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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...
Distance to beach: 22 yards to Public use + Private views Waldorf Astoria Resort
Key Amenities
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This beach view is beautiful and apartment in town can be yours EVEN IF FOR A SHORT VISIT! Just Blocks from downtown Key West? LIKE NO-WHERE ELSE! Like no where else in Key West, do Come + have YOUR, OWN OCEAN VIEWS! Yes! Secluded but not isolated? Yes! Check RATES AS NOW ARE DISCOUNTED, BOOK SOON!...
Featured review
Our stay at the studio was lovely. The proximity to the ocean and beach cannot be beat. The place was very clean, well appointed, comfortable, and creatively decorated too. Our host was very responsive...
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
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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...
Key Amenities
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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...
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Key Amenities
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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: 0.3 miles to Ft Zachary Taylor
Key Amenities
About this property
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theaters and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a huge, fabulous decks that overlooks the action on...
Featured review
We had 6 couples visiting key west for a week to celebrate milestone birthdays and get away. The houses were perfect for our group. Beautifully decorated,plenty of space for everyone to enjoy and not...
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
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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...
Key Amenities
About this property
2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys and 15 minutes to Key West. Located within the keys wildlife preserve, Sea View Estate is just a 15 minute drive to the shopping and nightlife of Key West and just minutes to some of the finest restaurants...
Featured review
This is the perfect place for a Florida vacation. It has everything we were looking for and more. Private beach, quiet location, mature trees with coconuts and bananas. Tiki hut with a wet bar and comfy...
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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TRANQUIL BEAUTY: 3 BR’s, 2 Baths Private Haven paradise with huge private heated pool and landscaped back yard!ENJOY KEY WEST at its peaceful best in your 3BR, 2 bath private hideaway in a quiet neighborhood near Higgs and Smathers beaches and only a 10 minute bike or Uber ride from Duval Street....
Featured review
Location was great. Quiet neighborhood, lush garden and good accommodations. The tile in the pool is excessively dirty. Pool guys came several times during our stay and never cleaned them.
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...
Key Amenities
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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!!
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...
Distance to beach: 0.5 miles to South Beach
Key Amenities
About this property
This Simonton Studio is neat, sweet and complete. *Cleaning fee of $100 is additional. * WiFi included * King size bed * Outdoor table and two chairs * spacious shower * excellent location for walking Old TownThis accommodation is the perfect location for exploring Key West. So, get out there...
Featured review
This property is perfect for a couple or a single wanting a getaway to the vibes of Key West. It has everything you need from a comfortable bed, a cool air conditioner, a functional kitchen with all the...
Distance to beach: 0.5 miles to South Beach
Key Amenities
About this property
This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key West. * King size bed * WiFi included * check-out cleaning is an additional fee of $100 * Split AC system * flat screen TV * porch with table and 2 chairs This accommodation...
Featured review
This small unit had everything we needed. Very clean and convenient to everything we wanted to do. Will rent again! Pam was so easy to work with.
Key Amenities
About this property
The Mile Zero House is a MONTLY VACATION RENTAL. Rent one or more months comes completely furnished. Charming conch home with true Key West character. Fenced for privacy with a open style front porch to enjoy the local flavor along with a passing Conch Train. Full size kitchen that is nicely stocked with...
Featured review
Historic Conch House Located Downtown Key West near Duval St and restaurants beach and many attractions ! Private Yard fully locked and fenced with beautiful plants Sitting on the front Porch you feel...
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
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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...
Key Amenities
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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
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...
Distance to beach: 528 yards to Fort Zachary Taylor Historic State Park Beach .3 M
Key Amenities
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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℠...
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...
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...
Key Amenities
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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...
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...
Key Amenities
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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
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.
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
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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...
Key Amenities
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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
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...
Key Amenities
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OWNER PAYS 12.5% TOURIST TAX ON YOUR BEHALF - $0. CHARGES ADDED TO YOUR RATECasa 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...
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...
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...
Key Amenities
About this property
Art-Filled 1,700SF 3BR/2BA Old Town Key West Home with 2 Decks, Pool, Parking,++Large art-filled, two story Key West condo boasts 2 large inviting bedrooms, including a king bed, queen bed, and large office or third bedroom for extra flexibility. Guests enjoy living and dining rooms, 2 full bathrooms,...
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...
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...
Key Amenities
About this property
Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida.*Saturday-to-Saturday Rentals OnlyProperty Overview:Prime Location: Casa Rosa is situated in a picturesque neighborhood, just one block away from Key West's renowned Duval Street. Casa Rosa...
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
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...
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...
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
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
Casa Papa Del Mar Two Bedroom Premiere Ocean View With a complete 2023 renovation, the décor is inspired by the life and travels of “Papa” Earnest Hemingway. This is a beautiful top floor two-bedroom ocean-view unit at 1800 Atlantic condos. It has pristine ocean-views from all rooms...
Featured review
BEST PLACE WE EVER STAYED AT. THERE WERE FOUR OF US. BEAUTIFUL LOCATION. SO COMFORTABLE. KIRK WAS SO HELPFUL TO HELP US GET SETTLED IN. ALL THE TREATS OF HOME. VIEW INCREDIBLE. WANTED OUR TIME THERE TO...
Key Amenities
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Coral Hammock – 3BR/3BA Home with Pool Views in Coral Hammock3 Bedrooms | 3 Full Bathrooms | Sleeps up to 8 | Backs to Community PoolWelcome to Coral Hammock, your home away from home in beautiful Key West! Built in 2004 and meticulously maintained, this spacious 3-bedroom, 3-bathroom home...
Featured review
Our family had a wonderful time staying in this townhome style rental. We relaxed and enjoyed the views of the bay and marina from the back porch. The boat slip worked great for our rental boat. This...
Key Amenities
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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...
Key Amenities
About this property
Location,Location, Location!! Old Town cottage!! Great location! 2 bedrooms 2 full bathrooms, Both bedrooms have King beds and french doors to outdoor sitting areas. Great front porch to watch the conch tour train go by.
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
$575/night
| $575 × 3 nights | $1725 |
| Cleaning + damage waiver | $300 |
| Tax (12.5%) | $253 |
| Booking fee | $0 |
| Total | $2,278 |
WEEKLY STAY
7 nights
all in
$571/night
| $571 × 7 nights | $3997 |
| Cleaning + damage waiver | $300 |
| Tax (12.5%) | $537 |
| Booking fee | $0 |
| Total | $4,834 |
MONTHLY STAY
30 nights
all in
$281/night
| $281 × 30 nights | $8430 |
| Cleaning + damage waiver | $300 |
| Tax (12.5%) | $1091 |
| Booking fee | $0 |
| Total | $9,821 |
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 gulf temp | Avg. gulf temp | What’s going on |
|---|---|---|---|---|---|
| January | $399 | +29% | 75° / 65° | 71° | Literary Seminar; Food and Wine Festival |
| February | $417 | +35% | 76° / 66° | 71° | Art and Craft Festival at Truman Waterfront |
| March | $398 | +29% | 79° / 69° | 73° | Conch Shell Blowing Contest; Taste of Key West; spiny lobster season ends |
| April | $327 | +6% | 82° / 72° | 78° | Conch Republic Independence Celebration |
| May | $300 | -3% | 85° / 76° | 81° | Songwriters Festival; Minimal Regatta, Memorial Day weekend |
| June | $249 | -19% | 88° / 81° | 83° | Pride, closing with the parade down Duval |
| July | $250 | -19% | 89° / 80° | 85° | Hemingway Days, with the look-alike contest at Sloppy Joe's |
| August | $233 | -25% | 90° / 79° | 87° | Spiny lobster season opens |
| September | $250 | -19% | 88° / 79° | 85° | WomenFest; Just a Few Friends; BrewFest |
| October | $295 | -5% | 85° / 76° | 83° | Fantasy Fest, ending the last Sunday; Goombay on Petronia Street |
| November | $300 | -3% | 81° / 72° | 78° | Film Festival; Harbor Walk of Lights from Thanksgiving eve |
| December | $333 | +8% | 77° / 67° | 75° | 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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