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Green Cottage - The Green Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their own personality and characteristics. All five cottages share the property's amenities: pool, boat basin, tropical sprawling grounds, ping pong table, kayaks, paddle boards...
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This grand peninsula retreat is embraced by the Ocean and lush mangroves, offering privacy to the heated pool with its tiki bar, expansive sandy playgrounds and lounge areas. Nestled along the tranquil shores of Florida Bay, its array of indoor and outdoor living areas, BRING YOUR BOAT - dock with ocean-access...
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Welcome to Oasis4rent!Escape to 2.75 acres of private oceanfront paradise in the heart of Islamorada. Two beautifully appointed homes sit directly on the Atlantic with 200 feet of sandy beachfront, a heated saltwater infinity pool, and views of Alligator Reef Light on the horizon.The PropertyMain...
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Sunrise is a spectacular unit within the Maison Matecumbe gated community. Maison Matecumbe is a small 9 unit condo located just off the old road in Islamorada at mile marker 81. Newly done pool and hot tub! 3 bedrooms, 3 baths, sleeps 6, pool, sandy beach.Dockage can be obtainable through Islamorada...
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The home is meticulously clean and spacious. It has all the comforts of home. We cooked several meals and had everything we needed. The views from the balconies are amazing. The complex itself is well maintained....
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Come enjoy this beautiful OCEAN VIEW condo located in Key Colony Beach on the 2nd floor!!! This two bedroom & two bathroom condo offers all the amenities of home!!! Enjoy a cup of coffee in the morning, or a glass of wine anytime on one of the two ocean view balconies. Coin laundry right outside the...
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The Royal Plum was very nice. The location was perfect. It was less than 15 minutes away from everything you'd want to see in Marathon. The room was very nice, had everything we needed for a weeks stay....
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Mar Azul is a High-end Oceanfront Residence overlooking the tranquil 'Bonefish Flats' of Marathon. Enjoy a Private, Secluded 3-Story Home with Spectacular Views of the Atlantic Ocean! Densely surrounded by Nature, the Property includes a Private In-Ground Pool Deck featuring an Outdoor Gazebo...
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My husband and I stayed here for a week over our wedding anniversary. Our stay was perfect in every way. The house was super clean, private, comfortable, and the views went on forever. There are plenty...
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Leatherback Cottage - The Leatherback Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their own personality and characteristics. All five cottages share the property's amenities: pool, boat basin, tropical sprawling grounds, ping pong table, kayaks, paddle...
Distance to beach: 3 miles to Founders Park
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Welcome to the Conch & Lobster Homes, a rare dual-home getaway located in the heart of Islamorada, just minutes from iconic Alligator Reef. Perfect for large families, multi-generational vacations, or group getaways, this tropical property comfortably sleeps up to 14 guests across two coastal designed...
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Both houses were great for our families. We will come again. Very close to everything you would want to do. Private drive and gates with access code. If I were to change anything it would be the...
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Casa Feliz~ Experience, enjoy, relax, and rejuvenate in luxury accommodations on the Atlantic Ocean.~ Secluded sophistication can be your vacation destination.Welcome to Casa Feliz! We are located on the quiet Grassy Key in the middle of the Florida Keys.Concierge Level Luxury vacation...
Distance to beach: 2 miles to Founders Park
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This tropical waterfront beauty has it all...heated pool, spa, dock and custom elevator. Beautifully appointed and fully equipped for your ultimate holiday rental. Located on a deep water canal with direct access to the Bay or Ocean. Enjoy unforgettable sunsets while relaxing on one of several patios...
Featured review
This was the nicest home overall I have rented. If you have a boat, don't look elsewhere. Everything in the house functioned and the house had everything one would need, even for people who do cook while...
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Great for Family Reuions, and Large Groups vacationing in the Florida Keys! Fabulous 6500 sq ft. vacation paradise. Includes everything you need for a perfect Family Reunion or large destination vacation.Private Vacation Rental Waterfront Home with 6 Bedroom 5 Baths Private Pool and Spa ~Tiki Hut,...
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This 3 level rental did not disappoint!! spacious, lots of cookware, linens, baby furniture, pool, dock, very nice park/ beach short walk, Publix minutes drive away! this was paradise! Liz was very attentive....
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Blue Shell is a delightful new canal front vacation home with a pool, just a minute to the ocean and open water and lots of fun amenities! It is also about 10 minutes from both Coco Plum Beach and Sombrero Beach.The dock is 50' and there is parking on the side of the house for truck and trailer....
Distance to beach: 4 miles to Founders
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Rare Summer Openings! Your Private Resort Awaits in IslamoradaIf you’ve been dreaming of an island escape with all the luxury of a high-end resort but none of the crowds, this is your chance.Your Own Private Resort in the Florida KeysFrom the moment you arrive, this estate feels more...
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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: 50 yards to Private sunning beaches at Anglers
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Book here and SAVE VRBO's $500-700 Booking fee for any stay!! PLUS our diect rates are the same or usually lower than on VRBO. Click on the "Link" to the left to see our many great reviews on our direct rental site.Welcome to Anglers Reef, a very special community of vacation homes....
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Our stay couldn't have been better. Great gated community beautifully landscaped, the house is great everything you could need. Very nice layout, Cold AC Great Pool just steps away, Location is exactly...
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Newly renovated 3/2 Canal front home with brand new pool, deck and front gates for privacy!The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra clean and has modern furnishings. It has 3 bedrooms, 2 baths. Upstairs there are 2 bedrooms,...
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2022 was our 2nd time renting this wonderful home. The location is fantastic, and the house and property offer everything you can imagine. Outside is a paradise with a refreshing pool (with fun lights...
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Mile Marker 83 – OceanfrontTwo adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada! This stunning property is truly a tropical paradise with a private, sandy beach and skiff dock. Relax at the beach or cool down in the beachside pool.The front home...
Featured review
Just finished a week at Osprey Bay nice house a little too much up and down with all the steps but spacious Need a larger trash can in the kitchen put it next to the wall near toaster Also new pillows...
Distance to beach: 6 miles to Pennekamp
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Recently renovated large 6 bedroom, 7 bathroom Ocean Front House on 5 Acres. Gated from the main road. It can comfortably sleep up to 16 people. Covered parking for up to 6 vehicles and outside parking for several more. This estate is surrounded on 3 sides by park lands and the Atlantic ocean. If...
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The Main House is a fully furnished, two-bedroom, two-floor house facing the bay that can sleep up to two adults and six children.On the second floor, the master bedroom is at the top of the stairs and contains two queen-size beds, a large closet, and access to the full-size bathroom, which is also...
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Adorable home just moments to the ocean. Lovely pool 10 X 20 (goes from 3′ to 5′) Pool heat is $200 add’l if paid in advance, or $250 on arrival plus taxes. 8 X 15 tiki to relax under the shade. 4 Flat screen TVs all w/DVD players. 55″ in L/R, 42″ in master bedroom and both...
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Canal front 4BR/3BA duplex in Marathon, just a 2 minute drive to Sombrero Beach! Perfect for families or friends, this home features a private pool (heating optional for a fee), shared dock for one 30’ boat, and a fenced yard. Enjoy modern comforts, a fully stocked kitchen, and easy access to all...
Featured review
Excellent stay, everything in the house worked smoothly, nice big pool, kayaks at our disposal, Sombrero beach, groceries in just few minutes of drive. One ctisism: no garbage recycling option.
Distance to beach: 900 yards to Sombrero Beach
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"BELLA VISTA" - a Spectacular Oceanfront home in Marathon, Fla. with an Invisible-edge heated salt water pool that overlooks the Atlantic Ocean. Open Water Unobstructed VIEWS. VERY PRIVATE. Newly renovated! This 4 bedroom/3.5 bath home can comfortably sleep 8 people. Three bedrooms have King...
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The best part of this home is the view. The house had everything we needed for a perfect vacation but it was the front row seat to the dazzling waters of the Keys that has us dreaming of coming back. We...
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Welcome to ‘The Beach House’ at Tarpon Point in Islamorada – This luxurious oceanfront home is in a private gated enclave of 12 houses. This home sits directly on ‘The Beach’. Being the end home, it is nestled next to lush mangroves and the ocean offering a lot more privacy....
Featured review
This unit on Islamorada provides wonderful oceanfront views. Our group included five retired women who all worked together in the past. We try to make a reunion vacation happen once a year. This is the...
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Welcome to the home with one of the best sunset views on Big Pine Key! This is a great location, with awesome views, and super quick boating access to both the Gulf and the Ocean. This three bedroom, three bathroom home is setup perfectly for the avid fisherman, boater, paddleboarder, or just the relaxed...
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Mile Marker 77 – Oceanfront – Lower Matecumbe Key.Six bedroom/ four bath luxurious oceanfront premier rental estate on Lower Matecumbe Key in Islamorada. Enjoy a walk around the lush, native garden or take a dip in the oceanfront pool. Catch palm tree shade or sun on the private beach,...
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"Wow beyond wow! This place had everything we needed and more. We like to rent a house where we can spend most of our time there enjoying family time. The pool and all the games with the game room and infinity table and the dining turned ping pong was amazing. Eric was very responsive..." -...
Featured review
Eric was the perfect host. We escaped a cold and snowy winter for Marathon and this home offered us the perfect get away! It included everything we could have needed…games, pool, grill, plenty of space...
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Experience the relaxed lifestyle of the Florida Keys.3 Bedrooms + Loft, 2 Baths, Sleeps up to 8 comfortably. There are 2 large bedrooms on the 3rd floor, each with queen size beds. The first floor bedroom is small with 2 bunk beds. The 4th floor loft is a general purpose room. Newly remodeled, decorated...
Featured review
Norman was extremely communicative. The place was spotless, updated and great value.We intend on booking with Norman when visiting Key Largo.Kawama offers great amenities and the accommodations...
Distance to beach: 1 miles to Cabana Club
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Lovely full duplex that sleeps 14! Upstairs there are 3 bedrooms, 2 and a half bath’s with a wide open concept. The half bath is off the living room area. Four flat screen TV’s, hi speed wireless internet, gas grill and a lovely pool (heat is $200/wk optional). Pool is 10 X 20 and 4′...
Featured review
The location is great! The home, yard, and pool are beautiful. We would recommend the place to others.Some minor issues that should be addressed: the outside fish / bait cooler was very dirty and unusable...
Distance to beach: 3 miles to Founders Park
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"It's just the best rental we have ever seen...beyond what we have had!" - GuestOceanfront retreat for families, groups & special occasions:Speakeasy for cocktails & karaoke Community pool & paddleboarding from private dock 4 bikes to explore Ocean views from...
Distance to beach: 0.3 miles to Anne's Beach
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Enjoy this modern and recently updated lagoon front 3 bed/3 bath single-family home on the Gulf side of Islamorada at MM 73.5, minutes from the Channel 2 and Channel 5 Bridges, offering immediate access to the oceanside of Lower Matecumbe Key. Dockage is available for up to a 35' boat, or use the...
Featured review
We have rented this property for 3 years and have been extremely pleased with all aspects from great hosts, nicely appointed house, heated pool, canal/dock access , easy out to ocean or bay, plenty of...
Distance to beach: 100 yards to Port Antigua Private Beach
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This spectacular 3/Bed 2/Bath canal front home is located in Lower Matecumbe Key, a part of Islamorada island. Enjoy the exclusive neighborhood of Port Antigua—just a 5 minute walk to our private beach.The house is nautically designed, with a spacious and open floor plan. There's a large...
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Take in the BEST VIEW from your living room and two private balconies, with breathtaking views overlooking the Atlantic, marina, and clubhouse. This beautifully appointed 1-bedroom, 1.5-bathroom retreat offers the perfect blend of luxury, comfort, and tranquility. Start your morning with coffee in the...
Featured review
Thank you so much for an amazing stay. We couldn’t have asked for a better rental. The rental had so many amenities that other places have not. Will definitely stay here again.
Distance to beach: 0.5 miles to White Marlin Beach
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Bring your boat!Nestled on a canal, less than a 2 minute boat ride to the bay and 10 minutes to the ocean with key access to private White Marlin Beach. Heated pool and hot tub, 70' dock with fish cleaning table, commercial ice machine, and two floors facing the canal and a private sanctuary....
Featured review
We stayed in this home for a month, the location is amazing if you love to paddle board, kayak and discover the many mangrove islands that are a five minute paddle from your dock. The outside area has...
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Play all day in Key Largo! If you like fishing, snorkeling, diving, kayaking, paddle boarding, wakeboarding, and nature, you can do it all here at Easy Livin’! Bayfront home on open water with dock and small private ramp. Love fishing? House is close to Flats, Backcountry, Reefs and Offshore. Dock...
Featured review
Beautiful recently built 3 bedroom 2 bath pet friendly bayside home with boat ramp and dockage. The owners have attended to every detail for accommodating on site water recreation, comfortable outdoor living,...
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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...
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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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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: 3 miles to Founders Park
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Welcome to Blue Palm Oasis!Escape to paradise at Blue Palm Oasis, a charming 4-bedroom, 3-bath home located on Plantation Key in Islamorada. This contemporary Keys villa seamlessly blends modern comfort with laid-back island charm, making it the perfect place to unwind, recharge, and soak up the sun....
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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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With thoughtful and creative touches, both inside and out, mixed with a keen attention to the smallest of details, this top floor oceanfront condo in building two, exudes a breezy sense of magic, whimsy and laid back Florida Keys style.Upon entering the home you’ll be greeted by the blue-green...
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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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⭐ 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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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,...
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Welcome to our 5 bedroom with optional 6th bedroom home, “Reel’em Inn” Big Pine Key, an excellent location for a relaxing vacation with family and friends 31 miles from Key West’s Mile Marker 0. This spacious 5-bedroom home is on a double lot with plenty of parking and 150 feet...
Featured review
We've stayed in this home for a month for 3 years, 2025 being our 4th year we added a month. We stayed in the home before Jeff and Christine bought it and loved it then. They've made so many improvements...
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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...
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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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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 #107 and I also rent 109 and 111 in case you need more than one. We are 140 feet from the water's edge facing Southwest. Lounge...
Featured review
Susan & Jennifer are great to deal with, this was our 3rd trip to the property, and we can't wait to go back!!
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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: 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.
| 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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