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Looking for a tropical escape with a unique island vibe? Our monthly rentals in Key West, Florida, offer the perfect mix of relaxation, adventure, and charm. From iconic sunsets to lively cultural events, Key West is an idyllic destination for extended stays, whether you're planning a seasonal retreat or a long-term getaway
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The Sea View Cottage is a 2 bedroom, 1 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is...
Featured review
This gated estate is exceptional. The beach is just steps from the back door, and the ocean views are outstanding. The pool area is stunning and offers a beautiful place to relax and take in the scenery....
Key Amenities
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Looking to Relax Renew Recharge? We got you. Your own Key West Sanctuary awaits! Escape to a classic Conch family home perfectly tucked away for privacy yet, only 5 Blocks from famous Duval Street. The best of both worlds! Morning yoga class on the deck, late night dip in the pool, and sunset...
Featured review
We loved our time at Key West Sanctuary! The perfect location to bike to the sights and sounds of Key West; close to one-way roads with a bike lane going to/from Duval. The beautiful and peaceful surroundings...
Key Amenities
About this property
Adorable historical conch house 2 bdrm, 2 full bath on quiet street with all the modern day amenities & decor in convenient location, relax by your private heated/chilled pool surrounded by decking and palm trees. Enjoy your morning sitting on the front porch watching the breeze travel through the...
Featured review
Beautiful home on a quiet street and close to everything. No need for a car. You can walk or ride bikes to anywhere on the island. Outdoor area is just right for a group of six. Totally enjoyed the...
Key Amenities
About this property
Welcome to Island Paradise, your serene retreat in the heart of Key West, Florida! Located in Old Town, Island Paradise is just a half block from the world-famous Duval Street. This charming property offers 2 bedrooms and 2 bathrooms, perfect for small families or couples looking for a relaxing and convenient...
Key Amenities
About this property
Down a very quite lane the house has one off street parking spot. If you are familiar with Key West you understand what a treat it is to have off street Parkin !Enter from gate through lush and colorful walk to front door of main house . Walking over the front porch is the typical Key West style outside...
Featured review
We loved our stay at Hidden Cottage! Located on a perfect bike loop with bike-lane to Duval (one way on Southard to Duval and one way on Fleming home)! Also very close to the boat docks. Hidden Cottage...
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Key Amenities
About this property
Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into 5 condo units. Tony's Conch Retreat, unit 5, is on the 2nd floor, at the top of the stairs, and encompasses the rear of the home from end to end. It has a lovely view of the...
Distance to beach: 0.8 miles to Higgs Beach
Key Amenities
About this property
Seasonal rental - Fully furnished - beautifully painted in Keyzie colors, 1br/1ba rear cottage in the historic district of Old Town, Key West; 5 blocks to the beach and 4 blocks to the world famous Duval Street with shops, art galleries, restaurants, bars and night clubs.FEATURES: One off street...
Distance to beach: 528 yards to Fort Zachary Taylor Historic State Park Beach .3 M
Key Amenities
About this property
Welcome to Casa Del Sol ℠— your luxurious and elegantly appointed 2-bedroom, 2.5-bath island townhome with private carport, nestled within the 45 lushly landscaped acres of the prestigious Truman Annex in the heart of Old Town Key West.Designed for relaxing extended stays, Casa Del Sol℠...
Key Amenities
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Luxury island resort style living in Key West. 1800 Atlantic offers a private sandy sunning beach, Olympic style pool, gym, three tennis courts (one is clay), fitness center, community clubhouse, picnic areas and more. This condominium is updated and turnkey . Open living and dining spaces, eat-in kitchen...
Distance to beach: 2 miles to Smathers Beach
Key Amenities
About this property
**Peaceful Paradise in Key West Golf Club – Monthly Stays Welcome**Escape to serenity in this beautifully appointed 2-bedroom townhouse nestled within the gated Key West Golf Club community. Designed for monthly stays of 29 days or more, this home offers the perfect blend of comfort, convenience,...
Featured review
The townhouse and grounds are exactly as pictured and described! Staying on Stock Island was a great experience. Close enough to beaches and downtown Key West and the island itself offers a number of terrific...
Key Amenities
About this property
Just a few houses off Duval, this wonderful retreat occupies the ground level of an almost 100-year-old home in one of the most desired locations in Old Town Key West. A large covered front porch welcomes you to sit and watch the Key West world go by, imagining what life was like in the early days of...
Key Amenities
About this property
Just a few houses off Duval, this wonderful retreat occupies the upper level of an almost 100-year-old home in one of the most desired locations in Old Town Key West. The carefully restored Dade County Pine wood walls and Red Oak floors evoke a more relaxed era in the Southernmost City. The home opens...
Key Amenities
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Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discerning travelers for over 15 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenities and ideal location the perfect spot to enjoy all that Key West has to offer.Dos...
Featured review
Our family of 5 visited Dos Casas and had an absolutely wonderful stay! We were warmly welcomed and informed about the property-they were very attentive to details. The compound is beautifully maintained...
Distance to beach: 2 miles to Smarthers Beach and Higgs Beach
Key Amenities
About this property
This home sits in Key Lime Grove Subdivision which I was born and raised in. It is a neighborhood rich in history and conveniently located on the Island. This home welcomes you with a white picket fence! It has been nicely upgraded down to the wood floors and crown molding trim. Open living room and dining...
Featured review
Sunshine House on Harris Street, Key West is a Home away from Home. We enjoyed 2 months of comfort and convenience at this home. The home is furnished with tasteful Island Decor. The layout is 3 bdrms...
Key Amenities
About this property
The Sand dollar is a 3 bedroom, 2 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is just...
Featured review
This is our 2nd stay at this vacation rental. We love the view, pool, dock, house, privacy and the owners. A must for anyone vacationing in the Keys!!
Key Amenities
About this property
Relax with family and friends in your own tropical paradise at this spacious townhome in Key West's beautifully landscaped & maintained Golf Club. Located in a private gated community with resort style amenities, it is just minutes away from the beaches, world class restaurants, water sports...
Featured review
We had wonderful time enjoying the beautiful weather and the beauty of all the attractions at Key West. Our condo was all we needed to fulfill our stay. It was clean and we enjoyed being right on the golf...
Distance to beach: 0.8 miles to Fort Zachary Taylor State Park and Beach
Key Amenities
About this property
Due to a change in licensing we are only available for monthly rentals. However I will consider offering a last minute deal pay for 3 and stay for 4. Please contact me directly.Here in Key West we believe in One Human Family where everyone is welcome and treated like family.Our condo has always...
Featured review
Top notch place in great location. Very clean. Would definitely stay in this unit again sometime in the future.
Key Amenities
About this property
The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny...
Featured review
I came to this house with friends, completely unsure what to expect from Key West. The island itself moves at this fascinating, slightly calm/chaotic pace, but stepping into this rental felt like entering...
Key Amenities
About this property
Island Dreaming – Your Luxury Key West Getaway - MONTHLY RENTAL Welcome to Paradise*** Please note for 2027 High Season rentals Jan- February - Arrival after the 5th of January for 6 week minimum is required in order to get accurate pricing***Discover the ultimate island retreat at Island...
Distance to beach: 0.5 miles to Higg's Beach
Key Amenities
About this property
Private Luxury Key West Home with Private Pool, surrounded by lush tropical landscaping in the Casa Marina neighborhood of Old Town.The fusion of a mid-century Florida home with dramatic Caribbean design, has created an ideal contemporary “Floribbean” style villa in the Casa Marina district...
Featured review
We were so impressed with this Key West hidden gem. Along with it's beauty, you feel the love and care the owners have for this private home, as they provided you with all the amenities, plus so much more....
Key Amenities
About this property
Welcome to Key West Getaway in Old Town!In the heart of Old Town, Southard Square Condominiums is an award-winning condo development with stunning gardens, a clubhouse with changing rooms/baths, seating area, kitchenette and one of the largest private community swimming pools in Key West. Staying...
Featured review
Thank you for you help in researching a vacation rental . We love key west an we will be inquiring with you in the future
Key Amenities
About this property
Private home located in New Town available for 28 day minimum rental. Beautifully landscaped yard with secure private back yard and pool. The home features a kitchen with all appliances and granite counter top. The master suite opens onto the pool deck and is furnished with a king size bed and walk-in...
Featured review
We stayed a month in December(2022),had everything we needed,close to shopping,sightseeing, nightlife,beaches and airport. House is completely furnished and nothing is lacking.Pool was heated and had all...
Distance to beach: 0.2 miles to Fort Zachary Beach
Key Amenities
About this property
AMAZING LOCATION in TRUMAN ANNEX: SHABBY CHICKEN - come stay with the large & proud bird in town!! She's not too shabby after all, she is close to the action, but far enough from the riff-raff :) Large front yard and porch to watch Key West pass by. Beautiful and spacious in/outdoors. POOL within...
Featured review
Shabby Chicken was absolutely perfect. From the location, amenities, interior , exterior, proximity to Truman waterfront , Fort Zachary beach and the Green Parrot. Marie (and Tom) were awesome. Karen and...
Distance to beach: 1 miles to Fort Zachery Taylor State Park
Key Amenities
About this property
924 Southard Street... an Old Town cottage made famous by Country Home magazine! Featured in Country Home , in June 2001, this one-of-a-kind cottage was formerly owned and decorated by well known decorator Mary Emmerling. Southard Comfort is perfect for the guest who wants to feel like a local and enjoy...
Featured review
Southard Comfort is perfectly appointed and comfortable. There is nothing I can suggest to improve the experience. The house is nicely decorated, the kitchen is completely outfitted, the location is great...
Distance to beach: 800 yards to Ft. Zachary Taylor State Park
Key Amenities
About this property
SPECIAL OFFER. A GREAT 12 NIGHTS ARE AVAILABLE NOV. 9-21 FOR THE PRICE OF A WEEKAbout This Property A Touch of Bermuda is a privately owned, two-story Bermuda-style conch cottage in the Shipyard section of Truman Annex — one of only seven private townhomes available for rent in this gated,...
Featured review
Our stay for the month was perfect. A Touch of Bermuda has everything a guest could want in a perfect Key West location. However, the best part of our stay was dealing directly with the owner (Jack) throughout...
Key Amenities
About this property
This charming one bedroom cottage has everything you need. Full kitchen and living area to relax in. Outdoor backyard patio with gas grill. It is an easy walk to shopping and dining. If you have a car, this property offers a private parking space for your convenience. Please note this is a monthly...
Key Amenities
About this property
This estate has it all waterfront, large sun-filled pool and seawall dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and entertain your guests. The home was recently rented...
Featured review
Perfect spot to vacation!! Family friendly. This adorable house is downtown and close to everything!! I loved the yard and the porch was a favorite. Can't wait to return!
Key Amenities
About this property
2/2 Main House, 1/1 Bunglow, Large Pool And Hot Tub On Beautiful Old Town LaneMulti-month Discounts availableHidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion and quiet serenity. Nestled amongst mature tropical landscaping,...
Featured review
The location is perfect - about 3 blocks from Duval, and 3 blocks from Truman, and a short bike ride to Ft. Zachary beach. We did not have a car, and did two Uber runs for groceries at Publix, then used...
Key Amenities
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Suncatcher on the Ocean – Available at 1800 AtlanticWe’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...
Distance to beach: 600 yards to Simonton Street Beach
Key Amenities
About this property
Enjoy an unforgettable stay at a one-of-a-kind ship-builder's home in the heart of Old Town Key West. You will be on a quiet lane in the most desirable neighborhood, just a few short blocks from dining, boating, fishing, galleries, theatre and entertainment. Unique features include open air kitchen...
Featured review
Management was informative and responsive. The home was perfect for our needs. Everything was pristine and well cared for. I would give this rental and the management the highest recommendation.
Key Amenities
About this property
The welcoming views at Coral Cove are waiting for you! This brand new two-bedroom, two-bathroom home is located on the open water and canal on Saddlebunch Key, just a stone’s throw from the famous “Baby’s Coffee.” You’re at Milemarker 15 and Key West is just minutes away!This...
Key Amenities
About this property
A phrase the locals use quite often here in Key West is that we are "Living the Dream" - if you come and spend some time here you will see why! Steps away from the Key West Seaport and just a few blocks from world famous Duval Street this property is located on Eaton Street in Old Town Key...
Key Amenities
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Casa Atlantic is located in the upscale Casa Marina District on a quiet shrub lined street that has very little traffic, because it is not a through street. This luxury house that was built in 2013 with 1,672 sq. ft. of finished indoor space has everything that is needed, except refreshments and food....
Distance to beach: 2 miles to Smathers
Key Amenities
About this property
January-April 2027 is booked. December 1-29 is available along with the rest of 2026. 28 minimum nights required by city of Key west. One level home! Relatives have stayed and loved it. Rates: July-Sept 8k per month, October $10,000, November is $20,000 /month, December $22,000/month. January, 2027 $23,000/month,...
Key Amenities
About this property
Charming Pool Cottage in the Heart of Old Town Key WestPerfectly situated in historic Old Town Key West, this quaint and inviting pool cottage offers the ideal island escape for a couple, with room for occasional guests. Thoughtfully decorated and impeccably maintained, the home features a newly renovated...
Key Amenities
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Best Deal in Truman Annex – Céad Míle Fáilte! 2 Bedroom | 1 Bathroom | Sleeps Up to 5 GuestsWelcome to Innis-free, our little slice of paradise in Key West—where you're greeted with Céad Míle Fáilte, an Irish expression meaning “a...
Featured review
We really enjoyed the unit at Shipyard Condos. Very clean and well equipped. Walking distance to local restaurants and very convenient with a dedicated parking place. Pool was nice too. There were only...
Key Amenities
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Luxurious Renovated Monthly Rental at 1800 Atlantic – Ocean Views & Premium Comfort Step into elegance at this beautifully renovated, high-end condo at 1800 Atlantic. From the moment you enter, you'll appreciate the meticulous attention to detail and modern upgrades throughout the space. Enjoy...
Key Amenities
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Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of 2 full suites. The first floor has a roomy living room, huge screen porch, queen sleeper sofa, bath and bedroom connected by an exterior staircase to the second floor. The second floor...
Featured review
I have not stayed there yet, but will gladly take $5 for this review. I hope is as nice as it its described
Key Amenities
About this property
Escape to the laid-back charm of Key West with The Gumbo Limbo Cottage, a beautiful and beachy vacation rental. Nestled in the heart of the island, this charming 1933 shotgun house has been impeccably restored and uniquely decorated, creating a tranquil and inviting atmosphere for your month-long getaway.As...
Key Amenities
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When they say it's all about the location, this home says it all!By city ordinance, you must rent this property for 29 days or longer!!Welcome to this beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street.A stairway decorated with wainscoting will lead you...
Key Amenities
About this property
This nicely appointed home is located in Key Haven subdivision of fine homes. It offers an expansive living room with upgraded kitchen and appliances. The kitchen is nicely stocked with plenty of room for multiple cooks. The house can accommodate up to six people with 3 bedrooms and 2 full bathrooms....
Featured review
We absolutely love this home! The interior features plenty of space and storage. The kitchen is well equipped with everything you need and more. The bedrooms very comfortable. The shower in the master has...
Key Amenities
About this property
Located just 10 miles from Key West on beautiful Geiger Key. Cozy and comfortable canal front getaway perfect for the fisherman eager to explore the crystal blue waters of the Keys or the person wanting to experience all that Key West has to offer. Deep water with quick direct access to Atlantic Ocean....
Featured review
This location is amazing just minutes to downtown Key West and a few minute idle by Boat to the Ocean(we brought our own boat and docked out back!) Had fun Snorkeling in crystal clear water, and even tried...
Key Amenities
About this property
Welcome to Moveable Feast, a dreamy home in the heart of Bahama Village that sleeps 10 comfortably. Located on a quiet, friendly lane with two parking spaces right in the middle of all the action. Four bedrooms (one king and three queens) - each with their own attached bathroom - plus a half bath on the...
Distance to beach: 0.4 miles to Fort Zachary Taylor State Park
Key Amenities
About this property
Key West is just like the Caribbean, always warm with lovely turquoise waters. It's a short walk to Mallory Square, Hemingway's Home, the Truman White House, Duval Street and Zachary Taylor Park ( do yoga on the beach, swim, snorkel, or hang hammocks between the palms). Walk to shops, restaurants,...
Key Amenities
About this property
Very good location in Big Pine, deer paradise, a very quiet place to relax and rest if what you want is incredible peace to relax, believe me, this is your place, lots of outdoor space, the house is on a corner, very cozy inside and out, outdoor hammocks, many places to sit and spend a lovely afternoon...
Key Amenities
About this property
Welcome to your Key West escape! Nestled in the heart of 'Old Town', this charming townhouse is part of a wonderful twelve townhouse community with a lush, tropical garden courtyard that provides a tranquil, resort-like feel. You're just a half-block from the quiet end of Duval Street,...
Key Amenities
About this property
Beautifully Renovated 2BR/2BA Condo at Exclusive 1800 AtlanticExperience comfort and elegance in this beautifully renovated 2-bedroom, 2-bath condo located in the prestigious 1800 Atlantic community. Each bedroom features a king-size bed, generous closet space, and direct access to a private balcony...
Distance to beach: 0.8 miles to Simonton Beach
Key Amenities
About this property
AboutClassic Old Key West HomeThis home offers a rare combination of location, charm, and character. With a beautiful mix of historic details and modern updates throughout, it’s perfect for couples traveling together or anyone hosting visitors during their stay in paradise.Primary guest...
Key Amenities
About this property
Extremely rare for Key West: Oceanfront property with dock and swimming pool. Have your cake and eat it too! 10 minutes to famous Old Town and its many entertainments, or to luxurious Perry Hotel and Marina, or to famous Safe Harbor Marina with Artists studios and Hogfish Bar and Grill. or travel by kayak...
Distance to beach: 0.5 miles to Ft. Zachary Taylor State Park
Key Amenities
About this property
NEW YEARS WEEK DEC. 26 TO JANUARY 2 IS AVAILABLE DUE TO A CANCELLATION So welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations and since I am not a real estate salesman or property manager, allow me let the photos and description speak for themselves....
Featured review
A touch of Cuba was the perfect little spot. We are now spoiled to the conveniences of renting direct with the owner, having Class A rated efficiencies, Beach, Bikes, Pool, very quiet and well kept area...
Explore a variety of monthly rentals in Key West, including historic homes, beachfront condos, and private cottages. Whether you’re seeking serenity or excitement, you’ll find the ideal rental to match your lifestyle. Enjoy the comfort and convenience of a long-term stay in the heart of the Florida Keys.
Don’t wait to secure your long-term rental in Key West. Browse our listings to find the perfect property for your stay. Whether you’re planning a winter retreat or a summer adventure, Key West offers endless opportunities to relax and explore.
It’s never too early to book your next getaway. Reserve your spot in advance to secure the best rental for your preferred dates, whether for a seasonal retreat or a long-term escape.
Group-Friendly Rentals: Traveling with family or friends? Key West offers spacious rentals with private pools and large living areas, perfect for group vacations or reunions.
Romantic Retreats for Couples: Key West’s sunsets, vibrant nightlife, and luxury accommodations make it an ideal spot for couples seeking a romantic getaway.
Winter Retreats for Snowbirds: Escape the cold and enjoy warm weather, turquoise waters, and the laid-back lifestyle of Key West for your extended stay.
Secure your winter retreat in Key West by booking one of our monthly rentals today. Embrace the luxury, sunshine, and vibrant island lifestyle that make Key West a favorite destination for snowbirds and long-term visitors
💰 Highest rates
January and February
🎉 Busiest month
March
🏠 Popular home types
Historic homes and waterfront cottages
🔥 Hottest months
July and August
❄️ Coldest months
January and February
☔ Rainiest months
June through September
🌺 Best months for flowers
April and May
🌴 Peak tourist season
January through March
🍂 Quietest months
September and October
🌊 Best beach months
April through June
🏌️ Best golfing months
November through April
🎨 Top cultural events
Fantasy Fest (October), Hemingway Days (July)
🍽️ Best dining months
January through March
🦋 Best months for nature activities
March through May
🛶 Best water sports season
June through September
🏖️ Best months for shelling
May and June
📅 Local festivals peak
January through March
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