Vacation Home Rentals By Owner In Key West, FL

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!brbrTHE PROPERTY: brBegin to relax and unwind as you ferry between two Keys in less than 5 minutes. Feel the soft breezes on your face and your tensions melt away, as you traverse the calm waters between Key West and Sunset Key. brbrUpon arriving at this private island, you will immediately notice the peaceful quiet that car-free, traffic-free living affords. The security and privacy that this island offers make this a great place for families, children, or couples. Upon entering the home via its foliage-lined pergola, you can decide whether to take a dip in the shared pool just steps from the home or enjoy the partial water view from the third-floor covered deck. brbrThis lush island is home to a gourmet restaurant just a few feet from the home, a sunset bar, tennis and basketball courts, spa, and pool. Nightlife on Duval is another attractive option via the island’s 24-hour ferry service. Whether you choose to take day trips from Key West or enjoy its many shops, restaurants, and bars, you can always return to your stress-free vacation retreat on Sunset Key. If you return prior to dark, you will witness the most beautiful sunsets on earth.brbrThis 2-bedroom, 3 baths home sleeps 6 and features 3 levels of living. An open-concept kitchen/living and dining area as well as a full bathroom with walk-in shower are located on the first floor. An office nook is ready for your work or study time. The kitchen also has breakfast bar seating. Whether you prepare cocktails from the bar, read a book on one of the private decks, or enjoy the sunshine on the island’s beach, this escape to paradise is truly special.brbrBED CONFIGURATION:brThe bedrooms are located on the second floor. The primary suite includes a king size bed and ensuite bath with walk-in shower. The second bedroom has two twin beds that can easily be converted to a king and also has an ensuite bath with tub/shower combo. There is a queen sleeper sofa on the first floor along with the third full bathroom, which has a walk-in shower. Not an early riser You won't hear the Key West roosters from this secluded location.brbrOUTDOOR AMENITIES:brA beautiful swimming pool steps away, tennis and basketball courts, spa, private beaches just a few hundred yards away, hammocks, and comfortable lounges complete the outdoor experience.brbrLOCATION: Sunset Key, a private small island minutes from Key West. brbrNEARBY: All the attractions of Key West and Duval Street are just a brief ferry excursion from Sunset Key.brbrPETS: This is not a pet-friendly home. Please view our many other pet-friendly homes!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***Managed by Historic Key West Vacation Rentals***

~The Escape ~ Your own tropical escape on private island!

Key West, Florida, United States

Bed

Bath

Sleeps

$345.26

This 1-bedroom, 1-bathroom property is located in Key West. The property offers 450 square feet of living space with a private entrance and on-property parking spot. The 1/1 is completely renovated with marble floors, washer and dryer, and A/C units in both the bedroom and the living room. Kitchen is fully fit with a refrigerator, stove top, oven, microwave and dishwasher. Ideal for those seeking a compact living space in a quiet residential area in Key West. First, Last and Security.

Charming private one bedroom in Key West

Key West, Florida, United States

1

Bed

1

Bath

Sleeps

$312.2

Sans Souci is a gorgeous Key West vacation home with a pool and lush tropical foliage. Relax by your own private pool or go out on the town! Key West Seaport is only two blocks away!brbrIn a peaceful alley just a 10 minute walk from Duval Street, your private paradise awaits. Sans Souci is a completely restored Key West home that promises rest for the weary and access to the best entertainment the island has to offer. The 2 bed/2 bath main house is a relaxing gathering place with a guest cottage nestled in a tropical garden just behind. Throw open the French doors into your private deck retreat with heated pool and spa to suit all guests.brbrEntertain friends and family in Sans Souci's spacious interior with a wall of glass that invites the sun and colors of Key West's gorgeous flora into your living room. The fully equipped kitchen with brand new stainless steel appliances and granite counter tops finishes the completely modern layout. Each bedroom has a TV and full length mirror. There is a sleeper sofa in the primary bedroom.brbrYou'll feel right at home in your upstairs primary suite with full bath and copious closet space. A downstairs guest room with twin beds is perfect for 2 more with an additional full bath. The guest cottage in the rear lives in its own little world with queen bed, half bath and outdoor shower. Sans Souci is a home the entire family will adore.brbrTHIS IS A MONTHLY RENTAL IT RENTS THE FIRST OF THE MONTH TO THE END OF THE MONTH ONLY. WE DO NOT SPLIT MONTHS.

Historic Key West charm @ San Souci - A Monthly Rental

Key West, Florida, United States

Bed

Bath

Sleeps

$1190.43

Three bedroom, four bathroom private home with heated pool . Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition TV and surround stereo throughout the home. High Speed internet and faxing available as well.brbrHigh security inside: guarded and gated Truman Annex. Only three blocks to Jimmy Buffets, Sloppy Joes and Duval Street entertainment. One of the nicest homes in the best area of Key West. Watch sailboats and sunsets from the decks during the day and feel refreshing ocean breezes throughout home at night. brbrOne week minimum stay is required.br

Palm Trees Ocean Breeze Key West FL

Key West, Florida, United States

Bed

Bath

8

Sleeps

$902.1

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrThinking of flying south to Key West for your next vacation Consider a vacation home that blends comfort, style, and offers enough space to spread your wings. THE PLAYFUL PELICAN lives up to its name with plenty of room, both inside and out, for fun and relaxation. Inside, open living areas provide the perfect place for gathering and creating memories, while private bedroom suites allow guests to settle in comfortably after a day of exploring the island. Outside, a refreshing private pool and welcoming lounge area invite you to soak up the sunshine, and convenient off-street parking makes it easy to be ready for your next island outing. THE PLAYFUL PELICAN is just a short stroll or bike ride to Duval Street and the Historic Seaport, making it the perfect perch for groups ready to dive into the best of Key West. Coupled with Last Key Realty’s unrivaled Guest Services & In-house Concierge, a stay at this modern island home will surely be one you treasure forever!brbrTHE LOCATION...brbrImagine your vacation home being just steps in either direction from all of the shops, restaurants, and sites of Duval Street and the Historic Seaport. Take a stroll or ride your bike down to the best of Key West, three blocks down Olivia Street to hit local favorites like Moondog Cafe, Martin's, and Nine-One-Five. Just a few blocks down Windsor Lane and you'll be at BO's Fish Wagon or Schooner Wharf.brbrTHE LIVING AREA & KITCHEN...brbrTHE PLAYFUL PELICAN offers an upscale retreat defined by soaring ceilings and chic, contemporary design. Sunlight pours into the main living space, creating a fresh, open feel from morning to evening. The inviting living room features plush seating arranged around a large Smart HDTV, with a seamless connection to the impressive, fully updated kitchen. From mixing drinks at the wet bar to cooking with top-tier appliances, everything is in place for relaxed gatherings and entertaining. Enjoy meals together at the dining table for six, or opt for a casual bite at the three-seat breakfast bar. A conveniently located powder room can be found just off the hallway.brbrTHE PRIVATE POOL...brbrBeyond the doors, you’ll find the standout feature of the home: a secluded tropical haven all your own. Fully enclosed by a privacy fence and surrounded by vibrant, exotic landscaping, this inviting outdoor space is perfect for gathering and unwinding. Relax on the comfortable chaise lounges that can easily be adjusted to chase the sunshine or settle into the shade beside the private pool, with the option to add heat for extra comfort. In the evening, take advantage of the propane grill for a laid-back poolside cookout, then enjoy dining under the open sky at the refined table set for six.brbrTHE ACCOMMODATIONS...brbr** First Floor Bedroom: Queen bed and an en-suite bathroom with a walk-in shower.brbr** Second Floor Master Bedroom: King bed, private balcony, and an en-suite bathroom with dual sinks and a walk-in shower. brbr** Second Floor Guest Bedroom: Two Twins OR One King bed, private balcony, and an en-suite bathroom with a shower and tub combination. brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat & A/Cbr** Ceiling Fansbr** Flat Screen Cable 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 and full cable is includedbr** Full-Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to, the amenities on this list:brbr** Fully Fenced & Landscaped Backyardbr** Private Saltwater Pool with Available Pool Heatbr** Propane BBQ grillbr** Off-Street ParkingbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** Pets Consideredbr** 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.brbrNEED MORE SPACE...brbrLast Key Realty manages several neighboring townhomes in this intimate complex. Inquire for details!

**THE PLAYFUL PELICAN @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...

Key West, Florida, United States

Bed

Bath

Sleeps

$537.74

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrSOUTHERNMOST BLISS is a historic Key West eyebrow home that recently underwent a complete renovation, and the result is nothing short of pure bliss. This home was designed to combine the best of classic Key West with luxurious modern comfort. SOUTHERNMOST BLISS features 3 bedrooms in the main house and a 4th bedroom in the Guest House, each with its own private bathroom. The common areas of the living room, kitchen, and backyard all provide plenty of space for your group to spread out. brbrIn addition to the fresh renovation and fabulous design of this home, the location could not be better. SOUTHERNMOST BLISS is located at 518 Frances Street, a quiet street considered by many to be the 'Park Avenue' of Key West. You can stroll a few short blocks to the Key West Seaport or enjoy the nearly 20 restaurants within short walking distance of this amazing home.brbrTHE LIVING AREA & KITCHEN…brbrYou will undoubtedly fall in love with this home from the moment you enter. The porcelain tile floors and elegant light fixtures combined with the pine walls provide the perfect blend of modern and historic. The open living area offers plenty of comfortable seating options, including a plush sofa and love seat situated in front of a large flat-screen TV hanging on the wall. Next to the TV area is a versatile space that can be utilized as a separate sitting area or home office. brbrThe fresh and fully equipped kitchen is tucked away off the living room and features top-of-the-line stainless steel appliances. There is even a pass-thru window to the backyard for those cold drink refills and afternoon snacks. The indoor dining table offers seating for six. A convenient powder room is located just off the living area and features a laundry closet with the washer & dryer. brbrTHE BACKYARD & POOL…brbrA truly unique feature of this home is the back wall of the living area, with Euro doors that fold open to create an epic indoor/outdoor living space. The entire backyard is fenced and surrounded by mature tropical landscaping for maximum privacy. You’ll have plenty of room on the spacious pool deck for everyone to lay out in the chaise lounges or relax on the outdoor furniture. brbrTake a refreshing dip in the pool to cool off on those warm South Florida days or crank up the pool heat to your liking in the cooler months. Enjoy a poolside BBQ using the propane grill and outdoor dining tables. There’s a convenient passthrough window from the kitchen to the outdoor dining area.brbrThe front of the house features a delightful shaded porch with plush cushioned seating. It’s the perfect spot for a morning coffee, private phone call, or a chance to greet folks as they walk by.brbrTHE ACCOMMODATIONS…brbr** Master Bedroom: Located on the First Floor with a King bed, a flat-screen TV, a separate dressing room with double closets and a twin-sized sleeper sofa, a gorgeous en-suite bathroom with double sinks and a custom walk-in shower.brbr** Second Bedroom: Located on the Second Floor with a Queen bed, a flat-screen TV, double closets, and an en-suite bathroom with a walk-in shower.brbr** Third Bedroom: Located on the Second Floor with Two Twin beds OR One King bed, a flat-screen TV, double closets, and an en-suite bathroom with a shower and tub combo.brbr** Guest House: Located just off the pool area with a Queen Murphy bed, a flat-screen TV, a closet, and an en-suite bathroom with a private outdoor shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen Cable 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 and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced & Landscaped Private Yardbr** Private Heated Poolbr** Propane BBQ Grillbr** Off-street Parking in Drivewaybr** Twin Sleeper SofabrbrOther notes:brbrbr** In person welcomebr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 9 adultsbr** Small Dogs Allowed - Max of 2 dogs allowed and an additional fee of $200 per pet will apply

**SOUTHERNMOST BLISS @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVICE

Key West, Florida, United States

Bed

Bath

9

Sleeps

$286.79

Conch Key | Private Pool & Outdoor Bar Paradise!brbrWelcome to Sunset Palms Retreat — a beautifully renovated 2-bedroom, 2-bath vacation home designed for indoor comfort and outdoor living. This monthly rental offers the perfect blend of convenience, style, and resort-style amenities, featuring a private pool and an expansive entertainment-ready patio complete with a covered bar area.brbrThe Ambiance:brThoughtfully designed with a fresh, coastal-modern aesthetic, this home comfortably sleeps up to 4 guests. The fully equipped kitchen features stainless steel appliances, stone countertops, and all the essentials you need to cook or entertain with ease. The bright, open living space flows seamlessly to the outdoor area, where a sparkling private pool, shaded lounge areas, and a covered bar and entertainment zone await — perfect for relaxing days or evening cocktails under the stars.brbrGuest Access:brGuests enjoy easy, contactless check-in with a personalized access code and full access to the home and all outdoor amenities.brbrThe Neighborhood:brCentrally located with quick access to the best of Key West — including Duval Street's lively dining and nightlife, historic landmarks, pristine beaches such as Fort Zachary Taylor, and even Fausto's, a local grocery store. Everything you need is just a short ride away.brbrTransportation Tips:brThe home includes off-street and covered parking, a valuable perk in Key West. Explore Key West effortlessly by bicycle, scooter, golf cart, or on foot, as many attractions are easily accessible from the cottage. Feel free to ask for local recommendations!brbrOther Things to Note:br- Central A/C throughout the home.br- Washer and dryer included.br- Pet-friendly upon request.br- Mid-stay cleanings available upon request.br- Guests must be 25 years of age or older to reserve this property.br- A minimum stay of 30 days is required, in accordance with local regulations.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, driveway, walkways, pool, 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.

Conch Keys | Private Pool & Outdoor Bar Paradise!

Key West, Florida, United States

Bed

Bath

Sleeps

Select Dates for Price

( NEW LISTING SEE VRBO LISTING 1223004 for reviews on my other property ) Newly renovated, invitingly spacious, serenely quintessential two-bedroom , want-for-nothing original “conch home” conveniently located on one of Old Town's famously peaceful side streets . A secluded location with encapsulating foliage, immaculate amenities, and a clean aesthetic combine to create a Zen-like private getaway minutes from Duval Street. Float or lounge poolside in the newly-installed saltwater pool. The modern kitchen with touchpad Wolfe convection oven and Thermador induction cooktop, John Pawson Demeyere cookware, Georg Jensen flatware and Rosenthal china for a serious cook or to make a simple cocktail . Laundry closet with Electrolux 2020 washer/dryer; living room equipped with flat-screen 45-inch TV loaded with major streaming services nestled behind a recessed remote-controlled drop down piece of art -- all connected via high-speed wifi -- allow for modern amenities amidst unparalleled spa -like paradise. Outdoor relaxed lounge seating surrounding another television, a state-of-the-art propane-fueled Weber grill and large outdoor dining space with seating for 10 next to the pool provide world class spa-like accommodations. The overall beauty of this home provides an island oasis in close proximity to all that Key West has to offer, allowing guests a world of entertainment only a few minutes walk away.

NEW LISTING Old Town Private Pool in Garden Of Eden tropical spa-like Oasis

Key West, Florida, United States

Bed

Sleeps

Exceptional(22)

$196.73

We selected the best of everything to create paradise in Key West. Enjoy tropical breezes as you sip your morning coffee or celebrate another amazing sunset with an evening cocktail on one of four open air decks surrounding this beautifully appointed townhouse in the prestigious Key West Golf Club. Located directly off a gorgeous, heated pool complete with a waterfall, this is your home away from home to spend your days relaxing, playing a round of golf, fishing, snorkeling and enjoying all that Key West has to offer. Please note this is a monthly rental as stays with us require a minimum of 28 days. brbrKey West offers restaurant choices meeting all your needs from casual to fine dining, but we know sometimes you just want a home cooked meal. We offer a fully appointed kitchen with all the amenities as well as a Weber grill to cook up a fresh catch. Fully renovated in 2022, this modern and bright kitchen will meet all your needs. Seat six comfortably for in home dining if you would like to entertain guests. br brThere are plenty of places to relax whether inside in the beautifully appointed living room or outside with comfortable outdoor seating on the open-air porch located just off the living room. High speed internet and a 65-inch smart TV allows you to enjoy a movie, surf the internet and play your favorite music on a Bose sound system in the main living area. The living room also offers a comfortable queen-sized pull-out sofa to accommodate additional guests for short stays. br brWhen it's time to rest you can enjoy a wonderful night's sleep on 1,000 thread count sheets. The main bedroom on the second floor offers a king-sized bed with Tommy Bahama bedding, plenty of closet space and a 55-inch smart TV for your entertainment. The large open-air porch just off the main bedroom features a two-person hammock and a day bed perfect for naps. brbrThe guest room also located on the second floor features a full-sized sleigh bed and houses a full-sized washer and dryer (new in 2024) for your convenience. Enjoy a writer's desk in the guest room to send postcards home or work remotely with high-speed internet access. The guest room offers a 40-inch smart TV and additional closet space. The open-air porch off the guest room is the perfect spot to enjoy the morning sun or star gaze in the evening in reclining chairs. brbrA newly remodeled and modern full-sized bathroom is located on the second floor and an updated half bath can be found on the main floor. Rinse off from the beach or pool with an outdoor shower that provides plenty of privacy. All linens, towels and pool towels are provided for your convenience. Just pack a bag and come to paradise for a month or more. You will be so glad you did. brbrPET POLICY: As pet lovers ourselves, we understand that bringing your companion along to paradise is a priority. Dogs are welcome up to 35 lbs. for a one-time non-refundable $250 fee. Be sure to select this optional fee when booking if you are bringing a pet. Please contact the owner, Barbara, if you have any questions about the eligibility of your pet. brbrThe Key West Golf Club is a gated community offering the “Old Key West” charm, two heated pools, a fitness center, free parking for one vehicle, 24-hour security, and access to the only 18-hole golf course in the Florida Keys.brbrFor safety and liability purposes, the property is equipped with two exterior cameras, one above the front door and one on the roofline in the rear. The cameras in no way infringe upon the guests’ expectations of privacy in these public areas of the property.

Paradise found at the Key West Golf Club!

Key West, Florida, United States

Bed

Bath

Sleeps

$484.91

Welcome to our new fully renovated townhouse hosted by HomeAway Premier Partner Roy Svenningsen. This home is located in a lush, family oriented gated community across from the Key West Golf course.brThe home features all new stainless steel appliances, new furniture, all new flooring, marble counters, and top quality mattresses.brIn the center of the community is a beautiful pool and a clubhouse with a fitness area.brIncluded is parking for two cars, WiFi and high speed internet.brClose by there is Croissant de France a french bakery, a CVS drugstore and two family restaurants (Roostica and Chico’s).

Spotless Fully Renovated Family Home. Free parking WiFi Pool.

Key West, Florida, United States

Bed

Bath

8

Sleeps

$333.14

VINTAGE OLD TOWN BEAUTY...brA classic gem that checks all the boxes for the ultimate Key West experience! This island getaway gives a nod to traditional southernmost influences yet is permeated with modern touches that guarantee the best of both worlds. Situated on one of the quieter blocks, you are also in a prime location in the city center, just steps from the White Street Gallery District, less than .06 mile from Higgs Beach ,and all of the best restaurants and activities, promising a vacation of pure bliss. The front door of this home has a Ring doorbell for security purposes. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES…brStep into the fully fenced and lushly landscaped front yard with a cozy porch that invites slow mornings over quiet conversation and soothing mugs of coffee. This lovingly restored one-and-a-half story home greets you with stylish LVT flooring throughout, to the stunning and spacious kitchen that boasts all the modern appliances and tools for fashioning fresh meals surrounded by your favorite people. Unwind over your favorite movies in the intimate tv room or gather in the adjacent sitting room for hours of game playing, telling your best fish stories, or burying your head in a favorite novel. A full washer and dryer are located on the second level for your convenience.brbrSLEEPING ARRANGEMENTS…brThe loft style primary bedroom occupies the second floor of the home, with a king bed, flat screen TV, dedicated work space, walk-in dressing room and closet, and direct access to the rooftop sun deck and balcony. The other guest rooms are both on the ground level, one offers a queen bed and the other features twin bunk beds. Both the upstairs primary suite and downstairs room have direct access to a full bathroom with a walk-in shower. brbrOUTDOOR LIVING…brThe outdoor living is what makes this home an ideal Key West experience. Exhale your cares and indulge for hours in the relentless pursuit of relaxation, with a sparkling salt water heated pool, umbrella'd chaises and tropical foliage that creates a natural privacy fence. The outdoor kitchen is equipped with a sink and refrigerated drawers, and the propane grill will inspire BBQ aficionados to do their best work. The heavenly outdoor shower will feel glorious after a day at the beach or adventuring on crystal blue water.brbrPARKING...brThis home offers one off street parking space in the driveway, which can fit up to a mid-size SUV.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).brbrFIND YOUR PEACE IN PARADISE...

ISLAND BLISS ~ Renovated 3 BR, 2 Ba in Old Town w/ Heated Pool and Parking!

Key West, Florida, United States

Bed

Bath

8

Sleeps

$410.79

Your Island Escape Awaits – Tropical Luxury in the Heart of Key WestbrbrWelcome to your dream getaway in the Florida Keys—an enchanting, historic Eyebrow-Style home nestled in the desirable Meadows neighborhood of Key West. This spacious 2,064 sq. ft. tropical retreat blends timeless Key West charm with modern luxury and comfort. Just minutes from the excitement of Duval Street, yet tucked away in a peaceful residential enclave, this is where you vacation like a local.brbrFrom the moment you step through the white picket gate and onto the inviting front porch—with its cozy seating area and classic porch swing—you’ll feel right at home. Surrounded by lush, vibrant landscaping including banana, lime, and mango trees, the property exudes a sense of serenity and privacy.brbrInside, the home is bathed in natural light, with large windows adorned by Bahama and louvered shutters. The original Dade County Pine walls and newly white-painted floors reflect the light beautifully, creating a fresh and airy ambiance throughout. High ceilings, coastal-inspired furnishings, and carefully preserved architectural details make this a one-of-a-kind escape.brbrSpend your days basking in the Key West sunshine around the large heated saltwater pool, surrounded by swaying palms and lush tropical greenery. The expansive Ipe wood deck offers sun loungers for soaking up the sun and a covered lounge area complete with a ceiling fan and 55” TV—perfect for outdoor relaxation. Just beyond, in the beautifully landscaped garden, you'll find a spacious dining table that seats eight and a tucked-away loveseat nestled in a secluded corner—an ideal spot for morning coffee or a peaceful afternoon escape. Rinse off in the outdoor shower after a dip in the pool, or fire up the grill for island-style meals under the stars.brbrThe interior living spaces are both inviting and stylish. The living room is spacious and breezy with high ceilings, beachy lounge seating, a work desk, surround sound, ceiling fans, and a 55” TV. The dining room features cathedral ceilings, whitewashed Dade County Pine walls and floors, and a dining table for six (with additional seating available). The bright kitchen is well-appointed with high-end appliances, an induction stove, island seating for three, and beautiful glass French doors that lead to the pool deck. A side door gives you direct access to the outdoor shower and grill area.brbrThe cozy sitting room, affectionately called The Buffett Room in honor of the legendary Jimmy Buffett, features two leather lounge chairs, a bar, ceiling fan, and French doors that open to the outdoor living area. A sturdy ladder leads up to a tucked-away loft with a futon mattress—perfect for reading, napping, or simply escaping into a good book.brbrThe primary suite is located on the first floor and features a king-size bed, a 44” TV, lounge chair, ceiling fan, spacious walk-in closet, and a full ensuite bathroom with private garden access. Upstairs, you'll find two additional large bedrooms and a full bathroom. One bedroom includes a king-size bed, ceiling fan, reading chair, and 40” TV, while the other offers a king bed, ceiling fan, and a convenient work desk with a printer.brbrWhether you’re planning a laid-back family vacation, a couple’s retreat, or a friends’ getaway, this Key West gem offers the perfect balance of peace, proximity, and pure island charm. Sip your morning coffee under the mango tree, take a dip in the pool by day, and stroll to the lively heart of Key West by night. Your island escape is waiting. Book now and start living on island time.

The Meadows Retreat

Key West, Florida, United States

Bed

Bath

Sleeps

$651.38

Get ready to relax in this 3-bedroom townhome in Key West. This superb property boasts 2 queen beds, 1 king bed, and 1 full bed, perfect for a group getaway. With 3 bathrooms featuring a shower and jetted bathtub, guests will feel pampered. The living room offers additional sleeping space with a queen sleeping sofa and full sleeping sofa. You're sure to make fantastic memories with a stay at our place. Enjoy the resort style pool in Coral Hammock. Very short walk to the pool

Another Day in Paradise

Key West, Florida, United States

Bed

Bath

Sleeps

$532.24

Charming Historic Bungalow with Private Pool & Detached Cottage – Steps from Duval Street!brbrExperience the best of Key West in this beautifully restored 2-bedroom, 2-bathroom bungalow with a spacious 1-bedroom, 1-bathroom detached cottage — perfect for multi-family trips or groups seeking privacy and comfort.brbrPrime Location:brNestled on a picturesque Old Town street, you’re just 3 blocks from the vibrant Duval Street and only 1 block from the waterfront. Enjoy easy access to world-class dining, unique shops, and iconic Key West attractions.brbrThe Space:brOriginally built in the 1860s and thoughtfully updated, this light-filled home features an open great room with French doors that lead to a generous deck surrounding a large 12 x 24 heated pool. Lounge on ample seating, relax in the covered outdoor media den, or unwind on the charming front porch.brbrBedrooms & Living Areas:brbrMaster Suite: King-size bed with en-suite bathroom, located on the first floor (also serves as a powder room).brbrUpstairs Guest Bedroom: King-size bed, private bathroom, and 32” TV.brbrDetached Guest Cottage: Queen-size bed, private bath with outdoor shower, kitchenette, and TV — perfect for added privacy.brbrOffice Space: Built-in office area for any work or quiet time.brbrLiving Room: Comfortable seating with a flat-screen TV.brbrDining & Kitchen: Breakfast bar and dining area with seating for six, plus a fully equipped kitchen with new stainless steel appliances.brbrOutdoor Paradise:brSpend your days lounging by the pool with full sunshine, enjoy coral-paved walkways through the fenced yard, and relax in the private keystone coral patio behind the guest cottage.brbrAdditional Info:brbrPool heat available November 15 – May 15 for an additional daily fee.brbrStreet parking only, no assigned spots (first come, first served).brbrThis historic Key West retreat offers a perfect blend of island charm, privacy, and convenience. Book your stay today and immerse yourself in the laid-back lifestyle of the Florida Keys!

Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$360.93

Experience the Timeless Charm of Historic Key West — Your Perfect Island Retreat!brbrStep into this stunning historic Key West home where classic elegance meets comfortable island living. Bathed in natural sunlight from the inviting sunroom entrance, this residence immediately welcomes you with a warm “I am home” feeling.brbrFeaturing soaring ceilings and an open, flowing floor plan, this home balances spaciousness with intimate charm. The handcrafted mahogany kitchen cabinetry, paired with elegant stone countertops, showcases master craftsmanship and timeless beauty.brbrAccommodation:brbr3 bedrooms, including a luxurious primary and guest suite with king-size bedsbrbrA versatile third bedroom/office with a queen sofa sleeper and workspacebrbrTwin daybeds in the sunroom, perfect for extra guests or loungingbrbrBathrooms:brbrTwo full baths, including a brand-new ensuite featuring an 84-gallon freestanding soaking tub—ideal for unwinding after a day in paradisebrbrDirect access from the main bath to a private outdoor shower to refresh under the open skybrbrIndoor/Outdoor Living:brbrAntique French doors with leaded glass transoms open from the dining room to a private deck, seamlessly blending indoor comfort with outdoor beautybrbrLarge landscaped yard with native trees and tropical foliage offers a peaceful retreatbrbrAdditional Highlights:brbrOff-street parking for two cars (stacked), plus additional street parking availablebrbrPrime location just 1 mile from Key West Airport and local markets, and only 2.5 miles from Old Town’s vibrant shops, restaurants, and nightlifebrbrWhether you’re visiting for a quick getaway or an extended stay, this historic home provides the perfect base to soak in the unique Key West lifestyle.

Last Stop in Paradise

Key West, Florida, United States

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Sleeps

$431.0

Experience crystal clear waters, picturesque beaches, and famous historic sites with a stay at 'Boho Breeze!' This 2-bed, 1.5-bath vacation rental townhome is located in a quiet, serene neighborhood and features a boho-inspired interior and multiple tranquil outdoor living and dining areas. Soak up the sun at Smathers Beach, stroll along Duval Street, and explore popular museums, followed by stunning sunsets over Mallory Square. At day's end, return to your peaceful retreat to relax and unwind.brbr-- THE PROPERTY --brbrOutdoor Living + Dining | Community Perks | 5 Miles to Historic District | Monthly Rentals OnlybrbrThis charming retreat welcomes beachgoers and snowbirds to enjoy the white-sand beaches, famous key lime pie, and close proximity to the best restuarants, attractions and vibrant nightlife in Key West.brbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Living Room: Sleeper SofabrbrCOMMUNITY AMENITIES: 2 outdoor pools, fitness center, tropical landscaping, clubhouse, 18-hole golf course (additional fees)brOUTDOOR LIVING: Furnished screened porch w/ bistro lights + ceiling fan, patio w/ dining table, chairs + gas grill, 2nd floor balcony w/ bistro table + chiars, front porch w/ chairs + table brINDOOR LIVING: Smart TVs, 4-person dining table, open floor planbrKITCHEN: Fully equipped, dishwasher, microwave, coffee maker, blender, knife set, dishware/flatwarebrGENERAL: Free WiFi, washer/dryer, linens/towels, A/C, ceiling fans, beach towelsbrSUITABILITY: Bedrooms + full bathroom on 2nd floor, stairs required for accessbrFAQ: Month-to-month rentals onlybrPARKING: Street parking (2 vehicles)brbr-- THE LOCATION --brbrON THE WATER: Dream Catcher Charters Key West Fishing Guides (1.7 miles), Dolphin Safari Charters (1.9 miles), Lazy Dog Adventures (2.0 miles), Fun in the Sun Charters & Boat Rentals (2.1 miles), Key West Express (5.4 miles)brBEACHES: Smathers Beach (4.4 miles), Higgs Beach (5.7 miles), Fort Zachary Taylor Historic State Park (6.5 miles), Calusa Beach & Loggerhead Beach (33.1 miles)brAREA ATTRACTIONS: Key West Tropical Forest & Botanical Garden (1.9 miles), Historic District (5.1 miles), Key West Lighthouse (5.5 miles), The Hemingway Home and Museum (5.6 miles), The Key West Butterfly and Nature Conservatory (5.6 miles), Southernmost Point of the Continental US (5.6 miles), Mallory Square (6.1 miles), Key West Aquarium (6.1 miles), Truman Little White House (6.3 miles)brEATS: Hogfish Bar & Grill (1.8 miles), Hurricane Hole (2.0 miles), The Stoned Crab (3.2 miles), Conch Republic Seafood Company (5.7 miles), Blue Heaven (5.7 miles)brAIRPORT: Key West International Airport (3.6 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs to enter and access all bedrooms. It may be difficult for guests with limited mobilitybr- NOTE: For stays longer than 1 month, guests will be required to pay for and under go a monthly cleaningbr- LIC 2021- 000294br- Business Tax Acc #130178 RCT#25230-130178

Charming 'Boho Breeze' Retreat w/ Pool Access

Key West, Florida, United States

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Bath

Sleeps

$916.08

Discover unparalleled luxury at Autograph House, an exclusive private oasis just one block from the center of Key West. Immerse yourself in the vibrant energy of Duval Street, explore Mallory Square's breathtaking sunsets, or discover the island's many unique shops, restaurants & attractions – all just steps away. The Main House boasts 4 bedroom suites, outdoor kitchen, plunge pool and outdoor shower. Complementing is the adjacent 2 bed/2 bath cottage, complete with a second heated plunge pool.brbrTHE PROPERTYbrAutograph House is an architect designed luxury compound in the heart of Old Town Key West. Comprised of a main house and guest cottage, the newly built property infuses casual island elegance with modern sophistication. Unrivaled location just steps to the action, your tropical oasis draws inspiration from the rich literary history and the eponymous Autograph Tree. The property is available for monthly and longer rentals; contact us for custom trip lengths.brbrMain House: The principal residence is a two story home with four well appointed bedrooms, each with en suite bathrooms featuring showers and custom millwork. The ground floor is an open plan living, kitchen and dining area with an expansive chef’s kitchen, including Miele appliances, column refrigeration and a large entertaining island with stool seating. A workspace desk area is also available for any requisite work check-in.brbrCottage: The adjacent guesthouse is part of the compound property yet affords privacy for folks who prefer a little separation. The two bedroom two en-suite bath single-story cottage includes all the necessities for a fully standalone stay, including a private entrance, fully featured kitchenette with cooking, living area with TV, workspace and private plunge pool hot tub with sun loungers.brbrAmenities: The property includes custom designed bath products featuring our signature scent evoking the heritage of tropical Key West. The kitchens include a well curated collection of utensils and appliances. High speed WiFi is included. A Sonos sound system blankets the property for audio indoor and out. Two Roku streaming TVs are included in the main house and one in the cottage. Full size laundry is available in each house.brbrPools: Two private pools are perfect for a morning soak or afternoon splash, beverage in hand. The main house has a heated cocktail plunge pool with waterfall and bench seating. Sun loungers on the patio are the perfect spot to catch some rays or read your latest book. The cottage includes a second plunge pool hot tub. Rinse off in the heated outdoor shower just steps away down a garden path. The lush landscaping creates a feeling of tropical oasis with secluded moments.brbrOutdoor Entertaining: A luxuriously sized covered porch includes a lounge seating area, outdoor kitchen with grill, sink, beverage fridge and outdoor dining table. Connecting to the main house via sliding glass wall system, the indoor and outdoor entertaining spaces can be opened up for completely open seamless entertaining.brbrLOCATION:brA quick walk around the block puts you in the absolute center of Key West action. Sloppy Joe’s, Hard Rock, Fat Tuesday, Mallory Square and local highlights are steps away. Stroll down the street to the Southernmost Point, Ft. Zachary beach access and other must do’s.brbrGUEST ACCESS:brParking available on property for one car and one golf cart.brHouse access is provided via smart lock key code prior to arrival.brbrOTHER THINGS TO NOTE:brAutograph House is a monthly vacation rental for 28 or more days. Contact us for special offers for custom length stays.

Luxe Designer Oasis + Guest House steps off Duval

Key West, Florida, United States

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Sleeps

$843.75

The historic William Skelton Home is ideally located on Eaton Street in Old Town Key West, steps from Duval Street, hundreds of bars and restaurants, and all major attractions. This rental listing includes the second and third floors of the home, which features three bedrooms, a private swimming pool, spacious living areas inside and outside, off-street parking, and a newly renovated chef's kitchen to prepare meals.brbrThe first story of the home will be left vacant when this listing is rented. See the many great reviews on the listing for the entire home rental, #3519858.

3 Bedroom Key West Home - Perfect Location & Private Pool

Key West, Florida, United States

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Sleeps

$253.91

Heron House | Canal Front 3-Bedroom Home with Private Boat Docking in Key HavenbrbrLocated in the serene and sought-after Key Haven neighborhood, just minutes from Key West, Heron House offers a peaceful and picturesque escape on the water. This 3-bedroom, 3-bathroom canal-front home boasts private boat docking, making it the perfect destination for water enthusiasts and those looking to enjoy the laid-back island lifestyle while being close to all that Key West has to offer.brbrThe Ambiance:brStep inside Heron House and enjoy the open, airy layout designed for easy living. The well-equipped kitchen boasts beautiful marble countertops and modern appliances, ideal for preparing meals with family or friends. The master suite features a king-sized bed and a private ensuite bathroom for ultimate comfort and privacy. The two additional guest bedrooms, each with a queen-sized bed, are spacious and perfect for guests or family members.brbrOutdoor Living:brHeron House offers an inviting outdoor space with a private boat dock, allowing easy access to the canal and nearby waters. Enjoy the tropical surroundings on the patio or take advantage of the boat dock for fishing, kayaking, or a relaxing day on the water. Whether you're enjoying a quiet evening outdoors or gearing up for a day of adventure, the home's outdoor space is perfect for island living.brbrGuest Access:brEnjoy a smooth, contactless check-in process with personalized access codes sent prior to your arrival. Our team is available for any assistance or recommendations you may need during your stay.brbrLocation Highlights:brLocated in the peaceful and desirable Key Haven neighborhood, Heron House provides the perfect balance of tranquility and convenience. Just minutes from Key West, you'll be close to everything the island has to offer, from its top attractions and world-class dining to vibrant nightlife and historic landmarks. The private boat dock gives you quick access to the canal, making it easy to enjoy a day on the water, or head out to explore nearby beaches and parks.brbrTransportation Tips:brGetting around is a breeze at Heron House! You'll have private off-street parking, making it easy to explore Key West by car. For a fun and eco-friendly way to see the island, consider renting bikes, scooters, or a golf cart. Taxis and rideshare services are also readily available for any off-island excursions.brbrOther Things to Note:br- Private washer and dryer available for guest use.br- Pets are welcome—just reach out for additional details. br- Mid-stay cleaning available upon requestbr- A minimum stay of 30 days is required, in accordance with local regulations.br- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrAt 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.

Heron House | Canal Front Home w/ Private Dock!

Key West, Florida, United States

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