Vacation Condo Rentals By Owner In Key West, FL

Life is best lived from the balcony of this tranquil oceanfront condo. Feel like your feet are touching the sand, but yet your balcony is a floor above the actual sand with both sunrise and White St Pier views. This two bedroom, two bath condo is about to have an owner change and these photos are temporary until the owners complete the personalization of their new getaway.brbrThis oceanfront oasis is located in the Key West Beach Club, an upscale, gated community with two oceanfront pools, pavilion area, workout room and tennis court. The Key West Beach Club is one of the very few condo communities on the island that sits directly on the coastline.brbrEnter the open living, dining, kitchen with your eye drawn immediately to the view. The living room has light blue walls with dark wood flooors and features a modern sectional leather sofa with leather accent chairs & natural wood accent tables. The dining area has a spacious natural wood Room and Board dining table for 6. The kitchen features a full wall of cabinets and stainless appliances The coffee bar is a nice feature to enhance the kitchen. It is the counter height table in the kitchen that steals the show, with its surfboard inspired design and bar stools as another dining space or perfectly used as a serving area.brbrThe Primary Bedroom is being updated with a king tropical style bed and new mattress. The ensuite bath has a long vanity and large walk in shower. A concealed window in the shower allows you to see the ocean while showering, but the view is obscured from the bedroom for privacy. The guest room will feature a queen bed and desk for multipurpose use of the space. A hallway door between the guest rooom and guest bath will close to allow the large bathroom with walkin showere to serve as a second ensuite.brbrThe balcony offers a lounge area, outdoor dining and chaise loungers for relaxing oceansidde. brbrUnit Features:brCentral A/C, Wi-Fi, washer/dryer, security entry, garage parking and elevator access.brbrCommunity Amenities: Resort-type amenities include two oceanside pools (heated), tennis court, outside cooking facilities and pavilion, fitness center and sauna. Since the shoreline is natural, beach access is best at the public beaches on either side of the community. Smather’s Beach is around the corner to the right when exiting the property and Higgs Beach is just past White Street Pier to the left. There are plenty chaise lounges around the pool areas as well as the covered pavilion to enjoy during those sunny island afternoons.brbr**Construction Disclaimer** From mid May through the month of June, 2026, the pool area will be under construction. This will create noise and dust that could impact your stay and may lead to pool closure as well.

Casa Bonita Key West ~ by Rent Key West Vacations

Key West, Florida, United States

Bed

Bath

Sleeps

$271.69

Summary:brbr2 bed/2.5 bath townhouse on golf course with shared pool minutes away from downtown Key West, local beachesbrbrbrbrThe Space:brbrIndulge in the ultimate getaway experience with our stunning 2 bedroom, 2 1/2 bathroom townhouse nestled on the picturesque Key West Golf Course. Overlooking the lush #1 green, this oasis offers unparalleled tranquility and relaxation. Step outside and immerse yourself in luxury at our lagoon-shaped pool featuring a soothing waterfall - just a few steps away from your doorstep. Unwind in the extended rear yard adorned with vibrant grass and tropical landscaping, creating a serene backdrop for your vacation. Inside, discover a haven of comfort and style. The spacious living room opens up to a screened veranda, perfect for expanding your entertaining space while basking in streams of natural sunlight. A convenient downstairs powder room adds to the convenience of your stay. Upstairs, each bedroom boasts its own private bathroom en suite, providing the utmost privacy and comfort for you and your guests. Experience the epitome of Key West living at our vacation rental - book your stay today and start making memories that last a lifetime. The Key West Golf Club HOA is a gated community offers safe and beautiful paths to run, walk and play. Staying here also gives you parking for 2 vehicles. Prime Tee Haven, is located at Mile Marker 5 of US 1 and is 1 block from the Key West Hospital, Police Department, Community College and Tennessee Williams Theater. It is about 5 miles from door to door to downtown Key West. This is a pet & smoke free property.

Prime Tee Haven | Townhouse on golf course

Key West, Florida, United States

Bed

Bath

Sleeps

$851.78

Please choose a Saturday check-in, all rentals will be in seven night increments.brBedding configuration may vary, depending upon your travel week and the villa available, please inquire prior to booking.brThank you for your interest in booking with Dash Realty Group, Windermere Florida. brDash Realty Group is registered in Florida as a licensed Fla. Seller of Travel Ref. No. ST42435.brbrOverlooking the Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with friends new and old at the Tiki Bar, or relax and unwind in the swimming pool. The resort's observation deck guarantees a stunning view from sunrise to sunset, and even to gaze at the stars. Rent a boat for a private viewing of the Keys or take a jetski for a spin right from the resort's marina. Work up a sweat at the on-site exercise room and afterwards, relax your body and mind in the sauna.brbrThe resort's 90-slip marina accommodates boats up to 150 feet and hosts a variety of water activities. After you've had your fill of fun on the water, stretch out on the private beach or outdoor pool. If you want to venture out and explore the island, there are local attractions, art galleries, shopping and restaurants within walking distance of the resort's doorstep.brbrA two-bedroom suite sleep up to six, and include a full kitchen, dining area and decked out living area. Villa is furnished with sandy earth tones, rattan furniture and tropical prints that perfectly set the mood for your stay in Key West.brbrThe Galleon Resort is perfectly positioned, sitting only two blocks from Duval Street - a legendary road that boasts top-notch restaurants, dazzling nightlife and non-stop soirees. Party until dawn at a carnival, swing by a cuban cigar stand or bring your camera to the exotic butterfly conservatory, all located on this versatile street that's earned its reputation. At the northwest end of Duval Street lies Mallory Square, a plaza which is famous for its Sunset Celebration - tourists gaze at the sunset while arts and crafts displays and entertainers amuse the gatherers. Key West's oldest attraction, the Key West Aquarium is a hit with families - everyone will enjoy scoping out the menagerie of rainbow-hued fish.brbrLarge waterfront swimming poolbrPrivate beachbrBoardwalkbrObservation deck with a 360-degree panoramic viewbrof Key West ... one of a kindbrDock CafébrTiki BarbrSaunabrDiving & SnorkelingbrSun BathingbrSunset CruisesbrExercise Roombr24 hour securitybrWireless InternetbrbrThe Galleon's Marina offers dockage space to accommodate boats and yachts up to 140 feet. Outside of being the most highly protected harbor for your vessel, they also offer exclusive marina and resort amenities when renting a boat slip in the Marina. Wet slips are available for both seasonal and transient rentals.brbrFishing Charters, Sunset Cruises, Parasailing, Snorkeling, Dolphin Watching, Glass Bottom Boat Jet Ski Rental, Scooter rentals, all available onsite or nearby.brbrTHE BOOK IT NOW FEATURE IS A REQUEST FOR RESERVATIONS, NOT A CONFIRMED STAY. Please do not reserve your airfare until you have communicated with us and have an executed rental agreementbrbrBooking through VRBO is fast and easy. Dash Realty Group will email you the updated confirmation once you book thru VRBO. Please note that VRBO provides an instant quote that may not be accurate and may require us to send an adjusted price quote and adjusted dates based on what is available for your requested dates.brThis is based on higher demand weeks and resorts that may be higher than the initial quote. The VRBO calendar does help provide instant availability and estimated price quote. However, because availability and rates vary constantly, the calendar feature and instant quote feature is not always 100% accurate. brbrThe photos are a good representation of what your villa will look like. Layouts may vary. The resort updates and maintains the villas at this resort and your villas is assigned upon check-in.

The Galleon Resort, Waterfront Location, Well-equipped Two Bedroom Villa!

Key West, Florida, United States

Bed

Bath

Sleeps

$502.77

***This unit holds a City of Key West Transient License and will be permitted to continue offering weekly rentals beyond 2025*** brbr brbrWelcome to Cocktails & Dreams, an impeccably updated second-floor condo located in the coveted Shipyard Condominiums! brbr brbrPositioned at one of Key West's prime locations, this residence offers you an unparalleled Key West experience. Just a short 2-block stroll from the vibrant energy of Duval Street, Cocktails & Dreams places you at the heart of Key West's renowned dining, nightlife, and shopping. Explore a plethora of restaurants, bars, and unique boutiques, immersing yourself in the dynamic spirit of the island. Venture to Truman Waterfront Park for a day of family enjoyment, creating cherished memories. If relaxation is your goal, the soft sands and inviting turquoise waters of Fort Zachary Taylor Park are only moments away, offering a tranquil escape. When the allure of the complex beckons, retreat to your private front or rear balcony. Begin your day with a cup of coffee and the soothing morning breeze, or unwind in the afternoon with a cocktail as you soak in the island vibes. For those seeking refreshment, the community pool (closed August 2026 for renovations) offers a delightful way to beat the heat. Take a leisurely dip, enjoy the sun's warmth, and relish the ease of having your relaxation needs met right on-site. Inside, Cocktails & Dreams is meticulously updated, providing you with modern comfort amidst the vibrant island atmosphere. Discover a harmonious blend of convenience and style that enhances your Key West stay. Whether you're an adventurer or a leisure seeker, Cocktails & Dreams places all the wonders of Key West within your grasp. Uncover the magic of this island paradise, knowing you have a comfortable haven to return to. Discover the essence of Key West living at Cocktails & Dreams. Experience the luxury of convenience and the allure of the island lifestyle. Book your stay now and let your Key West dreams come to life! brbr brbrSLEEPS MAXIMUM OF 4 GUESTS: brbr brbrBedroom 1: Queen Bed, Smart TV brbr brbrBedroom 2: Two Twin Size Beds, Smart TV brbr brbrLiving Room: Sofa With Pull Out Bed, Two Chairs, Smart TV brbr brbrKitchen: Nicely Equipped (everything needed to prepare and serve meals) brbr brbrAMENITIES: brbr brbr- Shared Pool (Pool will be closed August 2026 for renovations) brbr brbr- One Designated Parking Space brbr brbr- Keurig, Drip Coffee Maker, Toaster brbr brbr- Linens and towels provided brbr brbr- ~3 blocks to Duval Street brbr brbr- 0.3 miles to Fort Zachary Taylor State Park Beach brbr brbr- 0.7 miles to Southernmost Point brbr brbr- 0.8 miles to Mallory Square Sunset Pier brbr brbr- 0.9 miles to Historic Seaport brbr brbr- 2.6 miles to Smathers 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 brbrPet Policy: Pets are not permitted for guest bookings less than 30 days per the HOA. For guest bookings 30 days or more, up to one dog 25 LBS or less will be considered with a $10/night pet fee. To help maintain a safe and welcoming environment for all, we require every guest to submit pet or assistance animal information through BetterPet Passport. Guests will simply submit household pet information, request an accommodation for an assistance animal, or confirm they are not bringing a pet/animal. It's free, and only requires creating an account if you're bringing a pet or animal. 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 brbrMilitary Discount: A 10% discount is offered to active duty, retired, or reserve armed forces personnel with a valid military ID. 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 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, one exterior security camera monitors the front door. The camera is for security purposes only and does not monitor any private interior or outdoor living spaces.

Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterpark, Beach & Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$358.88

Welcome to the tranquil, tucked away community of Sunrise Suites in beautiful Key West, Florida. When you choose to spend your vacation with us at the pet-friendly Castaway Cove Condo, you will be just 1 mile from Smather's Beach and a quick 10 minute drive to the fun and excitement of downtown Duval Street with tons of restaurants, bars, art galleries, museums, live music and people watching.br brCastaway Cove offers all of the creature comforts you are used to at home including a full kitchen with cooking/dining essentials, Keurig & drip coffee machines and dishwasher. Meals can be enjoyed indoors on the peninsula countertop (up to 4) or outside on the private patio (up to 4). br brA Master Suite with ensuite bathroom, queen bedroom with bathroom attached (also accessible from living room) and a pull-out sofa in the living room can accommodate up to 6 guests for a restful night of sleep after a day of island exploration. Our guests also enjoy central AC, Free Wi-Fi, multiple smart TV's with cable and streaming capabilities, and in-unit washer and dryer.br brThe Sunrise Suites community offers our guests access to the following shared amenities:br-Heated Pool & Hot Tubbr-Sunbathing decks & loungers br-Fitness Center br-Tennis Courts br-Free parking on a first come, first serve basis (not assigned, not covered, proximity to unit not guaranteed)br-Walking Paths/Biking Trails br-Corner Store a quick 5 minute walk away

Castaway Cove: 2/2 Condo near the beach with shared pool and hot tub

Key West, Florida, United States

Bed

Bath

Sleeps

$572.95

Key Lime has a large open kitchen, vaulted ceilings and tile floors throughout. This immaculate unit has two-bedrooms, 2 baths and private patio with tropical views. Amenities include: Central AC, Dishwasher, Washer/Dryer, Color Cable TV, VCR, CD Player, Ceiling Fans, Sleeper Sofa, Community Pool, Sleeper Sofa, Full Kitchen, brbrThis and all of my places rent only Saturday to Saturday in the winter months.br br

Truman Annex unit 254

Key West, Florida, United States

Bed

Bath

Sleeps

$325.54

WHERE LIFE IS PURE…brThis dreamy 3 bedroom, 2 bathroom island getaway is sure to captivate the true essence of Key West charm within its tranquil setting. Peacefully located with convenience to everything, this home truly has it all making your Key West love story one never to forget! br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brPull up to the first floor of this island beauty showcasing lush, vibrant foliage surrounding this quaint abode. Step onto a private front porch, perfect for a morning cup of coffee as you daydream of your island adventures. Slip inside to a bright and cheery living space with natural lighting inviting you in. Whip up your meals in a fully equipped kitchen with stainless steel appliances which can be enjoyed at the table for 4. Cozy living room furnishings surround a flat screen TV, perfect for movie and game nights. brbrSLEEPING ARRANGEMENTS…brTotaling 3 bedrooms, this home is perfect for bringing all your loved ones together in Paradise. A queen guest room with a TV and a full guest room both share a bathroom with a shower. The queen primary suite comes with a TV and an en suite bathroom with a shower. brbrOUTDOOR LIVING…brYour tropical fantasies will come alive outside in the lush backyard area with delightful foliage surrounding an outdoor shower and private pool that comes heated in the winter months. The pool is NOT shared with the guests upstairs. Grill up your fresh catch of the day to be enjoyed at the outdoor dining table. This home is just a short stroll or bike ride from Duval St., Historic Seaport and the beautiful beaches of Key West! brbrPARKING...brOff street parking for 2-3 vehicles is available making coming and going a breeze! brbrPETS...brSmall dogs are considered at this home on a case by case basis. A pet fee is required.brbrMULTI MONTH RESERVATIONS...brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay clean brPool/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). brbrLIVE LIKE A LOCAL…

THE WEEKEND HOUSE ~ 3 Bedroom, 2 Bath Condo Centrally Located w/ Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$409.92

MINIMUM STAY 29 DAYS/28 NIGHTS Welcome to Conch Republic and the Shipyard section of the Truman Annex. You have many choices of accommodations and since I am not a real estate salesman or property manager, allow me let the photos and description speak for themselves. My oversized two bedroom, one bathroom condominium or casita as Cubans would call it, is located on picturesque Southard Street, the main entrance to the best location on the island, the Truman Annex where you can walk to just about everything you want to see or do. I am confident you would like this vacation home away from home. It is impeccably designed, meticulously maintained and you are surrounded with restful colors on the wall and art work from my many visits to Cuba on educational and humanitarian trips. I have everything you need for a worry free island vacation. Top mattresses, high thread linens, thirsty bath towels, large deep beach towels, high speed WIFI, reserved and secure parking and cable TV. Your comfort is my first priority and between my home itself and the large back deck shaded with a large umbrella, you can rest assured that you will enjoy your stay. The furniture and beds are very comfortable. The kitchen fully equipped from the Bosch dishwasher to the exotic micro wave and the Keurig coffee maker. Need a hair dryer Got it. Iron In above the large front loading washer and dryer. Beach chairs On the large back deck. Ask me about other amenities. And yes, there is the mandatory blender. This is my personal home so I would like to deal with you directly on email and telephone before we make a booking. Guests must come and go on a Saturday for the most part. Now on to more detail. Oh one more thing. If your party is looking for additional space, check out my cottage five doors down which is # 361238 here on VRBO. BONUS OFFER I HAVE SOME NICE OPENINGS IN SUMMER AND FALL A ALLOW ME TO OFFER A GIFT CERTIFICATE TO ONE OF KEY WEST'S BEST RESTAURANT BLUE HEAVEN

A Touch Of Cuba In Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$634.6

Introducing Glimmer Glass, an oceanfront two bedroom, two bath condominium at the Key West Beach Club, the premier Key West oceanfront development! Decorated with the cool tones of the ocean that laps outside, light glimmers off the water into the space. brbrThis third floor fully air conditioned home has a spacious living / dining area that offers abundant space to entertain or simply relax. A large screen tv surrounded by comfortable seating allows for that streaming movie night or your favorite sporting event. A Sonos sound system provides surround sound for your movie or simply to stream your favorite music. Expansive sliding glass doors open directly to a large balcony with two sitting areas and teak table for outdoor dining (up to 6 people) overlooking the beach and ocean. Sun streams into the balcony each morning, transitioning to the glow of sunset off to the west in the evening. brbrThe large cook’s kitchen with newer appliances, including a Viking refrigerator with an ice maker, is ready to prepare meals to entertain friends and family. The range has a double oven for the ease of baking. A water filtration system has been installed on the kitchen sink, so pack your water bottles and skip the case of water at the grocery store. The coffee station features both a regular drip coffee maker and a Keurig so the options are covered. A stacking washer/dryer unit is also in the kitchen area, so you can pack less brbrThe two oversized bedrooms with king size beds (or one with two twins) features luxury cotton bedding. The main bedroom has a contemporary tropical feel with a king woven sleigh bed set against the backdrop of teal grasscloth. Sliding doors access the balcony to go straight from waking up to watching sunrise! A large walk-in closet will allow you to unpack for your vacation stay. The principal bathroom has a large walk-in shower of beautiful blue tiles with plantation shutters that can be opened to enjoy the ocean view while showering. The second bedroom is large with either a king bed or two (extra long) twins, backing up to a woven leather headboard wall. A built-in wall of shelves also provides a desk area for the working vacation. The hall door closes off to make the second bathroom ensuite or it serves as the general powder room for the common area. The second bath also has a comfortable walk-in shower.brbrThe breezeway entry can be utilized as an office for 1 or 2 people at the same time. French doors can close this off from the kitchen if privacy is needed for that work call or zoom that can be avoided on vacation.brbrThe Key West Beach Club complex provides a resort-like atmosphere complete with 2 heated swimming pools, jacuzzi, workout room, outdoor barbecues, dedicated covered parking, elevator and a tennis court! All securely inside a gated entrance with beautiful landscaping. Due to the tide schedules, the beach may disappear during normal beach hours. This is not a beach that people normally lay out on.brbrThere are very few direct ocean front residences in Key West with direct beach and ocean front access. Listen to the ocean waves lapping on the beach just steps away. Glimmer Glass has this and more! brbrReady for a night out Glimmer Glass is a short walk to Salute restaurant on the Beach and the features of the Casa Marina Resort or 10 minute bike ride from all the activities, attractions and excitement of Duval Street. Still close enough, but far enough away to enjoy the “getaway from it all” feeling! brbrStay for a week or two or a month or two! This home is a perfect retreat to feel the ocean breezes and soak in the beauty of the Key’s ocean literally feet from your balcony!

Glimmer Glass oceanfront condo by Rent Key West Hideaways

Key West, Florida, United States

Bed

Bath

Sleeps

$473.9

Key West Waterfront Paradise – Dockage Included!brbrEscape to our charming Key West condo, where relaxation and adventure meet! Located right on Garrison Bight Marina, you can start your mornings with coffee on the balcony, watching boats glide by, and soaking up the tropical sunshine.brbrA short walk or bike ride takes you to Duval Street’s vibrant shops, restaurants, and nightlife. After exploring, unwind in the heated pool, grill fresh seafood at the BBQ area, or take a sunset stroll to Bayview Park with its tennis and basketball courts.brbrWhether it’s a romantic getaway, family vacation, or friends’ retreat, this is your perfect home base in paradise.brbrThe Spacebrbr• Primary Bedroom: King bed • Marina views • Private balcony access • Ensuite bathroom • Walk-in closet • Flat-screen TVbr• Second Bedroom: Two Queen beds • Flat-screen TVbr• Living & Dining Area: Open-concept • Bright & airy • Plenty of space to relax, play games, or dine inbr• Kitchen: Fully stocked with cookware & utensilsbr• Laundry: Full-size washer & dryer for added conveniencebrbrDockage Detailsbrbr• FREE Private boat slip with fresh water, power, and covered fish cleaning stationbr• Commercial ice maker on-sitebr• Overnight stays on boats are not permittedbrbrAmenities you’ll Lovebrbr• Shared heated poolbr• BBQ grills & tiki areabr• Free on-site parkingbr• Adjacent park with tennis courtsbr• Private building elevatorbr• High-speed WiFi br• Just 9-10 minutes from Key West Airport (EYW)brbrNearby Attractionsbrbr• Duval Street & Historic Old Townbr• Smathers Beachbr• Bayview Park – right across the streetbr• Historic Districtbr• Mel Fisher Museum & Shipwreck Museum

Key West Condo 2B/2B with Pool & Boat FREE Slip

Key West, Florida, United States

Bed

Bath

Sleeps

$275.07

Rent a piece of paradise right in the heart of beautiful Old Town Key West. Walking distance to all major attraction (restaurants, bars, art galleries, nightlife). Condo is also located right near Fort Zachery Taylor State Park which has the best beach in Key West. We have a seven night minimum stay. There are 2 bedrooms, both have queen sized beds. There is one bathroom. Full kitchen, washer and dryer, all towels provided.brbrWe offer strong reliable ,strong internet for our guests!!!brbrKeywords: Condominium

Rent a Piece of Paradise, Best Location on the Island!

Key West, Florida, United States

Bed

Bath

4

Sleeps

$895.67

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

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

Key West, Florida, United States

Bed

Bath

6

Sleeps

$797.21

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

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

Key West, Florida, United States

Bed

Bath

Sleeps

$161.34

A Fish Bowl has been completely remodeled with attention to detail. A beautiful 1 bedroom, 1 bath downstairs condo located in The Shipyard section of Truman Annex. The new kitchen sparkles with brand new top-of-the-line appliances, cabinetry and every amenity needed. The gourmet kitchen opens nicely to a sunny living room with glass doors leading to a private garden area with room for outside dining and lounging.brbrFrom the private patio, the back gate opens to the refreshing waters of the Shipyard swimming pool, only steps away.brbrThe primary bedroom has a comfy king bed to doze and dream of the day's next adventure. The luxurious bathroom appointed with new tiles, new fixtures, the finest of linens and a stunning glass shower.brbrThis pristine residential community is one of the most requested locations in the heart of Old Town Key West. A wonderful mix of a private community yet easy walking distance to the Duval Street attractions, Mallory Square, and Fort Zachary Taylor State Park. Includes free Wi-Fi & one assigned parking space. brPlease note: This property will require a minimum of a 28 night stay.

A Fish Bowl at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$240.32

Welcome to Mai Tai Terrace – Your Tropical Getaway in Key WestbrbrLocated in The Shipyard subdivision of the sought-after Truman Annex, this bright and breezy 2-bedroom, 2-bath end-unit condo offers the perfect island escape just steps from the best of Key West.brbrSPACIOUS, SUNNY AND PERFECTLY POSITIONEDbrbrSituated on the second floor, this open-concept condo features vaulted ceilings, large windows, and a light-filled layout that flows seamlessly from kitchen to lanai—perfect for relaxing after a day of exploring.brbrBEDROOMS & BATHROOMSbrbrPrimary Suite: Queen bed, large closet, 42” Smart TV, and a private en-suite bathroom.brbrGuest Bedroom: Two twin beds (can be converted to a king upon request), large closet, 42” Smart TV, and adjacent full bathroom with shower/tub combo.brbrKITCHEN, DINING & LIVING ROOM brbrFully equipped kitchen with all the essentials for home-cooked meals.brbrDining area seats 6 guests comfortably.brbrLiving room features a sofa sleeper, accent chairs, and a 55” Smart TV.brbrLanai off the living room includes a cozy conversation seating area and privacy wall.brbrAMENETIES & EXTRASbrbrCommunal swimming pool within the complexbrbr2 bicycles provided – the best way to explore the island!brbrBeach chairs & towels includedbrbr1 assigned parking space (perfect for a rental car or golf cart)brbrSecure, gated entry ensures privacy and reduced traffic/noisebrbrPRIME LOCATIONbrbrWalk to everything! Just:brbr1 block to Truman Waterfront Park & Amphitheaterbrbr2 blocks to The Hemingway House, Key West Lighthouse, and Shipwreck Museumbrbr3 blocks to Duval Street and Fort Zachary Taylor Beach ParkbrbrClose to restaurants, shops, and all the top sights in Old Town Key WestbrbrWhether you're coming for sun, sea, or a slice of island life, Mai Tai Terrace is the perfect home base for your Key West adventure. We can’t wait to welcome you!

MAI TAI TERRACE - KEY WEST

Key West, Florida, United States

Bed

Bath

Sleeps

$481.48

Atlantic Hideaway at 1800 Atlantic – Luxury 2BR Condo with Resort AmenitiesbrbrWelcome to Atlantic Hideaway, your private escape in paradise. Located in the highly desirable 1800 Atlantic condo complex, this beautifully updated 2-bedroom, 2-bathroom third-floor unit offers spacious accommodations, resort-style amenities, and a prime Key West location. Just 1 mile from the Key West International Airport and 2 miles from Duval Street, you're perfectly situated to explore all that the island has to offer.brbrResort-Style AmenitiesbrbrGuests enjoy access to a wide range of upscale amenities within the 1800 Atlantic complex, including:brbrTwo large swimming pools and a relaxing spabrbrTennis courts and a fitness centerbrbrPrivate beach and walking pathsbrbrBBQ area, recreation room, and librarybrbrSecured covered parking with overflow options for an additional vehicle or golf cartbrbrThe CondobrbrThis third-floor unit offers garden and partial water views with a spacious, open layout designed for comfort and entertaining.brbrBedrooms and BathroomsbrbrPrimary Suite: Features a king-size bed, large closets, full-length mirrors, and sliding doors leading to the shared lanai. The ensuite bathroom includes dual vanities and a custom-tiled shower.brbrGuest Bedroom: Includes a queen-size bed, chest of drawers, large closet, and direct access to the shared lanai.brbrSecond Full Bathroom: Located in the hallway, with a shower/tub combination and custom vanity.brbrLiving and DiningbrbrThe living room includes a sofa sleeper, loveseat, and accent chair, along with wall-to-wall glass doors opening to the lanai.brbrThe formal dining area seats six and is adjacent to a convenient wet bar and beverage center.brbrPerfect for entertaining or relaxing after a day of island adventures.brbrFully Equipped KitchenbrbrModern kitchen with stainless steel appliances, quartz countertops, shaker-style cabinets, and a breakfast bar with seating.brbrPrivate Outdoor LanaibrbrEnjoy morning coffee or evening cocktails on the spacious lanai with outdoor dining and lounge seating, accessible from both bedrooms and the living area.brbrAdditional FeaturesbrbrFull-size washer and dryer in the unitbrbrBeach chairs and towels providedbrbrOne assigned covered parking space in a secure garagebrbrBook Your StaybrbrWhether you're visiting for a family vacation, romantic getaway, or extended stay, Atlantic Hideaway provides the perfect blend of comfort, convenience, and resort-style living in Key West.brbrbrNOTICE!!!!!brConstruction Notice: Balcony Restoration Project – 1800 AtlanticbrProject Start: May 2025brEstimated Completion: Spring 2026brbrWe would like to inform our guests that a balcony restoration project will be taking place at 1800 Atlantic from May 2025 through Spring 2026.brbrWhat You Need to KnowbrOnly units not affected by construction will be available for booking.brAll amenities—including the pool, spa, and sunning beach—will remain open and fully operational throughout the project.brWe appreciate your understanding as we work to enhance the property for an even better guest experience.

ATLANTIC HIDEAWAY- Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$386.4

Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get without sacrificing a good night's sleep. The one bedroom Villa Rosa is generously equipped for your Key West family gathering, reunion, destination wedding, and even just a romantic Key West getaway.brbrThe number one reason why people choose the Rose Lane Villas is our fabulous location and proximity to all things worth doing in Key West. br1/2 block to Hard Rock Cafebr2 blocks to Margaritavillebr1 1/2 blocks to Sloppy Joe’sbr3 blocks to the Historic Seaportbr4 blocks to Mallory Squarebr4.5 blocks to Schooner Wharfbr6 blocks to Hemingway’s HousebrbrEmail us for availability, even if we look full. Please be aware of scams asking for wire transfers or offers from Craigslist. If you have any questions, please call our reservations desk.

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

Key West, Florida, United States

1

Bed

1

Bath

4

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

$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