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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
The property was amazing the views of the water were fantastic. The dock area was super great for fishing off of every day. The elevator was a life savior for getting suit cases and groceries up stairs....
Key Amenities
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Sun Kissed Tails is a beautiful 3 bedroom 3 bath townhome, with a modern coastal feel, in the Hawks Cay resort on Duck Key, MM61. ENJOY THE POOL AND BEACH AT THE OCEAN FRONT CABANA CLUB, just a 15 min drive to Key Colony Beach. The Cabana Club has an olympic size pool, Tiki Bar and restaurant, ocean...
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WELCOME TO SALT & SKY SALT & 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...
Key Amenities
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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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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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Distance to beach: 100 yards to Sombrero Beach
Key Amenities
About this property
Seaside Sandpiper is truly a unique property that can accommodate as few guests as you want and up to 30! Rent the 6 bedroom main house by itself or rent the entire 14 Bedroom Main house and Addition! Weddings, family reunions and business retreats are all possible at our home! Our pet friendly home...
Distance to beach: 3 miles to Sombrero Beach
Key Amenities
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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...
Key Amenities
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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...
Featured review
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....
Key Amenities
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*NEW!*Life is a Marathon~VIEWS!~Pool~Dock~HotTub! Summary Welcome to Life is a Marathon! This peaceful 4-BR sanctuary has everything you need for the perfect getaway. Enjoy open-water views, a dock just steps from the home, and a prime location minutes from the Ocean or the Gulf . Relax by 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...
Key Amenities
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Stunning rooftop views from this gulf side Tuscan style Villa 3 Bedroom 3 Bathroom Freestanding villa located in Bougainvillea, a Gated Community, with a pool exclusive to Bougainvillea Clients overlooking The Gulf of Mexico. There is Great Fishing at this location! You can bring your boat in for...
Distance to beach: 1 miles to Sombrero Beach
Key Amenities
About this property
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...
Key Amenities
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"The furnishings/decor are beautiful. This is one of the nicest houses we have had the pleasure to rent, everything is spotless/brand new. It was hard getting our kids ages 8 and 10 to leave the house each day for adventures. " -Kristie Krueger As a boating enthusiast, I designed Captain's...
Distance to beach: 4 miles to Sombrero Beach
Key Amenities
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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: 1 miles to Sunset Park
Key Amenities
About this property
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...
Key Amenities
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DOCKSIDE RETREAT is a 4 bedroom 3 bath canal front home that has a private pool, private dock, fish cleaning station, with a green light under the dock, two paddle boards, a kayak, four bikes, and a Tiki Hut for the ultimate Keys vacation! There are 4 parking spots for vehicles and one boat trailer (you...
Featured review
Dockside Retreat was such a treat to experience for one week. The owners are very helpful and gracious. We went all out for us and rented a boat for fishing and cruising. Our Captain (son-in-law) is an...
Key Amenities
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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...
Featured review
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: 0.1 miles to Sombrero Beach
Key Amenities
About this property
Waterfront 6 Bedrooms , 5 Baths, canal views. On the HIGHLY sought after Sombrero Beach !!! (We rent weekly only, and our Check-in is on a Saturday and Check-out is on a Saturday dates only so we can optimize our months.) Our houses are safe and clean because we disinfect them with the highest...
Featured review
The house was very clean, and location could not be better. The house was more amazing than the pictures showed. The outside tiki hut, (2) barbeque grills and pool made a perfect end to a day of fishing....
Distance to beach: 4 miles to Sombrero Beach
Key Amenities
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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...
Key Amenities
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"SOMBRERO HEAVEN" is a canal front 4 bedroom 3 bath attached Villa with neighborhood ocean front beach just down the street! It has a private pool that can be heated or chilled (for a fee), private dock (up to 35' boat), fish cleaning station, bait freezer and 4 new bikes! Additionally,...
Featured review
Meredith is prompt and helpful. Everything you could want at the beach or for your boat is provided. This is a big plus if flying in. Hope to return here. Highly recommend!
Key Amenities
About this property
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,...
Featured review
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....
Key Amenities
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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′...
Key Amenities
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NEW!!! FULL BACKYARD REMODEL!!! NOW OPEN FOR BOOKING!!! INGROUND POOL INSTALLED HEATED! FIRE PIT! PUTTING GREEN! PRICES STILL REFLECT PRE RENOVATION PRICES HURRY IN BEFORE THEY GET RAISED! The Keys Hideaway ~ your private paradise in beautiful Marathon, the heart of the Florida Keys! Gorgeous...
Key Amenities
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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...
Distance to beach: 1 miles to Sombrerro Beach
Key Amenities
About this property
Lemon Key Cottage Welcome home… Thanks to Hurricane Irma, we now have a beautiful newly renovated home! We've spent over $150K on a complete restoration and modernization. (check out the new pics) Lemon Key Cottage is absolutely stunning with new: bathrooms, kitchen, appliances, flooring,...
Featured review
We loved our stay at Lemon Key! The home was lovely and we enjoyed the pool everyday! We were able to buy fresh lobster from their neighbor Paul. What a treat!
Key Amenities
About this property
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...
Key Amenities
About this property
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...
Key Amenities
About this property
Sailfish Villa, unit #6, is a brand new gorgeous, professionally decorated 5 bedroom 4 bath Villa with open water views on Vaca Cut! Enjoy sunrise and sunset colors and direct ocean and Gulf access! It has a private pool and boat slip for a boat up to 35' including motors. There is no additional...
Featured review
I have been coming to marathon with family for many years and have had many rentals.. Meredith I have to say is the best.. she worked with me with every question and plans that I had . Definitely would...
Key Amenities
About this property
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...
Key Amenities
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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.
Key Amenities
About this property
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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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: 3 miles to Sombrero Beach
Key Amenities
About this property
Come and live the KeyZ life for the week or the month! Gorgeous home just off the open water on a deep water canal gulfside. This is a boater/fishing paradise with 60 feet of docking space, deluxe fish cleaning station located on the gulfside! Relax poolside at our signature swimming pool/tiki gar with...
Featured review
We came with our family of 10 and had a wonderful time. The house was perfect for us. It is beautiful and spacious. The outdoor area is fantastic with a sun deck, two sofas and large sun umbrella. The...
Key Amenities
About this property
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...
Key Amenities
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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...
Key Amenities
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4 Bikes 2 Kayaks Hot Tub Covered Outdoor Space 37 Ft of Dockage Fresh Interior Well-Equipped Kitchen Quick Walk to Sombrero Beach Lots of Parking Cozy and comfortable Sombrero Beach cottage! This light and airy single family home offers an open concept living, kitchen and dining area with large...
Distance to beach: 2 miles to Sombrero Beach
Key Amenities
About this property
Welcome to Turtle Cove – Your Ultimate Oceanside Getaway! Turtle Cove is a premium, single-family waterfront oasis designed for effortless Florida Keys living. Located just five houses from open water, this pristine 3-bedroom, 2-bathroom home puts Marathon’s legendary boating, fishing, and...
Featured review
nice house and pool. owner was great to work with. the road is a little tight for boat with trailer.
Key Amenities
About this property
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...
Key Amenities
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MARATHON ANGLER'S RETREAT in Marathon is a brand new property with every modern convenience and warm coastal decor! Located right on a canal (just 15-20 minutes from open water) it has its own private dock (can accommodate up to a 30' boat), fish cleaning station, private pool, hot tub, and...
Featured review
Meredith and Pineapple Properties were very accommodating, and answered all of our questions. The home, the pool, and the hot tub are all in great working shape, well-maintained, and clean. The property...
Key Amenities
About this property
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...
Key Amenities
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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: 3 miles to Sombrero
Key Amenities
About this property
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...
Key Amenities
About this property
Quiet, secluded townhouse that has amazing views of the tropical surroundings. The unit has two levels, so that no one is living above or below you. The two spacious wrap around decks reveal the Canal feeding in from the Gulf of Mexico and the heated swimming pool. There is a large 10 slip Gulfpointe...
Featured review
Great place to stay . Good location. Very nosey tenant's made the stay a little uncomfortable at times.
Key Amenities
About this property
NWelcome to your dream Serenity Oasis! This 3 BR sanctuary in the heart of the Florida Keys has been redesigned so every detail lets you indulge in the ultimate getaway in Paradise . Enjoy evening swims under the stars in your private heated pool , morning kayak adventures or bike rides , foosball or...
Featured review
The name of this property, Serenity Oasis, is exactly how you feel when you are here. Stunning decorated house in a very quiet neighborhood. The pool is wonderful with several different levels of built-in...
Key Amenities
About this property
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...
Distance to beach: 900 yards to Sombrero Beach
Key Amenities
About this property
"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...
Key Amenities
About this property
"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...
Key Amenities
About this property
Welcome to Paradise Point! Indescribable Views! This stunning sanctuary offers Water Frontage on 3 sides giving over 180° of unparalleled Atlantic Ocean Views, Direct Ocean Access from your Private Dock, perfect for boating or fishing right from the backyard After a day on the water, unwind in...
Key Amenities
About this property
Welcome to Morton Street Charmer! This coastal cottage, nestled on the open Gulf of Mexico, offers 2 bedrooms and 2 bathrooms, with recently updated furniture for a fresh feel. Enjoy stunning water views and unforgettable sunsets from the spacious dock, perfect for boats up to 30 ft. Don't forget...
Featured review
Location location location! Absolutely perfect view every morning. House is a tad bit outdated and one of the tvs didn't work but overall a really good vacation. Everything was clean and comfortable.
Distance to beach: 0.1 miles to On site
Key Amenities
About this property
BEST SUNSETS in the Keys, Key Colony Point unit #15, Ocean Beach Front, 2 bedroom, 2 bath ensuite, newly remodeled Condo with new furniture. COMPLEX: KEY COLONY POINT UNIT #15 Perfect get away for a week or a month. BEACH is 30 feet from our balcony. 150 feet to pool with hot tub. Great fishing...
Featured review
Absolutely the best view and pool in Key Colony. Spacious and well appointed condo. Would repeat #15 Very quiet and relaxing without crowds and annoying children!
See the approximate cost before you contact the owner. Owners list cleaning fees, taxes, and any extras up front, and because you book directly with the owner there's no booking fee stacked on top. The 12.5% tax is Florida sales tax plus the Monroe County bed tax.
SHORT STAY
3 nights
all in
$431/night
| $431 × 3 nights | $1,293 |
| Cleaning + damage waiver | $350 |
| Tax (12.5%) | $205 |
| Booking fee | $0 |
| Total | $1,848 |
WEEKLY STAY
7 nights
all in
$417/night
| $417 × 7 nights | $2,919 |
| Cleaning + damage waiver | $350 |
| Tax (12.5%) | $409 |
| Booking fee | $0 |
| Total | $3,678 |
MONTHLY STAY
30 nights
all in
$363/night
| $363 × 30 nights | $10,890 |
| Cleaning + damage waiver | $350 |
| Tax (12.5%) | $1,405 |
| Booking fee | $0 |
| Total | $12,645 |
Winter and spring are the high season overall, and rates ease to their lowest in October, at the height of hurricane season. A nice stretch to visit is March through May, when the days are warm and dry and the water climbs from the mid-70s to the low 80s.
| Month | Median nightly | Difference from annual | High / low air temp | What’s going on |
|---|---|---|---|---|
| January | $467 | +7% | 77° / 56° | Sailfish season; Nautical Flea Market, Big Pine Key |
| February | $500 | +14% | 78° / 57° | Gigantic Nautical Flea Market, Islamorada |
| March | $525 | +20% | 80° / 60° | Original Marathon Seafood Festival |
| April | $450 | +3% | 83° / 64° | Seven Mile Bridge Run |
| May | $429 | -2% | 87° / 69° | Marathon Offshore Bull & Cow mahi tournament |
| June | $473 | +8% | 89° / 73° | Battle in the Bay dragon boat races; tarpon peak |
| July | $500 | +14% | 90° / 74° | Spiny lobster mini-season, last Wednesday and Thursday |
| August | $446 | +2% | 90° / 74° | Regular spiny lobster season opens |
| September | $400 | -9% | 89° / 74° | Peak hurricane season; reef and backcountry fishing |
| October | $371 | -15% | 87° / 69° | Florida Keys Hawkwatch at Curry Hammock; stone crab season opens |
| November | $399 | -9% | 83° / 64° | Stone crab in full swing; high season begins |
| December | $433 | -1% | 79° / 59° | Holiday lighted boat parades |
Based on the median Marathon nightly rate on FloridaRentals.com.
Marathon anchors the Middle Keys, strung along US-1 by mile marker (MM), so "where to stay" comes down to how far north or south you are and whether you want a canal home with a dock or an oceanfront condo. The areas below all sit within a few minutes of central Marathon at MM 50.
Key West International (EYW) is the closest, about 48 miles and an hour down US-1. Miami (MIA) is the bigger gateway at about 2.5 hours, with Fort Lauderdale (FLL) a little farther as the budget alternate.
Marathon is strung along 13 miles of US-1, so a car is effectively required. Two commuter buses run the highway: the 301 Dade-Monroe Express north to Florida City and the Lower Keys Shuttle south to Key West, each just a few dollars a ride. Both are built for commuters.
In Marathon's residential areas, licensed vacation rentals run 7 to 28 nights, and stays under a week are generally prohibited. The exact minimum still varies by property, zoning, and HOA, and oceanfront condo associations add their own age and parking-decal rules.
Hurricane season runs June through November, and September is both the statistical peak and the lowest-demand month to book. The other season to time is sargassum, the harmless drift seaweed that washes onto Marathon's Atlantic-facing beaches from about May through August.
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