Vacation Rentals By Owner In Key West, FL

$253.13

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

Key West, Florida, United States

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

4

Bed

2

Bath

5

Sleeps

$293.66

/ Nightly

Condo

On the Rocks, 3 Bedroom, 2 Bath Condo right on the beach

Key West, Florida, United States

Welcome to On the Rocks – Your Oceanfront EscapebrbrExperience coastal living at its finest in On the Rocks, a spacious and beautifully designed 3-bedroom, 2-bathroom condo with breathtaking views of the Atlantic Ocean. Located just steps from the shore, this open-concept vacation home offers the perfect retreat for relaxation, entertaining, and soaking in the natural beauty of Key West.brbrKey Features:brStunning Ocean Views: As soon as you step inside, you’ll be greeted by floor-to-ceiling sliding glass doors that offer an uninterrupted, panoramic view of the Atlantic Ocean. The wrap-around balcony is perfect for dining al fresco, morning coffee, or simply taking in the fresh ocean air and stunning Key West sunsets.brbrOpen-Concept Living & Dining: The expansive living area is filled with natural light and is perfect for both relaxation and entertainment. With ample seating, you and your guests can enjoy the sea breeze while lounging or hosting a gathering. The sliding glass doors can be opened in the winter to let in the refreshing ocean breeze.brbrGourmet Kitchen: The large, fully equipped kitchen is ideal for whipping up anything from a quick breakfast to a full dinner party. With counter seating for four and a dining table that also seats four, there’s plenty of space for everyone to enjoy meals together.brbrGuest Bedrooms: Down the hall, you’ll find two beautifully appointed guest bedrooms. One features a queen bed, while the other has a king-size bed. Both rooms are equipped with their own TVs and share a spacious bathroom with dual sinks and a large shower.brbrMaster Suite: The master bedroom is your personal sanctuary, complete with a luxurious en suite bathroom featuring a jetted tub, separate shower, and a walk-in closet for all your belongings. Like the guest rooms, the master bedroom also has its own private entrance to the balcony, where you can enjoy your morning coffee or relax with a good book.brbrOutdoor Living: The wrap-around balcony is the highlight of the condo, offering breathtaking views of the ocean and providing the perfect setting for outdoor dining or lounging. Each bedroom has direct access to the balcony, allowing you to step outside and take in the beauty of Key West at any time.brbrImportant 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. brbrGuests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check. brbrAdditional Amenities:brbrTVs in every bedroom for your entertainmentbrHigh-speed Wi-FibrAmple closet and storage spacebrProximity to local dining, shopping, and attractionsbrOn the Rocks is the perfect choice for those looking for a luxurious oceanfront getaway with all the comforts of home. Whether you're traveling with family or friends, this condo has everything you need to make your Key West vacation unforgettable.brbrBook your stay today and enjoy the beauty and tranquility of On the Rocks!

Bed

Bath

Sleeps

$169.15

/ Nightly

Private Vacation Home

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

Key West, Florida, United States

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!

Bed

Bath

Sleeps

$346.21

/ Nightly

Private Vacation Home

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

Key West, Florida, United States

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.

3

Bed

2

Bath

8

Sleeps

$403.12

/ Nightly

Private Vacation Home

In the heart of Midtown

Key West, Florida, United States

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!

Bed

Bath

Sleeps

$164.72

/ Nightly

Condo

1800 Atlantic Condo in Key West – Stylish 2BR with Pool, Tennis & Beach

Key West, Florida, United States

Stunning Renovated 2-Bedroom Condo with Island ViewsbrbrWelcome to your perfect island retreat! This beautifully renovated two-bedroom condo offers breathtaking island views and a prime location with easy access to everything Key West has to offer.brbrInside, you’ll find a spacious master bedroom with a king-size bed, a guest room with a queen-size bed, and a queen sleeper sofa in the living area—comfortably accommodating up to six guests. The modern kitchen is fully equipped with sleek stainless steel appliances, making it easy to prepare meals during your stay.brbrEnjoy peace of mind with one assigned parking space (vehicles under 6'2).brbrAs a guest at 1800 Atlantic, you'll also have access to exceptional amenities, including:brbr Olympic-sized heated poolbr 20-person jacuzzibr Three tennis courts (including a clay court)br Lush tropical gardensbr BBQ picnic areasbr Private sunning beachbrbrWhether you're here to relax or explore, this island-view condo is the ideal home base for your next Key West getaway.

Bed

Bath

Sleeps

$350.63

/ Nightly

Private Vacation Home

Mermaid Landing, with Private Beach and Mini Golf Course

Key West, Florida, United States

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!

Bed

Bath

Sleeps

$1624.48

/ Nightly

Condo

**MAYA’S SECRET TREASURE @ DUVAL** Pool & Balcony over Duval + LAST KEY SERVICES

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrWalking along Duval Street dreaming of the ideal Key West vacation destination, scanning the rooftops for possibilities, at first you’ll miss this hidden gem completely…but once you discover MAYA’S SECRET TREASURE, you will know you have found the ultimate home base to enjoy Key West. Perched above Duval Street, this beautifully modern condo offers the best of all things downtown Key West mixed with the best of a high end vacation home: a private rooftop deck overlooking Duval, a location just steps from all of the action, all with the privacy of a hidden entrance off a tiny lane, a private pool all your own, and three large bedrooms with en-suite bathrooms to steal away and enjoy your space. Pair this once-in-a-lifetime vacation home with Last Key Realty’s Five Star Guest Services and your vacation in paradise will be the lasting memory you treasure (until your next visit of course…)brbrYOUR PRIVATE POOL AREA & LANAI...brbrThe entrance to this property takes you through the private pool area, a fully fenced oasis of sunshine you won’t believe is just a stone’s throw from the famous Duval Street. Plenty of lounge furniture and chaise lounges offer a variety of sunbathing options by the pool. The pool can be heated upon request to your desired temperature (additional fees apply.) The BBQ grill is perfect for a poolside cookout, and we include the propane. Climb the stairs to the covered lanai area with a designer lounge swing, an outdoor dining table, and even an outdoor TV for watching the game in the island breezes.brbrYOUR EXCLUSIVE ROOFTOP DECK…brbrThe true crowning gem of this exceptional condo is the private rooftop deck perched right over Duval Street. A front row seat to the magic of the most desirable location in Old Town, this deck has been designed to host the evening of your dreams. There is a custom bar with bar stools to sit and look down on the action below or gather around the tables with inset fire pits to enjoy evening cocktails. You won’t find a better, more exclusive location in all of Key West, and this one is all yours!brbrTHE LIVING AREA...brbrMAYA’S SECRET TREASURE is the ultimate discovery for a group ready to experience all that Old Town Key West has to offer just outside your door, while offering the privacy of luxurious separate bedrooms with en-suite bathrooms. The living area is ideal for relaxing after a day full of adventure on island or out on the water, or for game planning the day's festivities over breakfast as a group. Around a large flat screen TV you'll find comfortable seating for the group. There is a dining set off the living area for a quick bite in. The artistic kitchen sits off the living area with luxury appliances and tools, equipped with everything you'll need to prepare a meal at home in between enjoying the fantastic array of Old Town restaurant options, all just a few blocks walk away. There's also a queen size sleeper sofa in the living room and a private reading nook with a sofa and armchair situated above the living area .brbrTHE ACCOMMODATIONS....brbrFirst Floorbr** Master Suite #1 - One King bed, a flat screen TV, walk-in closet, seating area, luxurious Master bathroom with soaker tub & glass shower.brbr** Master Suite #2 - One King bed, a flat screen TV, built-in cabinetry, en-suite bathroom with a glass shower.brbrSecond Floorbr** Bedroom #3 - Two Twin beds OR One King bed, a flat screen TV, a desk overlooking the pool area, en-suite bathroom with a glass shower, access to the rooftop balcony overlooking Duval.brbrFor the room with Twin beds that convert to a King, just give us a heads up of how you'd like these beds prepared for your particular group and we'll have them ready for your arrival.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced & Lushly Landscaped Private Yard br** Private Pool with available Pool Heatbr** Propane BBQ Grillbr** Rooftop Deck overlooking Duval StreetbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** Max of 2 Pets Allowed with Additional Fee of $200 per petbr** THIS HOME DOES NOT INCLUDE OFF STREET DESIGNATED PARKINGbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

3

Bed

3

Bath

8

Sleeps

$617.63

/ Nightly

Private Vacation Home

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

Key West, Florida, United States

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!

Bed

Bath

Sleeps

$702.29

/ Nightly

Private Vacation Home

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

Key West, Florida, United States

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.

Bed

Bath

Sleeps

$537.85

/ Nightly

Condo

Henry's Piece of Paradise on the Ocean in Key West - Weekly / Nightly

Key West, Florida, United States

Thirteen-hundred-fifty square feet of fabulous living space located on the second floor with garden and partial ocean views from a 38-foot private balcony accessible from the living and both bedrooms will make your vacation a memorable one and keep you coming back year after year.brbrClick on the calendar icon to check dated that are available. If the dates you need are not available check my other Key West vacation rental (Henry's Penthouse) located in the same (1800 Atlantic) complex.brbrBoth these Key West vacation rental properties were decorated and are managed (and maintained) by me personally, assuring you of a memorable vacation in a property that is way above the average investor owned rentals offered by management companies.brbrCall me now or any time within reason (9am to 11pm 7 days a week) to make the reservation or if you have any other questions. - I'm easy to reach and easy to talk to. Henry. brbrNotes:br1. My on line calendar is active and updated dailybr2. After reviewing you’ll know you found the right property with the right location at the right price.brbr

Bed

Bath

Sleeps

$1157.63

/ Nightly

Private Vacation Home

Waterfront Views from Dolphin Watch

Key West, Florida, United States

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

Bed

Bath

Sleeps

$379.11

/ Nightly

Apartment

Mesa House Uno - One block from Duval St

Key West, Florida, United States

Summary:brbrMesa House, Uno, is a charming condo in a prime location with a large front porch. Great for couples on a weekend getaway or friends looking to be in the heart of Old Town Key West. The fresh, modern space and full amenities make this 1-Bedroom Suite at The Mesa House the perfect spot for your next getaway. Walk a couple of blocks north and you're at the docks and about a mile south you'll find Southernmost Point and Higgs Beach. Historic Duval Street is also walking distance from this condo!brbrbrbrThe Space:brbrUp to four can stay at this one bedroom Suite at The Mesa House, with a sofa-bed provides the extra sleeping space. The entire compound can be rented for larger groups. (Please contact us for more information!) brbrbrbrA private washer and dryer make post beach cleanups easy, and the full kitchen gives you plenty of room to cook your fresh catch from a day of fishing.brbrbrbrCentral air conditioning cools the condo on the hottest days and rocking chairs await you on the porch when the mood strikes. The home is outfitted with two cable TVs and free WiFi.brbrbrbrReserve the one bedroom Suite at The Mesa House for your next getaway!brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guest will receive a personalized access code prior to arrival.brbrbrbrThe Neighborhood:brbrPlaced perfectly in-between Downtown and the Historic seaport, enjoy attractions like Mallory Square at sunset, Fury’s water adventures for a day at sea, and the Shipwreck and Mel Fisher Maritime Museum for some Key West History.brbrbrbrHalf a block from Duval Street, The Mesa House, is steps away from Key Wests most famous bars and kitchens. Local’s favorite restaurants, such as First Flight, Bagatelle and Two Friend’s patio are less than a 5 minute walk from your front door. Got a sweet tooth Keep an eye out for Kermit’s Key Lime Pie Shop in the Historic Seaport known for the best Key Lime Pie in Key West, or grab some homemade fudge and candy from River Street Sweets.brbrbrbrForgot something or need a quick fix Shorty’s Market has your last minute necessities for your weekend getaway. Just 2 blocks away you can also find Fausto’s food market for locally sourced groceries.brbrbrbrGetting Around:brbrOne of the best parts of staying in Key West is how close in proximity you are to everything. Don’t feel like walking Peddle your way to breakfast, or take a bike ride along the water at sunset. Rent your bikes from Fury or Island Bicycles who offer both pick up & drop off services to your home! Feel like you’re on island time when you rent from Minty’s where you can enjoy exploring Key West on a scooter or golf cart. In addition to these non-traditional modes of transportation, you can also Uber, Lyft or Taxi to your next destination. Pink Taxi is an easy, reliable and affordable way for getting to your rental from the airport.brbrbrbrThere is no on-site parking for this unit. brbrFor overnight parking here are some parking lots:brbr• 204 Simonton Street (This is directly next to your unit and the most affordable on the island!)brbr• Caroline Street Outdoor Parking Lotbrbr• Park N Ride Old Town Garagebrbr• Fleming Street Overnight Pay to Park lotbrbrbrbrStreet parking information:brbr• There are pay-to-park spots and meters and it is free from 12AM - 8AM. With a 3 day limit.brbr• The neighborhoods of Old Town offer some free parking spaces, but be aware that many of the spots are marked “Residential Only” and visitors are NOT permitted to park in them.brbrbrbrOther Things to Note:brbrThere is no parking provided for this unit. brbrNo pets or smoking allowed.brbrPrivate washer and dryer

Bed

Bath

Sleeps

$600.69

/ Nightly

Apartment

Mesa House Dos - One block from Duval St

Key West, Florida, United States

Summary:brbrWhether you're lounging on the front porch or enjoying a seafood dinner inside, this 2-Bedroom Suite at The Mesa House is the perfect home base for relaxation or adventuring Key West. This home's great location and relaxed atmosphere invite you to embrace the island lifestyle. Placed perfectly in between Downtown and the Historic seaport, enjoy attractions like Mallory Square at sunset, Brightwild Adventures for an afternoon out at the sandbar, or the Shipwreck Museum for some Key West History.brbrbrbrThe Space:brbrThe two bedroom Suite at the Mesa House is a part of a larger property that can be rented all together for bigger groups. (Let us know if this is something that you're interested in!) brbrbrbrYou can expect a full kitchen, including a fridge, oven, stove, and microwave.brbrbrbrBedroom 1: KingbrbrBedroom 2: Two TwinsbrbrExtra Sleeping: Queen pullout couch in the living areabrbrbrbrA private washer and dryer make post-beach cleanup easy. When choosing to relax at home, enjoy the home's two cable TVs, as well as free WiFi. Central air conditioning helps keep everybody comfortable.brbrbrbrBook the 2 bedroom Suite at The Mesa House, Dos, for your group's next Key West adventure!brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guest will receive a personalized access code prior to arrival.brbrbrbrThe Neighborhood:brbrThis home is located in the heart of Key West's action, with plenty of dining and entertainment within walking distance, including historic Duval Street. Stroll a few blocks north to the docks, where snorkeling, boating, and other aquatic adventures await you.brbrbrbrHalf a block from Duval Street, The Mesa House, is steps away from Key Wests most famous bars and kitchens. Local’s favorite restaurants, such as First Flight, Bagatelle and Two Friend’s patio are less than a 5 minute walk from your front door. Got a sweet tooth Keep an eye out for Kermit’s Key Lime Pie Shop in the Historic Seaport known for the best Key Lime Pie in Key West, or grab some homemade fudge and candy from River Street Sweets.brbrbrbrForgot something or need a quick fix Shorty’s Market has your last minute necessities for your weekend getaway. Just 2 blocks away you can also find Fausto’s food market for locally sourced groceries.brbrbrbrGetting Around:brbrOne of the best parts of staying in Key West is how close in proximity you are to everything. Don’t feel like walking Peddle your way to breakfast, or take a bike ride along the water at sunset. Rent your bikes from Fury or Island Bicycles who offer both pick up & drop off services to your home! Feel like you’re on island time when you rent from Minty’s where you can enjoy exploring Key West on a scooter or golf cart. In addition to these non-traditional modes of transportation, you can also Uber, Lyft or Taxi to your next destination. Pink Taxi is an easy, reliable and affordable way for getting to your rental from the airport.brbrbrbrUnfortunately, there is no on-site parking for this unit. brbrFor overnight parking here are some parking lots:brbr• 204 Simonton Street (This is directly next to your unit and the most affordable on the island!)brbr• Caroline Street Outdoor Parking Lotbrbr• Park N Ride Old Town Garagebrbr• Fleming Street Overnight Pay to Park lotbrbrStreet parking information:brbr• There are pay-to-park spots and meters and it is free from 12AM - 8AM. With a 3 day limit.brbr• The neighborhoods of Old Town offer some free parking spaces, but be aware that many of the spots are marked “Residential Only” and visitors are NOT permitted to park in them.brbrbrbrOther Things to Note:brbrThere is no parking provided for this unit. brbrNo pets or smoking allowed.brbrPrivate washer and dryer

2

Bed

1

Bath

6

Sleeps

$266.97

/ Nightly

Private Vacation Home

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

Key West, Florida, United States

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...

Bed

Bath

Sleeps

$369.7

/ Nightly

Condo

Dee's Dream Sunset Condo with WiFi and AC in Key West - 2 bdrm - Shipyard #151

Key West, Florida, United States

This beautiful 2-bedroom condo in the quiet and private gated Shipyard Community. It has rave reviews & 2 blocks from famed Old Town & Duval St. with its legends like the original Margaritaville, Sloppy Joe's, the Hemingway House and Treasure Museum. Outdoor deck for relaxing or secluded dining. Enjoy our pool and nearby Fort Zachery Taylor's sand beach. First-Floor Convenience: Easier access and no stairs to climb.brbrUnique Features:br* Gated Community: Enhanced security and peace of mind.br* Private Terrace: Outdoor living space for relaxation and entertaining.br* Swimming Pool: Enjoy refreshing dips on hot days.br* Proximity to Duval Street: Easy access to the heart of Key West's entertainmentbrbrOld Town Key West is packed with iconic landmarks and attractions! Here are a few of the most famous:br* The Southernmost Point Buoy: This iconic landmark marks the southernmost point of the continental United States.br* Duval Street: The heart of Key West, Duval Street is a vibrant mix of bars, restaurants, shops, and street performers.br* Mallory Square: This waterfront park is famous for its nightly sunset celebrations, with street performers, musicians, and artists.br* Ernest Hemingway Home and Museum: Explore the former home of the renowned author and see his famous six-toed cats.br* Key West Lighthouse & Keeper's Quarters Museum: Climb the lighthouse for stunning views of the island and learn about its history.br* Fort Zachary Taylor State Park & Beach: Relax on the beach, explore the historic fort, and enjoy water activities.br* Key West Butterfly & Nature Conservatory: Discover a tropical paradise filled with colorful butterflies.brThis is just a small taste of what Old Town Key West has to offer. You'll find something to fascinate everyone, from history buffs and art lovers to beachgoers and nightlife enthusiasts.

Bed

Bath

Sleeps

$570.53

/ Nightly

Private Vacation Home

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

Key West, Florida, United States

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**

2

Bed

1

Bath

4

Sleeps

$226.53

/ Nightly

Private Vacation Home

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

Key West, Florida, United States

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.

2

Bed

2

Bath

5

Sleeps

$314.6

/ Nightly

Condo

The Salt Cay | Updated! Stunning Sunset View, Pool

Key West, Florida, United States

The Salt Cay | Updated! Stunning Sunset View, Pool!brbrEscape to The Salt Cay, a serene, beautifully updated, and well-appointed 2-bedroom condo nestled in the tranquil Sunrise Suites community on east side of Key West. Just a mile from the beach, this charming getaway offers the ideal combination of relaxation and adventure. Whether you're lounging by the pool, exploring nearby attractions, or enjoying the comfort of your condo, The Salt Cay is the perfect place to unwind and make lasting memories.brbrThe Ambiance:brStep into The Salt Cay and experience a tasteful blend of modern coastal charm, where sleek quartz countertops, modern white cabinetry, and an open-concept layout create the perfect space for gathering with family or friends. This gorgeous two-bedroom suite accommodates up to six guests, featuring a king-sized bed in the master bedroom, a queen-sized bed in the second bedroom, and a queen pullout sofa in the living area for additional guests. The fully equipped kitchen, complete with a Keurig and electric stove, makes meal preparation a breeze, while the private balcony offers spectacular sunset views. For added comfort, enjoy cable TV, WiFi, and central air conditioning throughout your stay.brbrGuest Access:brEnjoy a smooth arrival with our contactless check-in process, where you'll receive a personalized access code to enter your unit. During your stay, take advantage of the shared amenities, including:brbr- Shared heated pool and hot tubbr- Tennis courtbr- Walking paths and biking trailsbrbrLocation Highlights:brThe Salt Cay is ideally located within the peaceful Sunrise Suites Resort, just a short distance from Key West's best attractions. A quick 10-minute drive will take you to the lively Duval Street, where you'll find a vibrant mix of restaurants, bars, and entertainment. For added convenience, the Key West airport is just a short drive away, making travel easy and stress-free.brbrGetting Around:brWith parking available, you'll have easy access to explore the island by car. If you prefer to travel by bike, scooter, or golf cart, rentals are nearby for your convenience. Key West's walkability means many attractions are just a short stroll away, and for longer distances, taxis and rideshare services are readily available.brbrOther Things to Note:br- Pet-Friendly! 1 dog (40lbs maximum) with a $20 per pet per night feebr- Private washer/dryer in unitbr- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, walkways, pool, parking areas, and common outdoor areas. No cameras are placed in private or interior spaces.brbrAt Colocada Vacation Rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

2

Bed

2

Bath

6

Sleeps

$920.62

/ Nightly

Private Vacation Home

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

Key West, Florida, United States

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!

3

Bed

2

Bath

6

Sleeps

Vacation Rentals By Owner In Key West, FL

$253.13

$293.66

$169.15

$346.21

$403.12

$164.72

$350.63

$1624.48

$617.63

$702.29

$537.85

$1157.63

$379.11

$600.69

$266.97

$369.7

$570.53

$226.53

$314.6

$920.62

Rent a place that suits your needs

Most popular vacation rentals in Key West

$2179.76

$2489.04

$2433.36

$2377.08

$2193.75

$2144.26

$2072.19

$2078.34

$2519.19

$2168.85

Most Popular Cities in Florida