Vacation Rentals By Owner In Key West, FL

LET THE REAL WORLD SLIP AWAY...brExperience quintessential island serenity within this charming and newly renovated home tucked away in the Old Town district of Key West. A laid back vibe with every desirable amenity at your fingertips, this retreat is sure to capture your tropical soul. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES...brStep onto your quaint front porch calling your name for a good book as you sip on your morning cup of coffee. Totalling 3 bedrooms and 3 bathrooms this home seamlessly suits a comfortable month long stay in Paradise. Step in to find an open and cheery space showcasing cool hardwood flooring, impeccable interior design with Dade County Pine accents, bright natural light from all around and stunning cathedral ceilings creating a happy space for everyone to gather. A fully equipped kitchen boasting top of the line appliances makes meal prep a breeze as you gather around for happy hour with a cocktail in hand at the bar area for 4. Cozy living room furnishings lie steps away with a flat screen TV for lazy nights in. This property is equipped with a Ring Doorbell located next to the front door of the home.brbrSLEEPING ARRANGEMENTS...brThe first guestroom comes with a king bed with plush linens, a flat screen TV and a stunning en suite full bathroom with a shower. The second guestroom resides off the Great Room and comes with a cozy king bed with access to the outdoor area and a nearby hallway bathroom with a shower/tub combination. Step outside to find a charming poolside cottage with a queen bed, a flat screen TV and en suite full bathroom with a shower.brbrOUTDOOR LIVING...brTruly immerse yourself in your private and magical outdoor oasis as you cool off in the sparkling pool (comes heated in the winter months) with a sweet island breeze and attractive landscaping surrounding you. Grill up your fresh catch of the day to be enjoyed around a table for 6 with a flat screen smart TV and a bluetooth speaker for your island tunes. Enjoy parking for 1 compact vehicle so you can come and go at your leisure (owner's golf cart is parked in driveway and not available for guest use).brbrPETS...brThe owner prefers no pets, but may consider a dog under 30 pounds and a pet fee would be required.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).brbrPARADISE AT YOUR FINGERTIPS...

CROOKED PALM ~ 3 Bedroom, 3 Bathroom Luxury Home w/ Pool & Compact Parking!

Key West, Florida, United States

Bed

Bath

6

Sleeps

$421.88

A camera roll full of the best family vacation memories is inevitable at The Kaleidoscope House: A Colorful Key West Stay. Tucked away on a quiet, foliage-lined street in Old Town, this vibrant tropical retreat is nestled in and amongst the best of Key West. This home is a newer construction, built in 2014 with a big porch, vaulted ceilings, and a calming sage green exterior. Inside, bold and bright design details create a playful yet serene atmosphere, perfect for everything from post-beach, lazy lunch breaks to lively evening get-togethers before you head out on Duval Street. brbrUpon entry, the burst of colors proves your tropical vacation is well underway. Parents can get settled first thing in the large master bedroom, complete with a huge walk through closet, a bright bathroom, and secret door to your own outdoor shower. brMake your way down the artful, turquoise entry hallway and you’ll notice this home is well-stocked with all you need for a great time. Carts and wagons for the beach, yoga mats, towels, boogie boards, and cabinets full of snorkel gear, pool toys, games for game night, books and more. brbrThis Key West getaway’s open format, soaring vaulted ceilings, and spacious common area are ideal for celebrations, birthdays, and spending precious vacation time together. It has a massive table for 8, ample fridge and freezer space for all your snacks and refreshments, and plenty of couch seating for everyone to gather. The party continues as you step right outside into your own private backyard paradise surrounded by fluffy tropical plants, blooming orchids, and darting lizards. The sparkling swimming pool, hottub, and spacious deck are the perfect for sunbathing, grilling, and unwinding. brbrBack inside and up the stairs, you’ll find two more colorful bedrooms, both with their own private, full bathrooms and huge closets. With the vaulted ceilings, happy hues, and skylights, upstairs feels like a jungle treehouse.brbrBefore and after a day of exploring Key West, we know you’ll be glad to be on your calm, quiet end of Nassau Lane. Everything is nearby yet you’re out of the way of passerby, traffic, and noise. Your designated parking space means no circling the block or hauling bags. Just pull in, unpack, and start enjoying yourself! We look forward to making your stay at The Kaleidoscope House as fun and comfortable as possible.

The Kaleidoscope House - A Colorful Key West Hideaway w Pool & Jacuzzi

Key West, Florida, United States

Bed

Bath

Sleeps

$154.03

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 Island Escape! brbr brbrThis beautifully adorned condo is your ticket to the best of Key West living. Nestled just steps from the iconic Duval Street and a short six-block stroll from the Southernmost Point in the Continental US, this is the perfect base for your island adventures. Step out of your front door, and you'll find yourself immersed in the vibrant culture of Key West. Sample the delectable cuisine at the many restaurants and bars the island is famous for. Explore unique shops and discover captivating attractions around every corner. For beach lovers, several sandy shores are within walking distance, while the sprawling Smathers Beach, with its powdery soft sands and crystal-clear turquoise waters, is just 8 minutes away. Whether you're seeking relaxation, adventure, or a taste of local life, Island Escape has it all. brbr brbrSLEEPS MAXIMUM OF 4 GUESTS: brbr brbrBedroom: Full Bed, En-Suite Bathroom, Smart TV brbr brbrLiving Room: Sofa With Pull-Out Queen Bed, Smart TV brbr brbrKitchen: Nicely equipped (everything needed to prepare and serve meals) brbr brbrAMENITIES: brbr brbr- Shared Pool brbr brbr- Private Patio brbr brbr- One Parking Space Included brbr brbr- Linens and towels provided brbr brbr- half block to Duval Street brbr brbr- 0.4 miles to Southernmost Point brbr brbr- 0.9 miles to Key West Historic Seaport brbr brbr- 1.0 miles to Fort Zachary Taylor State Park Beach brbr brbr- 1.1 miles to Mallory Square Sunset Pier brbr brbr- 2.3 miles to Smathers Beach brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAmenity Fee: HOA requires booking tenant to pay a $100 amenity fee. (Subject to change and collected at time of booking) 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 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.

Island Escape: Charming Condo Just Steps From Duval Street, Near Southernmost Point, Shared Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$359.98

Welcome aboard *Strictly Pleasure*—a stay that feels less like a rental and more like stepping into the rhythm of the Florida Keys.brbrMoored at Perry Marina in Key West, this classic yacht offers a kind of experience you simply won’t find in a hotel. Mornings begin with coffee on deck as the marina comes to life. Evenings end with sunset skies from the bow, the water reflecting colors that feel almost unreal. In between, you’re perfectly positioned to enjoy the best of the Keys—without ever giving up the calm of being on the water.brbrThe vessel is thoughtfully set up for comfortable overnight stays, blending the charm of a classic yacht with the essentials you need. Inside, you’ll find a comfortable salon, air conditioning, bathrooms with showers, and a galley (kitchen) for simple meals. The outdoor deck spaces are where most guests find themselves lingering—watching boats pass, enjoying a drink, or simply taking it all in.brbrSleeping Arrangementsbr*Strictly Pleasure* offers two private cabins and two full bathrooms. The master cabin features a queen bed, while the forward (bow) cabin includes a full-size bed—comfortable, cozy, and true to the character of a classic yacht.brbrAs our guest, you’ll also have access to Perry Marina’s amenities, including waterfront dining, two pools, and a complimentary shuttle that runs to downtown Key West. Whether you’re heading into Old Town for a night out or staying local for a quiet evening by the water, everything is within easy reach.brbrThis is, at its heart, a boat experience. While securely docked, you may feel gentle movement depending on marina conditions. Moving through the vessel involves a few steps, narrow companionways, and the natural layout of a yacht, so guests should be reasonably mobile and comfortable in that environment.brbrWe give our guests space to enjoy their stay, but we’re always close by if needed—whether it’s a quick question or a recommendation for a great local spot. We’ve spent years exploring the Keys and are happy to share the kinds of places you won’t always find in a guidebook.brbrA few things to keep in mind: the vessel remains docked at all times and is not available for operation. The space is best suited for those looking for a relaxed, low-key stay rather than parties or large gatherings. Quiet hours are observed to respect the marina community.brbrBecause we love traveling with our own dogs, we’re happy to welcome yours aboard as well. A small pet fee applies, helping us maintain the extra cleaning and care that keeps the vessel comfortable for all guests. The boat is thoroughly cleaned between stays, though occasional traces of pet hair may remain. Cats are not permitted.brbrOut of respect for the marina environment, we provide eco-friendly soaps for use during your stay, as all water from the vessel returns to the marina system.brbrStaying aboard *Strictly Pleasure* is about slowing down, enjoying your surroundings, and experiencing the Keys from a different perspective—one that’s a little more personal, a little more memorable, and unmistakably on the water.brbr— Kaitlin & Kyle

House Boat

Strictly Pleasure : Unique Yacht Stay in the Keys : Marina & Sunset Views

Key West, Florida, United States

Bed

Bath

Sleeps

$483.94

Key West Cottage. Located in the Historic Seaport Area of Old Town. 2 BR. 2 BR. Three HD TV's. Streaming on every TV. Will accommodate up to Five. 1 off street parking spot. Mostly updated and remodeled Conch Cottage. Large Front Porch and Large rear deck area with Umbrella Tables and other outside seating. Fantasy Fest, Boat Races, Christmas and New Year's still available. Great Location for a Key West Vacation. brbrThis property is a monthly rental. Rates are modified due to fluctuating demand during holidays and events. See Below:brbrSummer SeasonbrMay 16 - Oct 1br$9400 Per MonthbrbrAdditional Fees:brbrCleaning Fee $150brDamage Deposit $750.00brbrbrbrAll reservations require a deposit upfront,brrefundable with a 60 day notice.brAll reservations made less than 60 days frombrarrival require nonrefundable payment in full.br We do not allow Spring Breakers. brbrbrbrbrbrbr

Key West Cottage Located in Old Town Key West. Available February 2026-on!!!!

Key West, Florida, United States

Bed

Bath

Sleeps

$582.59

This Key West rental is a boater's paradise offering the rare luxury of onsite boat parking with a canal that provides direct access to both the Gulf of Mexico and the Atlantic Ocean. The property boasts a double lot, with the front fully walled in to create the feel of a private villa, ensuring ample privacy and space. Within this secluded haven, you’ll find one of the island's most impressive private pools. Conveniently located, the property is just a short drive from the soft sands of Higgs, Zachary Taylor, and Simonton beaches, as well as the vibrant attractions of downtown Key West.

Double Lot Private Villa and Pool with Direct Boat Entry to Atlantic and Gulf.

Key West, Florida, United States

Bed

Bath

6

Sleeps

$329.51

Your Dedicated Key West Retreat with Pool & Separate CabanabrbrWelcome to your ideal getaway in beautiful Key West, a peaceful island retreat designed for relaxation and easy living. This spacious property offers three bedrooms and two-and-a-half bathrooms, plus an outdoor shower, comfortably accommodating up to six guests—perfect for families, couples traveling together, or friends seeking a laid-back island escape.brbrSpacious & Comfortable Living - The main house features two bright, beautifully appointed bedrooms designed with comfort in mind. Large windows bring in natural light, creating an airy island feel throughout the home. What truly makes this property special is the third bedroom located in a private cabana, offering extra privacy and separation—ideal for guests who appreciate their own quiet space.brbrYour Outdoor Oasis - Step outside and enjoy your own slice of paradise. The dedicated swimming pool is the heart of the outdoor space—perfect for morning swims, cooling off after the beach, or relaxing poolside with a good book. The surrounding patio offers plenty of seating for lounging, dining, or enjoying warm Key West evenings under the palms.brbrAn outdoor shower makes it easy to rinse off after the pool or a day at the beach.brbrConvenient Parking - The property includes off-street parking, along with easy and free street parking nearby, making it simple for guests traveling with vehicles.brbrPet-Friendly Island Living - Your four-legged family members may be able to join you as well. Dogs are considered with prior owner approval and a pet fee.brbrQuiet Location, Close to Everything - Located in a peaceful residential neighborhood, this home offers the perfect balance of tranquility and convenience. You’re just minutes from Key West’s beautiful beaches, local restaurants, historic attractions, and vibrant nightlife.brbrExtended Stay Option - Planning a longer escape This property also offers a six-month rental option at a reduced rate, perfect for anyone wanting to fully experience the Key West lifestyle. For more information about longer-term rental options, please contact southernmoststays@gmail.com.brbrDiscover the Best of Key West - Spend your days exploring beaches, historic sites, art galleries, and waterfront restaurants—or simply relax by the pool and soak in the island atmosphere. However you choose to spend your time, this home provides the perfect setting for an unforgettable stay.brbrBook Your Island Escape - Reserve your dates today and start planning your perfect Key West getaway. We look forward to welcoming you and helping make your stay truly memorable.brbrPool Safety Notice:brThis home has a backyard pool. There is no lifeguard on duty. Swim at your own risk. Children must be supervised by an adult at all times while in or near the pool area. Guests are responsible for ensuring doors remain closed and locked when the pool is not in use. By booking this property, guests acknowledge the inherent risks associated with pool use and agree to exercise appropriate caution and supervision.brbrPlease note: All cancellations are subject to a cancellation fee, which varies depending on the cost of your booking.

Island Time Escape - Charming Family Retreat

Key West, Florida, United States

Bed

Bath

Sleeps

$329.96

Welcome to Blue Gem, your private paradise in the Lower Florida Keys! This 4-bedroom, 3-bathroom canal-front home offers the ultimate month-long escape for families, snowbirds, and professionals seeking sun, serenity, and adventure.brbr Prime LocationbrbrNestled on a wide canal with direct ocean access to the Atlantic, just minutes from Snipes Key and Jewfish Sandbar.brbrOnly 10.5 miles to Duval Street and 5 miles to beaches and Key West Airport.brbrLocated in tranquil Porpoise Point—a quiet residential neighborhood perfect for relaxing.brbr ️ Backyard OasisbrbrHeated private pool, shaded pergola, and hammock garden.brbrFully equipped Tiki bar: margarita machine, popcorn popper, fridge, sink, outdoor projector & screen, and poolside TV.brbrFire pits, a large grill, and string lights create the perfect nighttime vibe.brbr80’ seawall for boat docking (owner’s boat removed during your stay).brbr Spacious & Stylish InteriorsbrbrOpen-concept great room with cathedral ceilings, coral rock fireplace, and French doors to the pool.brbrFully equipped kitchen with stainless steel appliances and an island breakfast bar.brbrSmart TVs, family board games, and high-speed WiFi.brbr Room to RechargebrbrBedroom 1: King suite with ensuite bath.brbrBedroom 2: Queen with hall bath.brbrBedroom 3: Queen + office desk (perfect for remote work).brbrBedroom 4: Bunk room (full/twin) off the primary—great for kids!brbr Included ExtrasbrbrOff-street parking for boat trailer or multiple vehicles.brbrOptional concierge services.brbrAsk about included kayaks, paddleboards, or beach gear.brbr Booking InfobrbrLicensed for 29+ night minimum stays only.brbrIdeal for seasonal snowbirds, family relocations, or extended holiday escapes. brbrHave you own boat This home is perfect to spend your Winter or Summer vacation. Perfect access to all the local sandbars.brBring your own water toys, kayaks or paddle boards as the backyard has a deck you can float them right off of!brbrReady for your waterfront escape brBook Blue Gem today and enjoy the Florida Keys lifestyle from your own private dock!brbr Damage ProtectionbrThis rental includes a $125 non-refundable damage protection plan instead of a $5,000 refundable security deposit. Prefer the refundable deposit Just let us know! brbrGuests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check.

Blue Gem - Waterfront Luxury - Tiki Bar - Pool - Boat Dock - 4BD/3Bath

Key West, Florida, United States

4

Bed

Bath

10

Sleeps

$801.7

* We are activally cleaning and sanitizing this rental with extra sanitation methods with each stay.brbrLUXURY IN OLD TOWN...brbrCharming home in the Historic Meadows area of Old Town Key West. Tucked behind a canopy of palms this home was built by a local ship captain at the turn of the century. The property is located in the sought after meadows area of Old Town known for its tranquil, peaceful, and quiet surroundings.brbrLOUNGE...brbrRelax by the heated dip pool or on one of the 2 expansive Ipe wood porch/decks. Lush tropical landscaping throughout with tall palms offering generous shade to the grounds that houses one of the oldest Sapodilla trees on the island. brbrDINE...brbrThe cozy dining room is bright and cheery with wood flooring. Seating for 6 indoors or enjoy a casual BBQ in the yard. Living area boasts plenty of indoor seating and a flat screen TV.brbrSLEEPINGbrbrUp to 6 people can sleep in this rare gem. The main floor includes a master king bedroom with an adjoining full bath. The main floor also consist of a full bedroom/office. The second floor is made up of 2 bedrooms and 2 bathrooms. The first bedroom offers 2 full beds with a hall bathroom. The second bedroom has one queen bed and full hall bath. This bedroom includes a private porch with bird’s eye view. brbrOUTDOOR LIVING AND AMENITIES...brbrThe Meadows district is approximately 10 blocks off Duval. A short distance from all the action and yet far enough away from the hustle and bustle. The property consist of off street parking(driveway) and street parking is available. The Perfect Location where you will find quaint shops, restaurants, take a sunset cruise, go snorkeling, or grab a fishing charter.brbrRELAXATION IN STYLE!

Historic Old Town Charm

Key West, Florida, United States

4

Bed

Bath

6

Sleeps

$612.7

brOur vacation rental, Island Time Escape, offers the perfect blend of comfort and convenience, providing you with a home away from home in this idyllic destination. Located just minutes from popular attractions like Duval Street, the Ernest Hemingway Home and Museum, and Mallory Square, you'll have easy access to everything Key West has to offer.brbrUnwind in our beautifully appointed accommodations, complete with modern amenities and charming island decor. Enjoy your morning coffee on a private outdoor deck, take a dip in the pool, or fire up the grill for a delightful evening barbecue. With its warm hospitality and inviting ambiance, our rental is the perfect place to create unforgettable memories.brbrThe main house consists of 2 bedrooms, 2 full baths, a large open kitchen and dining room. Both bedrooms and the living room open up to a beautiful pool, deck and landscaping. Additionally, there is a separate pool cabana perfect for an office including a murphy bed, half bath and outdoor shower for guests. brbrExperience the magic of Key West and discover why it's a favorite destination for travelers from around the world. We look forward to welcoming you to your tropical retreat! br

Island living 3-bed oasis w large pool, lush deck, cabana, outdoor shower

Key West, Florida, United States

Bed

Bath

Sleeps

$320.63

This 2 bedroom (one King and one Queen, plus Queen size pull out couch in the living room), 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located one mile from Smathers Beach, two miles from Higgs Beach and just minutes away from the Key West Lighthouse Museum. Many species of birds inhabit the salt ponds preserve that borders this property.br

Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

Key West, Florida, United States

Bed

Bath

Sleeps

$250.29

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. This is a 2 story unit.brBedrooms: 2brBathrooms: 2.5brLocation: Front StbrSquare Feet: 1220brParking: One assigned parking space in lotbrAmenities: Shared heated pool, TVs, Wifi, walkable to shops & restaurants downtownbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No commercial vehicles permitted in the parking lot.brPet Policy: One pet under 25 lbs. allowed with approval prior to booking and a non-refundable pet fee.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.

Banyan Court downtown condo- 2 bedroom, 2.5 bath, walkable, parking, pool

Key West, Florida, United States

Bed

Bath

4

Sleeps

$188.36

Live Like a Local in the Heart of Key West!brbrWelcome to your next luscious Vacay getaway—where history, culture, and island living come together just steps from your door! Located only 500 feet from the iconic Hemingway House and the Key West Lighthouse, and just two blocks from lively Duval Street, this centrally located cottage puts you within easy walking or biking distance to the best restaurants, galleries, nightlife, and attractions in town! Mallory Square, the Mel Fisher Museum, and the Key West Aquarium are all less than a mile away as well.brbrAfter a day of exploring, return to your private oasis and cool off in the sparkling plunge pool--Nestled into an enviously secluded outdoor space & is the perfect place for relaxing or entertaining! The home's interior features bold, bright, & inviting colors & furnishings--Creating a cozy and fun atmosphere throughout!brbrEnjoy the flexibility of two separate living rooms—each with smart TVs and comfortable seating—plus a fully equipped kitchen, ideal for preparing your 'Catch of the Day' or favorites from the local Seafood Markets. You can also grill up some dinner pool-side, while you enjoy a sunset cocktail at the outdoor bar. Upstairs, the primary bedroom offers a private bathroom and furnished balcony--featuring an ethereal spiral staircase that descends to the pool deck!brbrThe home includes full bathrooms on both floors, along with distinct sleeping areas for added comfort and privacy—ideal for families or a couples retreat. Additional amenities like high-speed WiFi, a private washer/dryer, and discounted Long-Term pricing make this the perfect place to soak up all that the Florida Keys have to offer!brbrDon't delay--Book your stay T O D A Y!!!brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by the good neighborpolicy and shall not engage in illegal activity. Quiet hours are from 10 p.m. to 8 a.m.brNo smoking is permitted anywhere on the premises.brLong-Term & Snowbird Renters WELCOME! - Please contact us for further details!brThis property is managed by Seven Keys Vacations by Casago.

Tropical Cottage w/ Private Pool--Two blocks from Duval - Near Hemingway House!

Key West, Florida, United States

Bed

Bath

Sleeps

$243.61

Treat your family to an unforgettable stay in Key West with this dog-friendly condo. Modern conveniences combine with a great location and first-class resort amenities - you'll love this adventure so much, you'll never want to head back home!brbrWhen you're done swimming in the shared pool or soaking in the shared hot tub, you can towel off and head indoors to relax. The private balcony provides amazing views of lush plants and wide-open blue skies, with the flatscreen TV of the living room right nearby. Whip up a delicious meal in the kitchen before retiring with your loved ones when it's time for bed. A dog is welcome. brbrGet started on your next great adventure - save your dates today!brbrTHINGS TO KNOW

Breezy Condo with Pool & Hot Tub, Private Parking & Great Location - Dog OK

Key West, Florida, United States

Bed

Bath

Sleeps

$675.0

This estate has it all waterfront, large sun-filled pool and seawall dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and entertain your guests. The home was recently rented to Actor Matthew McConaughey and others. Expansive living room with vaulted wood ceilings and oversize couches leads to a large dinning room table that seats six. Gourmet kitchen with granite counters and lovely wood cabinets that focuses on the love of food and cooking. Indoor laundry area is located just off the kitchen for convenience. Large veranda overlooks the backyard sun-filled swimming pool and boat dock includes a table set and grills making outdoor cooking a breeze. Split floor plan makes the expansive master-suite with king bed, his and her sinks and Jazuzzi tub separate from two private guest bedrooms, one with king bed and the other offering a queen bed. Make Cameron's Luxury Waterfront Estate your next Key West Vacation Home and don't forget to bring your boat! Note: boat lift is owner's use only.brbr

LUXURY WATERFRONT ESTATE SEAWALL DOCKAGE & POOL

Key West, Florida, United States

Bed

Bath

Sleeps

$1725.51

Situated in the heart of Key West, this unbelievable retreat will be the perfect place for entertaining the whole family! With three stories, high-end furnishings, and ample areas to spread out, there will ample room for everyone to indulge in their own kind of vacation. As if that isn't enough, recent renovations to enhance your stay include new carpet, updates to the upstairs bathrooms, and adding a waterfall to the pool. The interior is absolutely stunning with a gourmet kitchen, French doors throughout, and sunrooms to dive into your favorite book, yet stepping outside to the lush backyard will also be a treat. When days heat up, everyone can take a dip in the sparkling pool or simply lounge under the shade of the palms and banana trees as the chef of the group cooks up some burgers on the gas grill. Dine al fresco or gather with the whole family in the formal dining room to reminisce about the day's adventures. When the sun dips below the horizon, cozy up on the sectional sofa and play a movie on the TV with a bowl of popcorn. With so much fun to be had right at your fingertips, no one will want to leave this southern oasis!brbrLocated in Truman Annex, an exclusive private residential community in Old Town Key West, this home is situated on a small cul-de-sac just off Duval Street and close to great entertainment, dining, shopping, and attractions. When you want to venture out a bit, head over to the Key West Aquarium or Mallory Square, both sitting within walking distance of your front door. Little White House, the Key West Lighthouse, the Hemingway House, and Mel Fisher Maritime Museum are all great options as well within a few miles of home base. Don't forget to pop into some of the local restaurants and grab some seafood!brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brThis property is managed by Seven Keys Vacations by Casago.

Southern snowbird-friendly house with pool, stunning backyard & great location

Key West, Florida, United States

Bed

Bath

Sleeps

$161.02

*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.*brbrThis dog-friendly cottage includes street parking, a shared pool, and a location near Duval Street.brbrNestled in a quiet neighborhood about a mile from Higgs Beach Dog Park and a little under a mile to Mallory Square, you'll be able to get out and about with ease. With fresh seafood restaurants and dining spots right around the corner on Duval Street, you won't have to go too far to dive into it all. Take some time to wander through the unique shops to find that perfect prize to remember your trip. Do some stand-up paddleboarding or snorkeling while you're here.brbrSpend a relaxing afternoon by the shared pool. Connect to the free WiFi to book a reservation at a restaurant or cook a dish on the gas grill or convenient kitchen. Catch up with your favorite cable show in the central A/C while the private washer/dryer makes sure the laundry gets done. Chill out on the patio and slip into vacation mode. Two Dogs are welcome. brbrWhether you're taking in everything the beach scene has to offer, kicking back by the shared pool, or playing with your pups at the dog park, this Florida home makes it easy to let the stress melt away!brbr**This is a pet friendly unit with a two dog limit and a 35 pound weight limit for each dog.**brbrThis property is managed by Vacasa Florida LLC.

Cute Dog-friendly Tropical Condo with AC, WiFi, & Shared Pool - Snowbirds OK

Key West, Florida, United States

Bed

Bath

Sleeps

$419.76

The ideal location of this super-comfortable corner property makes it the perfect blend of convenience, tranquility, and tropical Key West scenery. Sit back and relax as you sip cocktails on the balcony, prepare a light meal in the newly renovated kitchen, and unwind in front of the living room smart TV after a day at neighboring Fort Zachary Beach. Or head down to the community's newly renovated, heated swimming pool to work on your tan.brbrWhat's nearby:brThe Shipyard Condos enjoy an enviable location in the Truman Annex area of Key West, just a short walk from the white sands of Fort Zachary Beach. You'll be amazed by how quiet this location is, despite being half a mile south of Mallory Square and two blocks from Duval Street's renowned shops, restaurants, and nightlife. You can easily stroll to the famous Ernest Hemingway House (a quarter-mile east) and the USCGC Ingham Maritime Museum (half a mile west) as well.brbrThings to know:brFree WiFibrFull kitchen

Alluring corner unit w/ full kitchen & pool - close to beach/ nightlife

Key West, Florida, United States

Bed

Bath

Sleeps

$293.21

Welcome to Julia Whitehead Guest Suites! Built in the 1890s on the site of what had been a small provisions and butcher shop, this charming building has a rich and captivating history. In the 1930s, while Hemingway was living a few houses down, it was home to a popular Cuban bodega. From the1980s through the turn of this century, potter Charles Pearson created ceramic masterpieces which are still collected today. If you keep a watchful eye, you will find some of his ceramic fish adorning buildings and homes in the neighborhood still. brbrIts current guardians have spent nearly a decade painstakingly bringing the building back to life, with three one-bedroom apartments, and hosting Dog Tired Studio gallery up front as the proud face of the building. Julia Whitehead, the patron mermaid of the building, has been keeping an eye over this landmark since she first surfaced here in the 1800s, and she invites you to come and live like a local, just steps from Duval, in the shadow of the lighthouse.brbrHere, at Mermaid's Retreat, you'll find a beautifully updated space, with colorful, eclectic decor and abundant natural light. Balconies off both the living room and bedroom upstairs are ideal for languid afternoons with a good book and some sweet tea, while the comfortable living room is a cozy hideout for a quiet evening spent watching TV or using the free WiFi to scroll social media. The full kitchen holds everything you need to whip up meals and snacks. When bedtime calls, head upstairs to drift off in your serene Key West sanctuary.brbrTHINGS TO KNOWbrA booklet inside the apartment features the full story of Julia Whitehead Guest Suites.

Apartment

Charming, colorful two-story apartment with two balconies - walk everywhere

Key West, Florida, United States

1

Bed

Bath