Vacation Rentals By Owner In Key West, FL

Fabulous waterfront two level condo in the beautiful Historic Mills Place Hospital Building in the Truman Annex awaits! This spacious palace enjoys tall ceilings on the main level with sweeping french doors leading out to the refreshing covered deck and spectacular views of the water, sunsets and the new Truman Waterfront Park! The entrance level includes the kitchen, dining and living rooms plus a full bathroom. Recently re-decorated, this terrific space is light-filled and yourself indoors in the spacious area or lounge in the hammock on the d eck... | On the lower level there are two wonderful bedrooms with baths ensuite and walk out private decks! | This condominium association is very private with only 19 units, a huge pool area with tables and chaises and assigned street parking. | The Truman Annex is a convenient location close to Duval Street, nightlife, dining, shopping, Ft. Zachary Taylor Park and Beach and the Truman Waterfront! | This property can be rented by the month - contact us for more details... brbrPlease note: This property is monthly rental

Gypsy's Palace at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$235.11

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrThis unit is a 30 night minimum.brbrFEATURES:brBedrooms: 4 (1 king, 2 queens, 2 twins)brBathrooms: 3brLocation: Near Smathers & Higgs BeachesbrSquare Feet: 1898brParking: There is gravel parking outside the front yard gate.brAmenities: Wifi, TVs, in-unit laundry, private pool, fenced yard, mother-in-law cottage with a kitchen, living area, and bathroom onlybrbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.brbrPool heating is $100 per week and must be requested prior to check in

Tranquil Retreat by the Beach-4 bedroom 3 bath home w/private pool, parking

Key West, Florida, United States

Bed

Bath

Sleeps

$280.13

Welcome aboard your Key West getaway!brThis charming one-bedroom boat is anchored in a peaceful, protected channel with breathtaking views and unforgettable sunrises and sunsets. Inside, you’ll find a cozy living area featuring a plush queen-sized V-berth, plus a couch and dining nook that each convert into twin beds—perfect for extra guests. Stay cool and comfortable with refreshing AC after a day in the sun.brbrWhen adventure calls, drop the ladder and dive into the crystal-clear shallow waters, or set out on a kayak for a beautiful paddle. A complimentary water taxi is also available daily for easy trips in and out.brbrCome relax, soak up the island vibes, and make your stay in paradise unforgettable!

House Boat

Super-Cozy boat in Key West!

Key West, Florida, United States

Bed

Bath

Sleeps

$479.23

This 4 story Townhouse is in Old Town Villas. A Caribbean inspired community in the heart of Key West. Built in 2017. This upscale, luxurious, townhouse is steps away from Sloppy Joe's and the Historic Seaport District. Lagerhead beach is a short walk away. All bedroom have attached baths. There is a private elevator, 2 car garage, an entertainment area on the 4th floor with a sofa bed, large TV, wet bar, and half bath. The top floor outdoor patio provides great views of Key West and yet has the privacy for personal sunbathing.

Unlock your Paradise Adventure - Between Sloppy Joe's and the Harbor

Key West, Florida, United States

Bed

Bath

Sleeps

$431.75

Experience the ultimate Key West lifestyle in this serene sanctuary overlooking the 8th hole of the Key West Golf Club. Whether you’re here for a month of remote work or a long-term tropical retreat, this elegant vacation rental townhome offers the perfect balance of Old Town energy and resort-style relaxation. Spend mornings sipping coffee on the porch, watching the golfers play, and afternoons lounging by one of the sparkling pools. Then, end evenings with a BBQ in a secluded, fenced yard.brbr-- THE PROPERTY --brbrModern Furnishings | Lush Views | Resort Perks | Gated Community Security brbrSLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 queen bedbrbrCOMMUNITY AMENITIES (access card provided): 2 outdoors pools, fitness center, golf course (addt’l fee, paid on-site)brOUTDOOR LIVING: Private deck, fenced patio, dining area, BBQ grill, beach chairs, furnished porchbrINDOOR LIVING: New appliances, 4-person dining table, ceiling fan, 3 Smart TVs w/ Amazon Firesticks brWELL-EQUIPPED KITCHEN: Cooking basics, microwave, refrigerator, stove/oven, dishwasher, Keurig coffee makerbrGENERAL: Free WiFi, linens/towels, central A/C, ceiling fans, in-unit washer/dryer, starter complimentary toiletriesbrFAQ: 3 exterior security cameras (facing out), quiet hours (10:00 PM-8:00 AM)brACCESSIBILITY: Steps required to enter, all bedrooms on 2nd floor, 2-story homebrPARKING: Driveway (1 vehicle, parking pass required)brbr-- THE LOCATION --brbrPRIME LOCATION: Nestled in a lush, gated community just a short drive or bike ride from the neon lights of Duval Street and the white sands of Smathers BeachbrAREA ATTRACTIONS: Key West Golf Club (on-site), The Hemingway Home and Museum (5 miles), Key West Lighthouse (5 miles), The Key West Butterfly and Nature Conservatory (5 miles), Key West Aquarium (6 miles), Mallory Square (6 miles)brEXPLORE THE WATERS: Lazy Dog Adventures (1 mile), Dream Catcher Charters (1 mile), Dolphin Safari Charters (2 miles), Key West Express (5 miles)brSEA & SAND: Smathers Beach (4 miles), Rest Beach (2 miles), Higgs Memorial Beach Park (4 miles), Fort Zachary Taylor Beach Area (6 miles)brAIRPORT: Key West International Airport ( 2 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking. This is a 100% smoke-free property, including the patio and deckbr- No pets allowed. We love animals, but our home is strictly pet-freebr- No events, parties, large gatherings, or unauthorized overnight guests.br- The primary booker must be at least 25 years oldbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: Please observe quiet hours from 10:00 PM to 8:00 AM and respect our peaceful Key West Golf Club neighborsbr- NOTE: This is a classic 2-story townhome. It requires steps to enter, and all bedrooms are located on the 2nd floorbr- NOTE: A temporary parking pass is mandatory for all guests. Please reach out to the Guest Contact at least 48 hours prior to arrival, so your pass is waiting for you at the security guard shackbr- NOTE: The world-class Key West Golf Club is open to the public for a separate fee, which can be paid directly at the Pro Shopbr- NOTE: Your safety matters. This property features 3 exterior security cameras: camera 1 is located on the front porch facing the front side of the house, camera 2 is on the back porch facing the back side of the house, and camera 3 is at the doorbell facing the front outdoor entry. The cameras do not look into interior spaces. The cameras record video and sound when activated by motion. They will record when they first sense motion and 30 seconds after the last motion is detected. The cameras will be off during your stay

Golf Course Oasis w/ Private Yard, 5 Mi to Duval!

Key West, Florida, United States

Bed

Bath

Sleeps

$367.08

Welcome to The Hideout, where luxury meets location. brbrLook no further than The Hideout for upscale luxury and single-story living. Tucked away in the beautiful, historic Casa Marina neighborhood, this fully renovated 3 bedroom, 3 bath home includes a spacious outdoor living area & pool with two dwellings connected via a covered lanai space. Perfectly suited to host guests who crave privacy, upgraded living and a location just steps from some of Key West’s most popular attractions, beaches, restaurants and Duval Street. brbrThe main home boasts two bedrooms, two bathrooms, a bright living area and spectacular kitchen. The lofty ceilings, natural lighting, pool view and open concept make this space perfect for entertaining. Upgraded finishes include quartz countertops, white shaker cabinets, shiplap walls, hardwood floors, Subzero refrigerator, Wolf gas range and a large island with seating. The spacious primary ensuite bedroom features high ceilings, plenty of storage and direct access to the pool. Its ensuite bath with dual sinks, water closet and large walk-in shower is finished in shades of white. The comfortable guest bedroom enjoys plenty sunshine and a large closet. Tasteful, tropically inspired local artwork is sprinkled throughout the home to add to the fresh, island aesthetic. brbrThe beautiful, heated pool and magnificent lanai connect the main home to the second dwelling. The sizeable pool suite features a bedroom with vaulted ceiling and cross beams, living area, bathroom with walk-in shower and private entrance. The living room area includes a kitchenette with cabinets, microwave and KitchenAid drawer style refrigerator, along with queen-size sleeper sofa. Both the living room and bedroom have access via sliding glass doors to the outdoor entertainment area.brbrAdditional features: brbr• Impact Windowsbr• Impact Doorsbr• Two off-street parking spaces br• Heated Poolbr• Outdoor Showerbr• Outdoor smart TVbr• High Speed Wi-Fi br• Smart TV's throughout

The Hideout! Where Luxury Meets Location. Fully Renovated, with Pool.

Key West, Florida, United States

3

Bed

3

Bath

8

Sleeps

$267.76

Experience luxury and space in this studio suite at Blue Flamingo Resort, offering uninterrupted ocean vistas. The suite features a king-size bed, a sitting area, and modern amenities for a comfortable stay.brbrThis listing is for a room within a hotel.brbr✦ Your room is 480 sq. ft, equipped with complimentary toiletries, high definition TV, available with Standard cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Outdoor pool available all year, opened from 7:00AM to 11:00PM.brbr✦ Paid parking lot – 1 space(s), available for $15 per day.brbr✦ Shuttle service operates according to a schedule.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $56.25 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). Max weight limit of up to 50 lbs per petbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.

Hotel

Live the Island Life | Pool, Lawn Games, Cabanas & Karaoke Nights

Key West, Florida, United States

Bed

Bath

Sleeps

$4253.21

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrCoordinating the entire gang for a dream Key West wedding, reunion, or simply a vacation of a lifetime is hard enough... let Last Key Realty make the accommodations easy for you. ALL TOGETHER NOW is an entire block of private homes just steps from Duval Street, all yours to enjoy and with everything needed for a large group getaway: a total of thirteen bedrooms, three open living areas, three spacious outdoor areas each with a private saltwater pool, three fully equipped kitchens, and a location that allows for easy accessibility to all the favorites of Old Town. So, round up your entire crew and head south for what is sure to be an epic vacation 'all together now' in America's Paradise.brbrTHE LOCATION...brbrDuPont Lane is a quiet nondescript lane that you wouldn't be able to find without directions, and this compound of homes is tucked away at the very end. If you decide to pull yourself away from this relaxing retreat, you'll realize that Key West's best restaurants, live entertainment and attractions are all within a block or two of your front door. While you won't need a car to get around from this fabulous location, there are three designated off-street parking spaces included.brbrTHE LIVING AREAS...brbrAll three homes have large living areas with plenty of space and seating for everyone to unwind after a day on Duval Street or out on the water. Each living room boasts a large flat screen SMART TV that can be enjoyed from comfortable furniture options, including plush sleeper sofas in each. The kitchens are fully equipped with top of the line appliances and every tool needed to prepare a meal from home. Each home also offers indoor and outdoor dining.brbrTHE PRIVATE SALTWATER POOLS...brbrAll three pool areas are connected via open gates that allow your crew to pass through and mingle amongst the homes. Fully fenced for privacy, these saltwater pools can be heated in the cooler months to your liking and get equal amounts of sunshine and shade throughout the day. Comfortable chaise lounges and patio furniture on the pool's decks offer the perfect outdoor lounging options. 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 ACCOMMODATIONS...brbrThis compound will keep your whole group satisfied, with ample space for everyone to escape to their own accommodations.brbrHouse #1 has 5 bedrooms:brbr+ 2 Twins or 1 King - First Floorbrbr+ 2 Twins or 1 King - First Floorbrbr+ 2 Twins or 1 King - Second Floorbrbr+ Queen - Second Floorbrbr+ King - Second FloorbrbrHouse #2 has 4 bedrooms:brbr+ 2 Twins or 1 King - First Floorbrbr+ 2 Twins or 1 King - Second Floorbrbr+ 2 Twins OR 1 King - Second Floorbrbr+ King - Second FloorbrbrHouse #3 has 4 bedrooms:brbr+ 2 Twins or 1 King - First Floorbrbr+ 2 Twins or 1 King - First Floorbrbr+ 2 Twins OR 1 King - Second Floorbrbr+ King - Second FloorbrbrFor rooms with two twin beds that can convert to a King, we ask that you communicate to us at least one week prior to arrival with these requests.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr+ Washer & Dryerbr+ Central Heat & A/C br+ Ceiling Fans br+ Flat Screen HD TVs in Living Room & All Bedrooms + + Fully-Equipped Kitchen br+ Basic stock of spices br+ Starter supply of paper products br+ Starter set of cleaning products br+ Linens and Towels provided br+ Wireless high-speed Internet access and full cable is included br+ Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr+ 3 Fenced & Lushly Landscaped Backyards br+ 3 Private Saltwater Pools with available Pool Heat br+ Outdoor Shower br+ 3 Propane BBQ Grills br+ 3 Queen Sleeper Sofas br+ 3 Off-Street Parking Spaces (with restrictions - NO LARGE VEHICLES)brbrOther notes:brbr+ In person welcome br+ Interim housekeeping provided upon request br+ Max of 2 Pets Allowed with Additional Fee of $200 per pet br+ This property will accommodate up to 26 adults in beds, 32 adults total.br+ 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.

**ALL TOGETHER NOW @ OLD TOWN** Three Homes & Pools + LAST KEY SERVICES…

Key West, Florida, United States

Bed

Bath

Sleeps

$400.28

Island Oasis @ the Truman Annex is beautifully renovated town home in the historic Foundry. | The living area is the entire first floor and has an open plan, with 11-foot ceilings and double French doors that provide plenty of natural light to enter. Enjoy the natural light of being an end unit with large bay 's a large flat screen TV and multiple comfortable seating options. There's also a convenient powder room located on the first floor. The kitchen has top-of-the-line stainless steel appliances, with granite counter tops and all the tools needed to prepare a meal from home and also indoor dining seats six comfortably. | Master Suite: Located on the Second Floor with a King bed, a large flat screen TV, a private balcony, a large closet, and an en-suite bathroom with a walk-in shower. | Second Bedroom: Located on the Third Floor with Two Twins OR One King bed, a flat screen TV, a closet, and an en-suite bathroom with a walk-in shower. | Washer & Dryer Central Heat and A/C Ceiling Fans Flat Screen TVs in Living Room & All Bedrooms Fully Equipped Kitchen Starter supply of paper products Starter set of cleaning products Linens and Towels provided Wireless high-speed Internet access & full cable included Assigned off street parking for one car and access to a refreshing community pool... brbrPlease note: This property has a 28 night minimum stay

Island Oasis at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$287.42

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrThis property is a 30 night minimum.brbrFEATURES:brBedrooms: 4 (1 king, 1 queen, 2 twins)brBathrooms: 3brLocation: Mid Town on GulfviewbrSquare Feet: 1640brParking: One reserved, covered parking space & first-come first served designated guest parkingbrAmenities: Wifi, TVs, in-unit laundry, private pool, Gulf of Mexico viewsbrbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

4 bed 2.5 bath home w/ ocean views, private pool oasis on Gulfview

Key West, Florida, United States

4

Bed

2

Bath

6

Sleeps

$503.09

A FUSION OF LUXURY AND HISTORY…brThis stunning Victorian estate has been meticulously renovated, offering the elegant allure of cosmopolitan tropical style with a nostalgic nod to the charming refinement of the early 19th century. Situated in the Historic Seaport neighborhood of Old Town, the graceful exterior is permeated with respect for its architectural history as your eyes take in the delightful Victorian wooden facade. Once you step inside, however, you are greeted with all the modern amenities and opulence expected in an upscale contemporary residence. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brA serene and elegant ambiance infuses the interior space as you step inside. You are immediately greeted by an entrance hall that features an elegant wooden staircase from the 1930s, which leads to 4 upstairs guest room suites. brThe great room offers a wide open layout with a large sitting area (Youtube TV live streaming available), infused with an abundance of sunlight flooding the welcoming gathering area. The stylish dining space and adjacent state-of-the-art chef's kitchen invite hours of happy conversation over tropical culinary feasts with loved ones. Just off the kitchen is a modern half-bathroom and a laundry room that offers two sets of washers and dryers. There is a Ring doorbell located on the front door for security purposes. brbrSLEEPING ARRANGEMENTS…brAll 4 guest suites reside on the 2nd floor with their own shower bathrooms. Each is uniquely decorated and furnished with high-quality furniture. There are two queen beds and two king beds for guests to enjoy. The living room has a sofa sleeper with a nearby powder room. brbrOUTDOOR LIVING…brExpansive gingerbread porches span the entire front of the house, inviting you to enjoy the lush surrounding views. The backyard evokes a sense of cozy tropical privacy, boasting a beautifully crafted lap swimming pool which comes heated in the cooler months. Dine al fresco after grilling your fresh catch on the luxurious sun deck with soothing cascading waterfall sounds from within the pool.brbrPARKING...brThis homes comes with 1 off street parking spot. brbrPETS...brThis is NOT a pet friendly home. 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 only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. 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).brbrENDLESS CARIBBEAN CHARM…

THE BLUE PINEAPPLE ~ Old Town 4 BR/4.4 Bath Home w/ Private Pool & Parking!

Key West, Florida, United States

Bed

Bath

Sleeps

$329.06

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrThis property is a 30 night minimum.br brFEATURES:brBedrooms: 2 (1 king, 2 twins)brBathrooms: 2 brLocation: Salt Ponds CondosbrSquare Feet: 772brParking: There is a 2 car MAXIMUM policy.brAmenities: Wifi, TVs, in-unit laundry, shared pool (not-heated), tennis courts, close to the beachesbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.

Seaside Serenity-2BD 2BA condo w/ pool, parking, tennis courts, near beaches

Key West, Florida, United States

Bed

Bath

Sleeps

$785.2

Your Treetop Condo awaits. The welcoming garden atmosphere of this adorable tropical property is perfect for a tranquil getaway. We are located in the heart of historic Old Town. Relax and refresh with ocean breezes on your treetop balcony. For your security and peaceful enjoyment, this property is surrounded by a bamboo privacy fence. This desirable property is highly recommended and reasonably priced. No resort or parking fees.brbrLocationbrOur Treehouse Condo is situated in a prime island location on the southern side of Key West in the prestigious residential Casa Marina neighborhood surrounded by majestic and luxurious homes with beautiful tropical gardens, perfect for pleasant walks any time of day. We are only a 3 minute stroll to Higgs Beach, Salute's Restaurant and West Martelo Tower, a Civil War Fort which is now home to the Key West Garden Club and walkable tropical gardens. We are a 13 minute walk to the Southernmost Point and a 12 minute walk to the Butterfly House. We are also close to several excellent restaurants and only a 9 minute drive from the airport.brbrOther Nearby Restaurants and AttractionsbrNearby access to the free Duval Loop Bus, provides access to the Historic Seaport, aquarium, Sloppy Joes, Truman Waterfront Park, Southernmost Point, Butterfly House and Nature Conservatory, Mel Fisher and Sails to Rails museums, art galleries and other attractions. Walking minutes to several nearby restaurants include: Dorada's (2min), Ana's Cafe and Southernmost Grocery Store (8min), El Siboney Cuban (8min), Oasis Mediterranean (7min), White Street Pizza (7min) and famous Sandy's Cafe for authentic Cuban coffee and sandwiches (5min).brbrBeach, Pool and Outdoor LivingbrJust steps from the beach, your condo is surrounded by lush gardens and palm trees. You can lounge on your treehouse style private balcony, 10 feet above the garden floor, among the treetops overlooking the common area complete with hammock swings and a dining table for six guests under our mango, a shared grilling area and a putting green. During your stay, relax and refresh in our intimate Cocktail Spa Style Pool, which is veiled by a wall of flowering vines and located immediately at the base of your staircase or escape to Higgs Beach just down the street. Higgs Beach is also ideal for romantic evening walks for stargazers.brbrFurnishingsbrOur decor reflects a true Key West vibe. The dining table in the open concept livingroom seats four, a day bed couch and the balcony includes two comfortable lounge chairs for relaxing in the treetops under the stars. The kitchen is complete with a two burner cook top, microwave, drip coffee maker, toaster, Cuisinart Griddler Grill/Panini Press, silverware, pots/pans, sink, refrigerator and a dishwasher. The full bathroom is complete with a shower and shelves for your toiletries. Bodywash, shampoo, conditioner, extra toilet paper, large bath sheet towels and a hair dryer are provided. Our bedrooms are equipped with cozy Tommy Bahama comforters. There are 3 televisions complete with cable channels and free WiFi for your entertainment and convenience.brbrSleeping ArrangementsbrYour condo sleeps up to six guests and includes 4 beds, a primary California King bedroom, a queen bedroom and two twin beds in your livingroom, perfectly arranged for families or couples with friends. The balcony lounge chairs are perfect for an outdoor nap any time of day or night.brbrDetails and AmenitiesbrYour second-floor Treetop Condo is 514 sqft. A shared Cocktail Spa Style Pool, bike rentals, washer/dryer service are all available on our property. We are family and pet friendly. Wrapped breakfast bars, nuts, fruit snacks, gourmet meatsticks, cheese and crackers, mini muffins, coffee/teas are provided in the condo along with fresh Florida oranges and grapefruits in our common area. Higgs Beach city park is nearby, complete with tennis, pickleball, sand volleyball, professional bocce courts, two playgrounds for children, White St. fishing and observation piers, an oceanside restaurant and a dog park. The White Street Pier is a quarter mile over the ocean with spectacular views of sunrise and sunset and excellent fishing.brbrConcierge ServicesbrEnjoy our concierge service to assist you before or during your stay with planning activities with the very best of Key West. From bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset sails, sandbar excursions, scuba diving, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. We can also arrange licensed massage therapy for you and your party, in our gardens or in your suite and have your condo stocked with groceries, adult beverages and all the necessities in advance of your arrival.brbrParkingbrFree off-street parking in front of and around the condo.brbrYou Need To KnowbrOur property is equipped with fire extinguishers and smoke detectors.brOnsite parties, weddings and other events can be scheduled with prior approval by property owner.brGovernment issued photo ID and a credit or debit card or cash deposit may be required at check-in for incidential chargesbrExtra person charges may apply per the property's policies.brReport any damages prior to check out.brKey West Quiet Time may apply after 10pm on weekdays and 11pm on weekends through 8am in the morning. Thank you for supporting our efforts to be a good neighbor. Please note that your condo is located in a noise sensitive area. When you return from the parties, celebrations and live music on Duval street you will have a quiet, tranquil and restful sleep.brbrMake marvelous memories that will last for a lifetime while staying at our condo in paradise.

Treehouse Condo 2nd Floor Balcony sleeps 6 free parking

Key West, Florida, United States

Bed

Bath

Sleeps

$581.06

This beautiful houseboat is the best way to stay in Key West. Recently Featured in Old Dominion‘s music video “I was on a boat that day”, it has a sleep number bed, hot water and full-size fridge. The Boat is nestled in a very calm bay protected from waves. The beautiful sites surround you as you wake up on the water and the sunsets and stars give you great experiences as you relax on the top deck in the evening. Included in the rental is use of a 13 foot motor boat to get to and from the houseboat. brbrYou have 360° ocean views sunsets sunrises stargazing. You can jump right off the boat into the golf of Mexico. Rental of the houseboat includes use of a 13 foot skiff to get yourself to and from land as well as plenty of parking. brbrBoating experience is required as you will be out on the water and get yourself to and from the boat. It is important that you are aware that this is a houseboat. Your electric is coming to the form of solar or generator power. There is a water heater and For size shower. There’s also a fridge and microwave. The bed is a sleep number which is adjustable on either side of the bed. There is AC in the bedroom. However the rest of the boat is called with the Ocean breeze in box fans. The top deck is beautiful place to watch sunsets or gaze at the stars. An extra cleaning fee will be charged if dishes are left in the sink or the house is left in very unclean conditions.brbrbrThis is the best place to stay in The Fl Keys great location beautiful views and an amazing experience, hosted by a six generation local. This is on a houseboat so basic knowledge of the water is recommended. You will have to get yourself to and from the houseboat on a 13 foot skiff. I’ll meet you to check you in and show you the way out to the boat as well as how everything on the boat works like the generator and solar power. The boat does have a full-size fridge, microwave oven, stove top, hot water full size shower, sleep number queen size bed, top deck for sunsets and star gazing , everything you’ll need to be more that comfortable. br brI am a six generation local to Key West. And also a licensed captain. I will be available during your stay to take you out to secluded islands in sandbars for snorkeling dolphin watching light tackle fishing or to just relax and enjoy the beautiful scenery. If you are interested in booking one of these charters during your stay I will be available weather permittingbrbr Plenty of free safe parking is available at the check-in location where the dock is that you will use to get to and from the houseboat. That being said there is not a captain on this boat and I will not be there to assist you with everything so it is important that you can start a generator and the motor on the boat to get you to and from the house boat. They are in perfect working condition however this can be an issue for some people.brbr This is a houseboat in the Caribbean. It can get hot. you will be using a generator and solar for power. If you check into this house boat and then realize that it is not a hotel room you will not be refunded. This is similar to camping however on a boat that has the amenities however you will have to use a generator and solar for any electrical needs.brbr This boat is not for complainers nor land lovers. This is a boat I repeat this is a boat.brbrCheck inbrbrI will meet you at the check-in location at a time we scheduled prior to your arrival to show you where to park in the Skiff you will use to get to and from the houseboat. You’ll then follow me out to the houseboat so I can show you have everything on the houseboat works. I’m available if you need assistance during your stay. But everything is very simple to use as long as you do have basic knowledge and our somewhat familiar with the water.brbrGuest access brbrThe entire boat is yours and your nearest neighbors are far away in the bay. So you’ll feel very private and secluded as you enjoy this unique experience. Access to and from the boat is made to use of a 13 foot kayak provided with the use of the rental. As well as one ride in when you check in and out. Water taxi is available however it is a very short kayak trip.brbrOther things to notebrbrThere is a full-size fridge. There is AC in the bed room however the rest of the boat is cooled with the ocean breeze. Most people don’t use the AC as the breeze and a fan make it very comfortable. However this is a boat in the Caribbean so on some days it can be hot. The toilet is a little different than yours at home main difference being that you won’t put toilet paper down the head it will go into a trashcan. An extra cleaning fee will be charged if dishes are left in the sink or the house is left in very unclean conditions. If you plan to do a lot of barhopping or partying on Duval this may not be the place for you either although you can get to and from land very easily and quickly this boat is special because it offers the other side of Key West like peaceful calm ocean views sunsets snorkeling.

House Boat

Happy’s Houseboat Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$1319.33

Breathtaking waterfront view from this 4 bedroom, 4.5 bath condominium in Harbour Place in the Truman Annex is ready to receive you! Enjoy a sprawling floorplan with endless views of the Atlantic Ocean and the Gulf of Mexico! This one of a kind gem has recently been COMPLETELY renovated. The four bedrooms all feature luxurious king sized beds and bedding with gorgeous ensuite bathrooms. The full kitchen enjoys a eight seated bar and island with all of the modern conveniences of a chefs kitchen. Relaxation is the cornerstone of this beauty which includes several lounging areas and a spectacular waterfront dining room! There are four decks, two facing the ocean and two featuring a private place to make those reservations for dinner, fishing and beyond! While enjoying your stay, there is a refreshing waterfront pool complex and immediate access to downtown, Duval Street. Come to unwind, and linger for as long as you sunsets will keep you coming back for more!brPlease note: This property has a 28 night minimum stay

Sublime Sunsets at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$594.88

City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to Poseidon's Paradise, your ultimate luxurious waterfront escape in Key West! brbr brbrNestled on the picturesque Riviera Canal, this retreat offers seamless access to the Gulf of Mexico and the Atlantic Ocean. As you step through the gate, you'll discover a haven designed for larger extended families or groups, perfectly suited for embracing the quintessential Key West lifestyle. Recently updated with a modern coastal chic aesthetic, the interior features sleek granite countertops and stainless steel appliances in the fully equipped gourmet kitchen. This property boasts the latest in technology, with fully automated landscape irrigation and lighting. You'll find ample parking for your convenience, ensuring an stress-free arrival and departure. The true jewel of Poseidon's Paradise is the heated concrete pool, which takes center stage in the backyard, overlooking the serene canal. Keep your eyes peeled for the frequent visits from friendly manatee families, who often grace the waters with their presence. Across the canal, a lush green mangrove provides a natural privacy screen, allowing you to relax in your own tropical oasis. For a closer encounter with Key West's incredible wildlife, embark on a paddleboarding adventure along the canal and through the enchanting mangroves. At Poseidon's Paradise, you'll discover the perfect blend of luxury, nature, and modern comfort, all coming together to create an unforgettable Key West experience. brbr brbrSLEEPS MAXIMUM OF 10 GUESTS: brbr brbrBedroom 1 (Main House, 2nd Floor): King Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV) brbr brbrBedroom 2 (Main House, 1st Floor): Queen Bed, Smart TV (no cable/satellite TV) brbr brbrBedroom 3 (Guest House,1st Floor): King Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV) brbr brbrBedroom 4 (Guest House, 2nd Floor): King Bed, Smart TV (no cable/satellite TV) brbr brbrBedroom 5 (Guest House, 2nd Floor): King Bed, Smart TV (no cable/satellite TV) brbr brbrLiving Room: Loveseat with Pull Out Queen Bed, Two Sofas, Smart TV (no cable/satellite TV) brbr brbrKitchen: Nicely equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- 85' Private Dockage (bridge clearance ~12' at high tide) brbr brbr- Private Heated Saltwater Pool (heated to ~85 degrees Nov-Apr, small separate dip pool is not a hot tub) brbr brbr- Gazebo with Outdoor Dining Set brbr brbr- Outdoor Seating brbr brbr- Propane BBQ Grill brbr brbr- Propane Fire Pit brbr brbr- Keurig, Toaster, Blender brbr brbr- Linen's and towels provided brbr brbr- 2.1 miles to Smathers Beach brbr brbr- 3.4 miles to Duval Street brbr brbr- 3.4 miles to Southernmost Point brbr brbr- 3.7 miles to Key West Historic Seaport brbr brbr- 4.2 miles to Mallory Square Sunset Pier brbr brbr- 4.4 miles to Fort Zachary Taylor State Park Beach brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. brbr brbrNo Pets: Pets are strictly prohibited. To help maintain a pet-free environment for all, we require every guest to confirm they are not bringing a pet/animal. It's free, and does not require creating an account. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrBoating & Dockage Advisory: Due to bridges and varying water depths, it is your responsibility to ensure that your boat can safely navigate local waters, access the canal, and fit the listed dockage before booking. While we are happy to provide general information based on our knowledge of the area, guests must exercise extreme caution when boating and ensure all activities comply with local regulations. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time. brbr brbrSecurity Cameras: For the safety and security of our guests and property, five exterior security cameras monitor the property. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.

Poseidon's Paradise: Luxury Waterfront Rental in Key West, Stunning Backyard Oasis and Private Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$361.08

**NEW LISTING** As soon as you arrive to this newly renovated, new town home you will be impressed at every turn. Privacy, a gorgeous backyard, and a one and only custom Key West pool design that will WOW you. Enjoy all of the five star amenities, including four complimentary beach cruiser bikes, with lights, baskets, and locks.brbrTHE LIVING AREAbrbrWith all brand new furniture, and 65 smart TV, you will have plenty room for entertaining. Poseidon's Paradise is loaded with high-end finishes, and elevated ceilings allowing for lots of natural light.brbrThe open living area leads you into the fully equipped chefs kitchen. With top of the line appliances, laminate countertops, a Keurig as well as a regular coffee maker, you will find all the pleasantries you have at home. Cook 5 star meals, grill your fresh catch on our new Webber grill, and entertain family/friends during your spectacular vacation.brbrTHE BACKYARD & POOLbrbrStepping outside through the set of French doors , you will be mesmerized by your very own private resort-like oasis, starting with the huge comfortable outdoor couch and sitting area. Relax and enjoy a movie or the big game on your new 65 outdoor smart TV. The custom pool is what sets Poseidon's Paradise apart from the rest. Whether you want to hang out along the long bench seating, relax in one of the two in water pool loungers, or swim laps for exercise in one of the largest residential pools in Key West, this pool offers it all. On the other side of you full outdoor bath, you will find an excellent place to enjoy outdoor dining from our six top dining table. Listen to the water coming from the waterfall and enjoy the custom LED lighting as you sit back and enjoy the vacation of your dreams.brbrACCOMMODATIONSbrbr- Bedroom One: Master King bed with luxury linens; 55 smart TV, en-suite bath with shower/tub, and vanity.br- Bedroom Two: Junior master - King bed with luxury linens, 55 smart TV, with French doors leading to backyard and pool areabr- Bedroom Three: Twin beds (can be converted into a King) and a 32 smart TVbr- Bedroom Four: Junior pool - Queen bed with luxury linens, 55 smart TV, with French doors leading to backyard and pool area.br****Poseidon's Paradise is all one level, and has up to 3 King beds!brbrADDITIONAL AMENITIES:brbr- Highest Wifi speed internet in Key Westbr- Washer and Dryerbr- Iron/ironing board and hand steamerbr- Central ACbr- Indoor and Outdoor ceiling fansbr- Linens and towels, including pool towelsbr- Weber propane BBQ grillbr- Private, fully fenced and tropical landscaped yardbr- Plenty of off street parkingbr- Pool heater (additional cost)

**Welcome To Poseidon's Paradise** Midtown Home & Incredible Pool *28 Nights Min

Key West, Florida, United States

Bed

Bath

Sleeps

$240.09

*Please note that this home is available for 28+ night stays only.*brbrPLEASE READ PRIOR TO BOOKING THIS PROPERTY:brThe Shipyard Pool will be closed beginning August 1, 2026, for the Pool Deck Replacement Project. The project is expected to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. During this time, no pool will be available to the guests. *The rates for the month of August have already been discounted to reflect the loss of the amenity.*brbrA Siesta Bay brings easy Key West living to one of the island’s most loved locations: Truman Annex. Bright, breezy, and surrounded by tropical palms, this two-bedroom condo is made for guests who want a relaxed retreat with the best of Old Town close enough to explore on foot or by bike.brbrInside, the home feels light and coastal, with soft blue tones, island-inspired details, and a comfortable living area that opens to the balcony. Start the morning with coffee outside, come back for a quiet afternoon break, or wind down with a drink while the palms sway around you. The updated kitchen is fully equipped for easy meals at home, and the dining area seats four for casual breakfasts, snacks, or dinner after a day out in town.brbrJust steps away, the shared community pool offers a refreshing place to cool off between adventures. Lounge in the sun, take a swim, or enjoy a slow afternoon in the shade before heading back out to experience Key West.brbrA Siesta Bay sleeps up to four guests across two bedrooms. The primary bedroom features a queen bed, while the second bedroom includes two twin beds, making the layout ideal for couples, small families, or friends traveling together. A full bathroom sits conveniently between the bedrooms, and in-home laundry adds extra ease for longer stays.brbrSet in Truman Annex, the location is one of the biggest highlights. You’ll be close to Duval Street, Mallory Square, Fort Zachary Taylor State Park, local restaurants, shops, nightlife, and some of Key West’s most iconic sights. Whether your plans involve beach days, sunset strolls, poolside afternoons, or exploring the island by bike, A Siesta Bay keeps you close to it all while giving you a peaceful place to come home to.brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrLocal Attractions: Key West Shipwreck Treasure Museum, Hemingway Home and Museum, Mel Fisher Maritime Museum, Harry S. Truman Little White House, Conch Tour Train, Dry Tortugas National Park, Lazy Dog Adventures, Dolphin encounters, Ghosts & Gravestones Tour, Old Town Trolley, Sloppy Joe’s Bar, Audubon House & Tropical Gardens, Florida Keys Eco-Discovery Center, Bike Tours, Seaplane adventures, Key West Aquarium, Sebago Day Tours, Private boat charters, Sportfishing, Rick’s Entertainment Complex, Duval Street (shop strips, shops, bar, and cafes), Mallory Square (waterfront plaza), Key West Garden Club, Sunset Pier, Grand, Cafe Key West, Island House, El Meson de Pepé, Cafe Sole.brbr*Home Truths:*br- This home has access to a shared pool and is part of a gated community.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that the twins at the property can not be converted into a king.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- All bookings 28 days or longer require a security deposit to be charged after booking.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.br- PLEASE READ PRIOR TO BOOKING THIS PROPERTY:brThe Shipyard Pool will be closed beginning August 1, 2026, for the Pool Deck Replacement Project. The project is expected to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. During this time, no pool will be available to the guests.brbrParking Details:br- One parking space per unit, no guest parking.br- No vehicle over 18’ long or 80” wide allowed.br- No large trucks, trailers, mobile homes, vans, campers or similar vehicles shall be parked in the Truman Annex.br- Motorcycles and scooters must be parked in the parking lot and not on sidewalks or porches.br- All vehicles parked within the community must either have a permanent parking sticker or a temporary parking pass (obtained at the Security Guardhouse).br- All others will be subject to ticketing and towing.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bed brBedroom 2 / Two twin bedsbrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. All bookings over 30 days require a security deposit.brbrWe report and prosecute all Credit Card Fraud.

Tropical Condo • Shared Pool + Near Duval St | Month-Long Stays | A Siesta Bay

Key West, Florida, United States

2

Bed

1

Bath

4

Sleeps

$148.66