Vacation Rentals in Marathon Florida Keys.
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Vacation Rentals by Owner in Marathon Florida -- We have partnered directly with a major provider for By Owner Rentals, and now have the selection and value to offer our visitors searching for places to rent in Florida.
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Manatee Bay , Pool table, Pool, Kayaks, Jacuzzi not working.
The Manatee Bay has the best of all worlds. It has a large custom fiberglass pool situated next to a 20 ft+ deep and beautiful swim able and fish-able lagoon. The Lagoon is filled with all sorts of different wildlife, including an occasional manatee, turtles, and all sorts of fish. It is the perfect place to learn to Paddle Board, Snorkel, or Kayak. There is Quick access to the open Gulf at the end of the lagoon, with a large dock out into the deep water with room for 3 boats. The back deck .......
\"Your own private resort\" - Mockingbird Pointe - Waterfront, pool and dockage
Mockingbird Pointe is a quiet secluded 1/2 acre tropical waterfront paradise in the heart of the Florida Keys with private heated and/or chilled 16' x 32' in ground cement swimming pool with splash deck custom Tiki hut and spectacular tropical landscaping. This two bedroom, two bath home features a newly remodeled kitchen and dining area and updates through-out the home with new bathroom updates, furniture, artwork and interior finishes. Private office is located off of main bedroom. Wrap aroun.......
10.0 Star Review
2 Bedrooms
- Sleeps 6
Marathon Vacation Rental
Pets Allowed 
Atlantic side, quiet neighborhood ~ 3 Bed 2.5 Bath, dock, pool / hot tub, kayak
This 3 bedroom, 2.5 bath single-family modern home is great for entertaining! Enjoy the outdoor area with a pool and a separate hot tub or catch a game of pool on the main floor. This home is located on the 63rd Street canal and being ocean-side, it's just a quick trip out to sea where you'll enjoy cruising, fishing or maybe even snorkeling!
This spectacular home boasts 2 levels of living space with canal views enjoyed from the dining room and living room. With these cathedral ceilings, y.......
Perfect Paradise
Perfect paradise is located in the heart of marathon. Only 9 minutes away from sombrero beach. Restaurant, supermarkets, ice cream, aquarium, and much more less than 7 minutes away. Public boat ramp is 5 minutes away. The house has plenty of parking spaces in the front to park your boat and 3 vehicles. 4 parking spaces in total. The home was recently remodeled completely and is fully stocked with everything you will need during your stay.
Perfect paradise rentals provides a complimen.......
Yellowfin Fun! 4-Bedroom, 3-Bath, Pool & Dockage
Summary:
Yellowfin 4BR/3BA half-duplex home by Sombrero Beach with Pool and Dockage!
Just minutes from Sombrero Beach, you’ll create memories that will last a lifetime in this lovely half-duplex home with private heated & chilled pool plus a private 30 ft. dock with a fish cleaning station to prep your catch of the day!
The Space:
Designed to offer you the perfect vacation with your family and friends whether you are a fisherman, beach goer, sightseer or a c.......
9.4 Star Review
4 Bedrooms
- Sleeps 10
Marathon Vacation Rental
Pets Allowed
Private Pool, Hot Tub, Boat Dock, Putting Green
Bikini Bottom
Stunning 4 bedroom, 3 bath stilted canal home on Marathon’s “Gulf Side”. Enjoy instant access to either the Gulf of Mexico or Atlantic Ocean, just seconds from your canal.
This Coastal getaway comes equipped with amenities the whole family will love. Enjoy outdoor dining on a wrap around deck that overlooks the putting green, private pool, and private dockage.
Equipped with a fish cleaning table, bait freezer, and 40’ of dockag.......
Sun of a Beach – Waterfront 7BR Home with Pool, Spa & Dock Minutes from Sombrero Beach
Indulge in the charm of this splendid split-level residence nestled in the heart of the captivating Florida Keys. This distinctive property comfortably accommodates up to 16 guests across its seven well-appointed bedrooms, offering an ideal haven for two families seeking both shared moments and personal privacy within its thoughtfully designed layout.
The main level of the home hosts the primary kitchen, a charming dining area, a welcoming living room, and three inviting bedrooms, ...comp.......
10.0 Star Review
7 Bedrooms
- Sleeps 16
Marathon Vacation Rental
Pets Allowed
Island Time in Marathon!
If you are looking for a home which will allow you to wake up to the noise of the ocean, has breathtaking views of the turquoise sea lined with snow white sand and gorgeous blue water, look no more.
This luxury front retreat includes five bedrooms and four full bathrooms. The view from the living room couch is jaw-dropping. A large balcony overlooking the ocean extends the living area outdoors. This vacation home also includes access to fishing dock, boat and jet ski ramp, private beach, boa.......
Waterfront luxury Villa (43) with spectacular sunset views and boat slip
This beautifully remodeled, spacious 3BD, 2.5BA Villa is the perfect blend of comfort and coastal charm. Each bedroom features its own television, and the living room offers a large flat-screen TV, ideal for relaxing after a day on the water. Step outside to enjoy direct sunset views over the Gulf from either your private porch or the upper balcony. Just off your back porch is your private boat dock, perfect for boating enthusiasts.
Dock Details:
Maximum overall vessel length (tip .......
Beautiful Waterfront Gulf of America Great location.
This property is like having your own private resort. On the Gulf of Mexico. Million-dollar waterfront views & sunsets. Next to Dolphin Research Center.
4BR + bonus room w/queen bed & futon. 6 TVs. Pool, Private Dock, Kayaks & Corn hole boards, and more.
Watch the Dolphins shows daily. Were located next to the World-Famous Dolphin Research Center.
House has wrap around deck plenty of seating inside/out. House has 2 sides.
Side1
Has kitchen, dining area, living room, king be.......
10.0 Star Review
4 Bedrooms
- Sleeps 10
Marathon Vacation Rental
Pets Allowed
Cozy beachfront oasis heated pool ocean view U13
Summary:
Experience the quintessence of Florida Keys charm in our cozy beachfront hideaway, praised by guests for its sparkling cleanliness, effortless check-in, and idyllic location. With a screened balcony offering sweeping ocean views, it’s the perfect retreat for small families or couples seeking a peaceful escape. Delight in the little luxuries of our quaint complex, from the heated pool to the sun-kissed tiki picnic area, and find out why many have made it their repeat vacation sp.......
Waterfront, dock, easy ocean access, heated pool, walk to beach! Great location!
One room with a king sized bed and the other has a queen sized bed – both with cool comfort memory foam mattresses. Pull-out queen sized sofa and twin love seats add additional sleeping options. Bathrooms lined in elegant tile with glass block showers. The well-stocked chef’s kitchen has all stainless appliances (including fridge with ice maker) with an eat-in breakfast bar and everything you need, from toaster oven to blender, to feel at home. The skylight adds openness and light to the ent.......
Isla Marlin 28: Palm lined luxury villa w/dockage and sunset views
Island Life at its Best at Isla Marlin, Indigo Reef 28! Located in the premier gated, waterfront marina resort of Indigo Reef. Follow the palms to your 27 ft boat slip, directly in front of your back porch rocking chairs. Spend the day on the water, fishing, snorkeling the reef or lounging by the resort pool. Indigo Reef is located just 90 miles south of Miami and 45 minutes from Key West. Isla Marlin boasts spectacular views of the Gulf of Mexico and easy access to the Atlantic Ocean via Va.......
10.0 Star Review
3 Bedrooms
- Sleeps 8
Marathon Vacation Rental
Pets Allowed
Beach House is a stunning and spacious 2bed/2bath with private pool & steps to Sombrero Beach!
The Beach House is a stunning and spacious 2bed/2bath with private pool & steps to Sombrero Beach!
This home offers an open concept living, kitchen and dining area. The living room is spacious with comfortable furnishings and large flat screen TV. Dining table seats up to 6 and the counter seats another 2. Off the kitchen is a storage area wtih the washer & dryer.
Master bedroom features queen bed, comfortable chair with ottoman, flat screen TV and a desk. The en suite bath has .......
Pozitively Bliss updated 3bed/2bath single family home near Sombrero Beach with private pool & dockage
Welcome to Pozitively Bliss, your updated 3-bed, 2-bath haven nestled in Sombrero Beach. Modern amenities seamlessly blend with laid-back style, promising an unforgettable escape in the Florida Keys. Step inside to discover an expansive living space, a well-equipped kitchen, and a charming screened porch, beckoning you to unwind in the tropical breeze.
The master suite, boasting a king bed and plush seating, offers a sanctuary within the home, complete with an en-suite bathroom ...boastin.......
Casa Del Mar~ Luxury Pool Home w/ Kayaks and Bikes!
4BR 4.5BA Home w/ Fantastic Outdoor Entertainment Area, Outdoor Bar and Private Heated Pool!
Casa Del Mar
This stunning vacation rental features 4 spacious bedrooms, each with en-suite baths, including two master suites with king-sized beds and patio access. The open great room boasts a chef's kitchen and expansive glass doors that seamlessly connect indoor and outdoor living. Outside, enjoy a private oasis with a large swimming pool, fire pit, top-of-the-line grill, and an.......
Waterfront - Large dock and large fenced yd. 1950 era knotty pine conch cottage.
Perfect for Boaters - Deep water, 115 foot private dock on Gulf half way between Vaca Cut and Seven Mile Bridge. Very close to public boat ramp. Tiki hut on water with fish cleaning station, bait/fish freezer, pool table and gas grill. Public bus to Key West stops four blocks away. Walking distance to restaurants and bars. 3 Bedroom, 2 Bath House; Sleeps 8. Large Fenced Yard for parking several boat trailers. Pet Friendly........
Pirate Point, Luxe 5BR Escape w/ Pool, Tiki, & Dock Minutes from the Beach
Welcome to Pirate Point – your private slice of paradise. Tucked away at the end of a peaceful canal street on lush, landscaped grounds, this upscale waterfront estate offers the ultimate blend of luxury and comfort. Set on nearly an acre at the corner of Avenue G canal and Coco Plum Bay, the compound boasts expansive bay views, a private dock, and exceptional outdoor living spaces.
The property includes a 3BR/3BA main home, a separate 1BR/1BA apartment, and a detached 1BR suite — off.......
10.0 Star Review
5 Bedrooms
- Sleeps 10
Marathon Vacation Rental
Pets Allowed
COZY FAMILY HOME-POOL-SPA -5 minute drive to sombrero beach-private property
Welcome to Your Marathon Paradise!
This beautiful home features 2 bedrooms, 2 bathrooms, and a spacious open-concept living, dining, and kitchen area—perfect for entertaining or relaxing after a day in the Florida Keys.
Inside:
• Dining area with comfortable seating
• Fully equipped kitchen with silverware, baking and cooking pots, utensils, and updated appliances
• King bed in the master bedroom, Queen bed in the guest room, plus a Queen pull-out sofa
• A.......
10.0 Star Review
2 Bedrooms
- Sleeps 6
Marathon Vacation Rental
Pets Allowed
Waterfront Luxury Living Inside & Out, Gulf View, On the Water!!
Fabulous Florida Keys outdoor living! 1br/2bath sleeps 4. Luxury living inside & out. Spend your days swimming in the deep waters of the beautiful Gulf of Mexico or under the palms in the fresh water swim spa which is solar heated in the winter and shaded and cool in the summer. Enjoy evenings overlooking spectacular sunsets from the waterfront patio. Deep water dockage on the gulf with easy access to the ocean (available for additional charge). Outdoor marble wet bar with many amenities. Marble.......
10.0 Star Review
1 Bedrooms
- Sleeps 4
Marathon Vacation Rental
Pets Allowed
Papa's House On Vaca Cut, fabulous location, views and amenities!
This single-family home (now 6 bedrooms, 6 baths) is located just in from Vaca Cut with unobstructed views of the Cut and the Ocean beyond.
Protected dockage and a 30' freshwater pool and poolside Spa. This home offers a perfect blend of gracious 'Old Keys' casual style and the location offers the sought-after boating access to the Ocean or Gulf within minutes. The ground level access, with 4 bedrooms and 4 baths, contributes to an easy lifestyle, no stairs or steps, the living areas flow un.......
9.4 Star Review
6 Bedrooms
- Sleeps 14
Marathon Vacation Rental
Pets Allowed
Indigo Reef #34 | Waterfront + Boat Slip +Sunset
This spacious 3BD, 2.5BA Villa is the perfect blend of comfort and coastal charm. Each bedroom features its own television, and the living room offers a large flat-screen TV, ideal for relaxing after a day on the water.
Step outside to enjoy direct sunset views over the Gulf from either your private porch or the upper balcony. Just off your back porch is your private boat dock, perfect for boating enthusiasts.
Dock Details:
Maximum overall vessel length (tip of bow to end of eng.......
10.0 Star Review
3 Bedrooms
- Sleeps 6
Marathon Vacation Rental
Pets Allowed
Absolutely Perfect! Reel Vacation Villa w/Pool, Dock, Close to Beach w/Extras!
This stunning home on the Intracoastal Waterway is loaded with amenities including a private pool and patio with boat dockage, a large balcony and a spacious, updated interior that can accommodate up to 10 guests. A perfect rental home for you and your family or friends with all of the amenities needed for a relaxing vacation. This home that has all the home away amenities to make your stay at Marathon Key unforgettable! When you need to book 3 or 4 bedrooms for the family, you can book this bea.......
10.0 Star Review
4 Bedrooms
- Sleeps 10
Marathon Vacation Rental
Pets Allowed
Island Adventure I 4 Bedrooms 4.5 Baths, Pool, Ocean View with Dock & Kayaks
Vaca-22-75
Welcome to Island Adventure: Your Ultimate Florida Keys Retreat
*Island Adventure* is the perfect home for families, fun-seekers, luxury lovers, and water sports enthusiasts. Built in 2021 and designed with relaxation and adventure in mind, this stunning 4-bedroom, 4.5-bath home is located in Marathon, offering direct access to the open waters of the Atlantic. With ample parking for up to a 30-foot boat trailer and two cars, your adventure is ready to begin as soon as yo.......
BEST House in Marathon With Ocean View!
Ocean side Newly remodeled home. 2 queen beds with private bathrooms. Cabana is 3rd private bedroom with memory foam sleeper sofa & full private bathroom. Lg Rm with memory foam sleeper sofa. House has outside patio, private 60 ft dock (Space avail is for 27 ft. boat including engines), fish off dock. Pool & whirlpool with water falls/lighting. Parking Max 4 cars including boat trailer. Boat rentals available in the area close by also 2 Grocery stores, many restaurants, 7 Mile bridge........
Oceanfront with Pool near Sombrero Beach
Welcome to Seascape Point! Perfectly situated at the end of a quiet block, this stunning property juts out into the Atlantic Ocean to offer amazing water views from every angle. Its incredible location next to a nature preserve provides you with additional privacy and daily sightings of exotic, tropical birds.
The spacious layout of the house consists of 2 floors which are not connected inside. Each floor has its own living area, kitchen, 2 bedrooms, and 1 bathroom (total o.......
Pool, Dockage, Walk to Sombrero Beach, Kayaks, 4 BR, large Ice Maker
Check out Anglers at Sombrero Canal Front Townhome with a private pool and 40 ft of dockage! Just minutes to the stunning Sombrero Beach, this Villa-style home is perfectly located in the heart of the Florida Keys. This newer built villa offers beautiful views of the canal and surrounding neighborhood. Island Living at it's best, this home offers a beautiful pool and covered patio area to relax or you can enjoy the beautiful islands of Marathon by boat and dock right outside the back door from.......
Adventures in Paradise at Sombrero Beach ~ Pet friendly waterfront pool home, 26' dock
Property Highlights:
• Sleeps: 10
• Bedrooms: 4
• Bathrooms: 3
• Dock: 26' private dockage with deep water and easy ocean access through Sister Creek and a jet ski dock (can fit 2 jet skis).
• Pool: Dive into your own private 152 sqft saltwater pool for refreshing swims. Can be heated for a fee. Pool towels are provided.
• Pet-friendly: Pets are welcome! Please notify us in advance and adhere to our pet policy. Fully fenced.
• Fishing Enthusiasts: Bait free.......
9.0 Star Review
4 Bedrooms
- Sleeps 10
Marathon Vacation Rental
Pets Allowed
Yellow Fin Ocean front Breeze- M#11
This 2BR, 2BA freestanding home sits on a spacious double lot and features breathtaking ocean views, a private 50-ft dock and 70 feet of waterfront—perfect for fishing, kayaking, or simply relaxing—and modern amenities throughout. Enjoy a fully equipped kitchen, King Master,Twins Guest & Queen sleep sofa, Lazy Boy recliner, plenty of parking. Minutes to the Ocean or Bay by boat, and close to local restaurants and shops........
Tropical Island Pool Villa- Ocotillo#14
This stunning vacation home is the perfect setting for your tropical getaway. The private heated pool becomes the heart of your island retreat, while the deep-water dock offers easy access for boating and fishing in the Atlantic or Bay. Featuring three stylish bedrooms, this luxurious escape blends comfort and convenience. Located near pristine Sombrero Beach, you’ll enjoy the best of the Keys—from relaxing poolside to exploring this vibrant island community........
Boater’s Seaside Dream 45 ft dock M#13
Waterfront Keys Retreat with 40-ft Dock & Tiki Porch
This neat 3-bedroom, 2-bath home is in the heart of Marathon & sleeps 8 guests (King, Queen, 2 Twins + sleeper sofa) & offers the ultimate experience. Relax on the seaside porch, grill by the tiki hut, or head out from your deep dock—perfect for kayaking, fishing or boating with quick access to the marinas, bridge ,ocean or bay. Walk to the 7 Mile Bridge or drive to Sandy Sombrero Beach. Parks 2 cars & boat trailer. PET FRIE.......
Beach House, Waterfront, Sombrero Beach, Florida Keys Rental, Private Pool, Dock
New Listing - Family Reunion Large Vacation Rental 6 bedrooms 5 baths steps to Sombrero Beach. 6 bedrooms (5 King size beds in 5 bedrooms) the last bedroom has
2 bunkbed sets (2 full size beds on the bottom and 2 single beds on the top bunks)
Welcome to the world of azure blue waters, tropical warm weather gently ocean breezes and the island sun of the Florida Keys. The Florida Keys is one of the most sought after destinations for anyone wanting to get-away from the mainland and rela.......
9.8 Star Review
6 Bedrooms
- Sleeps 14
Marathon Vacation Rental
Pets Allowed
Paradise Without A Passport New Home Ocean Views
Brand New Home, Brand New Furniture, Sunset and Ocean Views, Outdoor communal Fire Pits, Outdoor Kitchen, Grill, Possible Dock Rental, Bicycles, Snorkel Gear, Beach Chairs, Umbrella Sunrise and Sunset Views.......
2 Bedrooms
- Sleeps 8
Marathon Vacation Rental
Pets Allowed
Garden Oasis Ocean Views Pool Beach U27
Summary:
Uncover a hidden gem in our charming condo overlooking a tranquil garden with two unexpected side views of the ocean. It’s perfect for couples seeking a value-packed Keys getaway. A peaceful retreat, it is steps from the beach and pool, featuring a king bed, updated decor, and a screened balcony. With a full kitchen, it's your cozy base for exploring Marathon's beauty. Dive into relaxation or adventure, all while enjoying the comforts of our island home. Discover your Maratho.......
Atlantic Ocean views, Canal front, 3 bed, 3 bath, private heated pool, tiki hut
Fisherman's Paradise with Atlantic Ocean Views. "Keys Release" is located in Marathon Florida, the heart of the Florida Keys. Only one house in from the Atlantic Ocean, with quick easy access through a well navigated deep water canal, you will be fishing, snorkeling, diving in no time. Or if you would rather relax by the pool (heating of hot tub is not available only pool for additional fee), or enjoy the ocean breeze under the Tiki hut, that is always an option.
Keys Release offers a 2 .......
Waterfront,100' seawall W/ Dockage up to 30', Pool, Easy Ocean & Gulf Access!
VACA -23-147
Sharing our Family Home in Paradise! This house is a rare find!! Nice Florida Keys home with an old Florida Keys feel. The home is not on a canal, so the view is not obstructed! And it has shade on back deck for evening cookouts! Located on the Bay with 5 minute access to BOTH the Gulf and the Atlantic!! 100' seawall with up to 30' Boat Dockage and boat trailer parking. Island Time Boat Rental will deliver a boat to the house for free!
2 King Beds
1 Queen
2 Full
.......
Find the Top Vacation Rentals in Marathon, Florida.
We have 2,3 or 4 Bedroom beachfront Condo Rentals with ocean view or a Beach House for the entire family. Book Direct Here!
Marathon is a 10-mile-long stretch of islands located in the middle of the Florida Keys. When vacationers and snowbirds visit Marathon, they come here primarily for its fishing and boating activities, the private waterfront vacation homes, small hotels and inns or the annual seafood festivals and waterside restaurants.