Holiday rentals with a kayak near Sombrero Beach

A two-story house is surrounded by lush greenery and palm trees. A spacious backyard features a heated pool and a wooden dock. Loungers are arranged near the pool, providing a relaxing outdoor space. The exterior showcases large windows and a balcony with seating.

4.98 out of 5 average rating, 84 reviews

Sombrero beach vacation paradise, great location

Your family will be close to everything when you stay at this centrally-located home. Close to Sombrero beach you can walk ride a bike, kayak or take a short drive there. Many attractions near by. Publix and winn dixie and many restaurants near by. Key West just one hour away for any day trip. House has an ice maker, refrigerator and freezer downstairs to keep bait or fish .Private pool and Dock, back yard oasis There is a paddle board and 4 bikes and 2 kayaks for your use. Amazing location!

4.96 out of 5 average rating, 188 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 Getaway - Free Kayaks 2/2.5 Villa

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.

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 out of 5 average rating, 76 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

An aerial view captures the property's prime location along the waterfront, highlighting proximity to Sombrero Beach and the 7 Mile Bridge. The tranquil waters and nearby coastal homes enhance the inviting atmosphere of this tropical getaway.

5 out of 5 average rating, 6 reviews

Waterfront Oasis3/2 Direct Ocean

Welcome to our stunning vacation rental property located on the waters of the ocean, where you can enjoy the ultimate tropical getaway. Our property boasts of an exceptional location, featuring a private dock that provides direct access to the ocean. This beautifully furnished property has three spacious and comfortable bedrooms that can accommodate up to eight guests, making it perfect for families or friends. The two modern bathrooms are fully equipped with all the necessary amenities

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.

4.91 out of 5 average rating, 113 reviews

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

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' boat/trailer, and ocean views from the balcony~Kayaks, grill, beach toys await you for your beautiful day in the Florida Keys! Less than 5 min to Sombrero Beach, Dining & Local Bars! Experience the Florida Keys like a local and book Tiki Time today!

An aerial view showcases a vibrant orange house with a spacious pool surrounded by tropical palm trees. The scene is illuminated by a soft morning light, highlighting the outdoor area and canal in the background.

4.91 out of 5 average rating, 47 reviews

Sombrero Beach Home w/ Heated Pool, Kayaks & More

3 bed/2.5 bath home a block from Sombrero Beach - walk to beach, avoid parking fee! 3 bedrooms (2 ensuite): 1 king, 1 queen, 2 XL twins. Cook's kitchen, open plan living/dining room. Enjoy heated pool, incredible outdoor shower, chaise lounges, gas grill, outdoor dining, hammock, and sunsets over the ocean from our dock. House comes with beach chairs, sand toys, pool floaties, kids books and games. Strong Wifi, cable & streaming TV. 2 kayaks for your use. NO DOCKING FOR BOATS.

4.91 out of 5 average rating, 34 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

An airy dining area features a white stone-topped table positioned beneath a stylish light fixture. Large glass doors allow natural light to flood the space, connecting indoor and outdoor seating areas. The wooden floor adds warmth to the contemporary design.

4.86 out of 5 average rating, 14 reviews

SeaEsta! Bring your boat & 1 block to the beach!

Take a 1 Block walk to Sombrero Beach, dock your boat at this waterfront home or simply relax on the patio. 3 Bedrooms 3 baths. Large deck for cooking out. Direct access to the Atlantic. 65" TVs in all rooms. Enjoy your mornings by starting at our Coffee bar. Our home is fully furnished with all the essentials. We even include Kayaks, Bikes and Fishing Poles as well as Corn Hole and Giant Jenga. Boat Rental is offered at an additional cost. - VR License No: VACA -20-147

4.92 out of 5 average rating, 85 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. Toda una experiencia de camping para los huéspedes que les gusta lo divertido y diferente. Prueben y ustedes dirán. Ofrece un espacio para 2 personas

4.88 out of 5 average rating, 139 reviews

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

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, 150 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!

4.91 out of 5 average rating, 151 reviews

Condo in Marathon

Canal Front Retreat | Pool + Free Breakfast

Welcome to THE MAD MAHI — your ultimate waterfront getaway in Marathon! This stunning 1-bedroom condo comfortably sleeps up to 4 guests and is perfect for a relaxing Florida Keys retreat. Enjoy a full kitchen, private balcony, resort-style pool, Tiki Ba and restaurant. Conveniently located between Key Largo and Key West, with local shops, dining, and attractions just a short walk or bike ride away.

Popular amenities for kayak rentals near Sombrero Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

The modern beach house is set against a tranquil waterfront backdrop, featuring light-colored siding and a metal roof. Lush palm trees and landscaped grounds surround the property, complementing the natural waterfront area. The structure is elevated, with a staircase leading to the main level.

4.89 out of 5 average rating, 28 reviews

Salty Kisses Beach House

Aerial view of a two-story yellow home is shown, surrounded by a fenced yard with a spacious pool and patio area. Several sun loungers are positioned near the pool. Nearby, a boat dock and a grassy area can be seen, alongside other similar homes.

4.88 out of 5 average rating, 94 reviews

Summer Sale~New 4/3/pool/40f dock

5 out of 5 average rating, 25 reviews

Villa Serenity At Sombrero Private Pool Spa Dock

A serene waterfront view is captured, showcasing calm waters framed by lush greenery and palm trees. The scene includes a glimpse of a dock area with boats visible in the distance, enhancing the peacefulness of this tropical setting.

4.81 out of 5 average rating, 36 reviews

Waterfront, dock, easy ocean access, heated pool!

4.93 out of 5 average rating, 73 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

4.88 out of 5 average rating, 50 reviews

Oasis in The Keys-Kayaks-Paddle Boards-Cabana Club

A serene canal-side view features a spacious sandy area with palm trees. A thatched tiki hut and outdoor seating set the scene for relaxation. The home is positioned in the background, showcasing large windows that reflect the clear blue skies.

4.9 out of 5 average rating, 10 reviews

Twin Dolphin Marathon Deep Water Canal, 100’ Yard!

A private heated pool surrounded by a spacious patio area is complemented by a tropical tiki hut with seating. Lush green landscaping and palm trees enhance the outdoor oasis, while comfortable lounge chairs provide a perfect spot to relax under the clear blue sky.

4.53 out of 5 average rating, 15 reviews

Kon Tiki ~ Waterfront Pool Home, 30' Dock

Cabin rentals with a kayak

An inviting exterior view of the cabin showcases warm orange siding and a wooden staircase leading to the entrance. A picnic table is positioned in the foreground, surrounded by native vegetation and pebbled ground. Bright sunlight filters through the nearby palm leaves.

Cabin in Marathon

4.75 out of 5 average rating, 117 reviews

New Waterview 2/1 Cabins w Boat Ramp (No Loft)

An outdoor area features a large chessboard with oversized pieces set up on a sandy surface. Colorful lounge chairs and palm trees are visible in the background, alongside a glimpse of the ocean. Additional games can be seen in the vicinity, enhancing the recreational space.

Cabin in Marathon

4.69 out of 5 average rating, 36 reviews

Viamarhe Cabin-Private beach, Kayak, yard games

A rustic wooden cabin features a welcoming entrance with a sturdy set of steps leading to the front door. Large windows allow natural light to illuminate the exterior, which is complemented by a natural stone pathway and lush greenery in the background.

Cabin in Marathon

4.8 out of 5 average rating, 264 reviews

New Waterfront 2/1 Cabin With Loft at Bonefish Bay

Cabin in Layton

5 out of 5 average rating, 3 reviews

4BR Oceanfront Dog Friendly | Dock | Deck | W/D

Other holiday 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, 57 reviews

Flamingo Palms-BOOK Spring 2027 dates NOW!

4.96 out of 5 average rating, 28 reviews

Townhouse in Marathon

Beautiful View! 3BR 3 BA, Cabana Club Membership!

4.9 out of 5 average rating, 41 reviews

Golf Coast Oasis near Sombrero Beach

An inviting outdoor area features a swimming pool surrounded by a manicured lawn. Comfortable lounge chairs provide ample seating, and a large umbrella offers shade. A canal with docked boats is visible in the background, complemented by palm trees swaying in the breeze.

4.96 out of 5 average rating, 70 reviews

Waterfront Heated Pool 120 ft Boat Dock

A two-story home is depicted, featuring a covered balcony with blue chairs and a ground-level terrace. A kayak is positioned nearby on gravel, alongside two adirondack chairs near natural landscaping. The surroundings are lush with greenery, enhancing the tranquil setting.

4.91 out of 5 average rating, 23 reviews

Boaters delight! 1 min to open water, Dock & Beach

4.95 out of 5 average rating, 44 reviews

A shaded outdoor area features a small private pool surrounded by lounge chairs. A white table sits nearby, offering a space for refreshments. A view of the boat dock and palm trees creates a relaxing atmosphere perfect for enjoying sunny days.

Home in Key Colony Beach

Villa Bella 3/3 with Private Pool & Dock!

A clear view of a swimming pool framed by lush greenery and manicured grass, extending toward the Atlantic Ocean. The tranquil water reflects the blue sky above, enhancing the serene setting.

4.89 out of 5 average rating, 18 reviews

SAY'S BY THE SEA

A serene view of the canal is framed by swaying palm trees under a bright blue sky. A wooden railing offers a vantage point for observing the calm waters and nearby structures, including homes and boats. A kayak rests on the railing, adding to the outdoor ambiance.