Holiday rentals with a kayak in Marathon

A serene outdoor space features a clear swimming pool surrounded by palm trees. A covered lounge area provides shade, while lounge chairs offer spots for relaxation. The tranquil waters are visible in the background, enhancing the overall atmosphere of the private retreat.

5 out of 5 average rating, 14 reviews

Waterfront Oasis w/Private Pool-Dockage-Beach

Our beautiful spacious home has been recently renovated & features 3 bedrooms & 3 bathrooms, making it perfect for families or groups of friends. The open floor plan and large windows allow for plenty of natural light and stunning views of the water. The kitchen is fully equipped for all your cooking needs and the large private backyard provides the perfect spot for outdoor dining & relaxing poolside. Book your stay at our home today & get ready for an unforgettable vacation in the Florida Keys!

4.96 out of 5 average rating, 171 reviews

A serene waterfront view is framed by palm trees, with two green chaise lounges positioned for relaxation. The setting sun casts warm hues across the sky, reflecting on the water's surface. A Tiki structure adds charm, creating an inviting outdoor space.

Tiny home in Key Largo

Oceanfront Lookout Point w/two Kayaks & Deck

Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

4.96 out of 5 average rating, 162 reviews

A spacious outdoor porch features a round dining table surrounded by four chairs. A kayak is positioned nearby, and lush greenery and water views are visible in the background, enhancing the inviting outdoor space.

Villa in Duck Key

Beach House - Kayak 2/2.5 Villa - OS Slip/Ramp/Pkg

Welcome to Beach House Getaway, a charming villa tucked away on the serene island of Duck Key and perfectly situated in the heart of the Florida Keys. Nestled between Key Largo and Key West, Duck Key serves as a peaceful yet convenient base for your island getaway. Its central location means you’re just a short drive from some of the most iconic destinations in the Keys, including the natural wonders of Bahia Honda State Park, the famous waters around Islamorada, and the lively Key West.

4.97 out of 5 average rating, 175 reviews

A sunset view is captured from a covered outdoor seating area, showcasing a tranquil waterway. Silhouettes of kayaks and a table are visible, while the setting sun creates a warm glow across the horizon. Natural textures are evident in the thatched roof above.

Tiny home in Key Largo

Oasis2 in Key Largo With a million dollar view

Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

4.95 out of 5 average rating, 132 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.

4.93 out of 5 average rating, 362 reviews

The image features a distant houseboat silhouetted against a vibrant sunset, reflecting shades of orange and purple on the water's surface. The view is taken from a skiff, with gentle ripples seen in the foreground, creating a serene atmosphere.

Boat in Islamorada

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Superhost

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.

Home in Upper Sugarloaf Key

4.94 out of 5 average rating, 105 reviews

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.

4.97 out of 5 average rating, 169 reviews

Home in Key Largo

Key Largo Waterfront: Tiki, Dock, Kayak & Pool

This waterfront retreat is perfect for couples, families, or boaters looking to explore the best of the Keys. Snorkel right from the dock, paddle through mangroves with the tandem kayak, or relax with a drink while the sun sets over the canal. Steps from two heated pools, a playground, and a sandy beach, plus only 0.3 miles from groceries and restaurants. Whether you’re fishing, diving famous reefs, or just unwinding under the tiki, this home puts paradise at your doorstep.

4.88 out of 5 average rating, 25 reviews

A cozy sleeping area featuring a quilted bedspread in various patterns. A kitchenette with modern appliances is visible, complemented by cabinetry. Two refrigerators are nestled in the corner, and a large mirror reflects the space. Ambient lighting and decorative touches add character.

Houseboat in Marathon

b watervibe

Disfruta de los sonidos de la naturaleza cuando te quedes en este lugar único. Es algo diferente para disfrutar con tu pareja de un momento romántico y divertido y así relajarse y olvidarse de la vida cotidiana. Puedes disfrutar de la pesca ,de paseos en kayak ,vivir una aventura y disfrutar de otras actividades locales.Prueba de la expericiensa y ya ustedes diran.Esta casa flotante ofrece un espacio para 2 adultos. Está Esta es una experiencia de Acampada

Superhost

A cozy living space features a navy blue sofa adorned with nautical-themed throw pillows. A dining area with a glass table and chairs is visible in the background, alongside a decorative display of framed art and a potted plant. Natural light filters through the windows.

Houseboat in Marathon

4.89 out of 5 average rating, 123 reviews

Houseboat Getaway In Marathon

Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

4.95 out of 5 average rating, 140 reviews

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

Perfect for families, couples, groups, or solo travelers, this spacious home offers 5 bedrooms, 3 bathrooms, an open living room, and a fully stocked kitchen. Easy to reach and simple to access, it’s set in a peaceful neighborhood close to island fun and water adventures. Just a short walk to Sweet Savannah’s Ice Cream & Sweets Parlor, this retreat is ideal for relaxing or exploring. We look forward to hosting you!

An outdoor seating area features a thatched roof, providing shade over a collection of cushioned seating and a low coffee table. A swimming pool is visible in the background, surrounded by tropical greenery. Large glass doors lead into the interior of the home.

5 out of 5 average rating, 43 reviews

Discount Available! Pool 100' Dock, Fun Amenities!

This newly renovated tastefully decorated 3 bedroom, 3 bath home (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 2 bikes, 3 kayaks, and a paddleboard! It has a large pool with plenty of room for everyone to swim and play.

Popular amenities for Marathon kayak rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

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, 53 reviews

Flamingo Palms-Holiday Discount JAN 2-9 Available

A tranquil canal scene is depicted, lined with palm trees and private docks. Water reflects the clear blue sky, creating a serene atmosphere. Boats are moored along the canal, showcasing direct access to Gulf and Ocean waters.

5 out of 5 average rating, 45 reviews

Yellowtail Getaway with Boat Dock and Pool 2

A two-story home is showcased, featuring a spacious backyard with a swimming pool surrounded by lounge chairs and umbrellas. The exterior is illuminated under a twilight sky, while a stone walkway leads to the inviting entrance. Lush greenery adds a vibrant touch to the setting.

5 out of 5 average rating, 44 reviews

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

A private outdoor space features a heated pool surrounded by lounge chairs on a grassy area. Tropical palm trees provide shade, and the house displays large windows that allow natural light. An inviting patio area is visible, enhancing outdoor relaxation.

4.94 out of 5 average rating, 62 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

Superhost

Home in Key Largo

4.9 out of 5 average rating, 110 reviews

NEW! CASA AZUL - Golf Cart, 2 Kings, Pool, Kayaks

5 out of 5 average rating, 28 reviews

A modern duplex home features a spacious outdoor area with a swimming pool surrounded by lounge chairs. The structure is two stories with multiple balconies overlooking the pool, while tropical greenery provides privacy along the perimeter.

Home in Key Colony Beach

Cielo's Del Mar 1 - Pool/Dock/Beach Luxury in KCB

A private backyard features a hot tub and a shallow pool, surrounded by tropical greenery. Lounge chairs in teal are positioned nearby, and a grill is placed on the concrete patio. The canal is visible in the background, lined with palm trees.

4.93 out of 5 average rating, 45 reviews

Waterfront w/pool and hot tub

The exterior of the duplex is shown against a vibrant sunset sky. The structure features large windows and a covered patio area, with modern seating visible. Lush greenery and decorative plants border the property, enhancing the inviting front entrance.

4.88 out of 5 average rating, 58 reviews

The Mini Coconut

Cottages with a kayak

4.97 out of 5 average rating, 93 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

4.95 out of 5 average rating, 22 reviews

A coastal view features multiple white houses with balconies situated along the waterfront. Palm trees sway gently in the breeze, and clear blue skies create a serene backdrop. Vehicles are parked in the driveways, emphasizing accessibility to the beachfront.

Cottage in Cudjoe Key

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

An open living area features warm wooden beams on the ceiling and large windows allowing ample natural light. A rustic coffee table is centered on a patterned rug, with a comfortable sofa positioned nearby. Barstools line a counter, creating a casual dining space.

Cottage in Islamorada

4.76 out of 5 average rating, 177 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

4.94 out of 5 average rating, 150 reviews

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.

Cottage in Cudjoe Key

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

A guest room features a queen-sized bed adorned with a floral comforter. Two wooden nightstands with lamps flank the bed. French doors open to the outdoor garden, while light-colored curtains soften the sunlight filtering in from the windows.

Private room in Key Largo

4.58 out of 5 average rating, 745 reviews

Cottage Sunroom Waterfront Retreat 2 ppl

Cottage in Key Colony Beach

The private saltwater pool is framed by tropical plants and bright blue sky. Lounge chairs are positioned nearby, alongside decorative elements and pots. The serene atmosphere offers a refreshing retreat, inviting relaxation and enjoyment in the beautiful surroundings.

5 out of 5 average rating, 12 reviews

Luxurious Oasis on: 2BR w/Private Pool, Tiki, Dock

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.

Cottage in Cudjoe Key

4.82 out of 5 average rating, 104 reviews

OCEANIA... water front cottage retreat ~

4.91 out of 5 average rating, 89 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

Other holiday rentals with a kayak

4.96 out of 5 average rating, 90 reviews

A large heated swimming pool is set against a backdrop of lush palm trees and water views. The stone patio surrounding the pool provides ample space for relaxation, while vibrant greenery enhances the tranquil atmosphere.

Home in Key Colony Beach

Key Colony Paradise

4.97 out of 5 average rating, 62 reviews

A bright bedroom features a spacious bed with a white duvet cover and decorative teal throw. Art depicting fish adorns the walls. Natural light enters through the window, complemented by a stylish lamp. A wooden dresser occupies one corner, enhancing the room's coastal theme.

Bungalow in Islamorada

Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s

5 out of 5 average rating, 9 reviews

Townhouse in Marathon

Discount - Jan 31! 3 Bed/3 BA Cabana Club Access!

4.78 out of 5 average rating, 9 reviews

An inviting living area features a cozy sectional sofa adorned with patterned pillows. Large windows provide ample natural light, while a TV stands on a wooden console. A dining area with a light fixture and a view of the balcony is visible in the background.

Home in Summerland Key

Sailfish Dream on Cudjoe Key-28 day minimum

The outdoor area is softly illuminated with multicolored lights, outlining the space. A set of colorful stools sits invitingly near a grassy section, while a staircase leads to the entry. The façade of the home is visible, creating a welcoming ambiance at night.

4.97 out of 5 average rating, 34 reviews

COZY Family Home- 5 minutes from sombrero beach

5 out of 5 average rating, 15 reviews

An expansive view of turquoise waters is showcased, highlighting a private dock extending into the ocean. A swimming pool is visible adjacent to the water, surrounded by lush greenery, while the sky features a subtle blend of clouds and sunlight.

Townhouse in Islamorada

Oceanfront 3-Story Luxury, Dockage, Gameroom

4.96 out of 5 average rating, 68 reviews

A welcoming living area features a dark gray sofa and armchair, complemented by patterned cushions. A light wooden coffee table sits atop beige tile flooring. A large flat-screen TV is mounted on the wall, and natural light filters through window coverings, creating a bright atmosphere.

Apartment in Marathon

Dock POOL Kayaks Bikes Beach2mi WalkToStores

This aerial view captures a canal front home, showcasing two private pools on the lawn and a dock for boat access. The surrounding greenery complements the spacious outdoor areas, while the coastal setting is highlighted by the water's edge.