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Ocean-View | Family-Friendly | Resort Amenities | Tavernier / Upper KeysProperty Overview Welcome to Coastal Ways Suite at Ocean Pointe, a beautifully appointed 900 sq ft, 2-bedroom ocean-view condo in the Upper Florida Keys. Nestled between Key Largo and Islamorada, this resort-style retreat offers...
Featured review
Unit was nicely updated and exactly as advertised. The unit was nicely appointed including the kitchen. Close to pool and tennis courts. Loved the beach! We will be back!
Distance to beach: 5 miles to Anne's Beach
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Enjoy the sunrise from the balcony or from the condo through 50' of glass sliding doors. You can also view the sunset from our walkway on bayside. We have a full kitchen, dishwasher to microwave, washer/dryer, even beach towels. We have wifi,cable TV in living area and all bedrooms, master bath...
Featured review
Awesome peaceful location,clean and perfect amenities lots of birds and fish at marina manatee, sand sharks ,etc
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Swim. Sleep. Repeat., at Manatee Manor. This 3-bedroom, 2.5-bath home on Plantation Key has something for everyone. Enjoy a drink by the tiki bar, rack ‘em up at the billiard table, or soak up some vitamin D next to the pool. With an entrance just off the carport, the downstairs offers a comfortable...
Distance to beach: 3 miles to John Pennekamp State Park
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Enjoy the panoramic view this tropically decorated, fifth-story unit has to offer of the Atlantic Ocean and the adjacent Wildlife Sanctuary. The unit affords its guests the spectacular sunsets the Florida Keys are famous for, right from your balcony and living room.Kawama Yacht Club is situated at...
Featured review
Great atmosphere, two minutes to the Atlantic. Jose great host, very clean. Thank you Jose for sharing your home.
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⭐ 5 bedroom 4 bathrooms (One bathroom by pool) ⭐ Canal home in Venetian Shores with access to bay and ocean ⭐ 100 foot of dockage on 100 foot wide deep canal. Ask about bringing your own boat ⭐ Location of canal is off Snake Creek near MM86 ⭐ Beautiful large pool with hot tub in tropical...
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Property #27839 - silverEscape to your own Keys hideaway with cozy island‑inspired home, coastal décor and a bright open living/kitchen area that flows onto a huge screened terrace. Relax in your own private pool, tiki hut-gazebo, shaded lounge areas and serene canal views, perfect for lazy mornings,...
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1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a large boat basin with views of the Atlantic Ocean. Situated in Lower Matecumbe Key, Islamorada, the Sport Fishing Capital of the World. This very spacious 3 bedroom, 2 and half bath condo...
Featured review
Bay Harbor was delightful, from the condo unit to the grounds and amenities. We used the hot tub, exercise room and swimming pool, When we left there was 76 degrees, returned to 20 degrees in Pennsylvania.
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Gulf-Front Modern Luxury | 5BR w/ Rooftop Deck, Infinity Pool, Dock & More! Indulge in an unparalleled luxury experience in this breathtaking 5-bedroom, 5.5-bathroom estate in Marathon, Florida. With direct Gulf views, high-end amenities, and a sleek modern design, this home is a dream getaway for...
Featured review
The ocean view from the roof and 5 bedroom modern style home is 2nd to none in the keys! Each bedroom has it's own bathroom and the home is very modern and in excellent condition. The infinity pool is...
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Upon entering the home you’ll be greeted by laidback island decor and vast ocean views. The Tommy Bahama Tiki inspired apartment, over looking the marina located in the 5th building, offers two bedrooms and two bathrooms, Free Parking, High-Speed WiFi, Fully equipped kitchen- Washer and dryer. Self...
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Sunrise Drive, the perfect 3 bedroom, 3 bath home for your stay in the Keys. It’s located in Tropical Estates, a quiet upper scale community with water access throughout. A perfect location if you are looking for a tranquil island setting but close to the fun as Key West is just 25 miles south....
Featured review
I was lucky enough to stay here December and part of January! EXCELLENT owners. AWESOME pool area and a WONDERFUL comfortable home!!! Has everything you need and then some! It is close to Key West and...
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This rental offers beautiful Bonefish Bay views, private boat access, and everything you need for the perfect Marathon getaway. The home features a fully furnished kitchen, large living area, spacious balcony with open-water views, four bedrooms, three bathrooms, a laundry room, and comfortable sleeping...
Featured review
This property is beautiful. The views are great, and the beds are comfy. We enjoyed our stay here. The kayaks were a nice bonus as well! The only downside is guest experience. There is no bulk shampoo,...
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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...
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Welcome to your dream coastal escape! A peaceful and beautifully well maintained home where comfort meets adventure. Beautiful 3-story canal-front home, just 3 houses from the ocean. Boaters Dream!! Including an entertainment room, ideal for an executive office or a private guest retreat with sofa bed....
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Welcome to One Ten Palms!Escape to paradise at this private oceanfront estate in Islamorada, where the laid-back spirit of the Keys meets resort-style comfort. Set on more than two acres of lush tropical grounds, the property is graced with 110 swaying palms and 250 feet of natural oceanfront beach,...
Distance to beach: 10 miles to Bahia Honda
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Paradise awaits in the Lower Keys! Situated on a large corner lot, you have over 200 feet of concrete dockage so BIG BOATS are welcome! Featured on " American Dream Home," this vacation home will not disappoint. Whether you're looking to fish the Atlantic or Gulf, snorkel at Looe Key Reef,...
Featured review
This home was absolutely beautiful! My husband and I, along with his family, stayed here and it accommodated 6 adults, 1 teen, a baby, and even our dog—everyone was perfectly comfortable. We loved relaxing...
Distance to beach: 4 miles to Anne's Beach
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Enjoy the sunrise from the balcony or from in the condo through 50 ft of glass sliding doors. You can also see the sunset from our walkway on bayside. We have a full kitchen from dishwasher to microwave, washer/dryer, even beach towels. We have wifi, cable TV, and a Master Bath with whirlpool tub,...
Featured review
Condo was well equipped and tastefully decorated in an appropriate style. Direct ocean views from a 50' balcony overlooking docked boots with the occasional manatee swimming by was exceptional. Location...
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Welcome to our little slice of paradise! Your perfect Key Largo escape in the exclusive Landings of Largo community! This spacious and beautifully appointed 4-bedroom, 3-bathroom corner unit offers the ultimate blend of comfort, convenience, and resort-style amenities—ideal for families, groups,...
Featured review
I can't express how much we love this condo at the Landings at Largo. The community is fantastic and so friendly. The pickleball court and pool are steps away and the pool is temperature-controlled. Our...
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Welcome to Ananda Shala!Nestled at Mile Marker 92 in Tavernier, this beautifully appointed 3-bedroom, 3-bath bayfront retreat invites you to slow down from the moment you arrive. Inspired by the spirit of a “shala”—a space for practice, reflection, and mindful living—this home...
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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...
Distance to beach: 4 miles to Sombrero Beach
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Welcome to The Butterfly Cottage – Where Nature's Magic Meets Keys ComfortEscape to a truly unique Florida Keys experience at our certified Monarch Butterfly Garden sanctuary! This charming traditional conch cottage offers families a peaceful retreat where butterflies dance through native...
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Beautifully updated for your stay. This is not your typical vacation rental home, everything is new and curated for a wonderful stay. Conveniently located on deep water for Gulf or Atlantic access, no low bridges to navigate, with a natural preserve across the canal for privacy. Get ready to relax in...
Featured review
We absolutely loved our stay! The house was so cozy, clean, bright, and peaceful, and it had everything we needed to feel right at home. One of our favorite parts was enjoying our morning coffee on the...
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Welcome to Caribee Beach House!Discover the enchanting charm of Caribee Beach House, where the timeless allure of old-school Islamorada beautifully melds with stylish comforts. Tucked away in the heart of downtown Islamorada, this hidden gem offers an extraordinary retreat with 200 feet of private...
Distance to beach: 15 miles to Bahia Honda
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This luxurious home overlooking Cudjoe Bay on the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with 11 total homes. This is #111 and I also rent 109 and 107 in case you need more than one. We are 40 feet from the water's edge facing Southwest. Lounge...
Featured review
Well kept clean condo and good host. The host has a nice binder with information and local things to do with mile markers. I would have liked to have the list emailed to me before we came to plan more...
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SEAS THE DAY—or do absolutely nothing at all. You’re officially on island time.Welcome to your oceanfront retreat at Ocean Pointe Suites, where serene Atlantic views, coastal luxury, and resort-style amenities come together for the ultimate Florida Keys escape. Perfect for couples, friends,...
Distance to beach: 0.8 miles to Fort Zachary Taylor State Park and Beach
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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: 4 miles to Founders Park
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Welcome to Coral Key!Discover a refined yet relaxed waterfront retreat in the heart of Plantation Key at Mile Marker 90. Thoughtfully designed for comfort, relaxation, and effortless entertaining, this spacious home offers everything you need for a memorable Florida Keys escape.Upon entering,...
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Welcome to Mother Ocean!This stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfect for a family or group of friends. It features modern amenities and coastal decor throughout, providing a comfortable and inviting atmosphere for your stay. The spacious living room...
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You'll find coastal comfort in our oceanfront condo at Ocean Pointe Suites in Key Largo, located directly on the Atlantic. Situated on 60 lush acres, Ocean Pointe offers a newly renovated pool and jacuzzi, private lagoon beach, outdoor grills, marina, boat ramp, pier, tennis, nature trails, swings...
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Simply relax in this One bedroom One bathroom Oceanfront Condo at Ocean Pointe Suites in Tavernier.The comforting living room features a FLAT SCREEN TV, comfy pull out QUEEN SLEEPER SOFA and sliding glass doors that open to the step-out lanai offering sweeping views of the Atlantic.Visit delicious...
Distance to beach: 0.5 miles to Higg's Beach
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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....
Distance to beach: 1 miles to Founders Park
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Welcome to Morada Breeze! This 6-bedroom, 4-bath bayside slice of paradise is ready to make your next vacation an enjoyable one. Located on Plantation Key in Islamorada, Morada Breeze has the amenities to elevate your trip to the Keys.Step inside to discover an expansive kitchen perfect for preparing...
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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
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Welcome to Your Canal-Front Keys RetreatTucked away on Big Pine Key, this elevated canal-front home offers the relaxed rhythm of the Florida Keys with room to breathe, unwind, and reconnect with nature. From peaceful mornings on the deck to spectacular sunsets over the water, this home is designed...
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Discover your own private escape with this beautiful canal-front home, perfectly positioned for those who love nature, boating, and peaceful coastal living. Backcountry & Ocean Access Enjoy direct canal access leading to incredible backcountry waters ideal for kayaking, paddleboarding, and world-class...
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Look no further than this perfect place in the Keys for your next vacation! Our cozy condominium provides an ideal location to enjoy the best of the Florida Keys and has some of the best views in all of Key Largo!Located on the 5th floor, you are the top floor of the building with no one above to...
Featured review
Location of condo was excellent. Very nice condo complex . Condo was very nicely decorated and had the best washer/dryer and comfy reclining couch. We wouldn't hesitate to return especially if you are going...
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This condo is located in a tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada in Futura Yacht Club. FYC is a private 70-unit, gated community with a 53-slip marina and accommodations available for that tranquil tropical getaway you've always imagined. This condo offers...
Featured review
We have been searching for a unit in this area and found this. Islamorada has many restaurants, from fast food to white tablecloths, from waterfront dining to sports bars.
Distance to beach: 15 miles to Bahia Honda
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This luxurious home overlooking Cudjoe Bay on the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with 11 total homes. This is #109 and I also rent 111 and 107 in case you need more than one. We are 90 feet from the water's edge facing Southwest. Lounge...
Featured review
Great location, views were gorgeous from our waterfront decks, 30 mins. to airport! Rental was clean, comfortable & well equipped with everything you need & then some. Home owners thought of everything...
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Villa Sombrero – Private Waterfront Living with Sunset Views in the Florida KeysVilla Sombrero is a peaceful waterfront retreat overlooking Boot Key Harbor, offering breathtaking sunsets to the west and refreshing island breezes flowing in from the east through Sisters Creek. A natural waterway...
Featured review
It's the little things...... We had to call concerning changing the water filter on the refrigerator. The pool needed water added so that the filter and heater would work. The strainer was full of debris.......
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Escape to the heart of the Middle Florida Keys and experience laid-back island living at its finest in this beautifully appointed 3-bedroom, 2-bathroom waterfront retreat. Perfectly designed for families, couples, or boating enthusiasts, this inviting home combines comfort, convenience, and exceptional...
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Escape to paradise in this beautiful newly remodeled 2 bedroom 1 bath duplex unit on a canal nestled in the heart of Big Pine Key. Perfectly located near a grocery store, great local restaurants, parks, and just minutes from the famous Bahia Honda State Park. Whether you're looking to relax or head...
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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...
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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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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Stilt home on canal providing quick Bay access. Spacious master bedroom and bath. Bright and sunny kitchen and living area. Huge sundeck overlooking canal for ultimate relaxation. Covered patio underneath home, complete with picnic table, BBQ, hammock, outdoor games, and covered parking.Fenced in...
Featured review
I rented this home for three months during the winter/spring and had an incredibly positive experience. The location is excellent- quiet at night but also close to fun bars and restaurants. The house is...
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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...
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Open concept meets modern elegance in this stunning canal-front pool home located on sought after Coco Plum in the heart of the Florida Keys. No detail has been spared, from its spacious design to its functionality and huge outdoor living space, this home is sure to be your dream vacation location! Dedicated...
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Welcome to your ideal getaway in Key Colony Beach, FL! This charming 2-bedroom, 2-bathroom half duplex is brand new to the vacation rental market and offers everything you need for a relaxing and unforgettable stay. With deep water dockage, you’ll have easy access to the sparkling waters of 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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Adorable 2 bedroom, 1.5 bathroom half duplex. Conveniently located at the top of 4th Street in exclusive Key Colony Beach. Nicely updated, fresh and bright! Walk to the Cabana Club and enjoy the complimentary membership with a large swimming pool, bar/restaurant, beautiful sandy beach. Excellent deep...
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This super cozy, comfortable 2-bedroom, 2-bath vacation rental is located in the heart of Cudjoe Key, just minutes from the open ocean. Perfect for fishing, snorkeling, and diving enthusiasts, the home boasts easy access to some of the best spots in the Florida Keys.Relax and unwind in style after...
| 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.