocked kitchenette, a shower bathroom and a hanging closet for your convenience. brbrOUTDOOR LIVING...brTake in the island air and sip on your frosted cocktail on the upstairs wraparound porch that overlooks Duval street, a favorite people-watching spot. It has been restored to perfection for the pleasure of our guests.brbrPARKING...brParking is limited and not guaranteed, offered on a first come first serve basis at an additional fee of $15 per night. There are also some free as well as metered on street parking spaces on the surrounding streets. Most guests walk or bike ride to all of the nearby attractions once they secure a parking space.brbrPETS...brThis is not a pet-friendly inn.brbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrJOIN THE ADVENTURE...

AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

Key West, Florida, United States

Bed

Bath

Sleeps

$277.98

PICTURESQUE LANDMARK GUESTHOUSE WITH CELEBRATED RUM BAR...brSteeped in the rich 19th century lore of treasure hunts, romantic rum-running adventures, daring bootleggers, and notorious moonshiners and racketeers, the Quiet Pour room withi the Speakeasy Inn is nestled in true Key West magic. This unique conch-style adult-only retreat is brimming with authentic stories of derring-do during Prohibition days. The inn was the home of Raul Vasquez, a cigar selector at the local Gato cigar factory, whose true passion was rum running between Key West and Cuba. He cut a colorful swath in this southernmost community, smuggling rum and storing it in his secret cellar - one of the few basements in Key West! The Inn's tropical decor features hand-crafted beds and tables made from original 1876 Dade County pine, reflecting a respectful nod to its most illustrious history. You are right on Duval Street, renowned for its proliferation of whimsical art galleries, stellar restaurants and relaxing bars. Nestled in the heart of Old Town, you are only a couple blocks from the beach and the Southernmost Point.br***All guests must be 21 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.brbrDETAILS AND AMENITIES...brOn the first floor of the Speakeasy Inn resides the Rum Bar, which boasts an impressive selection of delicious rums from all over the globe. Join us for our rum tastings of both vintage and popular rums. Each guest room offers outdoor seating for its occupants. Amenities in the rooms include flat screen TVs, individually operated ACs, coffee makers, refrigerators, microwaves, and all rooms have PRIVATE bathrooms with showers.brbrSLEEPING ARRANGEMENTS...brThe Quiet Pour room is located upstairs and offers a king bed. Enjoy a stocked kitchenette and a shower bathroom that includes a shower and soaking tub for your enjoyment. The room also offers a convenient hanging closet.brbrOUTDOOR LIVING...brTake in the island air and sip on your frosted cocktail just outside of your room, with cushioned seating for your enjoyment. Upstairs features our wraparound porch overlooking Duval Street, a favorite people-watching spot! It has been restored to perfection for the pleasure of our guests. brbrPARKING...brParking is limited and not guaranteed, offered on a first come first serve basis at an additional fee of $15 per night. There are also some free as well as metered on street parking spaces on the surrounding streets. Most guests walk or bike ride to all of the nearby attractions once they secure a parking space.brbrPETS...brThis is not a pet-friendly inn.brbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrJOIN THE ADVENTURE...

QUIET POUR ~ On Duval St, Adult Only, Adjoining Rum Bar and Near Beach!

Key West, Florida, United States

Bed

Bath

Sleeps

$277.98

PICTURESQUE LANDMARK GUESTHOUSE WITH CELEBRATED RUM BAR...brSteeped in the rich 19th century lore of treasure hunts, romantic rum-running adventures, daring bootleggers, and notorious moonshiners and racketeers, the Bootlegger Bay room within the Speakeasy Inn is nestled in true Key West magic. This unique conch-style adult-only retreat is brimming with authentic stories of derring-do during Prohibition days. The inn was the home of Raul Vasquez, a cigar selector at the local Gato cigar factory, whose true passion was rum running between Key West and Cuba. He cut a colorful swath in this southernmost community, smuggling rum and storing it in his secret cellar - one of the few basements in Key West! The Inn's tropical decor features hand-crafted beds and tables made from original 1876 Dade County pine, reflecting a respectful nod to its most illustrious history. You are right on Duval Street, renowned for its proliferation of whimsical art galleries, stellar restaurants and relaxing bars. Nestled in the heart of Old Town, you are only a couple blocks from the beach and the Southernmost Point.br***All guests must be 21 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.brbrDETAILS AND AMENITIES...brOn the first floor of the Speakeasy Inn resides the Rum Bar, which boasts an impressive selection of delicious rums from all over the globe. Join us for our rum tastings of both vintage and popular rums. Each guest room offers outdoor seating for its occupants. Amenities in the rooms include flat screen TVs, individually operated ACs, coffee makers, refrigerators, microwaves, and all rooms have private bathrooms with showers.brbrSLEEPING ARRANGEMENTS...brThe Bootlegger Bay room is located downstairs and offers a queen bed. Enjoy a stocked kitchenette, a shower bathroom and a clothing hanging bar for your convenience. brbrOUTDOOR LIVING...brTake in the island air and sip on your frosted cocktail just outside of your room, with cushioned seating for your enjoyment. Upstairs features our wraparound porch overlooking Duval Street, a favorite people-watching spot! It has been restored to perfection for the pleasure of our guests. brbrPARKING...brParking is limited and not guaranteed, offered on a first come first serve basis at an additional fee of $15 per night. There are also some free as well as metered on street parking spaces on the surrounding streets. Most guests walk or bike ride to all of the nearby attractions once they secure a parking space.brbrPETS...brThis is not a pet-friendly inn.brbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrJOIN THE ADVENTURE...

BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

Key West, Florida, United States

Bed

Bath

Sleeps

$277.98

PICTURESQUE LANDMARK GUESTHOUSE WITH CELEBRATED RUM BAR...brSteeped in the rich 19th century lore of treasure hunts, romantic rum-running adventures, daring bootleggers, and notorious moonshiners and racketeers, the Smuggler's Cove room within the Speakeasy Inn is nestled in true Key West magic. This unique conch-style adult-only retreat is brimming with authentic stories of derring-do during Prohibition days. The inn was the home of Raul Vasquez, a cigar selector at the local Gato cigar factory, whose true passion was rum running between Key West and Cuba. He cut a colorful swath in this southernmost community, smuggling rum and storing it in his secret cellar - one of the few basements in Key West! You are right on Duval Street, renowned for its proliferation of whimsical art galleries, stellar restaurants and relaxing bars. Nestled in the heart of Old Town, you are only a couple blocks from the beach and the Southernmost Point.br***All guests must be 21 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.brbrDETAILS AND AMENITIES...brOn the first floor of the Speakeasy Inn resides the Rum Bar, which boasts an impressive selection of delicious rums from all over the globe. Join us for our rum tastings of both vintage and popular rums. Each guest room offers outdoor seating for its occupants. Amenities in the rooms include flat screen TVs, individually operated ACs, coffee makers, refrigerators, microwaves, and all rooms have private bathrooms with showers.brbrSLEEPING ARRANGEMENTS...brThe Smuggler's Cove room is located downstairs and offers two queen beds and is also our ADA compliant room for our guests who require special consideration (roll in shower and grab bars). Enjoy a stocked kitchenette with a large sink, an ample shower bathroom and a hanging closet for your convenience.brbrOUTDOOR LIVING...brTake in the island air and sip on your frosted cocktail just outside of your room, with a round table and 4 cushioned chairs. Upstairs features our wraparound porch overlooking Duval Street, a favorite people-watching spot! It has been restored to perfection for the pleasure of our guests. brbrPARKING...brParking is limited and not guaranteed, offered on a first come first serve basis at an additional fee of $15 per night. There are also some free as well as metered on street parking spaces on the surrounding streets. Most guests walk or bike ride to all of the nearby attractions once they secure a parking space.brbrPETS...brThis is not a pet-friendly inn.brbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrJOIN THE ADVENTURE...

SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!

Key West, Florida, United States

Bed

Bath

Sleeps

$810.78