Vacation rentals with a kayak in Marathon

4.93 out of 5 average rating, 82 reviews

Beach House, Private Pool, Dock, Gulf View Sunsets

You don’t come to the islands to stay in a town—you come to slow down. Welcome to our tropical keys beach home, tucked away from the traffic and noise of US Hwy #1. Sway with the palms on the wraparound deck, soak in wide-open panoramic bay views, and catch fiery sunsets right off your dock. Fire up the BBQ, brew a Keurig, float in the private pool, or cast a line from the 300’ private pier/dock. Easy going island living with ocean / gulf breezes, comfy beds, quality linens, Wi-Fi, and cable TV.

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4.73 out of 5 average rating, 26 reviews

Sunset Key Escape/Pool, Dock, Kayaks & Gulf Access

Welcome to Sunset Key Escape Your Private Waterfront Retreat in Marathon Bask in the beauty of the Florida Keys at Sunset Key Escape, a stylish and serene 3 bedrooms, 3 bathroom waterfront getaway designed for comfort, adventure, and unforgettable views. Whether you are unwinding poolside, launching a kayak at sunrise, enjoying dinner by the water under the stars, or challenging friends and family to a ping pong match, this home offers a true Keys escape surrounded by nature and coastal charm.

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5.0 out of 5 average rating, 18 reviews

Home in Key Colony Beach

Best Location in Marathon & KCB!

Luxury Meets Adventure at Seahorse Landing! 40’ of dockage, SUP, kayak & all the equipment you’ll need to explore the beautiful bays & wildlife frequented waterways. All that adventure is balanced by a newly renovated interior offering the perfect blend of comfort and style in a modern, spotless setting. Our family has created a home that is a perfect fit for adventurous couples or families seeking relaxation& exploration. Send us a message or book instantly & begin your luxurious adventure!

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5.0 out of 5 average rating, 3 reviews

Emerald Palms ~ Waterfront ~ Pool ~ Dock ~ Games

Welcome to Emerald Palms, a 4BR/2.5BA canal-front home in Marathon, Florida Keys. Built for groups who come to the Keys to be on the water, Emerald Palms pairs a heated saltwater pool and hot tub with a private dock, quick Gulf access, and a game room for the evenings — all minutes from the beaches, reefs, and fresh-catch restaurants of the Middle Keys. ✔ 4 Bedrooms (King Primary Suite, Queen, Full-with-Twin, Bunk Room) + 2 Sleeper Sofas — Sleeps 10 ✔ 2.5 Bathrooms ✔ Open-Concept Living ✔ Full

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4.77 out of 5 average rating, 162 reviews

Houseboat in Marathon

Tiny Home Aqua Lodges 2/1

This memorable place is anything but ordinary. Stay in our fully equipped aqua lodge with private surroundings. This lodge has 1 queen bed, 1 full bed, a sofa sleeper full size on the main floor, and 1 twin in the loft. It has a full kitchen, mini split ac, and full bathroom with hot water. This location has great sunset views and private BBQ waterfront area. All lodges have all bedding and dishes and cooking utensils. You will also have access to the Cabana Club located in Key Colony Beach.

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An inviting outdoor space features comfortable seating and a hot tub, surrounded by lush greenery. A large screen is set up for movie nights, and ambient lighting enhances the evening atmosphere as the sun sets.

5.0 out of 5 average rating, 81 reviews

Tropical Keys Retreat | Pool | Hot Tub | Cinema

Welcome to Paradise Palms: ⭑ 1750 sqft liveable space on 10,500 sqft estate ⭑ Private home, deck, patio & backyard, overlooking a beautiful scenic landscape ⭑ Crystal pool, hot tub, movie theater, remote workspace, game room with arcade & more ⭑ Secure parking for up to six vehicles, boat trailer parking, RV and EV charging ⭑ 10 min to sombrero beach & just minutes to all island attractions ⭑ Fully stocked kitchen ⭑ Extremely safe neighborhood License #VACA-24-20 License #VACA-24-32

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A boat is docked beside a light blue cottage, featuring large windows that reflect on the water's surface. Lush palm trees surround the property, enhancing the tropical atmosphere and offering a serene view of the canal.

4.98 out of 5 average rating, 58 reviews

Flamingo Palms-BOOK Spring 2027 dates NOW!

Flamingo Palms Cottage located on a deep-water canal with dockage and easy access to world-class fishing in the Atlantic and the Gulf. Nestled in a tropical setting amongst the native palms, Royal Poinciana and tropical landscape. Enjoy all the amenities needed for a perfect island vacation: airy open living areas, cozy screened porch, office nook off the kitchen, updated bedrooms and bathrooms, SUPs, beautiful yard, gas grill, parking for 2 cars/boat trailer. VACA-22-164/VRA-22-81

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4.95 out of 5 average rating, 146 reviews

A paved outdoor patio features two lounge chairs and a small round table, surrounded by tropical plants and palms. The tranquil canal is visible in the background, offering a serene waterfront view.

Home in Key Colony Beach

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

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4.92 out of 5 average rating, 120 reviews

The image showcases a vibrant living space within the Dapper Dolphin condo, featuring a stylish kitchen with granite countertops, a cozy dining area, and a comfortable bedroom with a king-sized bed. The outdoor area displays a large pool surrounded by lounge chairs, highlighting the resort's inviting atmosphere.

Condo in Marathon

Dapper Dolphin | Canal View + Breakfast + Pool

Escape to The Dapper Dolphin, a beautifully updated coastal 1-bedroom, 1-bath condo located at Skipjack Resort & Marina in the heart of Marathon. Sleeping up to 4 guests, this stylish retreat features a full kitchen, private balcony, and resort amenities including a pool, Tiki Bar, restaurant, Marina, and more. Situated in the heart of Marathon, it offers proximity to the beach, restaurants, activities, and all the essentials for an unforgettable vacation experience right on-site!

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Home in Upper Sugarloaf Key

The bungalow stands illuminated against a night sky, surrounded by swaying palm trees. Soft reflections shimmer on the water's surface, while the sandy beach extends along the shoreline. The structure features large windows, showcasing a welcoming interior visible from outdoors.

The Lighthouse - Beach Houses Key West

If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

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4.93 out of 5 average rating, 134 reviews

5.0 out of 5 average rating, 6 reviews

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

Wake up to open-water views at your private oceanfront retreat in Marathon. Bring the boat, step into your private pool, Perfect for families and boating groups.Your private 60' dock offers direct water access, freshwater for rinsing gear and flushing engines, while parking accommodates up to 4 vehicles. • Direct oceanfront setting • Private swimming pool • Private 60' boat dock • Complimentary kayaks • Sleeps up to 10 • Parking for 4 vehicles • Wi-Fi + dedicated workspace

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4.91 out of 5 average rating, 35 reviews

Private Dock| 5min beach| Kayak| Sunset view|RV

Relax in this serene beach house, just a 5-minute walk from Sombrero Beach and a quick drive to Publix. Located in the heart of Marathon, FL, this home features its own boating dock, perfect for water adventures. The master bedroom includes a king bed, full bathroom, and closet. The second bedroom offers a king bed, bunk bed with pullout, and a nearby full bathroom. Enjoy a fully equipped kitchen, washer/dryer, kayaks (3) and trailer parking. Your perfect vacation getaway

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Popular amenities for Marathon kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

A tropical backyard features a private saltwater pool surrounded by seating areas. A thatched-roof Tiki Hut is adorned with string lights. A gas fire pit sits centrally, while walls are embellished with colorful fish murals. Lush greenery completes this inviting outdoor space.

4.92 out of 5 average rating, 119 reviews

Tiki Time! Private Pool~Tiki Hut~Kayak~Grill!

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5.0 out of 5 average rating, 27 reviews

Villa Serenity At Sombrero Private Pool Spa Dock

LocationOutdoor spacesSleep quality

5.0 out of 5 average rating, 17 reviews

Canalfront Home Ocean accessible

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A waterfront property is depicted, featuring a contemporary two-story design with light blue and yellow exterior accents. A private dock is visible alongside the house, and a clear sky reflects over the calm water, enhancing the serene coastal environment.

5.0 out of 5 average rating, 21 reviews

Boating Paradise Villa rental Lic# VACA-25-124

Outdoor spacesLocationAccuracy

4.67 out of 5 average rating, 6 reviews

Blue Heaven Marathon

LocationOutdoor spacesBathroom

4.86 out of 5 average rating, 36 reviews

A private inground pool is surrounded by palm trees under a clear blue sky. A colorful rubber duck floats on the water's surface. A hammock can be seen in the background, while a red umbrella provides shade over two seated chairs nearby, creating a serene outdoor setting.

Home in Key Colony Beach

Welcome to Paradise! Private Pool, SUPs, Kayak!

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4.92 out of 5 average rating, 12 reviews

Blue Paradise Call for Weekend ONLY rates

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A two-story waterfront beach house features a spacious deck with seating, surrounded by greenery. A gravel area lies in front, with bicycles parked nearby, indicating easy access to Sombrero Beach. Palm trees and a clear sky complete the coastal setting.

4.96 out of 5 average rating, 48 reviews

Marathon Beach house w/45’ dock Ocean access

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Cottage rentals with a kayak

A serene waterfront view showcases clear turquoise waters under a bright blue sky. A boat can be seen cruising along the horizon, while a patio with seating is visible at the forefront, adjacent to a dock lined with black posts.

4.95 out of 5 average rating, 183 reviews

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

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4.95 out of 5 average rating, 106 reviews

A comfortable living area is highlighted by a light-colored sofa with textured cushions, accompanied by a woven coffee table. Natural light enters through multiple windows, revealing touches of coastal decor and a glimpse of a bedroom in the adjacent space.

Cottage in Islamorada

Islamorada bungalow 2 bed & pool

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A bright living area features light-colored furnishings with nautical accents. Large windows offer views of the water, while a flat-screen TV is positioned on a stylish stand. The adjoining dining area showcases a white table with matching chairs surrounded by plants, enhancing the airy environment.

4.79 out of 5 average rating, 121 reviews

OCEANIA... water front cottage retreat ~

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4.96 out of 5 average rating, 157 reviews

A spacious outdoor tiki living area features a thatched-roof gazebo overlooking the ocean. Two kayaks rest on the dock, with a fishing rod and tackle box nearby. The scene captures a serene sunset, reflecting light across the water and creating a tranquil ambiance.

Cottage in Key Largo

Oceanfront Getaway | Kayaks, BBQ & Stunning View!

ValueLocationParking

4.93 out of 5 average rating, 118 reviews

An outdoor lounge area features comfortable seating arrangements with cushioned chairs and a sectional. A striped rug covers the deck, while a thatched roof provides shade. The adjacent waterway is visible, lined with boats and marina structures in the background.

Cottage in Key Largo

THE PARADISE

LocationOutdoor spacesLayout

5.0 out of 5 average rating, 111 reviews

Cottage in Key Largo

My Little Paradise North Key Largo

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A tranquil pool is set against a backdrop of palm trees and a vibrant sunset. The water reflects the hues of the sky, creating a calming scene. Loungers are positioned along the poolside, offering a inviting space to relax.

4.81 out of 5 average rating, 37 reviews

2Bd/1Ba Waterfront Retreat w/35’ Dock

LocationOutdoor spacesRiver

4.85 out of 5 average rating, 46 reviews

Ocean Breeze @ VO - Kayaks, Bikes, 30 Min from KW

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Cabin rentals with a kayak

4.55 out of 5 average rating, 282 reviews

Cabin in Key Largo

2 BR/2 BA Oasis Kayaks, Pool, Beach & Dock Rental

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