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Distance to beach: 3 miles to Anne's Beach State Park
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This 3-bedroom bayfront property is located on Lower Matecumbe in Islamorada. The view is spectacular with sunsets on the water most of the year. There is plenty of room for boat trailers, RVs and other toys inside the fence. There is covered parking for your vehicles and a seawall out front to tie your...
Featured review
All I can say is that this place never fails to impress! The views from every inch of the property are the best in all of the keys! Great communication with Rich and his office. Would recommend every...
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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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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...
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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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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Reel Life 2 has everything! 4 bedroom 3 bathrooms, canal front, private dock (boat up to 35'), large private pool, Tiki Hut with flat screen TV, large grill, 2 bikes, 2 paddle boards, 1 kayak and a natural landscape view across the canal! Plus, Sombrero Beach is just down the street (1.3 miles)....
Featured review
We enjoyed our stay. The house was clean and had all those things (towels, beach toys, pool, kitchen essentials) that we were hoping for with our stay in Marathon. The location is great- walking/biking...
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Watch dolphins play in Shelter Cove while swimming in our oversized poolRelax in the private pool with the Spectacular Shelter Bay in the background...Our home is located directly on Shelter Bay in Key Colony Beach with some of the most spectacular views of open water a guest can ask for. We have...
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We enjoyed are stay at this well appointed and conveniently located vacation home. The setting is perfect and the home was loaded with every convenience you would need. Margie, the property owner, is...
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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...
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Tingler Retreat is a tastefully decorated 3 bedroom, 3 bath home with a pull-out couch, has a peek-a-boo view of the ocean and is seconds to open water in your boat! It has an open floor plan and is ground level with plenty of natural light and a fully fenced yard! Available for guest use are 4 bikes,...
Featured review
My husband and I hosted our daughter, son in law and 2 grandkids for a week. They loved the pool and the closeness to sombrero beach. It’s at nice quiet neighborhood with a lot of parking. The house is...
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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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Brand-new construction, expertly decorated single family home in Marathon. Whether you are vacationing with family, embarking on a fishing trip or looking to just relax Florida keys-style this is the perfect home for you. This spacious 1,800 square foot single-level stilt home offers 4 bedrooms, 3 full...
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Beautiful views from this condo!Bay Harbour is a gated community located at MM 77.5 bayside in Islamorada, FL.We are new owners of this condo that has never been in the rental pool. (that is why few reviews)Complete remodel with no expense spared!The location is quiet with the most beautiful...
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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...
Distance to beach: 1 miles to In the Key Colony Beach walking distance
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Hey there, fishing enthusiasts and families!Looking for the perfect Florida Keys getaway? Look no further! My beautiful waterfront home in Key Colony Beach is your dream vacation spot.Imagine this: You wake up to stunning sunrises over the open water, have coffee on the wrap-around porch, and...
Featured review
Stayed with a group of friends from around the country. The house was very clean and well provisioned Kitchen, bedrooms, bathrooms, outdoor cooking area. Met the host and hostess, who were very pleasant....
Distance to beach: 0.2 miles to Cabana Beach Club
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This is a large stilted duplex located in a tropical paradise. The water view property is located on the island City of Key Colony Beach in the Middle Keys (near Marathon). This is a canal-front unit with a 37.5 step down concrete dock with quick easy access to ocean. Dock comes with ladder access and...
Featured review
Our stay was wonderful. There were a couple of glitches that were handled immediately. Everyone was very friendly and accommodating. Accommodations were great. Would highly recommen
Distance to beach: 4 miles to Sombrero Beach
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Come stay with us! Why?71 FIVE STAR reviews!! It's literally the highest number of reviews for ALL properties listed here on !!! That's right ALL OF THEM!Welcome to the luxurious “Yellowtail” Villa, where luxury meets the Gulf of Mexico! The only problem with this vacation...
Featured review
We chose this amazing beach house for our summer vacation after considering many options. This spacious home with 3 bedrooms was perfect for our family of 5. We wanted a clear view of the ocean in a safe,...
Distance to beach: 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...
Featured review
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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We would love for you to come visit our renovated ground level Florida Keys home! We decided to call our home "TIGHT LINES", because my wife loves to fish. Our conch home consists of 3 bedrooms with king size beds with ensuite bathrooms. A half bath for guests. We have a 60 foot dock with...
Featured review
I can’t say enough about this property and the owners. From the ease of booking to our entire stay, we were more than happy. The home is top notch, great beds and very well stocked. The owners were...
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This home is a unique tropical paradise in Key Largo. Our kids named it Manatee Corner because it sits at the end of the canal and is often visited by friendly manatees. It is a large three-story duplex with a wraparound balcony. It has a canal that leads right out to the Atlantic, minutes from incredible...
Featured review
I rented jan.-mar and was very pleased with my accomodations. My rental was clean, spacious, and very naturally lit by all the large windows throughout. The owner was an absolute joy to work with. He even...
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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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The Jetson's House apartment (Located on the prestigious White Marlin Beach - which is considered one of the nicest natural sand beaches in the Florida Keys) features great swimming, snorkeling, and spectacular sunsets right off the beach! Have fun exploring an artificial reef! What makes the beach...
Featured review
This beautiful, perfectly maintained property was one of our best stays ever. This was our first time in Islamorada and we will be back. The accommodations were spotless, the patio, the view and the hammock...
Distance to beach: 0.0 miles to On Site
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This 2 bedroom, 2 bathroom, Ocean Front Condo has spectacular Ocean, Marina, Beach & Park views from the Living Room, Dining Room, Kitchen, Master Bedroom, Balcony and even the master bathroom.Included at no extra charge are free WiFi internet, Kayaks, Paddle Boards, Tennis equipment, Fishing...
Featured review
The condo has new furniture, beds are comfy, bathrooms are nice. We had everything we need for a great week. Restaurants, beach and shopping all close by. The owner has lots of extra items available to...
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Welcome to the Key House, a completely charming, canal front home located in the ultra popular Jolly Roger Estates on Little Torch Key.A cute tropical them from the outside in, you know you are in the Florida Keys! The exterior boasts an immaculately kept grounds with ample storage for your gear,...
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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....
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Tiki Time! Private Pool~Tiki Hut~Kayaks~Grill~Ocean View!Tiki Time ~ your private paradise in beautiful Marathon, heart of the Florida Keys! This is the perfect place for a family vacation or relaxing getaway. Gorgeous 3BR home with your own private salt water pool, Tiki Hut, space to park a 30′...
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Our oceanfront property with a rooftop patio, dock, heated pool, private hot tub and elevator makes this your own paradise!Stay 14 days and receive an 8% discount OR 28 days and receive an 18% discount!You can enjoy ocean views from both the hot tub and pool. The hot tub is completely private!...
Featured review
In summary, fabulous views! From the roof you get both the Atlantic and gulf. Unobstructed 180 degree gulf view. The house is great too. Everything you need to sleep comfortably, relax, cook. Space for...
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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,...
Featured review
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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Canal front, Dock, Hot Tub and Cabana Club AccessWelcome to Orchid House, a lushly landscaped canal front home located on the beautiful island of Key Colony Beach. This property comes with boat dockage , private hot tub and access to the Cabana Club pool and beach.When you first drive up to the...
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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...
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Pineapple Tides, located at "The Tides at Vaca Cut" (Unit #8), is a new 5 bedroom 4 bath home with a private pool and boat slip!Perfectly situated on the water with stunning views, sunrise and sunset colors, and direct quick access to both the Atlantic Ocean and the Gulf of Mexico via Vaca...
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Welcome to your spacious, five-bedroom waterfront pool home in Marathon, just steps from Sombrero Beach! Enjoy multiple entertaining areas inside and out, with a screened-in patio and sparkling pool (pool heat available for an extra fee). The open-concept interior features cathedral ceilings, a modern...
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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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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: 1 feet to on property or at Founders Park
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Beautiful new home on Florida Bay with sandy beach, spacious pool, beautiful views, and sunsets every night. The home accommodates up to 12 guests. Each suite can be rented individually or combined. Please note that there is no smoking and pets are allowed by special permission.Sitting on an acre...
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...
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Introducing Maison Residences Full floor for rent – Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE —Units 201 and 203 rented together. Private steps to pool, beach and Atlantic Ocean! 8 bedrooms, 8 full baths, 2 half baths, 2 full kitchens, 2...
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Looking to Relax Renew Recharge? We got you. Your own Key West Sanctuary awaits! Escape to a classic Conch family home perfectly tucked away for privacy yet, only 5 Blocks from famous Duval Street. The best of both worlds! Morning yoga class on the deck, late night dip in the pool, and sunset...
Featured review
We loved our time at Key West Sanctuary! The perfect location to bike to the sights and sounds of Key West; close to one-way roads with a bike lane going to/from Duval. The beautiful and peaceful surroundings...
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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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1440 sf - Sleeps 4 adults (also includes xtra bed in guest room plus EZ-Bed electric queen Bed and large sectional couch with chaise lounge and cuddler for larger families). Fully renovated and updated in 2021. 70ft foot dock and cleaning table. Great ambience, quiet home like feel. Private community...
Featured review
Here is the review I am trying to post via for our March 2024 stay.Wonderful! Fantastic! Amazing!Wonderful Hosts!!! Jay and Sharon are so welcoming and supportive! We felt at home before we...
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Turtle Cove - Turtle Cove is a true hidden treasure in Islamorada. This oceanfront gated estate consists of an enclave of four charming cottages nestled in beautiful landscaping with a total of seven bedrooms and seven bathrooms. When entering through the gate you will feel a sense a tranquility that...
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Mile marker 77. Deep Water ocean side canal with direct access to the Atlantic Ocean and a straight shot to Alligator Light House. Sunny Patio and splash Pool. 4 Bedrooms/4 Baths. Sleeps 8. There is no cable package with this home so please bring your passwords for live streaming from the smart TVs.The...
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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Welcome to Island Paradise, your serene retreat in the heart of Key West, Florida! Located in Old Town, Island Paradise is just a half block from the world-famous Duval Street. This charming property offers 2 bedrooms and 2 bathrooms, perfect for small families or couples looking for a relaxing and convenient...
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,...
Featured review
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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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...
Featured review
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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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 Tropical Sunsets, your tropical oasis in the heart of Marathon, Florida! This stunning 4-bedroom, 3-bathroom home offers a serene escape with breathtaking Gulf views and a perfect location for relaxation and adventure.*Saturday-to-Saturday Rentals OnlyProperty Overview: Prime Location: Tropical...
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Escape to this laid-back, oceanfront townhouse in Angler's Reef, where coastal vibes and easy living come together in the perfect Keys getaway. With three bedrooms, three baths, and plenty of charm, this spot is all about kicking back and enjoying the island life.The space has a cool, beachy...
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The Shores of Sugarloaf Luxury Waterfront Home with Gorgeous Pool, Tiki Bar and SunsetsWelcome to the Shores of Sugarloaf, the perfect Florida Keys Island Getaway. Check-in to this gorgeous coastal home and enjoy a lovely vacation on one of the Florida Keys most desirable keys-Sugarloaf. This house...
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The Blue Turtle 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 with a heater and a chiller, and all the amenities you would...
| 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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