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Sailfish Villa, unit #6, is a brand new gorgeous, professionally decorated 5 bedroom 4 bath Villa with open water views on Vaca Cut! Enjoy sunrise and sunset colors and direct ocean and Gulf access! It has a private pool and boat slip for a boat up to 35' including motors. There is no additional...
Featured review
I have been coming to marathon with family for many years and have had many rentals.. Meredith I have to say is the best.. she worked with me with every question and plans that I had . Definitely would...
Distance to beach: 0.5 miles to South Beach
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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.
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Brand-new construction, expertly decorated single family home in Marathon. Whether you are vacationing with family, embarking on a fishing trip or looking to just relax Florida keys-style this is the perfect home for you. This spacious 1,800 square foot single-level stilt home offers 4 bedrooms, 3 full...
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Welcome to Blue Wahoo, the perfect Florida Keys Island Getaway.Check-in to this gorgeous coastal home for a wonderful vacation on what is arguably the nicest of Florida’s lower keys. This house has it all. It is beautifully furnished; from a well-equipped kitchen and updated living room to...
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Turtle Cove - Turtle Cove is a true hidden treasure in Islamorada. This oceanfront gated estate consists of an enclave of four charming cottages nestled in beautiful landscaping with a total of seven bedrooms and seven bathrooms. When entering through the gate you will feel a sense a tranquility that...
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DOCKSIDE RETREAT is a 4 bedroom 3 bath canal front home that has a private pool, private dock, fish cleaning station, with a green light under the dock, two paddle boards, a kayak, four bikes, and a Tiki Hut for the ultimate Keys vacation! There are 4 parking spots for vehicles and one boat trailer (you...
Featured review
Dockside Retreat was such a treat to experience for one week. The owners are very helpful and gracious. We went all out for us and rented a boat for fishing and cruising. Our Captain (son-in-law) is an...
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1440 sf - Sleeps 4 adults (also includes xtra bed in guest room plus EZ-Bed electric queen Bed and large sectional couch with chaise lounge and cuddler for larger families). Fully renovated and updated in 2021. 70ft foot dock and cleaning table. Great ambience, quiet home like feel. Private community...
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Here is the review I am trying to post via for our March 2024 stay.Wonderful! Fantastic! Amazing!Wonderful Hosts!!! Jay and Sharon are so welcoming and supportive! We felt at home before we...
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Weekly rentals in the Keys {and generally elsewhere } are based on a Saturday to Saturday occupancy. Check - in is on Saturday at 4:00 PM, and check - out is on the following Saturday at 9AM . If other times are required \ requested , please inquire. This house is usually not available from the end of...
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This charming property offers 3 bedrooms and 2 bathrooms, ideal for families or groups looking to enjoy the beauty and tranquility of the Florida Keys.*Saturday-to-Saturday Rentals OnlyProperty Overview:Prime Location: Bird of Paradise offers stunning views of the Atlantic Ocean. Bird of...
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Escape to this laid-back, oceanfront townhouse in Angler's Reef, where coastal vibes and easy living come together in the perfect Keys getaway. With three bedrooms, three baths, and plenty of charm, this spot is all about kicking back and enjoying the island life.The space has a cool, beachy...
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We would love for you to come visit our renovated ground level Florida Keys home! We decided to call our home "TIGHT LINES", because my wife loves to fish. Our conch home consists of 3 bedrooms with king size beds with ensuite bathrooms. A half bath for guests. We have a 60 foot dock with...
Featured review
I can’t say enough about this property and the owners. From the ease of booking to our entire stay, we were more than happy. The home is top notch, great beds and very well stocked. The owners were...
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You will LOVE our condo.... location location, location! You'll love the waterfront heated and chilled pool during the summer! And it is a boater's dream! Great value and our reviews are awesome.Direct by owner. There are a lot of companies that promote on this site, and it will be less...
Featured review
Location, Location, Location!This place was perfect for remote work or a relaxing vacation, with the boat docked just steps from the door. It truly offers the best of both worlds!Graceful manatees...
Distance to beach: 528 yards to Fort Zachary Taylor Historic State Park Beach .3 M
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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℠...
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Front-Row Ocean Views – A Location That Cannot Be ReplicatedWelcome to Paradise Palms—the crown jewel of the exclusive Peaceful Palms gated community. The luxe upgrade! Perfectly positioned just steps from the water, this newly built three-story home offers sweeping panoramic views and...
Featured review
Paradise Palms was truly a paradise and Rebecca is the perfect host! Her oceanfront home was absolutely amazing; waterfront location, next to the pool, dock with amazing sunrise views over the ocean, every...
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Gulf side Gem, 45 ft. Dock, pool , hot tub and moreSpacious 3 Bedrooms and 3 Baths 1,600 sq ft home overlooking a canal with a brand new dock that spans the width of the property complete with a fish cleaning station and private pool and brand new hot tub. The Open Concept Living and Kitchen Area...
Distance to beach: 0.5 miles to White Marlin Beach
Key Amenities
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House, 3 Bedrooms, 2 Baths, Sleeps 6 Pure High End Luxury with all the Bells and Whistles Boat Friendly Vacation Rental with DockVilla Marlin , 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West....
Featured review
We had a wonderful week in Islamorada at Villa Marlin. This property has everything you need for a water-focused time, especially a beautiful little beach. It was perfect for our grandsons who could have...
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Welcome to Margarita Villa! Located in Jolly Roger Estates on Little Torch Key, where you’ll find some of the best deep water boating in the Lower Keys!Decorated in fine island-style this private home is definitely a 5-star property. Tile floors, open and airy kitchen, living and dining area...
Featured review
Not my first time with action keys, always had good result with everyone at this company! Wish they would rework there utilities policy , it’s hard enough to pay rent for a month.
Distance to beach: 1 miles to Sombrerro Beach
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Lemon Key CottageWelcome home…Thanks to Hurricane Irma, we now have a beautiful newly renovated home! We've spent over $150K on a complete restoration and modernization. (check out the new pics) Lemon Key Cottage is absolutely stunning with new: bathrooms, kitchen, appliances, flooring,...
Featured review
We loved our stay at Lemon Key! The home was lovely and we enjoyed the pool everyday! We were able to buy fresh lobster from their neighbor Paul. What a treat!
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"The furnishings/decor are beautiful. This is one of the nicest houses we have had the pleasure to rent, everything is spotless/brand new. It was hard getting our kids ages 8 and 10 to leave the house each day for adventures. " -Kristie KruegerAs a boating enthusiast, I designed Captain's...
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NWelcome to your dream Serenity Oasis! This 3 BR sanctuary in the heart of the Florida Keys has been redesigned so every detail lets you indulge in the ultimate getaway in Paradise . Enjoy evening swims under the stars in your private heated pool , morning kayak adventures or bike rides , foosball or...
Featured review
The name of this property, Serenity Oasis, is exactly how you feel when you are here. Stunning decorated house in a very quiet neighborhood. The pool is wonderful with several different levels of built-in...
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Welcome to Bay Harbour A-304, a waterfront penthouse in Islamorada featuring a private 50 feet deep water boat slip in a protected harbor with direct views of the marina and Atlantic Ocean. Atlantic Ocean views are visible directly beyond the protected harbor. Enjoy immediate Florida Bay access and quick...
Distance to beach: 4 miles to Sombrero Beach
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Come stay with us! Why?71 FIVE STAR reviews!! It's literally the highest number of reviews for ALL properties listed here on !!! That's right ALL OF THEM!Welcome to the luxurious “Yellowtail” Villa, where luxury meets the Gulf of Mexico! The only problem with this vacation...
Featured review
We chose this amazing beach house for our summer vacation after considering many options. This spacious home with 3 bedrooms was perfect for our family of 5. We wanted a clear view of the ocean in a safe,...
Distance to beach: 1 miles to Anne's Beach State Park
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This Condo sleeps 4 and comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key, Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks. Newly refurnished and refurbished,...
Featured review
This two bedroom apartment in the beautiful Bay Harbour condominium was special. The views of the ocean and the apartment complexes marina were exceptional. The apartment was well stocked with all the cooking...
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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...
Distance to beach: 100 yards to Sombrero Beach
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Seaside Sandpiper is truly a unique property that can accommodate as few guests as you want and up to 30! Rent the 6 bedroom main house by itself or rent the entire 14 Bedroom Main house and Addition! Weddings, family reunions and business retreats are all possible at our home! Our pet friendly home...
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VACA-22-238 BRAND NEW BUILD! 3- bedrooms with king beds and full size bathrooms, and 1/2 bath for guests. Large common area living room and open kitchen. Located on canal three houses from the ocean, with great open water views. Pool with sitting area under the house. Our home offers a 60'...
Featured review
Lynn and Freida are the best hosts. this is our second time down to their slice of Heaven. This time, do to a misunderstanding in our family, we had another 6 people that I was unaware of. Called Lynn and...
Distance to beach: 0.0 miles to On Site
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This 2 bedroom, 2 bathroom, Ocean Front Condo has spectacular Ocean, Marina, Beach & Park views from the Living Room, Dining Room, Kitchen, Master Bedroom, Balcony and even the master bathroom.Included at no extra charge are free WiFi internet, Kayaks, Paddle Boards, Tennis equipment, Fishing...
Featured review
The condo has new furniture, beds are comfy, bathrooms are nice. We had everything we need for a great week. Restaurants, beach and shopping all close by. The owner has lots of extra items available to...
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Tingler Retreat is a tastefully decorated 3 bedroom, 3 bath home with a pull-out couch, has a peek-a-boo view of the ocean and is seconds to open water in your boat! It has an open floor plan and is ground level with plenty of natural light and a fully fenced yard! Available for guest use are 4 bikes,...
Featured review
My husband and I hosted our daughter, son in law and 2 grandkids for a week. They loved the pool and the closeness to sombrero beach. It’s at nice quiet neighborhood with a lot of parking. The house is...
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Introducing the "Bonefish House" at Tarpon Point!This opulent, luxury, home is equipped to accommodate eight adults with 4 bedrooms & 4 full bathrooms. The open living space offers easy entertaining and direct panoramic views of the community pool and Atlantic Ocean. The well-appointed...
Featured review
A BEAUTIFUL LOCATION. This was a well appointed house which made for a wonderful stay for three couples. The house is listed for rental as four bedroom four bath. In reality two king bedrooms with bath...
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Welcome to Tropical Sunsets, your tropical oasis in the heart of Marathon, Florida! This stunning 4-bedroom, 3-bathroom home offers a serene escape with breathtaking Gulf views and a perfect location for relaxation and adventure.*Saturday-to-Saturday Rentals OnlyProperty Overview: Prime Location: Tropical...
Distance to beach: 3 miles to Anne's Beach State Park
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This 3-bedroom bayfront property is located on Lower Matecumbe in Islamorada. The view is spectacular with sunsets on the water most of the year. There is plenty of room for boat trailers, RVs and other toys inside the fence. There is covered parking for your vehicles and a seawall out front to tie your...
Featured review
All I can say is that this place never fails to impress! The views from every inch of the property are the best in all of the keys! Great communication with Rich and his office. Would recommend every...
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Tiki Time! Private Pool~Tiki Hut~Kayaks~Grill~Ocean View!Tiki Time ~ your private paradise in beautiful Marathon, heart of the Florida Keys! This is the perfect place for a family vacation or relaxing getaway. Gorgeous 3BR home with your own private salt water pool, Tiki Hut, space to park a 30′...
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Our oceanfront property with a rooftop patio, dock, heated pool, private hot tub and elevator makes this your own paradise!Stay 14 days and receive an 8% discount OR 28 days and receive an 18% discount!You can enjoy ocean views from both the hot tub and pool. The hot tub is completely private!...
Featured review
The property was amazing the views of the water were fantastic. The dock area was super great for fishing off of every day. The elevator was a life savior for getting suit cases and groceries up stairs....
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Sea Magic on Marlin – Panoramic Open Water Views & Spacious5-bedroom HouseYour Sugarloaf Key adventure begins at this beautifully located waterfront home. Panoramic water views and access allows for boating, swimming, kayaking, snorkeling, and fishing and this 5-bedroom house welcomes...
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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...
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Indulge in the epitome of coastal living in this expansive duplex penthouse boasting ocean views in Islamorada. Relish captivating tranquility with a grand open-concept layout seamlessly blending living, dining, and a wet bar, all framed by panoramic seascapes, a chef's kitchen and access to top-tier...
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"SOMBRERO HEAVEN" is a canal front 4 bedroom 3 bath attached Villa with neighborhood ocean front beach just down the street! It has a private pool that can be heated or chilled (for a fee), private dock (up to 35' boat), fish cleaning station, bait freezer and 4 new bikes! Additionally,...
Featured review
Meredith is prompt and helpful. Everything you could want at the beach or for your boat is provided. This is a big plus if flying in. Hope to return here. Highly recommend!
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One of the only white sandy beaches in the Fl Keys and 1 mile whole of it!Newly built,state of the art,beautifully done 5 bedroom home, 4 master suites w/ king beds and facing open water! Magnificent indoors and out! Each bathroom is exquisite,very large stone,glass and hand picked tiles. The...
Distance to beach: 2 miles to Smarthers Beach and Higgs Beach
Key Amenities
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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...
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Beautiful views from this condo!Bay Harbour is a gated community located at MM 77.5 bayside in Islamorada, FL.We are new owners of this condo that has never been in the rental pool. (that is why few reviews)Complete remodel with no expense spared!The location is quiet with the most beautiful...
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Mile Marker 75 – BaysideLarge, modern 4 bedroom canal front home with pool in Lower Matecumbe Key in Islamorada, Florida Keys. This gorgeous home overlooks the pool and canal.The main selling point of Latitudes is the home’s awesome outdoor area. Pool, Tiki Hut, grill and outdoor seating...
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Enjoy Beachfront Island Life from our condo right on the Atlantic Ocean. We are literally only 10-20’ from the water depending on the tide.Totally remodeled in 2022. All new kitchen with high end appliances. Beautiful master bath with large walk in shower for two.Huge wrap around...
Featured review
We are incredibly grateful to have spent April in this spectacular condo in Long Key, Florida. The 180 degree breathtaking views of the ocean on both floors; the fact that it's right on the water; the interior...
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Property Overview:Prime Location: Caribbean Sunsets is nestled in a quiet and picturesque neighborhood, offering breathtaking waterfront living with open Gulf views. Enjoy lush tropical surroundings and easy proximity to local attractions, dining, shopping, and Sombrero Beach. *Saturday-to-Saturday...
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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
About this property
Our oceanfront property with a rooftop patio, dock, heated pool, private hot tub and elevator makes this your own paradise!Stay 14 days and receive an 8% discount OR 28 days and receive an 18% discount!You can enjoy ocean views from both the hot tub and pool. The hot tub is completely private!...
Featured review
In summary, fabulous views! From the roof you get both the Atlantic and gulf. Unobstructed 180 degree gulf view. The house is great too. Everything you need to sleep comfortably, relax, cook. Space for...
Distance to beach: 15 miles to Bahia Honda State Park
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28-NIGHT MINIMUM RENTAL — PLEASE READ BEFORE INQUIRINGMonroe County requires a minimum rental of 28 consecutive nights to a single family or party. No subleases are permitted. We cannot accept reservations for fewer than 28 nights.This requirement is strictly non-negotiable. Monroe County...
Featured review
The home was clean and full of amenities. Great place to spend a month escaping harsh Wisconsin winters. Owners were attentive and easy to deal with. A great boat launch should you need one. Neighborhood...
Distance to beach: 0.1 miles to Sombrero Beach
Key Amenities
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Waterfront 6 Bedrooms , 5 Baths, canal views. On the HIGHLY sought after Sombrero Beach !!!(We rent weekly only, and our Check-in is on a Saturday and Check-out is on a Saturday dates only so we can optimize our months.)Our houses are safe and clean because we disinfect them with the highest...
Featured review
The house was very clean, and location could not be better. The house was more amazing than the pictures showed. The outside tiki hut, (2) barbeque grills and pool made a perfect end to a day of fishing....
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Welcome to the Key House, a completely charming, canal front home located in the ultra popular Jolly Roger Estates on Little Torch Key.A cute tropical them from the outside in, you know you are in the Florida Keys! The exterior boasts an immaculately kept grounds with ample storage for your gear,...
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Family House in Big Pine Key, Fl on the water. Bring your Boat and have easy access to the most beautiful waters of the Keys. Boat dock on the back of the house, and house comes with everything, it will make you feel at home.Welcome to your Ultimate Luxury Island Escape! This beautiful waterfront...
Featured review
This was our 2nd year staying at the Cloud 9 House home...if we could we'd stay a month instead of 10 nights the first year and 14 this year! The house has everything you could want and the hostess is amazing...
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We would like to invite you to stay at our peaceful keys getaway. Enjoy the spacious porch overlooking the pool and canal, this is great for my wife and I to watch our kids while they are swimming and fishing off the sea wall. As you can tell by the pictures you can catch hugh snapper right off the sea...
| Area | Median/night | Best for | The beach |
|---|---|---|---|
| Key Largo | $306 | Divers, snorkelers | No natural sand this far north, though there’s Harry Harris Park's protected swimming area |
| Key West | $395 | Walking to dinner, live music, culture | Fort Zachary Taylor, rocky enough for water shoes; Smathers, long and manmade |
| Marathon | $442 | Families with young kids, and anyone who wants a pool | Sombrero Beach, sand trucked in and kept up since the 1970s |
| Islamorada | $477 | Sport fishing in the backcountry flats | Anne's Beach, shallow and calm |
| The Lower Keys | N/A | Boats, docks, snorkeling, quiet nights | Bahia Honda is a protected tropical island |
Winter is the Keys' busy season, and Fantasy Fest was invented in 1979 to liven up a quiet Key West October. Summer is the slower season, so you might find deals between June and August. No month here is cold, with Key West air highs running 75° in January and 90° in August.
Air and water temperatures are Key West's, but all areas are within 1° of each other by day. Key West's nights are 1–4° warmer than Key Largo's, and Marathon's January low is 56° against Key West's 65°. Winter water in the Atlantic runs the other way, with Key Largo about 3° warmer than Key West from January through March.
| Month | Median nightly | Difference from annual | High / low air temp | Avg. gulf temp | What’s going on |
|---|---|---|---|---|---|
| January | $366 | +5% | 75° / 65° | 71° | Key West Half Marathon; Baygrass Bluegrass in Islamorada |
| February | $375 | +7% | 76° / 66° | 71° | Gigantic Nautical Market in Islamorada; Florida Keys Seafood Festival |
| March | $375 | +7% | 79° / 69° | 73° | Key West Orchid Festival; Marathon Seafood Festival |
| April | $357 | +2% | 82° / 72° | 78° | Seven Mile Bridge Run; Conch Republic Independence Celebration |
| May | $350 | 0% | 85° / 76° | 81° | KEYS100 ultramarathon; stone crab season closes |
| June | $350 | 0% | 88° / 79° | 83° | Key West Pride; Coralpalooza coral-planting dive |
| July | $363 | +4% | 89° / 80° | 85° | The two-day sport lobster season; Hemingway Days |
| August | $350 | 0% | 90° / 79° | 87° | Key West Lobsterfest, as the regular season opens |
| September | $310 | -11% | 88° / 79° | 85° | Swim for Alligator Lighthouse; hawk migration counted at Curry Hammock |
| October | $316 | -10% | 85° / 76° | 83° | Fantasy Fest and its Zombie Bike Ride; stone crab season opens |
| November | $327 | -7% | 81° / 72° | 78° | Race World Offshore world championship in Key West |
| December | $357 | +2% | 77° / 67° | 75° | Key West Lighted Boat Parade; Key West's New Year's Eve drops |
Based on the median Florida Keys nightly rate on FloridaRentals.com.
Miami is the shorter drive as far south as Tavernier, about 60 miles to Key Largo. From Layton down, Key West is closer, though it is a much smaller airport. Islamorada sits at the crossover, near enough the same either way.
They tell you which side of the Overseas Highway a place sits on, the Atlantic or Florida Bay. A listing called beachfront may be a canal house with a dock at the seawall, so pay attention to the location on the map and ask the owner if you’re unsure.
US-1 comes down from Florida City on the 18-Mile Stretch, and Card Sound Road is the tolled alternative beside it. They meet in Key Largo, and everything south of there is US-1 alone, so a closure has no detour. The toll is electronic or billed by mail, never cash.
Among the towns that set one, seven nights is the shortest. Key West works on licenses instead, so a licensed place there can rent for a night. Check the minimum on the listing and confirm it with the owner.
Learn how you can list your property free for 60 days.
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