Vacation Home Rentals By Owner In Key West, FL

This magnificent 5 bedroom Mediterranean villa has a landmark presence, complete privacy and a breathtaking outdoor plaza & refreshing pool. The gourmet kitchen features 'Blue Viola granite counter tops, custom cabinetry, stainless steel appliances and a large entertaining island including wine storage. There are 3 large bedrooms on the first floor; each beautifully appointed with luxury linens and furnishings. The generous living room and private dining room feature hand painted finishes, with sumptuous furniture while merging seamlessly with the indoor/outdoor lifestyle Key West is famous for. The second floor has two elegant bedrooms with walk in closets and baths ensuite. There is covered parking for one vehicle and plenty of space to bring in your island bicycles, mopeds or golf carts! Nearby enjoy Higgs Beach, Salute Restaurant, Louie's Backyard, and the White Street gallery district! NOTE: This property is monthly rental - 28 night minimum.

A Bella Capri in Key West by the Beach!

Key West, Florida, United States

Bed

Bath

Sleeps

$310.58

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 30 night minimum. brbrFEATURES:brBedrooms: 3 (1 king, 1 queen, 2 twins)brBathrooms: 3 (2 en suites)brLocation: New TownbrSquare Feet: 1651brParking: Driveway and street parkingbrAmenities: Wifi, TVs, in-unit laundry, office space, private pool, outdoor bar area, outdoor seating, outdoor grill, grass area to store a small boat up to 18 feetbrbrbrTHINGS 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.brbrPool heating is $100 per week and must be requested in advance

Margarita Villa-3 bedroom 3 bath home in prime location w/backyard pool oasis

Bed

Bath

Sleeps

$469.2

Hemingway Hideaway – Charming Townhouse in Truman Annex at Historic Foundry BuildingbrbrDiscover your perfect Key West retreat in this beautifully positioned 3-story townhouse within the coveted Truman Annex community. Just steps away from the vibrant heart of Key West, Hemingway Hideaway offers the ideal blend of comfort, convenience, and classic island charm.brbrProperty Highlights:brbrGated Entry & Private Courtyard: Enjoy privacy and tranquility as you enter your own peaceful oasis.brbrOpen Floor Plan: The spacious first floor seamlessly connects the living room, dining area, and fully equipped kitchen — perfect for relaxing or entertaining.brbrHalf Bath/Powder Room: Conveniently located off the kitchen.brbrMaster Suite on Second Floor: King-size bed, ensuite bathroom, two linen closets, in-unit washer/dryer, and a private balcony for morning coffee or evening relaxation.brbrThird Floor Bedroom: Queen-size bed occupies the entire level with its own ensuite bathroom.brbrDesignated Parking: One assigned parking space located at the rear of the unit.brbrPrivate Pool: Enjoy access to the Foundry building’s exclusive pool — a refreshing escape after a day exploring.brbrComplimentary Bicycles: Two bikes included to effortlessly explore Key West like a local.brbrPrime Location:brJust steps from the Truman Amphitheater & Splash Park, Fort Zachary Taylor, the Historic Seaport & Mallory Square, Truman’s Little White House, and popular spots like the Green Parrot. Within a 4-block radius of the lively 200 block of Duval Street — where all the action happens!brbrBooking Notes:brbrHemingway Hideaway – Charming Townhouse in Truman Annex at Historic Foundry BuildingbrbrDiscover your perfect Key West retreat in this beautifully positioned 3-story townhouse within the coveted Truman Annex community. Just steps away from the vibrant heart of Key West, Hemingway Hideaway offers the ideal blend of comfort, convenience, and classic island charm.brbrProperty Highlights:brbrGated Entry & Private Courtyard: Enjoy privacy and tranquility as you enter your own peaceful oasis.brbrOpen Floor Plan: The spacious first floor seamlessly connects the living room, dining area, and fully equipped kitchen — perfect for relaxing or entertaining.brbrHalf Bath/Powder Room: Conveniently located off the kitchen.brbrMaster Suite on Second Floor: King-size bed, ensuite bathroom, two linen closets, in-unit washer/dryer, and a private balcony for morning coffee or evening relaxation.brbrThird Floor Bedroom: Queen-size bed occupies the entire level with its own ensuite bathroom.brbrDesignated Parking: One assigned parking space located at the rear of the unit.brbrPrivate Pool: Enjoy access to the Foundry building’s exclusive pool — a refreshing escape after a day exploring.brbrComplimentary Bicycles: Two bikes included to effortlessly explore Key West like a local.brbrPrime Location:brJust steps from the Truman Amphitheater & Splash Park, Fort Zachary Taylor, the Historic Seaport & Mallory Square, Truman’s Little White House, and popular spots like the Green Parrot. Within a 4-block radius of the lively 200 block of Duval Street — where all the action happens!brbrBooking Notes:brbrMinimum 7-night stay required between January 1 – April 30, 2020, with Saturday-to-Saturday check-in/check-out.brbrOutside this period, flexible arrival and departure days.brbrDiscounts available for stays of 28 nights or longer.brbrIf this property is booked, we can recommend other great homes in the area.brbrPack your suitcase and get ready for an unforgettable Key West getaway in your home away from home!brbrOutside this period, flexible arrival and departure days.brbrDiscounts available for multiple months staysbrbrIf this property is booked, we can recommend other great homes in the area.brbrPack your suitcase and get ready for an unforgettable Key West getaway in your home away from home!

Hemingway Hideaway in the Truman Annex

Key West, Florida, United States

Bed

Bath

6

Sleeps

$247.54

Angel Fish Cove | Tropical Townhome Retreat Near Duval StreetbrbrWelcome to Angel Fish Cove, a charming tropical townhouse tucked away in the serene Presidents Walk & Southard Court community of the highly sought-after Truman Annex in Old Town Key West. This beautifully renovated two-bedroom, two-and-a-half-bath monthly vacation rental offers the perfect blend of island tranquility and unbeatable walkability. Just two short blocks from Duval Street and less than half a mile from one of Key West's best beaches, Angel Fish Cove places you close to everything—while still giving you a peaceful place to unwind and recharge.brbrWhether you're here to explore historic Old Town, soak up the sun, or enjoy world-class dining and nightlife, Angel Fish Cove is your private slice of paradise in the heart of Key West.brbrThe Ambiance:brStep inside Angel Fish Cove and immediately feel the relaxed island vibe. Tropical décor, thoughtful updates, and inviting indoor-outdoor spaces make this townhouse ideal for an extended Key West stay. Designed for comfort and ease, the home includes:brbr- Two comfortable bedrooms offering privacy and space for rest and relaxationbr- Two full bathrooms plus a convenient half bath for guestsbr- An updated kitchen with modern appliances, perfect for cooking at homebr- Three TVs throughout the home, including flat screens upstairsbr- Complimentary high-speed Wi-Fi to stay connectedbr- Covered parking for one vehiclebrbrThis home's layout and atmosphere make it easy to settle in, slow down, and truly enjoy the Key West lifestyle.brbrGuest Access:brGuests enjoy full access to the entire townhouse, including private outdoor spaces and a designated covered parking spot. Located within the secure Truman Annex community, Angel Fish Cove offers a quiet residential feel while remaining close to all the action of Old Town.brbrLocation Highlights:brAngel Fish Cove is perfectly positioned in the heart of Old Town Key West within the desirable Truman Annex community, offering the ideal mix of convenience and tranquility. Just two blocks from lively Duval Street, you'll have effortless access to the island's best restaurants, bars, boutiques, and nightlife. Historic landmarks, cultural attractions, and scenic прогул spots are all within easy walking distance, while one of Key West's most beautiful beaches is less than half a mile away. From sunset strolls and water adventures to dining and entertainment, everything that makes Key West unforgettable is just moments from your door—yet the home remains peacefully tucked away for true relaxation.brbrTransportation Tips:brWith a dedicated covered parking space, exploring the island by car is easy. Many guests choose to walk or bike everywhere, thanks to the home's central location. Scooters, bikes, golf carts, taxis, and rideshares are all readily available for getting around Old Town and beyond.brbrOther Things to Note:br- Covered parking includedbr- High-speed Wi-Fi and multiple TVs throughout the homebr- A minimum stay of 30 days is required, in accordance with local regulationsbr- Guests must be 25 years of age or older to reservebrbrCheck-in: 3:00 PMbrCheck-out: 11:00 AMbrbrAt Colocada Vacation Rentals, we take pride in offering thoughtfully curated homes that let you experience Key West like a local. If you have questions or would like recommendations for dining, activities, or hidden gems, we're always happy to help make your stay at Angel Fish Cove unforgettable.

Angel Fish Cove | Updated Townhome Retreat Near Duval

Key West, Florida, United States

Bed

Bath

6

Sleeps

$340.83

Welcome to Hemmingway's Paradise! brLocated on an almost hidden enchanting lane in Old Town Key West, this cottage is the perfect hideout for guests. Knowles lane is a very small 1 block single lane street with only a few historic homes built on it. Remodeled to historic requirements in 2023, this home has been meticulously maintained and outfitted for guest pleasure and comfort. brThis 3 bedroom and 2.5 bath home is sure to wow guests with its top-of-the-line finishes and decor. brWith two historic original front porches, you'll most likely find yourself front porch sitting enjoying your morning coffee or enjoying a glass of wine on the wooden porch swing as neighbors walk by and say hello, no traffic on this lane! Even though the home has 2 off street parking spaces, one for a car and one for a golf cart or small compact car, most cars won't drive the small lane.brThe home features a teak wrap-around deck with a new hot or cool spa and ladder stairs leading up to the rooftop tanning deck with loungers, a patio mister and tropical foliage where you can soak up the sun during the day and stargaze at night. All deck and garden areas are equipped with timed soaker hoses or drip lines and you can pick your fresh limes and lemons from the potted citrus trees and relax amid the lush tropical foliage and optimal privacy. brThe front suite with its large ensuite bathroom has your private front door entry and porch and an additional bathroom door leading to the outside deck. brFront Suite amenities include a Keurig coffee station, mini fridge and microwave to allow you to rise and shine or end your evening at your own pace. The main living area features full corner glass double doors leading to the outdoor deck living area and the weekly maintained new jetted Spa, outdoor patio lighting, outdoor shower, and the ladder to the rooftop tanning deck. brThe kitchen offers everything you'll need to create a gourmet meal in home or to chill out and blend up that perfect pitcher of Pina coladas. New stainless appliances including an in fridge craft ice maker to mold up the ultimate large round ice spheres, cubed or crushed ice, a wine fridge, a full pot or K-cup coffee maker and a Nespresso machine for your morning espresso. brTake a short leisurely walk or bike ride to Higgs beach, Duval Street, The Hemmingway House, the Key West waterfront, restaurants, world famous bars and shopping and all that Old Town has to offer. Bicycles with locks, beach chairs and beach towels are also included.

Hemmingway's Paradise! Walk or bike to all that Old town Key West has to offer

Key West, Florida, United States

Bed

Bath

Sleeps

$655

Newly renovated town home located on a charming lane in the Truman Annex. The generous open floor plan features 10 foot ceilings both on the first and second levels with hardwood floors and crown molding. Enjoy the theater style kitchen with new quartz counter tops and stainless-steel appliances with a gas cook top. The large living and dining area feature custom built-ins and ample storage. The beautiful rear tiled patio enjoys plenty of room for outdoor living and entertaining and includes an additional storage space. The second floor has two generous sized bedrooms with private baths. One assigned covered parking space. With access to a refreshing community pool right out side your front door.brbrPlease note: This property is monthly rental - This property has a 28 night minimum stay

Admiral's Paradise at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$565.75

Summary:brbrEscape to this cozy 1-bedroom, 1-bath cottage at the historic Curry Mansion Inn in downtown Key West. This fully equipped retreat features a kitchen, comfortable living area, and private parking. Just steps from Duval Street, enjoy easy access to top dining, nightlife, and attractions. Blending historic charm with modern amenities, it’s the perfect island getaway. brbrNote: Pool closed April 20–27.brbrbrbrThe Space:brbrThis comfortable 1 bedroom,1 bathroom offers everything you need for a Key West getaway. With its full kitchen and private entrance you will feel right at home!brbrAs part of your stay, you’ll have access to the beautiful shared outdoor spaces at Curry Mansion. Relax on the porch, or take a dip in the communal pool to cool off after a day in the Florida sun. brbrbrbrBed Layout:brbrBedroom: Queen BedbrbrLiving room: Full Sized Sleeper SofabrbrFull Kitchen: Stove/Oven, Refrigerator, MicrowavebrbrbrbrGuest Access:brbrOur contactless check-in makes the process seamless. Guests will receive a personalized access code before arrival as well as code to the front door code to the James House & Curry Mansion amenities. Guests will also have direct contact to a local guest experience manager for any questions, needs or recommendations during their stay.brbrbrbrThe Neighborhood:brbrEnjoy live music every Saturday from 6-8pm at George's Bar!brbrbrbrPlaced perfectly between downtown Key West and the Historic Seaport, enjoy walkable attractions like Fury Water Adventures for a day at sea, the Mel Fisher Maritime Museum for some Key West history and the famous Mallory Square for a Sunset Celebration. brbrbrbrSteps from Duval Street, the Curry Mansion is steps away from Key West's most famous bars and kitchens. Food is at your fingertips with locals favorite restaurants, such as First Flight, Bagatelle and Two Friends Patio, less than a 5-minute walk from your front door. Got a sweet tooth Keep an eye out for Kermit’s Key Lime Pie Shoppe known for the best key lime pie in Key West. Or, grab some homemade fudge and candy from River Street Sweets.brbrbrbrForgot something or need a quick fix Shorty’s Market has your last minute necessities for your weekend getaway. Just 2 blocks away, you will also find Fausto’s Food Market with locally sourced groceries.brbrbrbrGetting Around:brbrThere are a variety of great ways to explore Key West whether it be by bicycle, pedi-cab, Moke, scooter, golf cart, Uber, taxi or foot. Being in the heart of downtown Key West, many attractions are within walking distance. Please note we can not guarantee parking, but feel free to ask us for recommendations!brbrbrbrOther Things to Note:brbr- Laundry facilities are shared - to get you started we supply detergent and dryer sheets.brbr- Pet friendlybrbr•40lb maximum per petbrbr•$25/per nightbrbr•2 pet maximumbrbr- Private Parking Spot

Shared Pool & Parking - The Cottage at James House

Key West, Florida, United States

Bed

Bath

Sleeps

$412.62

HISTORIC ISLAND CHARM...brLocated in the Casa Marina Area of Old Town which is known for lovely and sophisticated homes, this unmatched retreat is no exception. Modern architectural elegance emanates from every corner, inviting you to bask in serenity and escape reality. Winner of the Ceramic Star from the Historic Florida Keys Foundation, your idyllic abode is filled with expansive entertaining space both inside and out. Enter through your white picket gated fence onto the delightful covered porch where your day begins with a morning coffee and an island song in your heart.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES..brThoughtfully designed and well appointed, the open-concept living-room, kitchen and dining area offers endless possibilities and dramatic ceiling heights. The kitchen includes every modern convenience with a gorgeous island with seating for 4, hood, gas stove top and sparkling stainless appliances. Dine on your fresh catch at the rectangular dining table that seats 8, then revel in your favorite tv shows from the inviting modern couch or plush seating on your large tv. Oversized windows invite Key West natural light in, coaxing you to your backyard oasis, just beyond the large sliding glass doors.brbrSLEEPING ARRANGEMENTS...brThe first bedroom resides just off the entrance hallway, a delightful space with two twin beds that can be converted to a king, TV, dressers, hanging closet and bathroom with quartz sink vanity and tiled shower, which can be entered from the hallway also. The second bedroom is also located on the entrance hallway and includes a plush king bed, TV, dressers and hanging closets, and a private bathroom with large tiled shower. Travel up the steps to the vaulted bonus room and primary suite. A perfect entertaining space, this intimate living area hosts a sitting area with TV and a workspace. Travel down the hallway that offers closets, storage drawers and a washer/dryer space. The bedroom is outfitted with a king bed, TV, storage cabinet and a luxurious bathroom with a shower and jet soaking tub.brbrPOOL AND OUTDOOR LIVING...brSink into outdoor seating and table for 4 on your patio under the stars or stretch out in one of the lounge chairs and gaze into your private sparkling pool (heated in winter months). Lush landscaping and balmy breezes surround you, captivating your island soul. Fire up the gas grill for your outdoor feast with a crafted cocktail in hand. This home is walking distance to the Key West Artisan Market and Higgs Beach so you can enjoy ocean views and pickle ball courts at your leisure. brbrPARKING...brOne larger off street parking is provided.brbrPETS...brThis is NOT a pet friendly home, and the owners do not make exceptions.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation.

SOUL OF THE SEA ~ Charming 3 BR, 3 Ba Home w/ Pool and Parking!

Key West, Florida, United States

Bed

Bath

Sleeps

$1409.57

Mermaid Cove features four separate units (two cottages and two apartments), each with a private entrance and all decorated and furnished in charming tropical fashion. The units surround a central courtyard with outdoor patio furniture and a large gas BBQ grill. Mermaid Cove allows you to gather as a group, but also enjoy privacy. With accommodations for up to 10 people, it is perfect for extended families, a bunch of friends, bachelor/bachelorette parties, or wedding parties.brbrMermaid Unit 1 is an upstairs unit with a king bed, full kitchen, full bathroom, and living room with full sofa and a mini-split air conditioner. The living room has a flat-screen Smart TV and French doors that open onto a deck with table and chairs. It sleeps two people.brbrFunky Unit 2 is downstairs with a queen bed, full bathroom, mini kitchen with under-the-counter fridge, microwave, toaster oven, coffee maker, blender, a smart TV, and a mini-split air conditioner. It sleeps two people.brbrOcean Cottage 3 is free standing and has a king bed with French doors that open onto the central courtyard. The bathroom includes a shower. The kitchen has a mini-fridge, microwave, toaster oven, coffee maker, blender, smart TV, and a mini-split air conditioner. It sleeps two people.brbrNautical Cottage 4 is at the rear of the courtyard and features natural cedar walls. At the entrance is a beautiful mosaic-tiled 20-foot wall with a one-of-a-kind mural of a Key West beach scene with a Mermaid! This unit features 2 queen beds, a bath with shower, kitchen with a mini-fridge, microwave, toaster oven, coffee maker, blender, a flat screen smart TV, a small sitting area/dining table, and a mini-split air conditioner. It sleeps four people.brbrThe courtyard has a large Weber Genesis grill and large outside stainless steel sink that can be used to clean your catch of the day from your fishing excursions. The lights on the patio at night can be casual with the blue rope or blue lamps, or you have the ability to turn on a powerful LED light to light up the entire patio. The courtyard also has a Mermaid bottle opener and a weathered bell to get everyone's attention for a special toast or occasion. brbrNote: Parking in Key West is very limited. This property has no assigned parking and is street parking only. You are responsible for finding parking for your vehicle.brbrPlease note that this property does not have a pool. brbrThe individual making the reservation must be 25 years or older with proper identification and be an occupant of the property. The maximum number of people allowed in this property is 10. If there are more than 10 people are in your party upon arrival, your party will be asked to leave without compensation. Violation of ANY house rules will result in your party being asked to leave without compensation.

MERMAID COVE - A collection of four units on Duval

Key West, Florida, United States

Bed

Bath

Sleeps

$1281.04

Elegance and modern sophistication are apparent as you enter any one of these six conveniently located townhomes in a quiet Old Town Key West neighborhood just three blocks from Duval Street.brbrWindsor Townhomes #5 boast over 1700 sq ft. on two levels for your vacation destination, with it’s own private garden with heated pool. The open living/dining area features comfortable sofas and chairs, and a dining table to seat six. Just off the living room is your complete and fully-equipped modern kitchen with top-of-the-line appliances and a center island/bar. The half-bath is situated in the hall between the foyer and kitchen. Sliding doors open from the living area to a deck and the pool edged by variety of tropical plants. An inviting deck surrounding the pool provides atmosphere for peaceful conversation and relaxation after a day of sightseeing. One bedroom is on the first level with a queen bed and en-suite bath with shower only. The second level of the house offers two bedroom suites with en-suite bathrooms. The bedrooms are expertly decorated to offer luxury without being overbearing. Spacious and plush, the main suite has an elegant king bed and a grand tiled bath with his-and-hers sink and large shower. The second bedroom has two twin beds with luxurious linens and an en-suite bathroom with tub.brbrThe villas are equipped with central air-conditioning system, flat-screen TVs, security system, and fully-equipped kitchen. These elegant villas are a destination for those expecting a special and exclusive holiday with the warm atmosphere of your own home! Located across the street from the Basilica of St. Mary Star of the Sea, it is the perfect spot for destination wedding parties.brbrBedding: 1 king, 1 queen, 2 twinsbrParking: One off-street parking space

Relax in Style at Windsor Townhomes #4

Key West, Florida, United States

3

Bed

3

Bath

6

Sleeps

$344.63

Your own private paradise awaits in this peaceful neighborhood just steps away from the buzz of Duval Street. “Soleil Chalet” is a completely restored cottage delivering easy access to all Key West has to offer while still providing a quiet retreat from the nightly celebrations downtown. A short walk from the most popular dining options on the island, as well as Fausto’s Food Emporium and Higgs Beach, this house comes with all the amenities you'll need for a single or multi-month stay. Relax in your private heated salt-water pool, cook delicious meals in your fully stocked gourmet kitchen, and work remotely from an adjustable standing desk (if you must!). Enjoy ample storage, a large washer/dryer, central air, a gas grill, free high-speed wifi, off-street parking for two cars, beach towels, floaties, and more!brbrStep into the world of Old Town Key West in this spacious dream home with 3 bedrooms and 3 baths. High ceilings in all bedrooms and the great room make this home feel extra large. All bedrooms have wall-mounted smart TVs, and the primary bedroom offers a king bed as well as an ensuite bathroom with a spacious shower. In the second bedroom you’ll find a king-sized bed and hallway bathroom. The pool house, aka “The Luna Lounge,” offers the privacy of a private studio apartment. It features a queen pull-down Murphy bed, an additional full-sized bed in the loft, and an ensuite bathroom. There is also a queen sleeper sofa in the main house for any additional overnight guests.brbrModern elegance meets classic style in this stunning Key West home. The full gourmet kitchen features all the state of the art appliances that any chef could dream of. The large kitchen island is the perfect gathering place for friends and family, and a pass-through window from the kitchen to the deck makes it easy to provide ingredients to the grill chef or frosty cocktails to your friends. Enjoy your morning coffee from the combo drip/Keurig machine while rocking on the front porch. The bright and airy living room offers all the comforts of home with a 55-inch flat screen TV and large U-shaped couch. Sliding glass doors open up to your lush outdoor tropical oasis, a deck with a private pool, lounge chairs, outdoor couch, a grill, dining table, and large umbrellas for those looking for shade from the Florida sun. brbrThis home is truly Key West living at its best!

Paradise Awaits @ SOLEIL CHALET

Key West, Florida, United States

Bed

Bath

Sleeps

$562.53

Relax with the whole family at this peaceful, pet friendly, waterfront oasis Remodeled in 2021 with kayaks, pool table, bbq with large outside dining areas, only a 15 minute drive to key west. his beautiful home is family owed. We manage the property ourselves and work very hard to ensure you receive the best quality of service from cleanings, stocking the property with everything needed and always available to answer any questions. Enjoy the blue waters surrounding the property perfect to explore in kayaks. Fully equipped kitchen includes coffee, creamer, teas, spices paper towels, cleaning supplies with enough stock for long term rentals laundry includes detergent, tv on every bedroom , as well as sleeper sofa and air mattresses for extra guests brbrbrYou will feel at home in this beautiful quiet neighborhood surrounded by nature and a crystal-clear canal, a chef's kitchen fully stocked for your entire stay with essentials like coffee, spices, cleaning supplies, paper towels, tp and more. Brand new beds and luxurious mattresses for a restful sleep, luxury hotel grade linens for extreme comfort . A Beautiful under-home patio with a pool table ample lounge area and BBQ , two outdoor dining tables , a hammock, a small fridge for your convenience and an ice machine, under-house covered parking for two vehicles, a private yard with plenty of space surrounding the property , and cohesive decor throughout . Guests have access to 3 kayaks, two two-person kayaks and one single person kayak, extra large float and single floats available also beach chairs and umbrellas brbrThe waters surrounding the Saddlebunch Keys and most of the Lower Keys coastal waters are very shallow – 1 to 3 feet deep, boats must not draft more than 18- 20 inches. Geiger Key Marina is located 10-minutes from our home and offers boat ramp access, there are several public boat ramps for open water access on both Shark and Sugarloaf KeysbrbrbrExplore nearby places like Baby coffee, located 2 minutes away, also key west sky dive located 10 minutes from the propertybr

Home in Blue water Key

Key West, Florida, United States

Bed

Bath

Sleeps

$429.51

****Welcome to the Parothdhideaway in Key West****brThis unique property offers an excellent place for groups or families looking to experience the vibrant island life. This central air-conditioned 3-bedroom home with two bathrooms—one equipped with a shower and the other with a relaxing claw-foot bathtub, both with a bidet, offering luxury and comfort. When you arrive at the house, you will have your own off-street parking spot and a handicap-accessible ramp leading to a large wraparound deck and an intimate pool. The washer, dryer, and ironing board ensure convenience and comfort. It's easy to see why you'll be able to unwind during the day and look great at night. brbrA secure bike rack is provided, and we also offer discounts on bike rentals. This is our way of ensuring that you can explore the island at your own pace and convenience.brbrThe house is located within minutes of the bustling Duval Street, the heart of Key West's entertainment district, where shopping, restaurants, and famous bars are just a quick bike ride or walk away. The property is also conveniently located near other popular attractions, making it an ideal base for your Key West adventure.brbrThe Layout of the house br- First Floor - br*Main bedroom with Queen Bed and Private entrance.br*Main bathroom with walk-in shower br*Living roombr*Kitchenbr*Dining roombrbr- Second Floor - br*2nd Bedroom with Queen bed, sitting area, and (rollaway bed available upon request)br*3rd Bedroom with 2 Double Bedsbr*2nd Bathroom with claw-foot bathtubbrbrAdditional features: brThe washer/Dryer is located in the shed outside.brCentral A/CbrCeiling fansbrFlat-Screen Smart TVs in the Living Room and all BedroomsbrFully equipped KitchenbrBasic stock of spicesbrStarter supply of paper productsbrAll beds come with linens and additional setsbrTowels providedbrHigh-Speed Wireless Internet accessbrFamily Games and Puzzles for those rainy daysbrbrUpon Request: br- housekeeping provided during your stay, additional costs (inquire by message for more information)br- Pets are considered - max of 2 allowed, and a fee of $200 per pet/stay will applybrbrWe kindly ask that you respect our neighbors and the residential area by keeping noise levels down past 11 PM. If we are notified of a violation of this, an additional charge of $200 may be imposed, and the rental may be terminated without refund. We appreciate you understanding and the cooperation in this matter.

Parothdhideaway - 3 bed w/pool and parking. Walking distance from Duval Street.

Key West, Florida, United States

Bed

Bath

Sleeps

$1105.86

This mid-town Key West home is recently refreshed with light colors and beautiful British Colonial furnishings. It features three bedrooms and three baths. The open living/kitchen area is decorated with light colored walls with striking tropical tones in the accent furnishings and tile, and soft fabrics. The dining room is outside in the attached pavilion. brbrEach of the bedrooms opens to a different part of the yard, extending the private space for each bedroom outside as well. The master bedroom opens to the pool area with two walls of French doors and windows. The master bath features a large tiled walk-in shower. The second bedroom is freshly painted with cool green tones and Key West art set to inspire. The third bedroom has two twin beds that can be also be made as a king. Villa Paradiso is in a very quiet residential neighborhood in close proximity to the beaches on the south side of the island. It is an easy bike ride to Duval Street and even closer to the Casa Marina area. A retreat vacation spot. Bedding: 2 kings, 2 twin beds

Villa Paradiso: A unique mid-town paradise

Key West, Florida, United States

Bed

Bath

Sleeps

$159.33

There's no better way to experience island time - that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this two-bedroom, three-story brick townhouse offers privacy and includes access to a gorgeous residents-only heated pool. Yet you are only several blocks from the main artery for entertainment-world-famous Duval Street-and in close proximity to Ft. Zach Beach, where you can claim your spot in the sand with a rented umbrella and chaise lounge or just stretch out your colorful beach towel and plop down.brbrOnce you've left your car in the designated off-street parking, enter through a six-foot white picket fence that opens into the front garden of the Royal Palm private residence. Up a few stairs puts you on a deck with a seating area. The entry door is an architecturally impressive facade of wood and glass panels covering one entire wall of the residence and flooding the first floor with ambient light. Inside a paddle fan adds charm, functionality, and accentuates the expansiveness of the twelve-foot ceiling. Below white travertine flooring stretches throughout an open floor plan. brbrTo the right is a conversation area delineated by a colorful oriental area rug. Classic wicker chairs, a deep-seated couch, wicker coffee table, and wicker end tables make this a perfect setting for reading or playing games like Cranium or Balderdash with family or friends. Directly across is a glass-top desk complete with wireless high-speed internet, phone/fax machine, and printer awaiting your computer hookup. Or if you've left the electronics behind on purpose, maybe use the space for handwriting wish you were here postcards to friends back home. Next to the desk is a flat-screen TV perfectly situated for comfortable viewing from the conversation area. Interesting art work and a charming bird clock (complete with different bird calls for each hour) add color and interest to the cloud white walls. It goes without saying that cable, stereo, and DVD player are available when you need them.brbrThe dining area consists of a glass-top table, four high-backed chairs, and a downlight chandelier/paddle fan whirring above. Steps away is the breakfast bar that also serves as a convenient pass-through from the kitchen to the dining area should you be motivated to make dinner salads or a three-course meal. The kitchen itself has a contemporary vibe with a double sink and all the modern amenities you'd expect right at your fingertips. Plenty of cabinet space above and below make it easy to keep countertops clear. A utility closet and half-bath complete this level of the residence.brbrHardwood stairs lead to the second-story master bedroom with en suite full bath. Up another flight to the third level is the guest bedroom, also with en suite full bath and twin beds that can be converted to a king if that's your preference. The master has a comfy king bed dressed in vibrant stonewashed cotton linens that beckon at naptime and/or bedtime. Bedside tables with lamps, a flat-screen TV, a six-drawer wicker dresser with large mirror, and a wicker armchair tucked in one corner complete the scene. But the best part is the large glass double doors flanked by large glass panels and the private balcony beyond. Sit here in your jammies (or even less) for your morning coffee or nighttime cocktail. No one besides gently swaying palm fronds or maybe a flock of water birds passing overhead can glimpse you in this space. A linen closet, a generous clothes closet for your hanging items, a full bath, and washer/dryer closet round out this floor. brbrIn the third-floor bedroom, panel after panel of windows flood this room with Florida's incomparable daylight and myriad stars at night, while another ceiling fan silently marks the 24-hour progression. Use this bedroom for children or guests while you maintain your own privacy on the floor below.brbrRoyal Palm is just minutes from the fun and frivolity you came to Key West to check out. Steps from your door enjoy the manicured landscaping, verdant palms, and interconnecting pathways that give your Truman Annex neighborhood its park-like atmosphere. Stroll out wrought iron privacy gates to find yourself immersed in the sights and sounds of Duval's tourist attractions. Check out the tours, museums, water sports, shopping, bars, and over two hundred restaurants, many with open-air seating, some right on the water. Don't miss the Butterfly & Nature Conservatory, boutiques, and especially the nightly sunset celebration at Mallory Square, where visitors and locals alike gather to applaud as the sun slips below the horizon. Then hang around afterwards for the spontaneous party. Unless you're been to the island before, pick up a guidebook to ensure you don't miss the vibrant art and culture scene that includes live music, lectures, plays, movies, art galleries, and artists' talks.brbrIf this is your first trip to the Conch Republic, a guidebook from Books & Books on Eaton Street or a stop at the Chamber of Commerce Information Center on Greene Street will help make sure you don’t miss anything. Other info on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section). Historic Hideaways' informative Area Guide/Events page located on our website also has a Calendar of Events. We DO NOT guarantee that the information VRBO (and affiliated sites) scrapes from our site to display on theirs is 100% accurate, particularly the amenities. If you come to us through them, be sure to look at all the information on our site related to your rental once you book to be sure you have accurate and up to date information.

Royal Palm

Key West, Florida, United States

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Bath

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$1287.01

These beautiful villas boast over 1700 sq ft. on two levels for your vacation destination, with it’s own private garden with heated pool. The open living/dining area features comfortable sofas and chairs, and a dining table to seat six. Just off the living room is your complete and fully-equipped modern kitchen with top-of-the-line appliances and a center island/bar. The half-bath is situated in the hall between the foyer and kitchen. Sliding doors open from the living area to a deck and the pool edged by variety of tropical plants. An inviting deck surrounding the pool provides atmosphere for peaceful conversation and relaxation after a day of sightseeing. One bedroom is on the first level with a queen bed and en-suite bath with shower only. The second level of the house offers two bedroom suites with en-suite bathrooms. The bedrooms are expertly decorated to offer luxury without being overbearing. Spacious and plush, the main suite has an elegant king bed and a grand tiled bath with his-and-hers sink and large shower. The second bedroom has two twin beds with luxurious linens and an en-suite bathroom with tub.brbrThe villas are equipped with central air-conditioning system, flat-screen TVs, security system, and fully-equipped kitchen. These elegant villas are a destination for those expecting a special and exclusive holiday with the warm atmosphere of your own home! Located across the street from the Basilica of St. Mary Star of the Sea, it is the perfect spot for destination wedding parties.brbrBedding: 1 king, 1 queen, 2 twinsbrParking: One off-street parking space

Modern Elegance at Windsor Townhomes #5

Key West, Florida, United States

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Bath

Sleeps

$328.81

CLASSIC OLD KEY WEST HOME...brThis home is boasting a rare combination of location and character. A mix of historic details and modern charm are evident throughout. Perfect for couples traveling together or those who have visitors during their stay in Paradise.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES.... brWalk in the door and be surrounded by Dade County pine and wood flooring. The main floor offers a large living room that is convenient for work and play and indoor dining for 6. You will find a full bathroom off the living room with a beautiful claw foot tub, pedestal sink and original mosaic tile. There is a fully stocked kitchen which over looks the private yard. Fabulous natural light through an abundance of wood windows finished in bright white moldings to compliment the home. The second floor is where the bedrooms lie in wait. There is abundant storage upstairs as well as the second full bathroom. brbrSLEEPING ARRANGEMENTS....brThe two bedrooms are located up the original wood staircase on the second floor. The master bedroom has a comfortable queen size bed, sitting area and a French door that opens to the rear deck. This room comes with a flat screen, smart TV so you can catch all your favorite shows on Netflix! There is an ensuite full bathroom with a shower stall and pedestal sink. The guest bedroom has two twin beds that can be converted to a king upon request. The hallway has a trundle bed with two twin beds. The downstairs living room has a sleeper sofa. br brOUTDOOR LIVING...brStep onto the front porch where there is seating to people watch while you take your morning coffee. If privacy is what your searching for then you can enjoy the refreshing dip pool with a beautiful backdrop of manicured tropical landscaping. Gather together under the pergola with cozy outdoor furnishings or enjoy dining together at the bench style table with plenty of seating available. brbrLOCATION...brThe location of this home is perfect for strolling through Old Town looking at the historic homes. Just a few blocks away you will run into Simonton & Duval street's where shops, galleries and restaurants line the area. There is always plenty to do or see like watching the sun set at Mallory Square or catching the Conch Train to hear the history of the island and how it became the coveted retreat it is today for visitors from all over the world!brbrPARKING...brOn street parking is available in the surrounding area for this home. Please park in unmarked spaces as residential permit spaces are only for Key West residents.brbrPETS...brPets are considered at this property and a pet fee is required. Please include the size and breed in the comments.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrLOCATION IN PARADISE!

ORCHID ESCAPE~ 2 bedroom 2 bath set in Old Town with private dip pool!

Key West, Florida, United States

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