Vacation Rentals By Owner In Key West, FL

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrWALKING ON SUNSHINE is a modern, tastefully decorated penthouse condo featuring a large wrap-around balcony that offers a front row seat to those famous Key West sunsets and overlooks the peaceful nature preserve and Atlantic Ocean beyond. Best of all, WALKING ON SUNSHINE is located in an upscale private community within walking or biking distance to all of your favorite Key West spots, including beaches, restaurants, shopping, and the beautiful waters surrounding the island. You'll be WALKING ON SUNSHINE throughout your stay in America’s Paradise at this beautifully appointed condo...And Don't it Feel Good! brbrTHE LIVING AREA...brbrA unique feature of WALKING ON SUNSHINE is the vaulted ceilings – in a lovely white wood that sets the tone for this gorgeous beachside condo. The floor-to-ceiling glass doors allow for plenty of natural light to fill the living room. There's a large flat screen TV in case you can tear yourself away from the stunning views off your balcony to catch your favorite show. The living room features a large comfortable sofa, that pulls out to a Queen sleeper for extra guests, and two leather armchairs. The fully-equipped kitchen has top-of-the-line stainless steel appliances and all of the tools the chef in your group will need to prepare a meal. There's an indoor dining table for six when you decide to stay in and an outdoor dining set on the balcony to enjoy an ultimate sunset dinner.brbrTHE POOL, THE BEACH & TENNIS...brbr1800 Atlantic offers Resort-style amenities, including an extra large Community Pool right downstairs. There are chaise lounges surrounding the pool for your comfort, and a cabana with restrooms for your convenience. Please note this is a shared pool with set rules, such as no music and no coolers. We ask that our guests be mindful of their neighbors and respect the rules.brbrFrom the pool, there's a walking path that leads to the on-site beach. The on-site beach offers a relaxing setting, with chaise lounges and soft sand. There is no direct water access from this beach, but Smathers Beach, Key West's largest public beach, is located within walking distance right next door. There is also an oversized Jacuzzi and a picnic area with BBQs available for guest use. You'll also have access to the newly built fitness center and Key West's only clay tennis courts, both located on-site.brbrTHE ACCOMMODATIONS...brbr** Master Bedroom: King bed, a large flat screen TV, direct access to the balcony, and an en-suite bathroom with an oversized shower. brbr** Second Bedroom: Two Twin beds OR One King bed, a flat screen TV, direct access to the balcony, and access to the full second bathroom.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Community Pool Accessbr** Community Jacuzzi Accessbr** Assigned off-street carport for 1 car (Parking Garage has a low clearance of 6'4)br** Key West's only clay tennis courtsbr** Handball courtsbr** Fitness Centerbr** Dry Saunasbr** Picnic areas with BBQsbr** Recreation rooms available for private partiesbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** This complex has both visitors and locals living here, we expect our guests to be mindful & respectful of the posted rulesbr** 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.

**WALKING ON SUNSHINE @ THE BEACH** Ocean Condo & Large Pool + LAST KEY SERVICES

Key West, Florida, United States

Bed

Bath

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

$341.0

Hyatt Vacation Club at Windward Pointe sits along the Atlantic side of Key West with beautiful oceanfront views and a relaxed tropical atmosphere. The resort features landscaped grounds, palm trees, and waterfront walking areas that highlight the beauty of the island setting.brbrGuests can enjoy a large oceanfront pool, hot tub, and barbecue areas designed for relaxing outdoor gatherings. The resort offers a peaceful retreat while still being just a short drive from the energy and nightlife of historic Key West.brbrThis two-bedroom villa provides a spacious layout designed for families or groups traveling together. The residence typically includes a primary bedroom with a king bed, a second bedroom with additional bedding, and a comfortable living area with a sleeper sofa.brbrThe villa also includes a full kitchen equipped with appliances, cookware, and dining space for convenient meals during your stay. A private balcony allows guests to relax and enjoy island breezes after a day exploring Key WestbrbrThe resort is located on the eastern side of Key West overlooking the Atlantic Ocean. Guests can easily explore the island’s famous attractions including Duval Street, Mallory Square, historic homes, and waterfront restaurants.brbrVisitors can also enjoy snorkeling, boating, fishing charters, and sunset cruises throughout the Florida Keys. The central island location makes it easy to explore the laid-back lifestyle and natural beauty that make Key West a unique destination.brKOALA Disclosure Summary:brbr-IMPORTANT: Payments appear as “KOALA VACATIONS” on credit card statements.brbr- BEFORE YOUR CHECK-IN: This booking requires the name and address of the person checking in. THE PERSON CHECKING IN MUST MATCH THE PHOTO ID PROVIDED TO US.brbr- This resort is part of a timeshare and you may be invited to attend a sales presentation. Any participation is always optional and never required when booking through KOALA.brbr- The primary guest checking in must be at least 21 years old.brbr- Resorts own and manage all units/amenities; unit assignments at check-in.brbr- Room photos are samples; actual furniture/layout may vary.brbr- The Resort is responsible for maintenance, may alter/close select amenities due to COVID-19 or other factors. KOALA is only responsible for ensuring your check-in and unit category.brbr- KOALA is not responsible for unit condition or resort services. For resort, unit or guest related issues after check-in, please contact the resort management.brbr- Check cancellation policy before booking. No refunds after the cancellation deadline due to any reason, including COVID-19 (except full resort closures), natural disasters, or personal changes. For these reasons we always recommend purchasing trip insurance for unforeseen circumstances like these. This resort is part of a timeshare and you may be invited to attend a sales presentation. Any participation is always optional and never required when booking through KOALA.

Hotel Resort

Key West 2BR Retreat – Ocean Views & Island Adventure

Key West, Florida, United States

Bed

Bath

Sleeps

$776.0

Hyatt Vacation Club at Windward Pointe sits along the Atlantic side of Key West with beautiful oceanfront views and a relaxed tropical atmosphere. The resort features landscaped grounds, palm trees, and waterfront walking areas that highlight the beauty of the island setting.brbrGuests can enjoy a large oceanfront pool, hot tub, and barbecue areas designed for relaxing outdoor gatherings. The resort offers a peaceful retreat while still being just a short drive from the energy and nightlife of historic Key West.brbrThis two-bedroom villa provides a spacious layout designed for families or groups traveling together. The residence typically includes a primary bedroom with a king bed, a second bedroom with additional bedding, and a comfortable living area with a sleeper sofa.brbrThe villa also includes a full kitchen equipped with appliances, cookware, and dining space for convenient meals during your stay. A private balcony allows guests to relax and enjoy island breezes after a day exploring Key WestbrbrThe resort is located on the eastern side of Key West overlooking the Atlantic Ocean. Guests can easily explore the island’s famous attractions including Duval Street, Mallory Square, historic homes, and waterfront restaurants.brbrVisitors can also enjoy snorkeling, boating, fishing charters, and sunset cruises throughout the Florida Keys. The central island location makes it easy to explore the laid-back lifestyle and natural beauty that make Key West a unique destination.brKOALA Disclosure Summary:brbr-IMPORTANT: Payments appear as “KOALA VACATIONS” on credit card statements.brbr- BEFORE YOUR CHECK-IN: This booking requires the name and address of the person checking in. THE PERSON CHECKING IN MUST MATCH THE PHOTO ID PROVIDED TO US.brbr- This resort is part of a timeshare and you may be invited to attend a sales presentation. Any participation is always optional and never required when booking through KOALA.brbr- The primary guest checking in must be at least 21 years old.brbr- Resorts own and manage all units/amenities; unit assignments at check-in.brbr- Room photos are samples; actual furniture/layout may vary.brbr- The Resort is responsible for maintenance, may alter/close select amenities due to COVID-19 or other factors. KOALA is only responsible for ensuring your check-in and unit category.brbr- KOALA is not responsible for unit condition or resort services. For resort, unit or guest related issues after check-in, please contact the resort management.brbr- Check cancellation policy before booking. No refunds after the cancellation deadline due to any reason, including COVID-19 (except full resort closures), natural disasters, or personal changes. For these reasons we always recommend purchasing trip insurance for unforeseen circumstances like these. This resort is part of a timeshare and you may be invited to attend a sales presentation. Any participation is always optional and never required when booking through KOALA.

Hotel Resort

Key West 2BR Retreat – Ocean Views & Island Adventure

Key West, Florida, United States

Bed

Bath

Sleeps

$684.0

Hyatt Vacation Club at Windward Pointe sits along the Atlantic side of Key West with beautiful oceanfront views and a relaxed tropical atmosphere. The resort features landscaped grounds, palm trees, and waterfront walking areas that highlight the beauty of the island setting.brbrGuests can enjoy a large oceanfront pool, hot tub, and barbecue areas designed for relaxing outdoor gatherings. The resort offers a peaceful retreat while still being just a short drive from the energy and nightlife of historic Key West.brbrThis two-bedroom villa provides a spacious layout designed for families or groups traveling together. The residence typically includes a primary bedroom with a king bed, a second bedroom with additional bedding, and a comfortable living area with a sleeper sofa.brbrThe villa also includes a full kitchen equipped with appliances, cookware, and dining space for convenient meals during your stay. A private balcony allows guests to relax and enjoy island breezes after a day exploring Key WestbrbrThe resort is located on the eastern side of Key West overlooking the Atlantic Ocean. Guests can easily explore the island’s famous attractions including Duval Street, Mallory Square, historic homes, and waterfront restaurants.brbrVisitors can also enjoy snorkeling, boating, fishing charters, and sunset cruises throughout the Florida Keys. The central island location makes it easy to explore the laid-back lifestyle and natural beauty that make Key West a unique destination.brKOALA Disclosure Summary:brbr-IMPORTANT: Payments appear as “KOALA VACATIONS” on credit card statements.brbr- BEFORE YOUR CHECK-IN: This booking requires the name and address of the person checking in. THE PERSON CHECKING IN MUST MATCH THE PHOTO ID PROVIDED TO US.brbr- This resort is part of a timeshare and you may be invited to attend a sales presentation. Any participation is always optional and never required when booking through KOALA.brbr- The primary guest checking in must be at least 21 years old.brbr- Resorts own and manage all units/amenities; unit assignments at check-in.brbr- Room photos are samples; actual furniture/layout may vary.brbr- The Resort is responsible for maintenance, may alter/close select amenities due to COVID-19 or other factors. KOALA is only responsible for ensuring your check-in and unit category.brbr- KOALA is not responsible for unit condition or resort services. For resort, unit or guest related issues after check-in, please contact the resort management.brbr- Check cancellation policy before booking. No refunds after the cancellation deadline due to any reason, including COVID-19 (except full resort closures), natural disasters, or personal changes. For these reasons we always recommend purchasing trip insurance for unforeseen circumstances like these. This resort is part of a timeshare and you may be invited to attend a sales presentation. Any participation is always optional and never required when booking through KOALA.

Hotel Resort

Key West 2BR Retreat – Ocean Views & Island Adventure

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

Bed

Bath

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

Bed

Bath

Sleeps

$324.37

Freshly updated Salt Ponds condo located on Key West minutes from the beach , airport and downtown. Enjoy a soak in the pool or hot tub and with a short bike or walk to Smathers Beach. Only steps form Key West Airport and close to all amenities in New town it’s still only 10 minutes from downtown and all the action. Enjoy the custom jetted tub or walk in shower along with two bedrooms with king size and queen size beds. Fully equipped kitchen with all utensils and appliances including a weber electric grill. Washer and dryer in unit along with cable, smart tv, and wireless internet. Beautiful Pool and Hot Tub along with tennis courts on property. Local store packed with snacks, drinks and beach amenities short 3 min. walking distance.br

Cozy Salt Pond Condo Hideaway

Key West, Florida, United States

Bed

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

Bed

Bath

12

Sleeps

$225.0

Enjoy all of Key West in this spacious condominium. The views of the natural salt ponds from your balcony are enchanting. The unit has two bedrooms and two full bathrooms, is a fully furnished home with three televisions and high speed internet. La Brisa has a large pool, tennis courts, clubhouse, barbecue grills, and many more amenities. This gated and secure community is steps from the beach on the Atlantic Ocean and a short bike ride downtown for restaurants and nightlife.

UPSCALE CONDO @ BELOW MARKET RATES

Key West, Florida, United States

Bed

Bath

Sleeps

$185.83

Suncatcher on the Ocean – Available at 1800 AtlanticbrbrWe’re thrilled to introduce Suncatcher on the Ocean to the rental market at the prestigious 1800 Atlantic community. This stunning, newly renovated condo has been upgraded from top to bottom with high-end finishes and thoughtful details throughout. Offered for rent for the very first time, this property is a perfect blend of luxury and comfort.brbrIsland-Inspired ElegancebrbrTastefully decorated with island décor and a touch of tropical flair, Suncatcher on the Ocean welcomes you with a relaxing, home-away-from-home atmosphere. Enjoy seamless indoor-outdoor living with balcony access from both bedrooms and the living room — perfect for taking in ocean breezes and serene views.brbrModern Comforts & Conveniencebrbr Dedicated workspace for remote professionalsbr Full-size washer and dryerbr Assigned covered parking for one vehicle (height limit: 6'4)brbrResort-Style Amenities at 1800 Atlanticbrbr Olympic-size heated poolbr 20-person jacuzzibr Fitness center and librarybr Small sunning beach and direct access to Smathers Beach, Key West’s largest city beachbr Three lighted tennis courts, including one clay courtbrbrThis is your opportunity to enjoy upscale coastal living in one of Key West’s most desirable communities.lay.brbrElevator Upgrade project taking place from June - September 2026 - Please note there will still be one working elevator in both the East and West building while this project is underway.

Suncatcher Luxurious 2 Bdrm Monthly Rental Fabulous amenities, Key West Best

Key West, Florida, United States

Bed

Bath

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

Bed

Bath

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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$1665.0

Location! Style! Elegance! This restored beach home is fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, this location can not be beat. The home's history is rich...neighboring the historic Gato Cigar factory which is now restored and used as county offices. Duval Square is directly across the street with three restaurants, shops, and even a salon and convenience store. The best homemade ice cream in Key West is just down the street!brbrThe house is beautifully decorated with warm colors, sophisticated furnishings accented with Cuban and beach themed artwork. There is both a living room and reading area in the front of the house and a indoor/outdoor room to enjoy the tropical lifestyle of Key West. A large farmhouse table sits in the sun room with french windows and doors overlooking the pool directly off the new kitchen with black granite counters and stainless steel appliances.brbrThe master bedroom is beautifully decorated with its black pencil post bed and unique bathroom with spa style vanity. The second bedroom sits to the back of the house and feels like the master suite with french doors to the outdoor sitting area and pool.brbrThe 21-foot long heat optional pool features benches on each side for relaxing (one with jets!) There is an outdoor table and nearby gas grill for outside/open air dining.brbrkeywords: House

Casa De Cuba A Beach House - Cuban Flair Steps From Duval

Key West, Florida, United States

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$179.58

City of Key West Business License # 28224brbrWe hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memorabilia welcome you into the abode our first guest affectionately called “The Writer's Retreat'.brThis two bedroom, one bath condo with bleached grey hardwood flooring throughout is highlighted by a massive 65 inch Plasma TV loaded with thousands of movies at your fingertips. Relax on the designer furniture while enjoying the full collection of Hemingway's books or lose yourself in The Master Bedroom retreat which has been luxuriously decorated with 1000 thread count bedding on the Romantic Canopy Bed with French doors leading out to a spacious rear patio overlooking the pool.brThe guest bedroom has two twin upgraded pillow top beds that can be converted to a King bed to accommodate a family or two couples. The King is stocked with a very thick down padding and luscious linens for maximum comfort. Enjoy the sounds of the keys or music of Buffet as the guest bedroom is decorated in tribute to crooner and the island lifestyle detailed in framed sheet music.brIf staying in for the evening or fixing breakfast or lunch have fun in the 1950’s themed state of the art kitchen equipped with an imported European SMEG Fridge and Stainless Appliances. Likewise, the bathroom has been decorated in an art deco style typical of an earlier time in the Keys. brThe front Family room area has features a queen sleeper sofa bed with a down pad and bedding for extra sleeping space. All pillows and bedding are down and of high quality in order to provide maximum comfort on your stay. Quite simply, we designed this home to fit in with the Keys lifestyle. It is bright, open and lends itself to a vibe which we hope catapults you to a great stay in our beloved Keys.brbrPlease enjoy the slide show of our new wonderful home in Key West and we hope to accommodate your vacation needs.brbrTO VIEW OUR OTHER PROPERTIES VISITbrVRBO Listing #412277 & #497962 for Catalina Island brVRBO Listing #316356 PGA WEST La QuintabrVRBO Listing #592709 for San Clemente BeachbrVRBO Listing #633858 for Park City UtahbrVRBO listing #724909 for Garden District New OrleansbrVRBO listing ID 815366 For Kiawah Island, Charleston South CarolinabrVRBO Listing ID 901935 for Newport BeachbrbrPlease see contract for additional details.

Hands-Down Best Deal in Key West!

Key West, Florida, United States

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$212.2

This one bedroom apartment on the ground floor is completely restored with a full kitchen and laundry. This unit has everything you need for an extended stay.Walk out to the private garden from your living room. Located on one of the best streets in Old Town. You are just 3 blocks from the Harbor, home to the freshest seafood restaurant and the best happy hours on the island. Or Walk down to Duval street to experience the local music scene and bar hopping, restaurants and shopping. Located in a privately owned historic home.brbrThis one bedroom has a California King and a queen pull out sofa in the living room. The kitchen is stocked with everything you need for cooking. There is a 55 TV in the living room and a 32 TV in the bedroom with cable and WiFi.brbrOutside enjoy the Tiki Bar for happy hour while sitting in the private garden, or jump in the hot tub to relax.brbrClose to everything, yet quaint and quiet, you will love your stay. We also have 2 other units in our home a 2 bedroom 1420448 and another 1 bedroom 1420515.

Just Restored One Bedroom Hideaway with Garden and Hot Tub 5 No Need For A Car

Key West, Florida, United States

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$840.38

This 2,000-square ft-condo is unique in that it has two large master bedroom suites with changing areas and private baths plus a third bedroom w/bath. A pull out sofa bed allows for total accommodations for 8 people. With the master suites on opposite ends of the condo, it is a great set-up for 2 or 3 couples as well as for friends or families who want additional space with luxury surroundings. There is a well equipped kitchen if you wish to dine in, free high speed internet, washer/dryer, iron & board, hairdryers, 3 TVs, DVD player and more. The sliding glass doors on each bedroom and living room all open to the large wrap around patio with a partial ocean view. The gated complex has a large beautiful tropical courtyard with grills and picnic tables, and the large pool and hot tub overlooking the ocean. brbrThe Olympic-size pool overlooking the Atlantic ocean with private beach is absolutely breath taking. The huge, tropical courtyard inside the complex truly makes you feel like you are in a tropical haven. In addition, for your enjoyment is an over-sized hot tub and men's & women's saunas to relax in. Feel free to use the barbecue grills and picnic tables to have your picnic in paradise, or you can get some exercise using the 3 tennis courts (1 clay), hard ball court, or walking the beach. The 400 ft. beach front is adjacent to Smather's Beach to the east, or walk a 1/2 mile to the west and arrive at Higgs Beach. All this helps set the tone for a fabulous vacation. brbrKey West is a Caribbean Island with all the luxuries and conveniences of America. It is surrounded by the turquoise water of the Caribbean and Atlantic oceans, loaded with history, art galleries, performing arts, symphony, tropical foliage, fabulous restaurants, sports activities, 7 public beaches, shopping, entertainment, music and watering holes. Weddings on the beach are a common site. brbrbrCONSTRUCTION NOTICE- Balcony Restoration Project – 1800 AtlanticbrStart Date: May 2025-Estimated Completion: Spring 2026brPlease be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026.brImportant Notes:br-Units available for booking will not be under construction.br-All amenities, including the pool, spa, and sunning beach, will remain open and fully operational throughout the project.

Spacious Ocean Front Resort - 3 Bedroom Condo

Key West, Florida, United States

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