Home Vacation Rentals By Owner In Key West, FL

Showing 1020 Of 2059 Vacation Rentals
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Exceptional(164)

$520.81

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Condo

CASABELLA@DUVAL SQUARE Lovely 2 Bedroom 2.5 Bath Townhome in a great location

Key West, Florida, United States

Duval Square is a charming community with shops and restaurants downstairs and secure, quiet, private residences, pool and pavilion upstairs. Although the condo includes one assigned parking space in the gated garage, you can stroll anywhere from this conveniently located condo. All of the shops, galleries, restaurants, and attractions on and around Duval Street and nearby beaches are just a leisurely stroll away. brbrWhen you enter the home you will find a fully equipped kitchen, dining area, spacious living room and a convenient half bath. French doors let in the natural sunshine and open to the private back deck with dining table and chairs perfect for outdoor entertaining. brbrOn the second floor, you will find 2 bedroom suites, each with their own private bathroom and an additional private balcony off the main suite.brbrBedding: 1 king, 1 queen, 1 queen sleeper sofa.brbrElevator access from ground level to the first floor of the condos. Stairs to the unit's second floor bedrooms.brbr**Construction Disclaimer** From mid May through the month of June, 2026, the pool area will be under construction. This will create noise and dust that could impact your stay and may lead to pool closure as well.
Bed 3

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Bath 2

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Sleep 6

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Exceptional(42)

$457.53

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Condo

205E La Brisa-2BR 2BA beachfront condo w/parking, shared pool, grills

Key West, Florida, United States

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrThis property is a 7 night minimum. 30 night stays also available! brbrFEATURES:brBedrooms: 2 (1 king and 2 twins-can be converted to a king)brBathrooms: 2brLocation: La Brisa Condominiums brSquare Feet: 1166brParking: Parking lot in front of condo buildingbrAmenities: Wifi, TVs, in-unit laundry, beachfront, shared pool, outdoor grills, private balconybrbrbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.
Bed 2

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Bath 2

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Sleep 4

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$343.14

/ Nightly
Condo

Casa Atlantica: A studio condo on the Atlantic shore of Key West

Key West, Florida, United States

Located just steps from the White Street Pier and Higgs Beach, Casa Atlantica truly lives up to its name: a home perched on the very edge of the turquoise waters of the Atlantic. Located on the quiet end of a waterfront townhome community, this property features simply the best views you will find in Key West. Best of all, Casa Atlantica is located just a short bike ride from Duval Street and the Historic District, so you get the peace and quiet of the tranquil shore without sacrificing access to Key West’s unsurpassed restaurants, shops, and attractions.brbrOpen the door to this property and you are welcomed by an entire wall of floor-to-ceiling windows, giving you unrestricted access to the most breathtaking view in the Keys. Slip outside on to the enormous, private, top-floor patio and enjoy the warm sunshine and salty breeze of the natural shoreline. Playful pelicans and majestic egrets swoop and dive into the cobalt-blue water directly in front of you! This is true coastal living at its best.brbrThe large patio doors can be left open to allow the ocean breeze in to the spacious studio living area, which features a king sized bed, comfortable chairs for lounging, a flat screen television and a large dining table. The fully equipped kitchen features a glass-top range. Down a short hallway is the large, unique bathroom featuring a glass enclosed shower and lots of closet space. The entire home features distinctive, Adobe-style rounded walls and charming brick tile floors. The whitewash walls reflect the lovely natural light and create an effect that is fresh and soothing to the senses.brbrIf you want to put your toes in the sand, head downstairs to charming tiki hut right by the water. This property also has a shared washer and dryer and limited street parking. Please be aware that this unit is accessible only via 3 flights of a centrally located staircase.brbrIf you are dreaming of a vacation by the shore, it doesn’t get any closer than Casa Atlantica!brbrBedding: 1 Kingbrbr*Disclaimer: Due to the property's oceanfront location, please be aware that Key West experiences seasonal occurrences of fermenting turtle grass along the south shore of the island brought on by our southern winds in the summer. This is a natural phenomenon that is outside of our control.
Bed 1

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Bath 1

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Sleep 2

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Exceptional(21)

$531.17

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Private Vacation Home

~ SOLARIS PAIR-A-DISE ~ A garden lover’s dream on a quiet Key West lane.

Key West, Florida, United States

THE PROPERTY: If you are looking for that tropical island vibe, look no further! Both sections of this casual home are comfortably furnished. Located on a teeny tiny quiet lane, you will find Bohemian bits indoors and lush landscaping outdoors. brbrThe front section of this duplex (SOLARIS COTTAGE) has a covered front porch, sunny walls, and Florida furnishings. The open concept living room and dining area lead to the fully equipped kitchen including a gas range, microwave, and dishwasher. From your white bedroom with reading chair and dresser storage you may access the outdoor area. The bathroom has a window, single sink, and tub/shower combination. brbrThe rear section of this duplex (SOLARIS GARDEN) has warm wood tones, exposed beams and an open concept living area. A bright kitchen and island seating have all you need to enjoy a meal. A white bedroom with dresser and closet storage is separated from the main living area by a partial wall and a draped entrance. The bathroom is cozy and bright with a pedestal sink, tiled walk-in shower, and shelf storage. Outdoor amenities meant to be shared with others in your group include a deck under a giant Banyan tree, a grill, and an outdoor washer and dryer. SOLARIS PAIR-A-DISE provides two separate spaces for you to enjoy a casual carefree vacation with your extended family or friends. brSOLARIS PAIR-A-DISE consists of both front and back sections of a first-floor duplex home, and each has their own entrance. SOLARIS COTTAGE occupies the front section of the duplex and SOLARIS GARDEN occupies the back section of the duplex.br brBED CONFIGURATION: Each queen bedroom is adorned with bedside tables, lighting and dresser storage. brbrOUTDOOR AMENITIES: This duplex home has an outdoor garden area, deck, chairs, grill, and washer/dryer. brbrPARKING: By renting both sections of this duplex home, you have access to a small parking space for a compact car. Please note this home is on a tiny, one-way lane.brbrLOCATION: The property is in Old Town, North of Truman Avenue and just a block and a half from Duval Street. You are just a short walk or bike ride to many tourist attractions, bars, restaurants, shops, and galleries including Mallory Square, known for breathtaking sunsets and performers. brbrPETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry, cats are not allowed.brbrSMOKING: This is a non-smoking home and property.brbr***Guests must be 25 years of age or older unless accompanied by an adult.br br***Managed by Historic Key West Vacation Rentals***
Bed 2

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Bath 2

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Sleep 4

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Exceptional(15)

$401.25

/ Nightly
Private Vacation Home

Beautiful Key West Townhome

Key West, Florida, United States

Come on in, relax and enjoy our wonderful slice of paradise. Over 2,000 square feet of luxurious living space. Our two bedroom, three bath town home is located in a very safe gated community, Seaside Residences.brbrOur town home is beautifully and tastefully decorated with designer touches throughout. After a fun & sun filled day in Key West, travel the three floors on your own private elevator. While in the living room open the two large double doors, to a stunning view of the Atlantic, or just put your legs up and enjoy the 75 inch lcd TV with surround sound. Each queen sized bedroom is also equipped with large flat screen tv's. Enjoy our fully equipped designer kitchen with beautiful granite countertops,& stainless steel appliances, with seating for ten, a perfect area for entertaining.brbrOpen the doors to four wonderfully furnished balconies. There is also a secluded roof deck for those of you that require that full body tan.brbrThe ground floor lanai and backyard is a very special area, with beautiful Travertine stonework, comfortable furnishings for a large group, lush landscapping, stainless steel gas barbeque, a beautiful outdoor stone firepit for those chilly Key West winter nights, a stunning stone Lion Head water fountain, and a quiet hammock area to read your favorite Hemmingway novel., and of course another flat screen TV. All beautifully accented with soft landscape lighting for your night time entertaining. brbrFor your morning exercise, we are located steps away from the pool, hot tub, and exercise facility. For your convenience we have included two new touring bikes. Start your day with a ride along the beach and view a spectacular quiet Key West sunrise, there is nothing like it. Also in the two car garage are four beach chairs, snorkel equipment, and coolers, for your day at the beach, and for you to use, to see & experience this very special, unique place called Key West.. Do enjoy!!!brbrPlease keep in mind, this is for a 28 night min. rental...brbrKeywords: Townhome
Bed 2

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Bath 3

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Sleep 6

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Exceptional(29)

$192.25

/ Nightly
Condo

Away From It All @ The Truman Annex

Key West, Florida, United States

Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval Street and all the Old Town Key West attractions. The properties are also ¼ mile from Fort Zachary Taylor State Park. The property is outfitted with washer/dryer, pots/pans, towels, linens, have central air conditioning, off street parking, and pool access. This corner second floor Shipyard Condo has big, beautiful French doors in the living room. They open onto both front and back balconies with views of the treetops and Old Town Key West. Away from it all has full amenities, including flat screen TV’s in the living room, both bedrooms and wireless internet access. The master bedroom has a queen size bed and the guest bedroom has the option of 2 twins or a king size upon request. After a full day of taking in the island’s many wonderful experiences, come back to the comforts of home. The manicured landscaping, verdant palms, and white picket fences give the Shipyard and Truman Annex a lovely park atmosphere. All this tranquility makes it hard to imagine that Duval Street, Key West’s central artery of entertainment is only two blocks away. Both bedrooms do have flat screen TV's. brPlease note: This property is monthly rental - the minimum rental period is 28 nights
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Bath 1

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Sleep 4

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Exceptional(150)

$1898.57

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Private Vacation Home

NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking

Key West, Florida, United States

Seaside Place welcomes guests from all states and follows all cleanliness and safety guidelines. Your safety and comfort is top priority - feel free to reach out to us with any questions, we are always here to help!brbrClassic Key West style, just off Duval Street with Atlantic Ocean view. Built in 1910, this 2700 square foot, classic revival style home is authentic Key West workmanship, complete with wood peg structure, traditional balconies and gingerbread trim. Refurbished by our current owners, Seaside Place is a spacious 5 bedroom, 5 bathroom home with private master suite (inclusive of kitchenette, living space, private entrance and balcony access), off-street parking, and the largest and deepest heated pool in Old Town private home. Space is your luxury here: our common areas comfortably accomodate all guests for dining and lounging, while large bedrooms allow for privacy and rest. Our pool deck offers covered dining space, chaise seating for all guests, shaded conversation nook, grill deck and full bungalow bathroom with shower. You'll never feel cramped or in tight quarters while staying with us!brbrSeaside Place Interior:brbrYour vacation begins as you enter our main foyer. Look down the hallway and you'll catch your first glimpse of our crystal clear pool. To the right is our sunlit living room, full of custom woodworked furniture, handcrafted by ownership. The living room opens to the colorful kitchen, complete with bar seating for a light breakfast and coffee, yet fully appointed to cook your catch and prepare a memorable dinner for all guests. Pass through window allows easy access to the dining room, with a panoramic view of the pool deck. Dining room features custom furnishings and a convenient banquette with ample seating for guests to dine and make memories together, or find a comfortable space for reading and relaxing. brbrThe back bedroom allows for both privacy and access - a king sized bed and western light ensure restful sleep without disruption. The en suite bathroom offers a wall length mirror with grooming station. A door provides access to the laundry room, featuring two sets of washers & dryers for your convenience, extra towels, housekeeping supplies and sunblock - there is a second door out to the pool, so wet pool towels can easily be transferred to the wash.brbrThe front bedroom features southwestern exposure and windows overlooking the porch. The king sized bed has decorative bedding and sheets by The Company Store. Stairs welcome you to the second floor and shared bathroom. The back bedroom has a queen sized bed and bonus daybed, with built in closet.brbrMove down the hall to the front room and enjoy bright natural lighting and en suite bathroom. Relax in the hallway sitting area and enjoy the ocean breeze through the porch door. Cozy seating adorns the balcony, where you'll easily pass time enjoying the Atlantic and people watching below.brbrThe private master suite is the gem of our home and our favored space. Enter the living space, featuring futon and chairs overlooking the front balcony. The king sized bed features an intricately detailed headboard and romantic bedding. There is a dining table for two just outside the kitchenette, with refrigerator, sink, small appliances and free standing ice machine. The en suite bathroom is spacious with a private linen closet. A private entrance provides access to the upper balcony, with a staircase to ground level.brbrInterior decor and furnishings are tropical and vibrant - the artwork themes for each room were curated by our owner and carefully considered to inspire a sense of place: you are experiencing vacation in Key West, this is the rest you deserve.brbrSeaside Place Exterior:brbrSeaside Place offers an extraordinary Key West experience. Our pool deck is second to none for a private residence: the 15' x 30', 7' deep heated pool is unique to our property - you will not find a pool this big, this deep or this private anywhere else in Old Town. The cabana bathroom provides the quintessential vacation experience by allowing you to bathe in the warmth and tranquility of nature. Dining outdoors under the moonlight or chatting in the shade of the sitting area are where the memories of vacations are made.brbrThe long driveway offers off street parking, a rarity in Old Town. Use the space for cars, bikes, golf carts or scooters; there is plenty of space available. The front porch is calm and luxe, and the perfect place to enjoy morning coffee or a happy hour cocktail and watch the world peacefully pass by. From the white picket fence to the detailed wooden craftsmanship, every aspect of Seaside Place is a reminder of your Key West experience. The side porch houses luggage storage, should you need space to store your items outside of check in/check out hours. Trash and recycling recepticles are tucked away at the back.brbrStaying at Seaside Place and indulging in our unique amenities will reimagine your idea of an island getaway. When you're ready to depart your haven and take in the thrills of Duval Street, a quick half block walk takes you to exquisite art galleries, exciting nightlife, fresh seafood and delicious dining, the Southernmost Point, the Butterfly Conservatory and access to the Duval Loop. brbrSeaside Place Bedrooms:brbr• Front downstairs bedroom - queen sized bed, en suite full bathroombr• Rear downstairs bedroom - king sized bed, en suite full bathbr• Front upstairs bedroom - queen sized bed, en suite full bathbr• Front master suite - king sized bed, futon, en suite full bath br• Rear upstairs bedroom - queen sized bed with twin daybed, hallway bathroombrbrAmenities: 15' x 30' heated pool with waterfall, tropical landscaping, wrap around upper and lower balconies with seating, outdoor covered dining, 3 fixture cabana bathroom, two off street parking spots, Atlantic Ocean view, luggage storage, full equipped kitchen, 2 free standing ice makers, twin washer & dryer sets, televisions in all bedrooms, central air conditioning, internet, cable television, master suite with kitchenette, concierge service. Mid-week housekeeping service may be scheduled.brbrRestrictions: Smoking permitted outdoors only, ashtrays must be used for refuse. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian. Pets are not permitted.
Bed 5

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Bath 4

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Sleep 12

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Exceptional(26)

$444.38

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Cottage

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

Key West, Florida, United States

Welcome to the Jolly Rooster!brbrWe’re thrilled to welcome you to our newly renovated, standalone cottage—proudly presented by the owners of the Dancing Rooster. Thoughtfully designed for relaxation and comfort, the Jolly Rooster comfortably hosts up to six guests and blends island charm with modern convenience.brbrNestled just one block from vibrant Duval Street, you’ll be steps away from Key West’s best dining, shopping, and nightlife—while still enjoying the peace and privacy of your own retreat. Our cottage comes fully equipped with all the essentials for a carefree and memorable stay.brbrCome unwind, explore, and experience the best of island living at the Jolly Rooster!br________________________________________brThe SpacebrbrThis thoughtfully designed retreat includes:brbr• 2 private bedrooms, each with a queen bed + ensuite bath (walk-in showers)br• Spacious living area with American Leather queen sleeper (memory foam, no bars/springs)br• Smart TVs + high-speed internet throughoutbr• Private entrances for both bedrooms and living roombr• Any use of the sofa bed—whether your group exceeds 4 guests or not—incurs an additional charge of $100 per night, plus applicable state and local taxes.br________________________________________brFully Equipped KitchenbrbrPerfect for prepping anything from snacks to full meals, featuring:br• Granite countertopsbr• Cooktop stove and Rangebr• Microwavebr• Refrigerator with ice makerbr• Coffee maker, toaster, and blenderbr________________________________________brLocation Highlightsbrbr• 1 block from Duval Streetbr• Walk to Hemingway House, Marina District, beachesbr• Across from Sugar Apple natural food cafébr• 1 block to CVS + bike/scooter/golf cart rentalsbr• Duval Loop (free shuttle) stops ½ block awaybr________________________________________brParking & TransportationbrbrNo dedicated parking. Free street parking on Simonton (first come, first served).brExplore by foot, bike, scooter, or golf cart!br________________________________________brOther Things to Notebrbr3-night minimum staybrNo smokingbrWe recommend travel insurance—especially during hurricane season (June 1–Nov 30). No refunds for weather or early departures.brbrTravel insurance is strongly recommended, especially during Florida’s hurricane season (June 1 – November 30). No refunds will be issued for weather-related disruptions or early departures. You may consider providers such as Travel Guard (AIG), Nationwide, Allianz, Berkshire Hathaway, or Red Sky.
Bed 2

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Bath 2

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Sleep 6

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Exceptional(13)

$448.82

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Condo

World's End at the Truman Annex in Key West

Key West, Florida, United States

Enjoy spectacular 3-way Key West views from the large wrap-around deck without leaving your rental unit. This 2 bedroom at, 2.5 bath Harbour Place condominium is in Key West's most prestigious community of Truman Annex, offering breath-taking, unobstructed sunsets over the Gulf of Mexico and Sunset Key, the harbor and boat marina, and adjacent to the beautiful Truman Waterfront Park. The large dining table, umbrellas, propane grill and cushioned deck furniture provide a fabulous gathering space, a quintessential Key West experience. The Truman Annex community is 2 short blocks from Duval Street, all of the Old Town Key West attractions and only 1 mile from the best beach/picnic area at Fort Zachary Taylor State Park. The historic Harry Truman Little White House, the Custom House Museum and the aquarium are next door and the world-famous Hemingway House is down the street. The unit sleeps 4 comfortably (renter may choose: 1 queen/2 twins or 1 queen/1 king) and is outfitted with a fully equipped kitchen, washer/dryer, abundant towels, linens, central air conditioning, WIFI, garage parking and a gorgeous waterfront pool area.brbrPlease note: This property has a 28 night minimum stay
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Bath 2

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Sleep 4

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Exceptional(1)

$330.83

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Private Vacation Home

Peak Of Duval

Key West, Florida, United States

Summary:brbrPeak of Duval- Sophisticated Bright & Breezy Duval Street ApartmentbrbrbrbrThe Space:brbrThis Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, and Entertainment in the heart of Key West. Ones you enter the property through your private entrance, you would be captivated by its expansive space. The oversized living room has an abundance of natural light coming from the Cathedral Ceiling Skylights. Comfortable couches and flat-screen TV will help relax after all the fun playing. Tastefully decorated two bedrooms have a Queen and Full-size bed. Double sink vanity and a shower tub are in Master Bathroom. Plush towels and high -end linens are provided for our most discerning guests.brbrbrbrFor those who love to entertain and cook, we offer fully equipped Chefs kitchen with new stainless steel appliances, granite countertop, and high top dining table. Kitchen opens to a second wing of the apartment where the casual entertaining area is located with a breakfast table, comfortable sofa,  flat-screen Tv, and a Glass Wall with two sets of French doors that open directly to the Duval Promenade view.  The second full bathroom with Shower is in the latter wing as well.brbrbrbrEnjoy people watching while sipping tropical cocktails in the privacy of your balcony.brbrbrbrThe great news is that your furry friends are all welcome to enjoy Key West with you.  A newly constructed dog-friendly park, Truman  Waterfront, is just 10 min walk away. On the weekend, Duval Street becomes a car-free promenade, and you have the front row seat.brbrbrbrGuest Access:brbrGuests will have access to the entire homebrbrbrbrThe Neighborhood:brbrThe famous Duval Street is the main street in downtown Key West, Florida, running north and south from the Gulf of Mexico to the Atlantic Ocean, just over 1.25 miles in length. It is named after William Pope Duval, the first territorial governor of Florida. It is a center of nightlife, restaurants, and shops. The closest beach is just 5 minutes away.brbrbrbrGetting Around:brbrA rental car is recommended.brbrbrbrInteraction with Guests:brbrWe value our guests’ privacy but are available if needed.
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Bath 1

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Sleep 6

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$325.92

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Private Vacation Home

POOLSIDE PARADISE ~ Charming 3 BR/2Ba Home w/ Pool!

Key West, Florida, United States

SPECTACULAR POOL HOME IN PEACEFUL SANCTUARY...brSpace, style and sunshine abound in this stunning 1926 single-story refuge, tucked in the tranquil neighborhood of Midtown Key West. This location offers the ideal balance between quiet residential charm and easy access to the island's most exciting attractions. You are minutes from all the adventures in paradise yet sequestered from the crowds as serenity and soothing escape lure you inside this perfect retreat.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brThis tropical abode blends historic architecture with modern creature comforts, ensconced in a sheltering landscape of dense vegetation and sultry palms. As you step inside, your spirit is soothed and serenaded by the charming architectural details throughout the interior, boasting a bright and airy open concept living and dining area for relaxing and unwinding after a day of outdoor diversions. The ample kitchen is appointed with all the tools and devices you'll need to craft your most ambitious cuisine. A full size washer and dryer reside inside the home for your convenience. Enjoy YouTube TV live streaming for binge-watching your favorite shows. There are outdoor cameras on the exterior of the home for security purposes.brbrSLEEPING ARRANGEMENTS...brWhen it's time to wash the day off and sink into bedded bliss, choose from one of the 3 plush bedrooms, outfitted with closet space and TVs for your comfort and pleasure. The primary bedroom features a king bed with a spacious en suite shower bathroom. One guest room offers a queen bed and the second guest room offers two double beds. There is a second full bathroom with a shower/tub combination for the guest rooms to share. All TVs are equipped with YouTube TV. brbrOUTDOOR LIVING...brYour backyard oasis is the hallmark of this home away from home, resplendent with a glorious heated pool, outdoor shower and a wide porch that's ideal for morning coffee and evening cocktails. Toss dinner on the grill and dine under the stars at your outdoor dining table. Let the southernmost breezes lull you into the ultimate state of relaxation in your tropical slice of heaven. 4 bikes are available for your evening island stroll and there is an additional cooler located on the back porch.brbrPARKING...brThere is off street parking for multiple vehicles at this home. brbrPETS...brThis is not a pet friendly home.brbrBOOKING DATES...brThis home is offered only 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.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).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!brbrUNWIND AND UNPLUG…
Bed 3

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Bath 2

Bath

Sleep 8

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Exceptional(5)

$545.59

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House Boat

Waterfront & Heated Pool - Away Awai Floating Villa

Key West, Florida, United States

Summary:brbrExperience Key West in a new way: aboard a luxury houseboat!brbrFrom watching sunrise on the dock to watching sunset from the rooftop, or enjoying one of the best happy hours in town, you won't even need to leave the Marina. Come aboard & see why life really is better on a boat.brbrbrbrThe Space:brbrEmbark on a unique getaway on our expansive houseboat, an aquatic haven that comfortably accommodates up to four guests.brbr Immerse yourself in the luxury of the master suite, complete with a queen-sized bed, private bath, and sliding glass doors that open up to breathtaking waterfront vistas from the back deck. Accompanying another couple Our second bedroom won't disappoint, boasting a queen-sized bed and direct access to a spacious bathroom. brbrRelax in the open living area or breathe in the salty air on one of the three deck areas. The fully stocked kitchen awaits your home cooked meals or venture out to the nearby Perry Marina restaurants for a delectable dining experience.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a code for the lock box to retrieve the key prior to arrival.brbrbrbrShared Features: This unique stay is located at the beautiful Perry Marina, where you have access to amenities including a pool, restaurants and barsbrbrbrbrThe Neighborhood:brbrThis property is located at the Perry Marina in Stock Island - the authentic and revitalized fishing and arts community located directly east of downtown Key West.brbrbrbrGetting Around:brbrArrive by boat, plane, or car. On-site golf cart rentals are available; or take advantage of the many taxi and ride-sharing services available for short trips around Key West and Stock Island.brbrbrbrOther Things to Note:brbr- The property is a houseboat docked at the Perry Marina. brbr- Shuttle service provided every hour to downtown (Key West Historic Seaport)brbr-The complimentary guest shuttle may also stop Publix and Higgs Beach by request. Call 786-862-6621 and allow one hour for the bus to arrive.brbr- It includes full service power and water. brbr- Other amenities include: Keurig coffee maker, private stackable washer/dryer, rooftop, steering wheel is for show (not use), first come first serve parking, and access to Perry Marina amenities.
Bed 2

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Bath 2

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Sleep 4

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Exceptional(2)

$220.82

/ Nightly
Apartment

Cozy spot next to Duval with swim spa - 2bed/2bath

Key West, Florida, United States

Fully furnished flat on the 2nd floor with 2brbedrooms (queen bed in each bedroom), 2 brfull bathrooms, futon/sofabed in the living room.brbrFull kitchen and laundry unit. Only a half abrblock off of Duval Street midway betweenbrMallory Square and southernmost point.brLess than a 2 minute walk to ErnestbrHemingway's home and steps to dining, barsbrand shopping. Available for monthly rentalbronly.brUse of the entire unit and shared outdoorbrspace with a swim spa.
Bed 2

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Bath 2

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Sleep 6

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$689.99

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Private Vacation Home

POPEYE'S COTTAGE ~ NEW! Historic 3 BR/3Ba w/ Pool in Perfect Location!

Key West, Florida, United States

NEW LISTING!brbrDISTINGUISHED LANDMARK GEM…brDiscover the irresistible appeal of Key West in this beautifully preserved Conch-style home, a true legacy of historic treasure. Originally built in the late 19th century, the property has been meticulously restored to give a respectful nod to its past, yet punctuated with state-of-the-art modern conveniences. Its exceptional renovation earned the prestigious Historic Florida Keys Preservation Award, highlighting the skillful craftsmanship and custom woodwork that showcase the beauty of Dade County Pine throughout the home. You are nestled in a private and quiet lane, yet a brief stroll from the vibrant local scene.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brInside, the home exudes refined comfort, with soaring ceilings and sleek stainless-steel appliances, complementing its elegant design. The kitchen serves as a central gathering space, thoughtfully designed to balance practicality and style—ideal for everything from casual meals to inspired cooking. Flowing seamlessly from the kitchen, the generous living areas create a welcoming environment for both relaxation and entertaining (with Youtube TV live streaming), merging indoor and outdoor living in classic Key West style.brbrSLEEPING ARRANGEMENTS:brEach bedroom offers a peaceful retreat, filled with character and a touch of island charm. Enjoy two bedrooms in the main house - the primary king suite and a queen guest room - both with ensuite shower bathrooms. Enhancing the property even further is a delightful poolside guest cottage with king bed and full shower bath, providing a private haven for visitors or family members. A versatile upstairs bonus room adds flexibility, perfect for use as a home office, sleeping area on the pullout, or cozy reading area.brbrOUTDOOR LIVING…brOutdoors, a lush tropical garden with an inviting pool (comes heated in the cooler months) and outdoor shower creates a tranquil setting, ideal for gatherings or simply unwinding in the sunshine. The vibrant landscaping captures the quintessential essence of Key West. brbrPARKING...brThis home offers 1 off street parking space in a moderately sized (no oversized SUVs) driveway off the narrow private lane. There is street parking on a nearby street, if needed.brbrPETS...brPets are considered and approved on a case by case basis with the required pet fee. Please include the size, breed and age when inquiring/booking.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).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!brbrCIRCA TIMELESS...
Bed 4

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Bath 3

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Sleep 8

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$176.04

/ Nightly
Private Vacation Home

Enjoy the best of Key West from this ideally located monthly rental just steps from the pool and close to Truman Waterfront, Fort Zachary Taylor State Park and Beach, Coffee Butler Amphitheater, and Duval Street. Private treetop deck.

Key West, Florida, United States

Cut and paste this video link https://www.youtube.com/watch v=9mv1bfrtnjI Just steps to the pool and close to Truman Waterfront sunsets, Fort Zachary Taylor State Park and Beach, Coffee Butler Amphitheater, and Duval Street. Walk to restaurants, bars, galleries, shops, live music, and waterfront events, return to a comfortable space designed for extended stays, seasonal escapes, and relaxed island living. Enjoy your mornings and afternoons on the Private treetop deck. brbrRoyal Palms Realty is available to assist before and during your stay. Guests will receive check-in details before arrival, and our team can help with questions about the home, the neighborhood, local recommendations, and anything needed to make your monthly stay comfortable.brbrThis property places you close to some of the best of Key West. Enjoy sunset walks at Truman Waterfront, beach days at Fort Zachary Taylor State Park and Beach, and concerts or events at Coffee Butler Amphitheater. Duval Street is also within walking distance, offering restaurants, bars, galleries, boutiques, live music, and the classic Old Town Key West experience.brbrGuests will have access to the rental, the pool area, and approved community amenities available to residents and guests. Any restricted owner areas, locked closets, or HOA-controlled spaces are not included. Parking and community access instructions will be provided before arrival.brbrThis monthly rental is set up as a comfortable Key West home base for extended stays. The location is the highlight: steps to the pool and close to the waterfront, beach, amphitheater, and Duval Street. It is ideal for seasonal guests, remote workers, couples, and anyone who wants to enjoy Key West with less need for a car.brbrKey West is easy to enjoy by walking, biking, scooter, rideshare, taxi, or local shuttle. From this location, guests can walk to Duval Street, Truman Waterfront, Fort Zachary Taylor, restaurants, bars, galleries, and events. A car is helpful for larger grocery trips or exploring the Lower Keysbrbr This is a monthly rental designed for extended stays. Please review the listing details, house rules, parking information, and community guidelines before booking. The location is ideal for guests who want walkable access to Old Town, waterfront sunsets, beach days, restaurants, galleries, and local entertainment. No pets, no smoking, this is a second story unit
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Exceptional(1)

$308.39

/ Nightly
Private Vacation Home

A Bit of Heaven is the perfect monthly rental in Key West

Key West, Florida, United States

This quintessential Key West eyebrow home is located in Old Town's prime Historic District, sitting just blocks away from Duval Street, the Historic Seaport, the Art District, and all of the amazing things Key West has to offer.brbrSituated on the upper part of Southard Street in Old Town Key West, A Bit of Heaven offers an inviting space for up to 6 guests. The welcoming covered front porch offers a great place to drink your morning coffee or your afternoon libations and watch the world go by. brbrThe first floor has a large living room with an abundance of comfortable seating, an open dining area, and an all new kitchen with stainless steel appliances, Corian countertops, and a large bar-top seating area.brbrDown the hall you will find the primary bedroom with a king bed, a desk area, spacious closet, and a completely remodeled bathroom, along with French doors opening to a deck. Upstairs is another master suite with a king bed for even more privacy. It features an ensuite bathroom, desk area, plenty of closet space, and a deck overlooking the beautiful back yard. The third bedroom containing a sleeper sofa is out back by the pool: a renovated pool house/cottage with all the essentials and a private entry separate from the main house.brbrThe rear yard outdoor living area is set up for outdoor entertaining. It features all new Trex decking in the rear, a bamboo privacy fence, and a huge 15x30 heated and chilled pool. You will find a new fully outdoor kitchen, a covered seating area, and plenty of space to lounge and/or entertain.  brbrThis is a monthly rental and only rents from the first of the month to the end of the month.  We cannot split months.
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Exceptional(2)

$362.71

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Condo

Paradise Found in Historic Key West

Key West, Florida, United States

Paradise has been Found at this beautiful Old Town Key West condo! Just steps away from the new Truman Waterfront, Fort Zach Beach, and only 3 blocks from Duval, Paradise Found is easy walking distance to delicious restaurants, lively bars, and plenty of shops. Situated in a quiet one way street, you're close to the action but rest assured, you'll sleep amazing in this peaceful home. Super fast WiFi makes this the perfect place to WFH.brbrThis spacious 2 bedroom, 2 full bathroom condo is open, airy and surrounded by swaying palm trees against the bright blue Key West skies. This home has a beautiful kitchen with granite countertops & stainless appliances, a custom master bath with a gorgeous walk in shower, and an assigned off-street parking space, which is very rare in Key West. Each bedroom has it's own en-suite bathroom making this great for a family or 2 couples or roommates. brbrEnjoy a shared heated pool with 3 other units (rarely crowded), grill out some fresh caught mahi on the grill and relax under the stars. brbrYou just steps from some of the best bars and restaurants - The Green Parrot, Blue Heaven, Cuban Coffee Queen, Kaya Eats and more. We Cycle bike shop is around the corner too, so you can rent a bike for the month and explore the Island! brbrCatch a show at the Coffee Butler Amphitheater, just a few minute walk down the street. brbrExplore The famous Hemingway House, just a 5 min walk from Paradise Found. Watch the sunset from Mallory Square while you watch street performers and locals mix and mingle. What are you waiting for It's time you find your paradise!
Bed 2

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Bath 2

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Sleep 4

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Exceptional(1)

$354.61

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Private Vacation Home

~SUNSET COVE~ Kayak or paddleboard right from your backyard!

Key West, Florida, United States

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!brbrTHE PROPERTY: This 2-bedroom, 3 full bathroom townhome with boat docking on the water is a rare find in Key West. Enjoy indoor-outdoor living as you saunter out the oversized French doors onto your lanai. From there you can entertain friends, take a dip in the pool, or walk out to the water and launch your kayak. The outdoor space is fenced and adorned with palm trees and lush landscaping. A composite deck and loungers surround the seasonally-heated pool. The outdoor shower is perfect for rinsing off after a day on the water. Enjoy cocktails on the furnished lanai then dine under the stars. Moving back inside, you will find an open concept family room, dining area and kitchen. Here you will find stainless steel appliances, counter seating, and all the conveniences of home. The family room has a TV, ample seating for everyone in your party as well as a twin pull-out sleeper chair. A convenient full bath with shower is in the hall. Also located on the first floor is the bonus room, currently designed as an office with French doors. brbrTwo ensuite bedrooms with closets and comfortable furnishings are located on the second floor. The primary king bedroom has a vaulted ceiling, which adds an airy ambiance to the room. Its full bath includes double sinks and a walk-in shower. Enjoy morning coffee on your bedroom’s balcony while taking in views of the dip pool. The queen guest bedroom also has a vaulted ceiling, and its full bath includes a sink and tub/shower combination. Enjoy the cool outdoor breezes from its balcony. A stackable washer/dryer is located on the second floor for your month-long visit. For a relaxed Key West vacation in a waterfront home, we invite you to experience island life at Sunset Cove!br brBED CONFIGURATION: The primary bedroom has a king bed. The guest bedroom has a queen bed. The living room has a twin pull-out sleeper chair for an occasional guest.brbrOUTDOOR AMENITIES: A pier leads out to the water, from which you can dock your 25-foot boat or view stunning Key West sunsets. The pool is heated seasonally (November-April) for an additional fee, which will be assessed at the time of booking. There is outdoor dining furniture and loungers, as well as an outdoor shower. brbrPARKING: This unit comes with one designated parking space. brbrLOCATION: Secluded location in the gated community of Gulfview Pointe on the Gulf. This home is just a short drive to bars, restaurants, and all the attractions on Duval Street. In the opposite direction, enjoy Key West pink shrimp with the locals at one of the many restaurants on Stock Island. brbrPETS: One (1) dog allowed, up to 25 lbs, for an additional fee and completion of Pet Information addendum. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations must be up to date. Please be advised some breeds are not permitted. Sorry, cats are not allowed.brbrSMOKING: This is a non-smoking home and property.brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Please note that the cleaning fee includes a full mid-stay clean***brbr***Outdoor only security camera(s) are in use at this property, and may be used to verify guest occupancy and guest safety. Security camera(s) are not active inside the property nor at the pool area.***brbr***Managed by Historic Key West Vacation Rentals***
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Exceptional(24)

$723.97

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Private Vacation Home

Breezy Retreat - 2BD/2Bath - Windward Park - Pool - 5min walk to Duval!

Key West, Florida, United States

The Breezy Retreat is situated in the Windward Park gated community, offering a convenient location within walking distance to the Historic Southernmost Point and one block away from the famous Duval Street, known for its vibrant atmosphere and attractions.brbrAs you enter the gated community, you'll be greeted by a large community pool surrounded by lush tropical plants. It provides a refreshing spot for swimming and relaxation.brbrThe living room space inside the home is cozy and open, seamlessly connecting to the kitchen and dining area. The kitchen is well stocked and equipped with everything you need to prepare meals, including the fresh catch of the day or your favorite dishes. The dining table comfortably seats four, and there are two additional seats at the countertop, offering plenty of space for entertaining.brbrThrough the French doors, you have access to a side porch, providing a pleasant place to spend time during the day or night. It's a great spot to enjoy the tropical surroundings and relax.brbrThe first floor features a guest room with two twin beds that can be converted into a king-size bed upon request. The room is perfect for accommodating guests and visitors. There is also a full shower bathroom on this floor, ensuring convenience and comfort for guests.brbrThe master bedroom, located on the second floor, features a king-size bed and an ensuite bathroom with a full bath/shower combination. It offers a private and comfortable space for relaxation. brStep onto the second floor balcony to enjoy the pleasant evening breezes. This balcony provides a peaceful setting to unwind and savor the end of the day.brbrWith its convenient location, cozy living space, well-stocked kitchen, and relaxing outdoor areas, the Breezy Retreat offers a delightful vacation rental option for guests looking to enjoy the attractions and ambiance of Key West.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. brbr7 night minimum stay, maximum stay is 14 days. brThis unit does have it's own washer and dryer which are located outsidebrNo pets allowedbrPool is heated during the Winter monthsbrBoth Bedrooms have TV'sbrOne assigned Parking SpotbrPool is Heated Seasonally
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Sleep 4

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$237.23

/ Nightly
Condo

Blue Horizon Hideaway

Key West, Florida, United States

Summary:brbrWaterfront 3BDR/2.5BA Key Cove Retreat, W/shared poolbrbrbrbrThe Space:brbrWelcome to Blue Horizon Hideaway, a spacious three-bedroom, two-story townhouse in the sought-after Key Cove community. This corner home is surrounded by water on two sides and tropical landscaping that sets the stage for a true island retreat. Guests enjoy access to a sparkling community pool, dedicated parking, and the comfort of being tucked away in a serene neighborhood while still just minutes from shopping, dining, and lively Duval Street.brbrbrbrThe first floor features an open-concept design with a chef’s kitchen, dining area, and a comfortable living room complete with a wet bar—perfect for entertaining. A half bath adds convenience, while sliding doors lead to a private outdoor patio ideal for alfresco dining and enjoying the tropical breeze.brbrbrbrUpstairs, you’ll find all three bedrooms and two full baths. The master suite offers a king-size bed and stunning water views. The second bedroom is furnished with a queen sleeper sofa, and the third bedroom includes a versatile trundle bed with two twins—making the home perfect for families or groups.brbrbrbrBlue Horizon Hideaway combines the best of Key West living: modern comforts, waterfront views, lush surroundings, and unbeatable proximity to the heart of the island.
Bed 3

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