Vacation Home Rentals By Owner In Key West, FL

This one bedroom apartment on the ground floor is completely restored with a full kitchen and laundry. This unit has everything you need for an extended stay.Walk out to the private garden from your living room. Located on one of the best streets in Old Town. You are just 3 blocks from the Harbor, home to the freshest seafood restaurant and the best happy hours on the island. Or Walk down to Duval street to experience the local music scene and bar hopping, restaurants and shopping. Located in a privately owned historic home.brbrThis one bedroom has a California King and a queen pull out sofa in the living room. The kitchen is stocked with everything you need for cooking. There is a 55 TV in the living room and a 32 TV in the bedroom with cable and WiFi.brbrOutside enjoy the Tiki Bar for happy hour while sitting in the private garden, or jump in the hot tub to relax.brbrClose to everything, yet quaint and quiet, you will love your stay. We also have 2 other units in our home a 2 bedroom 1420448 and another 1 bedroom 1420515.

Just Restored One Bedroom Hideaway with Garden and Hot Tub 5 No Need For A Car

Key West, Florida, United States

Bed

Bath

Sleeps

$253.13

Your Key West Hideaway home is located in the heart of Old Town. Key West landmarks, attractions, Duval St, restaurants, coffee shops and bars with live music are all within walking distance. A pleasant 10 minute walk (0.5 miles) will take you to the bustling entertainment part of town located primarily along Duval St. brbrIf you want to unwind and relax, lounge under the palm trees of the large pool located within this seven house gated community and soak in the Key West easy lifestyle you are all set here at the house.brbrEverything you need is located within one minute walking distance from the property. Start your day with a morning cup of Cuban coffee at locally famous Five Brothers coffee shop across the street. Have lobster bisque for lunch with Key Lime pie for desert at the modern French Caribbean Café Sole and your dinner at the Italian Mangia, Mangia restaurant. All three locales are located within 100 yards from the property. brbrKey West Hideaway is close to all the action in town and yet far away enough from the noise to let you enjoy a good night of restful sleep. Not only is this community peaceful and quiet, but the house itself is tucked away at the far end of the property away from the occasional noise from the street. brbrRide a bike! Your Key West Hideaway is equipped with three bikes for you to use. Within minutes you will be able to reach all the best beaches in Key West including South Beach (6 min), Smather's Beach (13 min) and Fort Zach State Park Beach (8 min). The Historic Marina is just a few blocks up from home too!brbrWe've recently made some improvements in expanding your comfort in our home. We've finally added a bathroom! Our large second bedroom now has its own private bathroom, complete with a shower. This allows for a bit more privacy for multiple couples, guests, and children. We also added an outdoor shower! Have a quick rinse off from the pool or when you get back from the beach! br

Hidden Treasure in Old Town: 3BR Home with Pool in Peaceful Gated Enclave

Key West, Florida, United States

Bed

Bath

Sleeps

$169.15

Welcome to Island Paradise, your serene retreat in the heart of Key West, Florida! Located in Old Town, Island Paradise is just a half block from the world-famous Duval Street. This charming property offers 2 bedrooms and 2 bathrooms, perfect for small families or couples looking for a relaxing and convenient escape. brbrBOOKING DATES... This home is only available as a monthly rental (28 day 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. brbrbrProperty Overview:brbrPrime Location:brEnjoy the convenience of nearby local attractions, dining, and shopping, all within just a few steps.brbrbrElegant and Comfortable Living Spaces:brIsland Paradise features two cozy bedrooms, each thoughtfully decorated with a coastal theme to enhance your Key West experience. The Master Bedroom has an ensuite bathroom. The open-concept living area boasts comfortable seating, a flat-screen TV, and large windows that fill the space with natural light.brbrbrOutdoor Features:brStep outside to a deck area where you can lounge by the small, refreshing pool. Enjoy the seclusion of a large tropical yard, surrounded by tropical foliage. This space is perfect for sunbathing, enjoying a morning coffee, or relaxing in the loungers. brbrbrHighlights Include:br-Private Pool: Cool off in your own private pool, complete with comfortable lounge chairs.brbr-Hot Tub: New March 2025brbr-Modern Kitchen: The fully equipped kitchen offers stainless steel appliances and ample counter space for preparing delicious meals. There is a Keurig.brbr-Cozy Bedrooms: Each bedroom is designed with relaxation in mind, featuring comfortable queen-sized beds, soft linens, and beach-themed decor.brbr-1 Designated Parking Space on property for guestsbrbrbrComfort Amenities:brbrLiving Spaces: The living room is comfortably furnished, creating a perfect spot for relaxing after exploring the city.brbrKitchen: Enjoy the convenience of modern appliances, including a dishwasher, microwave, and coffee maker.brbrDining Area: The quaint dining area seats five comfortably and is adjacent to the kitchen, making it easy to serve meals.brbrPets:br- This home allows 1 dog under 9 pounds for a $275 fee. If undisclosed pets are brought into the home without Dolphin Vacation's approval there is a fine of $500 per pet.brbrbrAccess for Guests:brGuests will have full access to the entire property, including the pool area. brbrbrExplore the Area:brDiscover the best of Key West with activities such as snorkeling, boat tours, and visiting the Ernest Hemingway Home and Museum. The lively Duval Street, with its eclectic mix of bars, restaurants, and shops, is just a short stroll away. There are a variety of great ways to explore Key West whether it be by bicycle, pedi-cab, scooter, golf cart, Uber, Lyft, Taxi, or foot. Being in the heart of downtown Key West, many attractions are within walking distance.brbrbrMake Your Reservation:brbrBook your stay at Island Paradise today! Don’t miss out on this charming Key West retreat!

Island Paradise 2BR House Pool, 1/2 Block to Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$346.21

This prime four-bedroom, three full baths, thoughtfully furnished and fully equipped home is a two-story townhome located on a quiet residential street within the Key West Golf Club Community and is the perfect place for your vacation to put you in A Key West State of Mind. There is a bedroom on the main floor with a full-size bed, SMART TV, desk, printer/scanner/fax machine and closet. A full bathroom with walk in shower is also located on the main floor. Three more bedrooms are located upstairs with the master offering a King bed. ensuite bath with double sinks, a sitting area with table, large closet and a screened in porch with cushioned lounge chairs and breakfast table to enjoy your morning coffee or afternoon refresher. Another bedroom has a Queen bed with storage under the bed, nightstand, nice size closet with table and chairs on the front balcony to enjoy any time of the day. The third upstairs bedroom offers two twin beds which can be converted to a King upon request, nightstand, a nice size closet, and an additional table and chairs on the front balcony which connect to the Queen balcony for everyone to enjoy. The Queen and Twin bedrooms share a bathroom with tub located in the hallway. All bedrooms have ceiling fans and SMART TV's. The living area has ample room for entertaining with plenty of seating – don’t miss our game drawers for fun things to do and our book collection for you to read and swap. The kitchen table has a removable leaf to accommodate more of your friends and bar stools to provide a convenient breakfast nook. There is also a spacious screened in porch off the living room with comfortable outdoor furnishings and a lovely view of the tropical flora and fauna as well as the Fairway. The fully appointed kitchen has everything needed to prepare your catch of the day - Pots/Pans/Cutlery, Blender, Toaster, Conventional Stove/Oven, Microwave, Coffee Maker, Ice Maker, Dishwasher and an outdoor gas grill with all utensils. The home also comes equipped with a Washer/Dryer, Iron and Ironing Board, Bed Linens, Pool Towels, blow dryers in each bathroom and more. The Golf Club Community offers a private gated entrance and 24-hour security services which provides a safe environment for an evening neighborhood walk, use of the large waterfall pool, smaller pool and the exercise room/gym. These complimentary amenities are located just a short walk across the street. This home provides a serene vacation setting when a lush private escape is needed, but still just moments away from the sights and entertainment of Historic Duval Street in downtown Cayo Hueso. Pets are welcome with prior approval and additional fee to help you live your best Key West State of Mind.

A Key West State Of Mind at The Key West Golf Club

Key West, Florida, United States

Bed

Bath

8

Sleeps

$403.12

smaller Bedroom with a separate entrance, plus 1 Bathroom, Central Air Conditioning, an enclosed outdoor Washer and Dryer, and covered Parking. The home has been freshly painted and a new Central Air Conditioning unit has been installed.A privacy wall and separate entrance to the unit in the back of the duplex, creates the perfect independent living situation from the main home. Enter to find a user-friendly kitchen, living room, and 1 Bedroom and 1 Bathroom. Step outside to the screened-in covered patio and tropical landscaping!

In the heart of Midtown

Key West, Florida, United States

Bed

Bath

Sleeps

$350.63

Dive into paradise at Mermaid Landing, your ultimate tropical escape nestled in the enchanting Florida Keys! Newly renovated with a magical mermaid-inspired décor, this 3-bedroom, 2-bath oasis offers the perfect blend of relaxation and adventure. Imagine waking up to the sound of rustling palms and a well-appointed kitchen where you can whip up tropical treats before stepping out to your own private beach, just a short stroll through the mangroves.brbrLounge under the sun as you gaze over the Gulf of Mexico, and if you're feeling adventurous, bring your flat-bottom boat for a seaside adventure. In the mood for fun Challenge friends and family to a round of pirate-themed mini golf or enjoy one of the many outdoor games in the spacious, turf-covered yard.brbrLocated at the end of a peaceful dead-end street, just 15 minutes from downtown Key West, Mermaid Landing offers tranquility with the perfect touch of excitement. Whether you’re watching Navy jets soar across the open sky or relaxing in front of a smart TV in each bedroom, this tropical paradise has something for everyone. With room for multiple vehicles, RV hookups, and space for your boat, it’s the ideal vacation spot for families, adventurers, and sea-loving souls alike.brbrBook your stay at Mermaid Landing and let your next vacation be one to remember!

Mermaid Landing, with Private Beach and Mini Golf Course

Key West, Florida, United States

Bed

Bath

8

Sleeps

$617.63

Flip Flop Inn is a beautiful 3 Bedroom 3 Bath home, (each bedroom has its own private full bath), and a Queen size Futon. We're located in the luxurious gated safe community of Coral Hammock. The grounds are beautifully landscaped and include a large community pool and a fitness room. Two parking spots are also included in your rental. We are ideally located at mile marker 5 which is only a 10 min hop to downtown Key West, Duval St, and all the action. The Key West golf course is directly across the street, and there are no less than 4 restaurants and a CVS within walking distance of the home. I invite you to come stay at Flip Flop Inn, guaranteed to add years to your life!

PET FRIENDLY! Completely REMODELED! 3 Bedroom 3 bathroom home. Sleeps 8

Key West, Florida, United States

Bed

Bath

Sleeps

$702.29

Location, location, location! Brand new and beautiful, this spacious house is conveniently located on a quiet street in the heart of Old Town Key West only 1/2 block from the fabulous shops, restaurants and bars that made Duval Street famous. brbrBeautifully furnished and luxuriously appointed, Bahama House has three bedrooms, all with private baths, graciously spread out over three floors. The ground floor features a fabulous gourmet kitchen, dining area, half bath, and sitting room with a wall of French doors that open onto the deck and private pool with waterfall. brbrThe master bedroom is located on the second floor and has a private balcony and marble bathroom. Just down the hall is a charming den with a sleeper sofa. The two third-floor guest suites are spacious and private with beautiful tree-top views of Old Town. brbrBahama House’s old world charm and modern conveniences are sure to delight! Amenities include private heated pool with waterfall, off street parking, laundry, wireless internet service, hard wood floors, central air conditioning, IPod dock, sleeps 6-8 people.

Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub

Key West, Florida, United States

Bed

Bath

Sleeps

$1157.63

Dolphin Watch is located in prestigious Truman Annex and is one of the few private waterfront homes. We are less than two blocks from Duval Street and beautiful Mallory Square sunsets. You can also see the sunset from your own private balcony! Walking distance to famous Fort Zachary State Park and Beach. The living area, master bedroom, bath, and kitchen are located on the second floor where you can enjoy the fantastic view of the harbour and sunsets. Downstairs offers 3 bedrooms/2 baths and leads outside to the large private pool.brbrKeywords: waterfront, private home

Waterfront Views from Dolphin Watch

Key West, Florida, United States

4

Bed

Bath

8

Sleeps

$266.97

NOSTALGIC AND INSPIRATIONAL HAVEN...brHistory permeates and echoes through the classic Dade Pine details of this lovingly preserved Conch cottage, once home of locally esteemed Liz Lear, the Duchess of Ashe Street. This retreat has hosted icons of literature and art such as Tennessee Williams, Leonard Bernstein, and other creative giants. Layered with cultural allure and situated on one of Old Town's most sought-after-streets, this home's storied past whispers to come in and find sanctuary here. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE***brbrDETAILS AND AMENITIES…brAs you enter through your white picket fence to the classic conch porch with intricate and whimsical woodwork into the welcoming interior, the style is Old World charm graciously restored to respect its historical weight, yet skillfully updated to satisfy modern convenience. A wall of French Doors, a stunning salvaged window and a 14 foot cathedral ceiling beckon soothing southernmost sunlight inside, enveloping you in its tropical warmth. A fully stocked contemporary kitchen and dining area encourage time spent breaking bread over lively debate with your favorite people. Choose from a library of novels to dive into or enjoy live streaming on Roku TV for all your favorite shows! A washer/dryer resides in an outdoor shed. brbrSLEEPING ARRANGEMENTS…brSlumber well in one of the two cozy bedrooms, one with a queen bed and the other with a queen futon and office space for those working remotely. Both rooms are equipped with a shower bathroom. brbrOUTDOOR LIVING…brA canopy of greenery and mature foliage shelter and shade you in your backyard hideaway, with a propane gas grill and seating for dining and dreaming under the sultry stars of Key West. A soothing turtle pond completes the experience and your island soul has found the garden of serenity it has yearned for.brbrPARKING...brThis home offers an off street carport.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)brbrCONCIERGE SERVICES...brEnjoy this service to assist you with planning activities for your trip. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night min.). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrMAKE YOUR OWN HISTORY HERE...

THE WRITER'S COTTAGE ~ Renovated Old Town 2 BR/2 Ba Home w/Parking!

Key West, Florida, United States

Bed

Bath

Sleeps

$570.53

Sun yourself on the back patio, then cool off in the pool. Rinse off in the outdoor shower with hot/cold running water. Dry yourself with the complimentary pool towels. Cycle along the convenient bike lanes on the complimentary bicycles—helmets, bike lights, and bike locks provided. *Just hanging out The delightful front porch is the perfect vantage point to watch the world drift by on island time on this quiet, three-block long street. Tuck into the cushioned porch sofa, sheltered from the street or on the sunny yellow Adirondack chairs with new cushions. *Working remotely Zoom from an easy chair in the sunny yellow bedroom or an oversized upholstered chair in the sunroom. Prefer a desk surface Choose among the dining room table, kitchen island, or more private bedroom desk. (High speed fiber internet, plus HP Deskjet 3755 printer & shredder.) br *Eat your breakfast by the pool, lunch at the kitchen island, dinner at the dining table. Or dine out after a short walk or easy bike ride. This bright, beautifully renovated Conch cottage is one of the most charming properties in Old Town Key West. Featuring Dade County Pine throughout, ceramic tile bathrooms and tasteful décor selections by a well-respected southeast designer. brbr*Two spacious bedrooms with en-suite bathrooms feature queen and full beds on opposite sides of the house for privacy, plus luxurious linens and towels. An open living room with expandable dining table leads to the gourmet kitchen plus a cheerful sunroom. The kitchen features Fiesta Ware dishes, Royal Worcester serving pieces, ample barware, pots and pans. Conveniently launder your clothes with the in-home washer/dryer. brbr*Located on one of the most desirable streets in Old Town, this quintessential Key West oasis is an easy walk from Duval St. and a short stroll from the Historic Seaport. Park your Mini-Cooper sized car off-street on a gravel pad.brbr*This is a private home, first rented out for the 2021 season (see our 5-star reviews!) and now very limited 2026 dates. Regretfully, no pets, no children, no smoking, no parties. No exceptions.brbr**30 day minimum stay**

OLD TOWN GEM in SEPT26! Private pool, stunning decor, 5-star reviews. NO PETS

Key West, Florida, United States

Bed

1

Bath

4

Sleeps

$226.53

Welcome to your Old Town Key West escape, located just one block from the legendary Duval Street. This charming two-level front unit at 415 Julia Street offers the perfect blend of historic character, tropical outdoor living, and unbeatable walkability—ideal for a monthly stay in paradise.brbrStart your mornings on the inviting front porch, a classic Key West feature and the perfect place for coffee while enjoying the island breeze. After a day at the beach or exploring Old Town, rinse off in your private outdoor shower, a favorite feature for island living.brbrInside, the home offers two levels of living space, creating a comfortable and spacious layout ideal for longer stays. Natural light, island charm, and relaxed furnishings make it easy to settle in and enjoy the slower pace of Key West life.brThe second level offers the sleeping quarters. The open loft offers a king bed while the guest bedroom, which is closed off to the loft offers a queen bed with en suite. The second full bathroom is located on the first floor.brbrLocated on picturesque Julia Street, this home places you just steps from the restaurants, galleries, and nightlife of Duval Street, while still offering the comfort of a quiet residential setting.brbrProperty Highlights:brbrPrime Old Town Key West locationbrbrOnly one block from Duval StreetbrbrTwo-level front unitbrbrCharming front porchbrbrWalk or bike to restaurants, nightlife, galleries, and historic attractionsbrbrIdeal for monthly vacation rentalsbrbrSpend your days exploring turquoise waters, historic streets, and vibrant island culture—then return home to your peaceful retreat in the heart of Old Town.brbrMonthly rental available. Inquire for availability and seasonal rates. There will be an annual renter in the rear cottage.brbrGuests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check. brImportant Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know.

Twin Palms on Julia - Heart Of It All - 2BD/2Bath - May - August 10% off!

Key West, Florida, United States

Bed

Bath

5

Sleeps

$920.62

Welcome to Elizabeth's Secret! You have found your secret!brbrA very private and secluded tropical oasis awaits you behind the private gated entrance at Elizabeth’s Secret, but just steps to all that Key West has to offer.brbrOnce inside the gate you will find a great space with plenty of outdoor seating and a private pool (NOTE: This pool can be heated for an extra cost, please inquire with your host prior to your stay).brbrYou find a wonderful covered front porch complete with a porch swing. The seating area is perfect for those times in which you want to get out of the sun but still be able to visit with family and friends lounging poolside. The side yard has room to relax while you grill your fresh catch of the day.brbrInside this charming 3 bedroom, 2 bath cottage you'll enjoy a bright and well-equipped kitchen inclusive of a breakfast bar, an open floor plan, cathedral ceilings, and a living area that has plenty of room for relaxation. Bring the outdoors inside by opening the French doors off the living room to the side deck where there is a space for outdoor dining.brbrThe master suite is decorated in bright colors, and has access to a private outdoor shower, (there is also a shower inside).brbrThe second bedroom is located upstairs over the living room in a large loft area. This loft-bedroom is open to the living-room below and has a king-sized bed.brbrThe third bedroom is downstairs and has access out onto the deck. It is a full sized bed.brbrWe are close to everything, even the Pickleball courts!brbrCome find out why Elizabeth Secret is perfect for you!

ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking

Key West, Florida, United States

Bed

Bath

Sleeps

$469.94

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

$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