Holiday rentals with a kayak near Sombrero Beach

The image showcases a modern two-story home with a light blue exterior, surrounded by lush landscaping. A heated pool is visible in the foreground, alongside kayaks and paddle boards. The ocean view offers clear, open water, enhancing the tranquil setting of 'The 7-Mile Villa.'

5 out of 5 average rating, 23 reviews

Seagrass-Free • New 5BR Pool Home w/ Ocean View

Brand new build 2024. This 5 bed/4bath luxury ocean gulf home with boat dock, heated/chilled pool/ spa, paddle boards kayaks, bicycles was meticulously designed and custom built like no other house in Marathon Key. You can see ocean water from every room in the house. and the interior design was chosen to maximize comfort, with a stress-free peaceful setting. Only three homes on this one-acre private ocean gulf lot that has the look and feel of a private island with 400 feet of bulk head

A tray displays two coconut cups filled with a refreshing beverage, each adorned with a pink paper umbrella. Slices of watermelon are arranged on a plate beside the drinks. The vibrant blue water of the heated pool glistens in the sunlight, surrounded by tropical greenery.

5 out of 5 average rating, 62 reviews

Luxury Boating Paradise+Pool+Sailing Kayaks

Captains Quarters, Your 4BR Waterfront Oasis on a deep-water ocean canal. This meticulously remodeled home provides a unique unforgettable Florida Keys experience for your entire family. 🏊‍♂️ Luxury heated pool & spillover spa ⛵ Private 75ft dock with sailing kayaks for ocean adventures 🕹️ Epic game room with Golden Tee, Pack Man, foosball table, Ping Pong & Infinity Game Table 🍳 Outdoor patio with BBQ grill & waterfront dining 💻 High-speed Wi-Fi for streaming & remote work 🛏️ Comfortable

The outdoor area features a private swimming pool accompanied by a spa, surrounded by lush palm trees. Colorful lounge seating is available nearby, and a staircase leads up to the elevated house, which is situated in a tranquil, well-maintained garden.

4.96 out of 5 average rating, 45 reviews

Dock Pool Home by Sombrero Beach

This spectacular home is in the heart of Paradise. Sombrero beach just a few blocks away, Golfing across the street and your boat in our dock, everything you need to enjoy paradise! Situated in a very quiet and desirable neighborhood close to the beach and shopping. This home is a private oasis. The golf course is directly in front of the home. The home offers a private swimming pool with spa. There is 75' of deep water dockage which offers a straight shot out to the Ocean or Bootkey VACA-21-493

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-NOV/DEC discounts on AVAIL DATES

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. Marathon License #VACA-22-164

A private backyard showcases a tranquil pool surrounded by a stone deck. Comfortable lounge chairs are positioned for relaxation, with a vibrant float placed in the water. The blue exterior of the house enhances the outdoor space under a partly cloudy sky.

4.93 out of 5 average rating, 83 reviews

New Private 4/3 Single Family - Kayaks & Bicycles+

Blue Treasure at Sombrero Beach is a 2020 built single-family home in a private community within walking distance to the beautiful Sombrero beach and 5 minute boat ride to the ocean. This house is a private fully equipped 4/3 that has three king memory foam beds and one queen memory foam & queen sofa memory foam. All the rooms have a TV w/ cable & Netflix. We also have a separate downstairs area that we provide kayaks, paddle boards, and bicycles at no additional cost. License #:VACA-20-150

4.96 out of 5 average rating, 158 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.

An aerial view captures the duplex home situated near a canal with multiple boats docked along the water. The vibrant homes are seen in a tangle of greens and blues, with sandy pathways and lush landscaping complementing the serene coastal environment.

5 out of 5 average rating, 27 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

This 2 bed/2 bath Duplex home is located on the water just 4 homes away from the open Atlantic Ocean. Bring your boat or rent one! Paddle with our 4 comp kayaks right from our dock. Go 8 min drive to Sombrero Beach. We have you covered with comp beach towels and beach chairs. We have fishing rods, nets, underwater green light, outdoor freezer and bait station for you to use while staying in our home. Fish right from your very own dock and cook the fresh catch in our BBQ. VACA-24-53

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, 55 reviews

Marathon Keys Escape • Pool • Hot Tub • Near Beach

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

4.95 out of 5 average rating, 128 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.

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.

4.83 out of 5 average rating, 6 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

4.84 out of 5 average rating, 19 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

4.89 out of 5 average rating, 123 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.

Popular amenities for rentals with a kayak near Sombrero Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

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, 43 reviews

Yellowtail Getaway with Boat Dock and Pool 2

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

A private pool is surrounded by a paved patio, featuring lounge chairs and a small table. Lush tropical plants provide a natural backdrop. In the distance, a boat dock is visible along with outdoor dining furniture and an umbrella. Soft lighting enhances the inviting outdoor space.

5 out of 5 average rating, 18 reviews

Waterfront home w/pool, dock & close to beach

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

An open-concept living area is featured with light wood flooring and large windows allowing natural light. A modern dining table is set for four, while a cozy seating area includes a sofa and decorative wall art. Nautical elements enhance the coastal ambiance.

5 out of 5 average rating, 14 reviews

Marathon Paradise

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.

4.95 out of 5 average rating, 42 reviews

Waterfront w/pool and hot tub

A modern home is showcased, bordered by lush greenery. A heated pool reflects the sky, with sun loungers placed nearby. The smooth patio leads to an inviting seating area, sheltered by a sun umbrella. Large windows provide a view into the airy interior, enhancing the spacious ambiance.

4.89 out of 5 average rating, 28 reviews

Golf Coast Oasis

5 out of 5 average rating, 26 reviews

Serenity Oasis~Pool!~Kayaks~Grill~Bikes~Spa

Other holiday rentals with a kayak

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!

An aerial view captures the oceanfront estate featuring a spacious house with a light green roof. A private pool is surrounded by lounge chairs, while kayaks rest on the sandy area by the water. A long pier extends into the clear, shallow water, framed by palm trees.

4.83 out of 5 average rating, 30 reviews

Million Dollar View

4.65 out of 5 average rating, 26 reviews

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

Viamarhe Cabin-Private beach, Kayak, yard games

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.

4.88 out of 5 average rating, 8 reviews

Twin Dolphin Marathon Deep Water Canal, 100’ Yard!

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

4.96 out of 5 average rating, 24 reviews

A modern kitchen features granite countertops and a large island with seating. Natural light floods the space through multiple windows. Light-colored cabinetry contrasts with vibrant blue tile accents, creating a welcoming atmosphere. The kitchen opens to a living area, showcasing comfortable seating and views of the outside.

Home in Key Colony Beach

Salt&Seaglass. Key Colony. Screen Porch. Pool Club

A two-story home with vibrant teal accents is nestled among tropical landscaping. The property features a private pool and a sand volleyball court prominently positioned in the foreground, complemented by shaded seating areas and palm trees surrounding the space.

4.89 out of 5 average rating, 9 reviews

Sea Haven~ Waterfront Pool Home, 35' Dock

An aerial view captures a waterfront property featuring multiple pools surrounded by lush greenery. The colorful houses are highlighted against the clear blue water, with the distant horizon blending into the sky. Nearby homes and a small marina are visible, adding to the serene setting.