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Florida Keys Vacation Rentals – Start your vacation in the Keys off right at Blackbeard’s Escape! This unique home has it all. Main living area on first floors is a 2-bedroom 1 bathroom home with gourmet kitchen, lovely finishes and details plus comfy king size beds. Cooling is great with...
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Relish ocean serenity in this residence set directly on a secluded beach, where an open-concept design seamlessly merges the living area and gourmet kitchen with a grand terrace, all framed by uninterrupted ocean views. Bask in the heated pool, unwind on the covered patio, or step onto your private dock...
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The Sea Glass House~LUXURY Oceanfront Estate~Pool Dock Views Jacuzzi Game Room FirePit Office More!The Sea Glass House is a Luxury Exclusive Oceanfront Treasure with more than 100’ of dock and stunning ocean views from virtually every room. Located perfectly in the Middle Keys with direct access...
Distance to beach: 2 miles to Smathers Beach
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**Peaceful Paradise in Key West Golf Club – Monthly Stays Welcome**Escape to serenity in this beautifully appointed 2-bedroom townhouse nestled within the gated Key West Golf Club community. Designed for monthly stays of 29 days or more, this home offers the perfect blend of comfort, convenience,...
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The townhouse and grounds are exactly as pictured and described! Staying on Stock Island was a great experience. Close enough to beaches and downtown Key West and the island itself offers a number of terrific...
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WELCOME TO SALT & SKYSALT & SKY is a spacious 4-bedroom, 3-bath Duck Key vacation home designed for relaxing, boating and enjoying everything the Florida Keys has to offer. With accommodations for up to 10 guests, a private 32-foot dock right outside your back door, multiple balconies and...
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INGROUND POOL WITH HEATING! THE ONE AND ONLY HOUSE WITH PICKLEBALL COURT AND PUTT-PUTT!! FIRE PIT! LARGER AND MORE SPACE THAN EVER!The Keys Hideaway ~ your private paradise in beautiful Marathon, the heart of the Florida Keys! Gorgeous 3BR home. Your own private pool, gas grill, beach chairs, all...
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Welcome to Anglers Paradise, your waterfront escape in beautiful Marathon, Florida Keys! Located on a peaceful deep-water canal with quick access to the Atlantic Ocean, our cozy condo is the perfect destination for boating, fishing, diving, or simply relaxing in paradise.~ Bring Your Boat (BYOB)~ Guests...
Distance to beach: 3 miles to Sombrero
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Plan your Marathon Trip - Stay at Manatee Cove-4BR/2BA vacation home. Pool with Spa, Tiki, Quick Atlantic access!Escape to the Florida Keys ~ Gorgeous 4BR/2BA Home on the Atlantic side of the canal in Marathon. Our home offers the best pool in our area; who can say no to a hot tub, pool, and bar stools...
Featured review
This was everything we had hoped and more. We stayed 10 nights and wished we had more time. The pool and hot tub was amazing, we were able to have the boat right out back at the dock. And the best part...
Distance to beach: 3 miles to Sombrero Beach
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Welcome to DragonFly Lite our home in Marathon, FL in the heart of the beautiful Florida Keys, the house has 2 bedrooms a Queen in the master and 2 twins in the guest room, one bathroom + our outdoor shower, all the towels you will need for the pool or beach (please leave the sand outside). It’s...
Featured review
Though Dragonfly Lite would be a marvelous place to vacation anytime, it proved especially so in a global pandemic. We had everything we needed right there on property. The pool is pristine, the home was...
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The Sea View Cottage is a 2 bedroom, 1 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is...
Featured review
This gated estate is exceptional. The beach is just steps from the back door, and the ocean views are outstanding. The pool area is stunning and offers a beautiful place to relax and take in the scenery....
Distance to beach: 0.5 miles to ANNE'S BEACH
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Located in the desirable Islamorada which is know as the “Sportfishing Capital of the World” and where you will find the most beautiful crystal clear waters. The house is just minutes from Channel 5 and Channel 2 which give you quick access to the best ocean and backcountry fishing. You are...
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You could not ask for a more beautiful and clean vacation home. Everything seems really new and well kept. The moment you walk through the home you see the balcony with the beautiful view of the water....
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Kara Pan - Islamorada's Premier Oceanfront Estate Home... Kara Pan 1. Discreet Key West style home is situated on a four-acre parcel surrounded by lush landscaping and a natural white sand beach dotted with palm trees. When entering the winding driveway, you will be intrigued with anticipation of...
Distance to beach: 23 miles to Marathon
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Charming house on a canal with all amenities like home. Bring your own boat and park it on the dock for the duration of your vacation. Convenient located 25 miles before Key West. Nice restaurants and groceries shopping 10 minutes from the house Marathon is only 30 minutes away. A short boat ride...
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After a several weeks stay on Little Torch Key, we are comfortable with these obserservations, cozy, clean, comfortable, and quiet. Just what we needed after traveling since mid-November. Easy access to...
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Beautiful bayfront house, private pool and dock, right in Downtown Islamorada Relaxing is made easy at Coral Cove 8, moving from open, airy living spaces to your own private pool. Bright modern finishes meld with traditional Key West style, Coral Cove 8 offers island living in style. This retreat is...
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Trade snow and cold weather for warm sunshine, tropical breezes, and the laid-back lifestyle of Key Largo!This oversized one-bedroom apartment is the perfect winter retreat for snowbirds looking for comfort, convenience, and easy access to everything that makes the Florida Keys so special.Enjoy...
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3 bedroom, 2 bath gulf front home with amazing views and meticulously manicured lot.Amazing Gulf and sunsets views from almost every room in this tropical retreat! The Palm Tree Resort is a private gated, three quarter of an acre resort located directly on the Gulf in a premier section of Morton...
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The Toasted Coconut ~ your private paradise in beautiful Marathon, the heart of the Florida Keys! Gorgeous 3BR home. Your own private pool, gas grill, bikes, beach chairs, all await you for your beautiful day in the Florida Keys! Less than 10 min to Sombrero Beach, Dining & Local Bars. We have everything...
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Mile Marker 83 – BayfrontWelcome to your dream waterfront rental home in Islamorada, located in the heart of the Florida Keys. This stunning 4 bedroom, 4 bathroom home sits on the bay and offers breathtaking views of the water and world class sunsets.As you enter the home, you’ll...
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The Artist's Cottage at Anglers Reef #136 - This beautiful home is located in Angler's Reef, a gated oceanfront community located in Islamorada. The owner has shared his own personal artwork throughout the unit for guests to enjoy. Angler's Reef is known for its beautiful tropical landscaping...
Distance to beach: 100 feet to 4 on site
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This is a 2 story, 2 bedroom, 2 bathroom townhouse that comfortably sleeps 6 in a 24 acre Resort / Condo complex.Included in the price are Taxes, Cleaning, WiFi, a Golf Cart, Kayaks, Paddle Boards, Bikes, Fishing Gear, Snorkeling Gear, Tennis Equipment, Towels, Linens, Kitchen utensils, appliances,...
Featured review
Great condo 3 pools, lots of grounds to walk. Loved the view , 4th floor. Would rent again.. was close to stores and restaurants.
Distance to beach: 0.0 miles to 4 small beaches on site
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3 bedroom, 3 bathroom Ocean Front / Beach Front Villa in Key Largo sleeps up to 6. It was completely renovated in 2020. It has dockage for boats up to 38 feet. This Villa is 35 feet from the Ocean and has a private beach 5 feet from the patio. I provide a Golf Cart, Kayaks, PaddleBoards, Fishing equipment,...
Featured review
This was my first trip since the passing of my husband 5 years ago. It couldn’t have been better. Sun, beach, and good food. The Villa was perfect for me, my son and his fiancé, and three grandchildren...
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Mile Marker 74 – Bayfront – Beachfront – Handicap Assessable – Dockage for 30′ boatThis amazing beachfront home is a must see! Located on one of the few white sand beaches in the Florida Keys, Gulfview is a private home located on Lower Matecumbe Key in Islamorada in...
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Seaglass-Paradise on the Gulf is located in Marathon—the heart of the the beautiful Florida Keys. The Keys are a series of 40 islands connected by 40 bridges , off the southern most tip of Florida. The chain of islands extends 120 miles into the Atlantic Ocean and Gulf of Mexico. The area is famous...
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So thankful we came across this listing. It was absolutely perfect. Honestly I wish I could post pictures to share, because it’s better than what we expected. The sunrise view while laying in the master...
Distance to beach: 4 miles to Bahia Honda State Park
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Beautiful waterfront home located in quiet Eden Pines neighborhood. Easy access to Pine Channel to fish, dive, and explore the Atlantic Ocean, the Gulf of America, or the backcountry. 60 feet of seawall with a set of davits, boat lift, and a tiki hut. Public boat ramp one block away. No neighbors across...
Featured review
We have stayed at alot of vacation homes in the keys over the course of the last 7years and this one is by far our favorite! Richard was an amazing host, he always made himself available for a text, email...
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Luxury island resort style living in Key West. 1800 Atlantic offers a private sandy sunning beach, Olympic style pool, gym, three tennis courts (one is clay), fitness center, community clubhouse, picnic areas and more. This condominium is updated and turnkey . Open living and dining spaces, eat-in kitchen...
Distance to beach: 0.5 miles to White Marlin Beach
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*******Check us out on VRBO No. 2003434******** Please go to ....**To our guests** Nautilus Getaway has always been proud to utilize a contact-less check in process. We use CDC recommended standards for disinfecting in our all our cleaning protocols.As soon as you walk into this home you will...
Distance to beach: 100 feet to 4 on site
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3 bedroom + den, 3 bathroom, 4 balcony, Lagoon Front Townhouse in Key Largo which sleeps up to 8. All bathrooms have been renovated this year.Located inside, private, gated Kawama Yacht Club & Marina. With access to: 3 pools, 2 tennis courts, a 4.5 acre salt water lagoon with tropical fish....
Featured review
I rented from Norman Wortman and he was absolutely outstanding.Kawama is a wonderful community that really replicates "Old Florida." The rental had a wonderful view of the lagoon. Lots of space and...
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Adorable historical conch house 2 bdrm, 2 full bath on quiet street with all the modern day amenities & decor in convenient location, relax by your private heated/chilled pool surrounded by decking and palm trees. Enjoy your morning sitting on the front porch watching the breeze travel through the...
Featured review
Beautiful home on a quiet street and close to everything. No need for a car. You can walk or ride bikes to anywhere on the island. Outdoor area is just right for a group of six. Totally enjoyed the...
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Hidden in the heart of Islamorada, this oceanfront villa offers an unmatched privilege of a secluded private beach—an experience few can claim. Expansive terraces stretch across both levels, framing ocean views. This haven's open design and spacious rooms blend seamlessly with serene surroundings....
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The Blue Manatee (formerly Sunshade Villa), located in Key Colony Beach, in the Marathon area, is a gorgeous, brand new, designer decorated canal front duplex with a modern coastal feel! Each side is rented separately and has 4 bedrooms, 4 bathrooms, a private pool and all the amenities you can imagine...
Featured review
The house was beautiful. Well stocked with all things anyone would need. Pool was perfect- we did add heating as we have small grands that wanted warm water!! We loved it and will be back next year!!
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Step into a private world in Islamorada's most coveted location. Heart of Morada sits in Coral Cove a gated community of just 8 homes giving you a private heated saltwater pool with waterfall, your own boat dock with electric and water hookups, and near-exclusive use of a second community pool and...
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Welcome to Coastal Charm, your serene seaside retreat located in Marathon, Florida! This charming condo offers 2 bedrooms and 2 bathrooms, making it ideal for families, couples, or small groups seeking a relaxing getaway.*Saturday-to-Saturday Rentals Only Property Overview:Prime Location: Situated...
Featured review
This place was nice, quiet, clean and on a private beach. Had plenty of room and we sat out on the balcony for several dinners and had great ocean views. Loved the area it was in. Condo and town were really...
Distance to beach: 1 miles to Sunset Park
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Family-friendly Waterfront Oasis with Private Heated Lazy River Pool and 70' Dock Summary: Welcome to Your Dream Florida Keys Getaway! Bring the family to experience the ultimate Florida Keys vacation! Nestled in family-friendly Marathon—right in the heart of the Keys—our...
Featured review
This is my 2nd year in a row staying at the Lazy River Inn and it has gotten better and better each time! Will definitely continue to come back each year! Thank you Roger and Amy for the amazing time and...
Distance to beach: 4 miles to Sombrero Beach
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New construction! This spacious and tropically decorated property includes 4 KING bedrooms, each with private ensuite bathrooms. There is an additional half bath for guest use, as well as commercial washer and dryer. State of the art kitchen with quartz counter tops and well appointed living area including...
Featured review
My wife and I have been many places around the country and a few out as well. Kraken Cove is a true gem! The house is perfect, clean and well stocked with everything you would want or need. It is beyond...
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Introducing Maison Residences Unit 201, Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE —A world-class oceanfront residence, located in the heart of Islamorada in the Florida Keys. This luxurious residence features unsurpassed vistas of the Atlantic Ocean...
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Wide Horizon is a bright beautiful upscale home where you feel immersed in nature. The house was custom designed, by the owners to take full advantage of its unique ocean location. All principal rooms, including bedrooms, have a minimum of 12 foot glass sliding doors to oceanfront balconies. Its...
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Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discerning travelers for over 15 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenities and ideal location the perfect spot to enjoy all that Key West has to offer.Dos...
Featured review
Our family of 5 visited Dos Casas and had an absolutely wonderful stay! We were warmly welcomed and informed about the property-they were very attentive to details. The compound is beautifully maintained...
Distance to beach: 3 miles to Sombrero Beach
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Trade the everyday for island time at our oceanfront home in Marathon, designed for guests looking to truly experience life in the Florida Keys.Located in the welcoming Ocean Breeze community, our modern 2-bedroom, 1.5-bath home sleeps up to six and is fully equipped for a comfortable extended stay....
Featured review
Newer, modern, comfortable, and well decorated oceanfront property. Had everything we needed and more. Beautiful views from the deck and very nice outside area. We appreciated that there were great...
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Just a few houses off Duval, this wonderful retreat occupies the ground level of an almost 100-year-old home in one of the most desired locations in Old Town Key West. A large covered front porch welcomes you to sit and watch the Key West world go by, imagining what life was like in the early days of...
Distance to beach: 100 feet to On Site
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This recently remodeled and upgraded, 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...
Featured review
This condo was perfect for our family of 4. We have two 21 year old daughters, we came to celebrate their birthday. The condo was spacious and had plenty of room for all of us. The kitchen was well stocked...
Distance to beach: 8 miles to Sombrero Beach
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Welcome to Marlin House – your perfect Keys getaway! This 2-bedroom, 2-bath coastal retreat offers the perfect balance of comfort and adventure. Relax in your own private plunge pool, enjoy fully stocked amenities for a stress-free stay, and make yourself at home with thoughtful touches throughout.Step...
Featured review
We had the most wonderful stay at Marlin House on Duck Key . Thank you Paola ! You were such an exceptional host !!!! The townhome is tastefully appointed , clean, great location, lovely patio with private...
Distance to beach: 100 feet to 4 on site
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This is a 2 story, 2 bedroom, 2 bathroom townhouse that comfortably sleeps 6 in a 24 acre Resort / Condo complex.Included in the price are Taxes, Cleaning, WiFi, a Golf Cart, Kayaks, Paddle Boards, Bikes, Fishing Gear, Snorkeling Gear, Tennis Equipment, Towels, Linens, Kitchen utensils, appliances,...
Featured review
It was our third time staying at the Kawama Yacht Club, but our first time at this lovely rental. We have rented with Norman every time, and we’ve always had a wonderful stay and a great vacation. My...
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Come enjoy the cool clear blue waters of the Florida Keys. The weather is great, lobster season is open from Aug.6th to April 1st. This is a spacious oceanfront home with breathtaking open water views! It is located on beautiful Ramrod Key 85 ft concrete seawall facing the priceless Atlantic ocean teaming...
Featured review
This 4 bedroom, 2 bath is more than a house, it feels like home! From the fully stocked kitchen to the various board games available, this house will keep you busy. You can also rest here as the nights...
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2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys and 15 minutes to Key West. Located within the keys wildlife preserve, Sea View Estate is just a 15 minute drive to the shopping and nightlife of Key West and just minutes to some of the finest restaurants...
Featured review
This is the perfect place for a Florida vacation. It has everything we were looking for and more. Private beach, quiet location, mature trees with coconuts and bananas. Tiki hut with a wet bar and comfy...
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Lovely and spacious 3 bedroom, 2.5 bath half duplex on Key Colony Beach. Very spacious townhouse style on the shady side of 9th St. All tile floors downstairs, with an open concept, large well equipped kitchen with a nice size bar that seats 5, along with a separate dining table. There is an adjacent...
Featured review
We have been staying in Key Colony for many vacations. Each time we have stayed in a different house, reason being that I usually wait too long to make reservations. This house definitely was by far the...
Distance to beach: 1 miles to Sombrero Beach
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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 9:00 AM. Check in directions are emailed to you the week prior to your arrival { please check "spam" } Pups...
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Have a truly blissful vacation at this charming, Gulf Front home that sits on one acre of pristine property on exclusive Morton St. Enjoy the magnificent open Gulf views from nearly every room. This unique home is reminiscent of the way the Keys used to be…..charming! Perfect area for walking,...
Featured review
Had a great family week at this lovely home with pool, hot tub and tiki hut. The furniture was comfortable and the kitchen was great. We visited many of the local state parks and beaches, the restaurants...
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Beautiful oceanfront apartment with easy access to pool, spa, and beach. Dock with boat slips and tiki hut overlooking the Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room BBQ, and tiki bar. Located...
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Welcome to Paradise Palms! This stunning 3-BR retreat has it all. Boating right from your private dock, easy open-water access, waterfront views, unwinding in your private heated pool Fire up the grill for a sunset BBQ, challenge friends to cornhole or game room fun, and set off on a kayak adventure...
Featured review
We have a great vacation, the house fit our needs perfectly. There recommended places to visit and eat at were great. Had a small issue with the dryer, we called them and they responded quickly.
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Awake to the sight of a glorious sunrise from your private oasis. This stunning 3-bedroom, 3-bathroom oceanfront villa is perched directly on the beach in Key Largo, offering panoramic marina-facing views and magnificent vistas of the sparkling ocean.With its soaring ceilings and open, sun-drenched...
Featured review
The place was absolutely beautiful. Norm did a great job he did everything we asked of him and more!! I’d recommend this place for anybody.
| 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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