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Escape to paradise at Anglers End Estate the ultimate vacation getaway with unobstructed open water views and an indoor heated pool. This stunning property boasts 5 bedrooms, 3 full bathrooms, and over 3600sq ft of living space, making it perfect for family and friend gatherings. Enjoy the amazing, landscaped...
Distance to beach: 0.5 miles to Sombrero
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We REALLY LOVE our Marathon house! Last canal before the Atlantic- quick trip to open ocean! 45 feet of open seawall for boats. Relax in your private pool! UPDATE 2024! We added a mini split AC to the twin bedroom! VERY COOL! We completed a major remodel In Dec 2019. All new kitchen and appliances!...
Distance to beach: 9 miles to Coco Plum Beach
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Our vacation rental is a historic 1 BR/1 BTH waterfront cottage in prestigious Duck Key in the Florida Keys. There are plenty of outdoor amenities on the more than 1/4 acre property. These include a 15 X 34 foot saltwater swimming pool, hot tub, and grill with counter prep and dining area. The backyard...
Featured review
Very cute little place. Perfect for one couple. Pool and hot tub are a bonus. MELINDA was great. Easy from day one til with left. Very good communication thru texting the whole time. Will till all my friends...
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Everything you need for your Islamorada vacation is here including 2 gorgeous private beaches, kayaks, paddle boards, heated resort style pool, porch seating with ocean view, and 2 balconies. Located in the middle row of Anglers Reef, this home accommodates up to 6. Boat slip can be reserved for additional...
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Key Lime Sunrise Watch the sunrise & feel the tropical breezes while sipping your coffee from the comfort of the upstairs screened terrace of this lovely and neatly maintained two bedroom two & a half bath home situated on Sombrero Beach Road. This charming getaway is within walking/biking distance...
Featured review
171 10th St. The duplex was very neat. We loved the screened in back porch (had to keep the fans going because of the heat). The pool chairs lacked comfort but we had seen that in the pictures and brought...
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Tea Table Key Private Island Estate and Wedding Venue An extremely rare and stunning private island, accessible by car, Tea Table Key is a gated Caribbean Island located at Mile Marker 79.7 in Islamorada.Jutting into the blue-green waters of the Atlantic Ocean, Tea Table Key features a 2,000′...
Distance to beach: 1 miles to Fort Zachery Taylor State Park
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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...
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Experience the best of Florida Keys living at Marin, a beautifully renovated 4-bedroom, 3-bath waterfront retreat in Marathon's prestigious Key Colony Beach community. Located just two hours south of Miami and one hour north of Key West, this boater's paradise offers direct ocean access, a private...
Distance to beach: 8 miles to Bahia Honda State Park in the keys
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Ocean access waterfront canal with 40’ dock and all the fixins. Looe key reef straight out canal. 2/2 house with nice size porch
Featured review
Let me start with the owner Vicki, she is wonderful! So responsive, helpful, and friendly. Now for the house....don't know where to start but to say we loved it. Great size and the sliding door in the living...
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Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, pickleball, heated pool, private beach, and dockage for...
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We stayed in unit 102. Glenn was a great guy to rent from, very helpful and followed up for any questions.a very nice condo, private bathroom for two main bedrooms. Most everything needed for making meals...
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Stay where the palm trees meet the ocean. The Egret House is a quaint and charming home nestled in the lower Florida Keys. This spectacular home is in the perfect location in the highly desirable side of the island. Cozy 2 bed, 1 bath property with open water access, heated and cooled saltwater pool,...
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We stayed from middle of June to middle of July this year and can tell you, you will not find a more relaxing vacation spot that this one. Scott was incredible from the first day we connected until we...
Distance to beach: 3 miles to Sombrero Beach
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*Modern updates, new furniture, new docks, pool etc- updated photos on mgmt site!* A spacious bayside 3 BR 2.5 BA retreat within Indigo Reef, a private resort community of Marathon FL- offers many extras for anglers, families, snowbirds, or tourists! Beautiful views from both levels of canals, spacious...
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Our stay at Indigo Reef was fantastic. Perfect weather and a perfect location. The unit had everything that we needed and was very comfortable for 5 adults. We truly hope to be back for a longer stay in...
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Come enjoy the breathtaking open water views from the multi-level porches of Waterside Bay!This 3-story custom home has 3-bedrooms and 3 bathrooms, and has upscale yet comfortable living on one of the best islands in the lower keys for open water location for boating, fishing, diving or snorkeling....
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Experience the epitome of coastal living in this exceptional half-duplex located in the prestigious Key Colony Beach. Situated on the picturesque blue waters of Key Colony Beach, this property seamlessly combines modern luxury with the relaxed charm of island life. With 3 spacious bedrooms and 3 beautifully...
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Welcome to Flamingo Island Paradise!Step into this updated spacious home and enjoy! Tasteful, fresh decor matched perfectly for this relaxation paradise. 2 Master suites with ensuite bathrooms and comfy King Beds. There is a pullout twin in the living area for an extra guest. Updated well stocked...
Featured review
This is a great location for two couples exploring what the Florida Keys has to offer. We did not have a boat or plan to fish so the residence could’ve accommodated both of those things. We did use the...
Distance to beach: 0.2 miles to Fort Zachary Beach
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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...
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Privacy galore at this great location on Sombrero Beach Rd with a brand new POOL! Famous Sombrero Beach is approximately half mile down the dedicated bike path from this stilted 3 bedroom single family pool home with dockage! Open concept living with expansive decks on both floors that boast open water...
Distance to beach: 3 miles to Sombrero Beach
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Start planning your perfect escape to the Florida Keys! Blue Ocean Bungalow is ideally located on a wide, deep-water canal with easy access to world-class fishing in the Atlantic and the Gulf. Enjoy all the amenities needed for a perfect island vacation: airy open living areas with canal views, cozy sunroom...
Featured review
Thank you . We had a great time..we fished, snorkeled and spent a wonderful time with family and friends.. we all highly recommend!!
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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...
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Seaside SerenityWelcome to your exclusive luxury retreat in Marathon, Florida. Seaside Serenity is a brand-new, 4-bedroom 4.5-bathroom, private pool home where paradise meets perfection. With 35' of dockage and nestled in close proximity to the Atlantic Ocean, Gulf of Mexico, and Coco Plum Beach,...
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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...
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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...
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DescriptionAdorable two bedroom, two bathroom half duplex on stilts overlooking the extra wide, deep canal and the Par 3 Golf Course on the streetside. This home is tidy and spacious. It offers soaring ceilings, tons of natural light, lots of covered seating, a beautiful concrete pool, 37 feet of...
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Updated two bedroom, two bathroom half duplex on 11th street. Excellent location towards the end of the canal yielding instant access to Vaca Cut and the Open Atlantic, 37 ft of deepwater dockage on an extra wide canal is perfect for fisherman and families alike! Enter through the street-side screened...
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No detail spared in this completely renovated, top of the line stilted half duplex on 9th Street in highly sought after Key Colony Beach. Excellent end of the canal location makes for instant access to Vaca Cut! Head to the open waters of the Gulf or Atlantic! Open concept living and kitchen area overlooking...
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DIRECT BAYFRONT | Mile Marker 99 | Gated Community | Resort-Style Living | 28-Night MinimumMulti-million dollar, unobstructed bay views + the peace and privacy you come to the Keys for. Located at Mile Marker 99 in Key Largo, this direct bayfront condo delivers a true resort-style experience in a...
Featured review
Absolutely loved my time here! The condo has all updated bathrooms, kitchen and laundry! The master bathroom is beautiful and felt like I was in a hotel! Views are gorgeous and the location is great! Will...
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You and your family will feel right at home in this charming Big Pine Key home. The Owners have totally refurbished this 2 bedroom plus den, 2 bath property in 2020. Soft sea colors and coastal décor make this a totally comfortable home away from home.Large and spacious living room, kitchen and...
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Welcome to your perfect slice of paradise in the heart of Key Colony Beach! This beautifully renovated 3-bedroom, 2-bathroom half duplex on 10th Street has been thoughtfully transformed from top to bottom with stunning finishes, modern coastal style, and everything you need to relax and enjoy the laid-back...
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Welcome to Yellowstone by the Sea! A spacious, two bedroom, two bathroom, vacation rental home located on Big Pine Key with excellent, quick, open water access. This home truly has the “Keys” vibe inside and out. Plenty of space to relax and chill canal side or poolside! The open concept kitchen,...
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Escape to paradise at this stunning 3-bedroom, 3-bathroom single-family home in Key Colony Beach! Nestled in a prime location, this spacious home offers everything you need for a relaxing and unforgettable getaway. Whether you're a boating enthusiast, a pool lover, or just looking to unwind in the...
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Direct oceanfront condo with stunning views of the Atlantic. Large heated pool, tennis, hi speed wifi. Stroll along the long span of beach or relax at the oceanfront pool. Or just sit on your private balcony and watch the world go by. Large open living area, master bedroom with King size bed, the guest...
Featured review
The condo well appointed with everything you would need for your stay. The pool beautiful and warm, unfortunately the railing on the stairs of the shallow end make it difficult for an adult to get in or...
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Welcome to your perfect Florida Keys escape in Marathon. This beautifully appointed 4-bedroom, 3-bathroom waterfront pool home offers everything you need for a relaxing week in the Keys—open water views, dockage for your boat, and spacious indoor and outdoor living designed for coastal comfort.Inside,...
Featured review
Spacious 5 bedroom/bath house near the beach, shopping, and restaurants. Tastefully decorated and comfortable beds.
Distance to beach: 6 miles to Baja Honda
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Conchcanary is located on Little Torch Key, in the heart of the Florida Keys. Come relax in our hammocks with a tropical beverage or bring your boat for some fantastic fishing.Enjoy your morning coffee with a canal views from the screened balcony. Newly updated kitchen with top of the line appliances,...
Featured review
My wife and I spent the first 7 days of our married life living it up in the Keys. We loved it. Kayaking in the bay. Trips to the beach (very different from other beaches). Snorkeling in the ocean! Live...
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2 bedrooms, 2 bath half duplex (left side) across from the pickle ball courts and Par 3 golf course, with community park which includes tennis and bocci ball courts. Great central location with easy walk (less than half a mile) to upscale restaurants and Sunset Park, a popular spot known for its stunning...
Distance to beach: 600 yards to Simonton Street Beach
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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.
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Escape to tranquility in this charming two-bedroom, two-bath half duplex located on the shaded side of 9th St. Newly installed, the sparkling 9 X 16 pool offers a relaxing oasis with therapy jets in the seating area. Indulge in comfort with a king-size bed in the master bedroom, while the guest bedroom...
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Located in the first of Ocean Pointe Resort's five buildings, Coastal Retreat offers peaceful views of the protected mangrove preserve with glimpses of the Atlantic Ocean from the living room and private balcony. This thoughtfully renovated 915 sq. ft. corner condo is designed to provide a relaxing...
Featured review
My family and I loved our stay here. Great location, super clean, and comfortable. The amenities were great, really liked the decor. Highly recommend if you are looking for a stay in the area.
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4 Bikes 2 Kayaks Hot Tub Covered Outdoor Space 37 Ft of Dockage Fresh Interior Well-Equipped Kitchen Quick Walk to Sombrero Beach Lots of ParkingCozy and comfortable Sombrero Beach cottage! This light and airy single family home offers an open concept living, kitchen and dining area with large...
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This lovely, brand new home is located in a private, quiet residential area just 3 blocks from Sombrero Beach and 5 minutes or less to the open Atlantic by boat! 3 bedrooms and 2 baths, all tiled floors, pretty kitchen with granite tile counters. The master bedroom has a queen bed and en suite bath with...
Distance to beach: 5 miles to Sombrero Beach
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A fisherman's delight! This perfectly located 2 bedroom house with a large loft is a perfect place to bring your family or friends for a great Keys experience. It has a 40' dock with access just yards away from the Atlantic ocean and the 7 mile bridge. The property has a large swim spa, ice...
Featured review
Great location to visit both upper and lower keys. Well stocked kitchen and we enjoyed the large deck and swim spa.
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Charming Canal-Front Retreat in Key Colony Beach with Exclusive Inch Beach AccessEscape to paradise at this stunning 3-bedroom, 2-bathroom canal-front home in the heart of Key Colony Beach. Perfectly positioned to offer breathtaking water views, this spacious retreat is the ideal vacation getaway...
Distance to beach: 800 yards to Ft. Zachary Taylor State Park
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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...
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Beau Soleil is located in the most sought after neighborhood in the Lower Florida Keys, Summerland Cove, on Summerland Key. A gorgeous gem, tucked away in privacy with tropical plants and fruit trees everywhere you turn!This home is situated on a great boating canal with plenty of dockspace for your...
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Bitter End Vacation Rental –This Summerland Key beauty is the one you have been looking for. Located on Summerland Key with superb boating and access to deep water. Just the perfect spot to see sunset views and peaceful water vistas. Feel free to bring your pet along too!!The interior is...
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INGROUND HEATED AND CHILLED POOL TO COME IN NOVEMBER!! Daydreamin’ blue in the super-desirable Summerland Cove neighborhood! There is plenty of room for family and friends here, with four bedrooms and a huge open concept kitchen and living room, you won’t ever feel crowded. Additionally, a...
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Welcome to Sunsets & Turtles at Moon Bay A301, a beautifully remodeled waterfront condo in Key Largo, Florida, overlooking Blackwater Sound toward Florida Bay. Located on the third floor of the gated Moon Bay community, our Florida Keys getaway combines beautiful bay views, spectacular year-round...
Featured review
We absolutely felt surrounded by sunsets & turtles during our stay. The condo is thoroughly decorated and thoroughly equipped with everything you might want or need for a good vacation, from the coffee...
Distance to beach: 7 miles to Bahia Honda State Park
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This newly remodeled home is cozy, yet spacious.This open concept, single family home is located on a canal and just a few seconds from the ocean. Fully furnished with Keys-inspired touches, this home comfortably sleeps 6 people with 3 bedrooms and 2 bathrooms.Spend the day at Bahia Honda State...
Featured review
We stayed in the rental for February and March of 2024 and loved it.Very quiet with friendly neighbors.Wonderful outside area and perfect boating with easy access to the ocean or gulf.Already have our reservation...
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Latitude Adjustment equals attitude adjustment! Location Location Location! This vacation rental home is located in the super desirable Summerland Cove neighborhood, with easy quick open water access!Whether you are coming for the weather, the boating, the diving or just to relax, this home has it...
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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...
| 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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