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Distance to beach: 2 miles to Smathers
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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,...
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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...
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Mar Y Sol – Luxury Oceanfront Condo in Key West Breathtaking Views. Unbeatable Comfort. Perfect Location.Welcome to Mar Y Sol, a stunning oceanfront condominium located at 1800 Atlantic, Key West. This beautifully renovated 3-bedroom, 2.5-bathroom vacation rental offers sweeping views of the...
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The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment * King size bed in the bedroom *accommodates 2 adults only * WiFi inlcuded * Parking included *Central AIr Conditioning * Check-out cleaning is $160 * This is not a hotel; it is a privately owned condo facing the...
Featured review
Just finished a 2 week stay and I have been renting from Pam for over a decade and she continues to make a great condo even better with her constant upgrades to the unit and she is a wonderful host. The...
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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...
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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,...
Distance to beach: 0.5 miles to Ft. Zachary Taylor State Park
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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...
Distance to beach: 0.4 miles to Fort Zachary Taylor State Park
Key Amenities
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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,...
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Atlantic Sunrise – 3BR/3BA Penthouse with Partial Ocean ViewWelcome to Atlantic Sunrise, the only 3-bedroom, 3-bath unit in the exclusive 1800 Atlantic complex. Spanning approximately 2,000 square feet, this spacious penthouse comfortably accommodates up to 8 guests, making it the perfect retreat...
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Spacious 2-Bedroom Condo with Ocean Views & Island ComfortsThis beautiful 2-bedroom, 2-bath condo offers a lovely view of the Atlantic Ocean and an extra-large floor plan with a slightly oversized private balcony—accessible from both bedrooms and the living room. It’s the perfect island...
Distance to beach: 0.4 miles to Fort Zachary
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Escape the winter and settle into this beautifully renovated 2-bedroom, 1-bath condo in the heart of Old Town Key West — perfect for snowbirds and monthly renters seeking the ideal balance of tranquility and convenience. Located in the prestigious gated community of Truman Annex at the Shipyard...
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Beautiful top floor ocean front 2 bedroom 2 bath condo at La Brisa in Key West. The property has a queen bed in each bedroom and the master has an en suite bathroom. Totally renovated Kitchen and a balcony with amazing Sunrise Views across Smathers Beach. The living room has a flat screen smart TV...
Featured review
Very thing was good the condo was perfect and the pool was great the parking was close to the elevator
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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...
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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...
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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...
Distance to beach: 0.8 miles to Simonton Beach
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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...
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Tom's Oceanfront PenthouseExperience coastal luxury at Tom's Oceanfront Penthouse, a stunning 3-bedroom, 2-bathroom unit ideally located in a prime spot within the complex. Just steps from the elevator, this expansive 2,000 sq. ft. penthouse offers the ultimate in comfort and convenience,...
Featured review
We went to Key West to attend my nephew's high school graduation. People extremely hospitable and easy to work with to reserve the condo. Comfortably fit 5 adults. The room, views, and landscaping are beautiful!...
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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...
Distance to beach: 300 feet to Southernmost Beach
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This beautiful one bedroom, one bath condo is located in the Historic District, Old Town Key West . The condo is approximately 50 feet to Duval Street. It sleeps up to 4 people, one bedroom with a queen bed, a sleeper sofa in the living room which sleeps 2. One bathroom with a stand up shower and...
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Welcome to “The Coconut” – Your Slice of Old Town ParadiseTucked into the heart of Old Town Key West, The Coconut is your dreamy island hideaway — where history meets laid-back tropical living.Built in the late 1800s and full of classic Key West charm, this sun-drenched...
Key Amenities
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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...
Florida and Monroe County require a 12.5% tax, which includes a 6% state sales tax, 1.5% county surtax, 4% tourist development tax, and 1% tourist impact tax. The owner sets the cleaning fee, damage waiver, and any additional costs, but because you book directly with them, there isn’t a booking fee on top.
SHORT STAY
3 nights
all in
$751/night
| $571 × 3 nights | $1,713 |
| Cleaning + damage waiver | $290 |
| Tax (12.5%) | $250 |
| Booking fee | $0 |
| Total | $2,253 |
WEEKLY STAY
7 nights
all in
$668/night
| $552 × 7 nights | $3,864 |
| Cleaning + damage waiver | $290 |
| Tax (12.5%) | $519 |
| Booking fee | $0 |
| Total | $4,673 |
MONTHLY STAY
30 nights
all in
$554/night
| $483 × 30 nights | $14,490 |
| Cleaning + damage waiver | $290 |
| Tax (12.5%) | $1,848 |
| Booking fee | $0 |
| Total | $16,628 |
The best time to visit Key West is spring, when the air sits in the low 80s and the water has warmed to the high 70s without the risk of summer storms. Winter runs a close second, since the water is still in the low 70s, making Key West a nice escape for snowbirds. Come June, the heat and the afternoon storms arrive together, with the majority of the area’s rain concentrated between June and October.
| Month | Median nightly | Difference from annual | High / low air temp | What’s going on |
|---|---|---|---|---|
| January | $393 | +31% | 75° / 65° | Literary Seminar; Food and Wine Festival |
| February | $400 | +33% | 76° / 66° | Art and Craft Festival at Truman Waterfront |
| March | $393 | +31% | 79° / 69° | Conch Shell Blowing Contest; Taste of Key West; spiny lobster season ends |
| April | $317 | +6% | 82° / 72° | Conch Republic Independence Celebration |
| May | $285 | -5% | 85° / 76° | Songwriters Festival; Minimal Regatta, Memorial Day weekend |
| June | $249 | -17% | 88° / 81° | Pride, closing with the parade down Duval |
| July | $250 | -17% | 89° / 80° | Hemingway Days, with the look-alike contest at Sloppy Joe's |
| August | $233 | -22% | 90° / 79° | Spiny lobster season opens |
| September | $258 | -14% | 88° / 79° | WomenFest; Just a Few Friends; BrewFest |
| October | $309 | +3% | 85° / 76° | Fantasy Fest, ending the last Sunday; Goombay on Petronia Street |
| November | $300 | 0% | 81° / 72° | Film Festival; Harbor Walk of Lights from Thanksgiving eve |
| December | $310 | +3% | 77° / 67° | Lighted Boat Parade; New Year's Eve drops |
Based on the median Key West nightly rate on FloridaRentals.com.
You can bike the length of the island in about 30 minutes. Lively Old Town holds the historic district, Duval Street, and the Historic Seaport. New Town runs east toward the airport. It’s more suburban, but the buildings are newer and city code requires each licensed rental to have an off-street parking space, a rule that does not apply inside the historic district.
Seven airlines run scheduled nonstop service into Key West International, three to four miles from Duval and about 15 minutes by car. Driving from Miami is about 160 miles (around 4 hours), and US-1 is the only road in.
On-street parking in Old Town's commercial blocks is paid through the Passport Parking app, and no vehicle may sit on a city street longer than 72 hours. The Old Town garage at Grinnell and Caroline is open 24 hours, and paying there covers the city bus for everyone in the car.
While evacuations are rare, if they do happen, Monroe County begins a mandatory visitor evacuation about 48 hours ahead of tropical storm winds and residents about 30 hours out. Key West is Zone 1, farthest from the mainland, and US-1 is the only road off the island.
The island has only so many short-stay licenses, so a week can be harder to find than a month. A licensed rental must post a medallion with contact information outside, and the city keeps a public list of licensed addresses.
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