Vacation Home Rentals By Owner In Key West, FL

$211.53

Emma's Secret by AvantStay | Heart of Old Town | Month Long Stays Only

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbrLocated in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you a cause to celebrate the island's way of life.brbrA fabulous location that will allow you to walk or bike to all the island highlights. In the heart of Old Town, Duval Street is an easy stroll to the live music, entertaining shops, and galleries along with Mallory Square where hundreds gather nightly to celebrate the setting sun and watch the local street performers. Fabulous food everywhere but the local's favorite and a Key West must, Santiago’s Bodega is just steps away and Blue Heaven where visitors flock for key lime pie and roosters run about your feet.brbrLocated in a private building with only four condominiums, this ground-level unit has been recently updated with appliances, granite countertops, and beautiful wood cabinets. The trendy urban feel to Emma’s Secret comes complete with flat-screen TVs, WIFI, and all you need in your home away from home. Cozy living spaces for the days you need a time out or place to hang your bag in between island adventures.brbrRelax by the breathtaking free-form pool and enjoy the hot tub as it spills over creating a soothing tropical retreat. A perfect place for collecting sunshine or just lazing the day away. Beautiful tropical foliage will surround you in this island oasis.brbrThis property will sleep 4 guests, with 2 bedrooms and 1 bath. Emma’s Secret features a queen bed along with a set of bunks for a dreamy night's rest and a fabulous full kitchen to whip up our favorite island fare or just a margarita.brbrThese properties are available on a monthly basis only but that’s OK, pack your bags, and bring a little extra because you might just not want to leave.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- Please note that all bookings 28 days or longer will require a security deposit of $2000 which will be collected after the booking has been made. Multiple months reservations might be subject to a higher security deposit fee.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br-This home has access to a community pool and hot tub. It is a combined pool & spa where water can flow.br- This home features a sleeper sofa for additional sleeping options.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:brStreet parking only,brNo assigned parking space, the parking next to the property is owner's parking ONLY.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bed brBedroom 2 / Queen bedbrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

2

Bed

1

Bath

4

Sleeps

$242.0

/ Nightly

Condo

2 Bedroom Townhome in Key West Golf Club

Key West, Florida, United States

Summary:brbrPet Friendly! 2-Bedroom, 1-1/2 Bathroom Townhome at the Key West Golf ClubbrbrbrbrThe Space:brbr10brbrbrbrStep into our Island Oasis! A very spacious 2-bedroom, 1 1/2 -bathroom home, perfect for your island getaway, in the coveted gated community of the Key West Golf Club. With beach-style flooring throughout and charming shiplap accent walls in the living area and main bedroom. This home exudes the island life and Key West charm. The open concept living and dining areas flow seamlessly from the fully equipped kitchen to a large, screened deck. Looking through the glass wall with sliding doors is a peaceful view of the yard and serene butterfly garden. Upstairs, enjoy a private balcony off the front bedroom and another large screened in porch off the rear bedroom. Just around the corner is the expansive heated lagoon-style pool, perfect for a refreshing swim, enjoy your favorite book, or a cocktail. Our Island Oasis is just minutes away from some of the island's best hidden gem restaurants and island activities. Whether you're looking to explore the vibrant nightlife on Duval Street or enjoy the laid-back atmosphere of downtown, you're only a quick 10-minute drive away. Don’t forget your golf clubs or rent theirs. This is a perfect Oasis and ideal for those who want to be close to the action but still enjoy a peaceful retreat. Your island adventure awaits! Pet Friendly

2

Bed

1

Bath

5

Sleeps

$408.04

/ Nightly

Private Vacation Home

Savor Margarita on Margaret w/ PRIVATE Pool

Key West, Florida, United States

Savor the Key West Lifestyle at Margarita on Margaret - Private All Oasis. Escape to your own private slice of paradise in the heart of Old Town Key West. This beautifully restored historic conch-style home with a charming guest cottage offers the perfect blend of classic island character and modern comfort. With three bedrooms and two and a half bathrooms, it’s an ideal retreat for families and friends looking to relax, recharge, and enjoy the best of Key West living.brbrStep through the white picket gate and into a lush, fully fenced property surrounded by vibrant tropical landscaping. A welcoming front porch with cozy seating sets the tone for the warm, inviting atmosphere you’ll find inside.brbrThe main house features an open-concept living room and kitchen with soaring tongue-and-groove wood ceilings, white beams, and plenty of natural light. A wall of accordion glass doors opens fully to the spacious deck and sparkling pool, creating seamless indoor-outdoor living. The kitchen is well-appointed with stainless steel appliances, a large granite island with seating, and everything you need to prepare meals at home.brbrBoth bedrooms in the main house are spacious retreats with en suite bathrooms, vaulted ceilings, TVs, and charming island details, including a Dade County Pine accent wall in the primary suite. The separate cottage overlooks the pool and features a cozy cabinet bed, high ceilings, sliding glass doors, and a half bath en suite — a private hideaway for guests.brbrOutdoors, you’ll find everything you need for the ultimate tropical escape: a large pool with sun loungers, an outdoor shower, a grill, and a dining area for six. Whether you’re swimming, sunbathing, or enjoying cocktails poolside, the private backyard is the perfect spot to unwind.brbrLocated in a desirable Old Town neighborhood, the home offers the best of both worlds: a quiet residential feel just steps away from all the action. You’ll be within walking distance of Duval Street’s restaurants, shops, and nightlife, as well as Higgs Beach, the White Street Pier, and the famous El Siboney Cuban Restaurant.brbrVacation like a local and make unforgettable memories in this one-of-a-kind Key West retreat.

Bed

Bath

Sleeps

$412.5

/ Nightly

Cottage

LAST MINUTE AVAILABILITY! architect designed OASIS in OLD TOWNE on a quiet lane!

Key West, Florida, United States

Turtle House. A Key West Artist's haven. Now available from January 8th through March 8th 2026! brbrDelight in the uniqueness of this property. It is a compound comprised of two former cigar maker’s cottages, redesigned and renovated by the artist and her late husband, an architect. Turtle House has been featured in several magazines, including the April 2009 edition of Coastal Living Magazine, and Design Within Reach summer catalogue 2019. Turtle House is located on a quiet lane in Old Town Key West near the cemetery. WAlk everywhere! brPrivate parking in front of the house.brbrCome finish your novel or work from home. A wonderful desk and computer monitor and printer set up for your use! brbrdip your body into the sunken black tiled jacuzzi. Dine under the covered breezeway beneath a bamboo pergola, protected from weather, with beautiful views of the garden illuminated at night by solar lighting. brbrFind magic and inspiration at Turtle House, along with all the comforts and amenities of modern living. Serenity abounds... br brFor those who seek elegant simplicity and a refuge in nature, this may be your dream come true! With privacy difficult to find in Key West... bike or walk to your favorite restaurant or cook at home on the gas grill and eat under the stars! Wake up to the song of birds and sleep peacefully to the sound of tree frogs and crickets. br brThe house is appointed with finr linens, dishes and cookware that offer a comfortable elegance to the rustic design of the cottages, The principle bedroom is its own cottage, furnished with a king size bed, an excellent mattress, a 24 x 68 desk and a bookshelf full of inspiration. brbrThere is a full indoor/outdoor bath attached to the cottage that can be accessed from the cottage or from the deck. The second bedroom is located in the main cottage. It is a cozy retreat, with a full size bed (brand new mattress) and its own bathroom which opens to both the bedroom and the living room. This bedroom faces the lane with a beautiful garden just outside the window. It is a wonderful place for an afternoon nap!brbrTurtle House is not for everyone! There are no marble countertops, no dishwasher, there are window aircondtioners, but no central air. But what there is cannot be overlooked or bought for all the money in the world....a magical oasis to provide a perfect retreat, a peaceful haven, for the sophisticated nature loving soul!brbr A perfect spot for a poet, or a poetic soul, a writer, an avid reader, an architect, a lover of architecture! a person who needs to continue working while on vacation. The lush gardens have been lovingly cultivated by the artist, herself. The owner, a well known Key West artist, hopes you will find inspiration and respite in this unique hide away!brbrCome and enjoy TURTLE HOUSE.brbrTurtle House has a 30 day minimum stay. Ideally, renting to a couple who would use the front bedroom (full size bed and private bath) as a guest room for friends or family to visit.brbr It is truly a little jewel. (Not for partiers, smokers, heavy drinkers, and revelers...sorry)

Bed

Bath

Sleeps

$321.01

/ Nightly

Private Vacation Home

The Local's favorite spot.

Key West, Florida, United States

The best of living on the water, just 10 miles from Key West on a canal with 35 ft. water frontage and direct access to the Atlantic. Excellent paddle boarding, kayaking, and boating! Beautiful, clean, and lovingly updated 3 bedroom, 2 bath home for your pleasure. Enjoy the wonderful local ambiance of Geiger Key Marina just a short walk or paddle from the house. Take in a waterfront happy hour and delicious fresh local seafood, or take a short 10 mile drive (or Uber) for the culture, nightlife, and dining experiences of down town Key West!brbrOur family home comes complete with 3 speed cruiser bikes for a casual ride down to Boca Chica beach, and we have beach chairs, BBQ, hammock, etc. to create your perfect vacation experience.brbrThe kitchen is stocked with utensils, pots and pans, dishware, glassware, toaster oven, coffee makers(Keurig and drip), blender, and microwave in addition to oven and fridge. Across from the kitchen is the 3rd bedroom, that functions as an office, exercise, playroom, and comes with a twin bed. You can also use a double bed blow up mattress provided (as pictured). As you proceed down the hallway, on the left side is the hall bathroom, and at the end of the hallway is the second bedroom complete with queen adjustable bed. On the right side is the master bedroom and bathroom with a queen adjustable bed, TV, and bathroom with shower and a Toto washlet.brbrDisclaimer: There are occasional naval jets that fly overhead. When flying overhead they are loud, although cool to see, especially when flying in formation. These instances are random and days can go by without hearing them at all. They never fly at night. That said, we want our guests to know that these fly-bys can occur.

Bed

Bath

Sleeps

$3027.32

/ Nightly

Private Vacation Home

Quaint Key West Getaway: Historic Knowles House w/Private Pool & Rooftop Deck

Key West, Florida, United States

Short walk to Duval Street. Central location. Restaurants nearby. Surrounded by charm of Key West. 7 to 8 rooms with ensuite bathrooms for the family. Explore the city then come back home to hang out with family & friends or by the plunge pool. There is an outdoor shower and propane gas BBQ available for use. 2 onsite parking spots included for regular & compact vehicles. Large/oversized SUVs may find it difficult to fit 2 vehicles side by side but there is a parking garage located just 1.5 blocks away.brbrWe offer a portable crib please request in advance. Subject to availability. brbrMain House:brRoom 1 - located downstairs w/ensuite bathroombrRoom 2, 3, 4, & 5 - located upstairs with ensuite bathroombrLiving room has TV and gamesbrKitchen, laundry room, & small dining areabrbrGuest House:brRoom 6: King bed, downstairs, ensuite bathroombrRoom 7: (couch/queen Murphey bed cabinet/kitchenette as seen in photo) flex space w/bathroombrRoom 8: King bed, downstairs, ensuite bathroom

7

Bed

8

Bath

16

Sleeps

$477.02

/ Nightly

Hotel

Close to Key West International Airport! Beachfront, 4 Pools, Shuttle, Parking!

Key West, Florida, United States

Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins herebrbrThis listing is for a room within a hotel.brbr✦ Your room is 376 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

1

Bed

1

Bath

2

Sleeps

$617.57

/ Nightly

Hotel

Beach Break in Key West! Beach Access, 4 Pools, Parking and Shuttle Service!

Key West, Florida, United States

Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins herebrbrThis listing is for a room within a hotel.brbr✦ Your room is 376 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

1

Bed

1

Bath

4

Sleeps

$349.86

/ Nightly

Hotel

Short Drive from Historic Old Town Key West! Beachfront Hotel, 4 Pools, Parking!

Key West, Florida, United States

Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins herebrbrThis listing is for a room within a hotel.brbr✦ Your room is 376 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Bed

Bath

Sleeps

$325.09

/ Nightly

Hotel

Ultimate Florida Getaway! Garden View, 4 Pools, Shuttle Service and Parking!

Key West, Florida, United States

Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins herebrbrThis listing is for a room within a hotel.brbr✦ Your room is 376 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Pool is available.brbr✦ Paid valet parking – 1 space(s), available for $32.25 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A mandatory resort fee of $51.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

1

Bed

1

Bath

2

Sleeps

Select Dates for Price

Spectacular Ocean Views, Refreshing Sea Breezes with an Island Atmosphere. KW

Key West, Florida, United States

CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 AtlanticbrStart Date: May 2025-Estimated Completion: Spring 2026brPlease be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026.brImportant Notes:br-Units available for booking will not be under construction.br-All amenities, including the pool, spa, and sunning beach, will remain open and fully operational throughout the project.brbrbrbrbrExplore the Best of Key WestbrbrExperience the perfect blend of comfort and island luxury in this beautifully renovated 2-bedroom condo at 1800 Atlantic, located less than 1.5 miles from the Historic District.brbrThis spacious, fully tiled condo features:brbrKing bed in the master suitebrQueen bed in the guest roombrHigh-speed wireless internetbrComfortable, modern furnishingsbrbrEnjoy breathtaking views of the Atlantic Ocean from the expansive private balcony, accessible from both bedrooms and the living room.brbrResort-Style Amenities at Your FingertipsbrbrLarge Heated Pool & Jacuzzi Spa – Just a one-minute walk from your doorbrOn-Site Sauna – Unwind and rejuvenatebrExclusive Clay Tennis Court – The only one on the island!brLush Tropical Landscaping – With direct beach accessbrSecure assigned parkingbrbrPlease note: During our prime season (December through April), we only accept monthly reservations beginning on the 1st of each month. Availability will not show for other dates during this period.

Bed

Bath

Sleeps

$123.69

/ Nightly

Cottage

The Ivy Cottage - Private Home in Key West

Key West, Florida, United States

Tucked away on a quiet street in the heart of Old Town Key West you will find the quaint and comfortable Ivy Cottage. This well-appointed home offers everything you will need to feel at home for your extended stay - a comfortable queen bedroom, fully stocked kitchen and living area, fast Wifi, private front and back porches, and a heated swimming pool. Here you are a quick stroll to the beach and lots of great dining, shopping, and attractions. One convenient parking space is included.brbrThe shotgun style cottage opens to the queen bedroom, which leads to a hallway with storage, laundry, and the bathroom. The living area, kitchen, and dining space are in the back of the home, which opens to a porch with seating and dining for four. The swimming pool is just steps from the back porch, shared with the three other cottages on-site.

Bed

Bath

Sleeps

$1959.71

/ Nightly

Hotel Resort

Sunset Harbor Resort & Spa, Hot Tub, Pool

Key West, Florida, United States

Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and beautiful contemporary design creates an environment of relaxation and restoration. Guests are encouraged to slow down and relax, to dip into the outdoor pool and whirlpool hot tub while soaking up some famed Floridian rays. Guests will also receive privileges at the adjacent Hyatt Key West Resort & Marina, offering even more ways to keep occupied even on your off days.brbrThe right size, the perfect view and the must-have amenities... Hyatt Sunset Harbor Resort's residences become the perfect home-away-from-home during your stay in Key West! Classic studios offer a king-size bed, casual living area, TV and DVD player. The one- bedroom tropical-style residence features a deluxe queen bed, fully-equipped kitchen, dining area, ceiling fans, seating area with TV, stereo, DVD player and private balcony. The beautiful two-bedroom residence is even more luxe, and includes a master suite with king-sized bed, adjoining bath and spa tub, a guest suite with queen bed and full bathroom. In addition, enjoy a fully-equipped kitchen, seating area, TV, DVD player and balcony!brbrHyatt Sunset Harbor isn’t just another Key West property - it’s in the heart of Old Town, the heart and soul of one of America’s most treasured vacation destinations. Nearby, you can also enjoy Duval Street shopping or nightlife and Mallory Square. Of course, if you're looking for more natural pursuits, you have plenty of options - Key West is a haven for fishers, and the unique ecosystem is well-suited to those seeking to explore by foot or bike. Plenty of unique attractions await those looking for a change of pace - check out the The Harry S. Truman Little White House, Key West Aquarium, Key West Lighthouse Museum and Mel Fisher Maritime Heritage Museum!brbrOn-Site Features & AmenitiesbrConciergebrInternet accessbrOutdoor poolbrShared laundry facilitiesbrWhirlpool/hot tubbrNearby AttractionsbrBarbrBoatingbrDrug storebrFitness centerbrGolfbrGrocery storebrHikingbrLive entertainmentbrOceanbrParkbrRestaurantbrRiverbrShopping areabrSnack barbrSpa servicesbrTennisbrWater skiingbrWind surfingbr** Policies **brNo PetsbrNo SmokingbrbrThe resorts require a credit card at check-in to cover potential charges for damages, liabilities, and incidentals. If there are resort fees those will need to be paid directly to the resort as well. The owner is responsible for providing the Guest with reasonable notice of any such inconveniences of which the owner becomes aware before or during the guest’s stay. Most resorts are amenable to requests for custom bed formats and/or unit views which can be requested at check-in. Please note parking fees may apply and are not included in the price quoted here. The room view is not guaranteed here and varies, if you would like an upgrade to a specific view please let me know and if available I can do that, additional fees may be required. Additionally some resorts have various towers/buildings and these may vary. Again, please check with us in advance to discuss the view/building/unit and any additional fees that may apply. Finally, Tourist Accommodation Taxes vary at resort and must be paid directly to the resort this is standart to resorts and may vary depending on location. For more information ask about the fees prior to making your Booking Request.”

Bed

Bath

Sleeps

$175.89

/ Nightly

Condo

1-bedroom 2 blocks to Duval, close to beach, parking, and pool

Key West, Florida, United States

Located in Key West 2 blocks from Duval and half a mile to Beach, enjoy what this 1-bedroom condo has to offer. This lovely property features a cozy bedroom with a queen bed and a comfortable living room with a sofa bed. Guests can relax in the peaceful atmosphere and take advantage of amenities like AC, WiFi, and a washing machine and dryer. You will have your own parking space and access to the common pool.

1

Bed

1

Bath

3

Sleeps

$391.46

/ Nightly

Condo

Art-Filled 1,700SF 3BR/2BA Old Town Key West Home with 2 Decks, Pool, Parking,++

Key West, Florida, United States

Large art-filled, two story Key West condo boasts 3 inviting bedrooms, including a king bed, queen bed, and an office or third bedroom for extra flexibility. Guests enjoy 2 full bathrooms, one with a large shower and one with bathtub. Furnished as a home not a vacation rental and filled with fine art, guests can settle in for longer stays and live like locals. Located within the prime Old Town Key West quadrant, a short stroll to and from the Duval downtown, Truman Ave., the Marina, White Street Arts walk, and more, and surrounded by flora and shade, there's no quieter place to unwind and rest, eat in or make home base for enjoying all Key West has to offer. Enjoy one of the largest pools on the island, heated and salt water, 2 TVs, stereo, coffee maker, blender, W/D, DW, etc. etc.. Feel free to reach out to us during your stay – we’re happy to suggest local spots to check out.

Bed

Bath

Sleeps

$534.38

/ Nightly

Condo

The Galleon Resort Best Resort Location in Key West

Key West, Florida, United States

June unit 1bd 1ba with pull out sofa-sleeps 4, 5th floor with large balcony, great marina views. The Galleon Resort has its own marina, fishing charters on site, tiki bar that serves food and drinks while you watch the yachts cruise by, pool with hot tub, beach with swim platform, 6th floor observation deck, sun decks, sauna, gym, covered parking and linen change once per week-more often if desired. Best location to stay in key West! Right on Front St, walk to Duval St and Mallory Square.

1

Bed

1

Bath

4

Sleeps

Select Dates for Price

Private Vacation Home

Sumptuous Home w/ Private heated pool, Central AC, WiFi & Private Washer/Dryer

Key West, Florida, United States

Prime Key West LocationbrbrEscape to laid-back island living in this inviting Key West retreat, where tropical beauty and everyday comfort come together seamlessly. Tucked away in a quiet, greenery-filled neighborhood, this single-story home offers a peaceful setting while keeping you close to everything that makes Key West unforgettable.brbrStep outside to your private backyard oasis, complete with a sparkling pool, tranquil garden views, and a charming avocado tree that adds to the authentic island vibe. Grill up your fresh catch on the gas grill and dine alfresco under the stars, or cool off indoors with central air conditioning after a day in the sun.brbrPerfect for couples, families, and remote workers, this well-equipped home features fast WiFi, a dedicated workspace, and a private washer and dryer for added convenience. At night, unwind in comfortable bedrooms designed for restful sleep, so you're refreshed and ready for the next day's adventure.brbrNearby Attractions:brLocated just one mile from Old Town Key West, you're moments from world-famous Duval Street, the Ernest Hemingway Home & Museum, and the Key West Butterfly & Nature Conservatory. Spend your days soaking up the sun at Higgs Beach or Smathers Beach, or enjoy a scenic walk to White Street Pier and the historic Martello Tower for breathtaking coastal views.brbrWhether you're exploring the island's rich history, chasing beach days, or simply relaxing poolside with a good book, this home provides the ideal backdrop for an extended stay in paradise.brbrThings to knowbr• Minimum stay of 28 nights requiredbr• Optional pool heat available for $7.50 per nightbr• Pool heat must be requested at least 48 hours prior to arrival and applies to the full staybr• Fully equipped kitchen with dishwasherbr• Flat path to the front doorbr• Located on a bike path and bus routebr• Beach towels providedbr• Futon in the living room offers additional sleeping spacebr• Snowbird-friendly—contact us for detailsbr• Please note: an active security camera is located in the garage and faces the carportbrbrThis property is managed by Vacasa Florida LLC.

Bed

Bath

Sleeps

$430.78

/ Nightly

Private Vacation Home

LATITUDE ADJUSTMENT ~ Prestigious 3 Bedroom, 3.5 Bathroom Home with Pool!

Key West, Florida, United States

UNMATCHED ISLAND RETREAT…brTucked away within one of the island’s most impressive lanes in the Casa Marina district, this retreat is sure to offer optimal serenity from your everyday reality. An expansive estate revealing a classy blend of luxurious details and everyday comforts, your Key West escape is sure to be spent to the fullest. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brPull up to a convenient off-street parking space and step into this generous, open layout with wood flooring throughout. Mesmerizing at a glance, exceptional décor and precise finishes reveal pure perfection. A bright gourmet kitchen offers top of the line stainless steel appliances with gorgeous custom cabinetry and a build in bar for happy hour. Come together among cozy living room furnishings and a flat screen smart TV with a powder room nearby. Cheery natural light pours in through multiple French doors creating an inviting indoor outdoor space. A desk lies in the upstairs hallway for those working remotely. Enjoy cable TV in the flex room off the living room and smart TVs throughout the rest of the house! This property is equipped with a Ring Doorbell located next to the front door of the home. brbrSLEEPING ARRANGEMENTS…brTotaling 3 bedrooms and 3.5 bathrooms, this home allows ample space and privacy for all your guests. Follow the stairs to the second level to find two guest rooms outfitted with king beds connected by a jack and jill bathroom with a shower. Down the hall is the primary suite with a king bed, flat screen TV and a private en suite full bathroom with a tub/shower combo. All upstairs rooms have access to an oversized balcony overlooking the lush outdoor oasis below. A convenient laundry room resides on the second level hallway. Off the downstairs Great Room is another living space with a sleeper sofa, TV and an en suite bathroom with a glass shower. brbrOUTDOOR LIVING…brStep out to a covered back porch with vibrant garden views surrounding a heated, lagoon shaped pool, dining table for 8, flat screen TV and outdoor shower. Unwind as your sip on your crafted cocktail and turn up the music on the Sonos system before you hop in to town for a taste of all the action! brbrPARKING...brThere is off street parking for your convenience. brbrPETS...brNo pets please.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).brbrFIND YOUR LATITUDE ADJUSTMENT…

3

Bed

3

Bath

6

Sleeps

$343.11

/ Nightly

Condo

Contemporary Dog-Friendly Cottage with Easy Beach Access & Shared Pool

Key West, Florida, United States

Book your well-deserved getaway to this dog-friendly Key West home. With a prime central location near Duval Street and access to a shared pool, this home will let up to four guests and your happy puppy (for a small nightly fee) unwind in style. brbrNotice: This is in a residential area, Quiet Hours are 10:00pm- 8:00ambrbrRight in the heart of the action, this home surrounds you with mouthwatering dining options, historical sites like the Ernest Hemingway Home and Museum, and of course, the Key West beaches. brbrBury your toes in the warm Florida sand while you catch up with a good book on by the waves. Book your spot on a deep-sea fishing adventure, or maybe explore the coast on a stand-up paddleboard. Toss a load in the shared washer/dryer then take your tropical cocktail out to the shared pool to catch some rays. Connect to the free WiFi and stream some gentle background music before whipping up a dish in the fully equipped kitchen. brbrWhether you're wandering through the charming shops, sampling the local fare, or slipping into vacation mode on the iconic beaches, this dog-friendly Florida Keys home makes it easy to enjoy it all.brbr**This is a pet friendly unit with a two dog limit and a 35 pound weight limit for each dog.**

Bed

Bath

Sleeps

Select Dates for Price

Private Vacation Home

Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin

Key West, Florida, United States

This beautifully home with quaint charm has a one month minimum stay requirement because of local zoning regulation. Colorful and breezy with covered front and back porches. Sliding back doors open onto lush landscaping and one of a kind lazy river heated pool. brbrEquipped with full kitchen, washer/dryer, local art that includes an original Shel Silverstein mural. (Shel was a beloved Key West artist and author.) brbrSteps from Blue Heaven Restaurant, Hemingway.House and Duval Street but you can retreat to a quiet home in one of the last authentic Key West neighborhoods. Two bicycles come with the property. One parking space is included with this property, however, you don't need a car! Everything is a short walk or bicycle ride away!brThe heated pool is shared within a five home community. Responsive and helpful and friendly owners live just across from the pool. brbrTwo bedrooms each have a queen size bed. Two bathrooms each have walk in showers. HDTV cable and high speed WIFI are all included.brbrThis is a one month minimum rental! Come join us and live like a Conch in the Conch Republic for a month or longer! If you can work from your laptop, you have two full desks and wifi so you can work in paradise and play in paradise when you are finished telecommuting.

2

Bed

2

Bath

4

Sleeps

Vacation Home Rentals By Owner In Key West, FL

$211.53

$242.0

$408.04

$412.5

$321.01

$3027.32

$477.02

$617.57

$349.86

$325.09

$123.69

$1959.71

$175.89

$391.46

$534.38

$430.78

$343.11

Rent a place that suits your needs

Most popular vacation rentals in Key West

$2168.85

$2433.36

$2377.08

$2193.75

$2179.76

$2078.34

$2059.55

$2072.19

$2489.04

$2144.26

Most Popular Cities in Florida