Vacation rentals with a kayak near Sombrero Beach

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.

4.94 out of 5 average rating, 93 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

Superhost

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.

4.77 out of 5 average rating, 148 reviews

4.96 out of 5 average rating, 192 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 | Waterfront | Free Kayaks

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.

A stilted beach house stands beside a serene canal, with lush green foliage lining the wooden dock. A kayak rests on the dock, while palm trees sway gently in the background, all under a bright blue sky.

4.94 out of 5 average rating, 35 reviews

Walk to Sombrero Beach, 50’Dock, SPA, Kayaks,Bikes

Cozy FL Keys stilted beach house ideally located in Sombrero Beach w/ 50’ private dock & large SPA whirlpool & attached bar. Walk/bike to beautiful Sombrero Beach down paved path. 4 bikes, 2 paddle boards, 2 kayaks included. Renovated home with new central A/C unit, new bathrooms & kitchen. Near supermarkets, liquor stores, pharmacy, great restaurants & more. Near Dolphin Research, Aquarium Encounters, Turtle Hospital, Bahia Honda State Park Beaches & more. Key West less than 1 hour away.

Superhost

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, 116 reviews

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

4.93 out of 5 average rating, 119 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!

4.89 out of 5 average rating, 47 reviews

Dog-Friendly • Pool & Boat Dock • Sombrero Beach

"We were welcomed by a manatee in the channel when we arrived." That's what guests keep saying about 61 Sombrero, our dog-friendly single-level home at the end of a quiet Marathon canal, a five-minute walk from Sombrero Beach. Cast off from the dock at sunrise, watch manatees drift past over coffee, then bike to Publix or back to the sand. Two kings, a queen on the quiet side, and a daybed-and-trundle room for the kids. Heated saltwater pool, gas grill, fenced yard, no pet fees.

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

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.

4.88 out of 5 average rating, 16 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

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.

5.0 out of 5 average rating, 50 reviews

Tiki Hut w/TV, Pool, Kayak, Paddleboards, Bikes!

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 4 bikes, 3 kayaks, and a paddleboard! It has a large pool with plenty of room for everyone to swim and play. The house legally sleeps 8 people, including infants and children.

5.0 out of 5 average rating, 26 reviews

Villa Serenity At Sombrero Private Pool Spa Dock

Relax and unwind at Serenity at Sombrero! This cozy canal front vacation home is perfect for a secluded and relaxing Florida Keys getaway! The three bedroom two bathroom, newer build stilt home comes fully apportioned with a 30' concrete dock with space for up to a 45' boat, optionally heated pool and spa, and large industrial sized ice machine! Centrally located and just minutes from Sombrero Beach and all major shopping and tourist attractions!

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

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.

4.87 out of 5 average rating, 141 reviews

Popular amenities for kayak rentals near Sombrero Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

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, 86 reviews

Sombrero beach vacation paradise, great location

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.

4.97 out of 5 average rating, 32 reviews

Get Hooked private pool & dock

A private pool is visible, accompanied by a basketball hoop and surrounded by a spacious patio with lounge chairs. The area features a covered balcony above, providing shade and an outdoor seating arrangement, while lush greenery creates a serene backdrop.

4.81 out of 5 average rating, 27 reviews

Casa Marquez

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, 80 reviews

Tropical Keys Retreat | Pool | Hot Tub | Cinema

4.93 out of 5 average rating, 76 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

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.

4.89 out of 5 average rating, 98 reviews

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

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 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.

4.96 out of 5 average rating, 45 reviews

Ocean Breeze Oasis with great boating access

Other vacation rentals with a kayak

5.0 out of 5 average rating, 17 reviews

A two-story house is set against a clear blue sky, featuring balconies and a light blue exterior. A wooden dock extends into tranquil water, with paddleboards and kayaks visible. A heated pool is surrounded by palms, offering a relaxing outdoor space.

Villa in Marathon

Marathon Villa w/ Priv Pool/Dock Sombrero Beach

4.93 out of 5 average rating, 96 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

A serene waterfront scene captures colorful sunset hues reflecting off calm waters. Palm trees sway gently in the breeze, while boats are moored along the canal. The peaceful atmosphere of the neighborhood is evident in the backdrop of charming docks and nearby structures.

4.92 out of 5 average rating, 78 reviews

Blue Ocean-AUGUSTSummer Deals AVAIL.

A spacious pool area is framed by tropical landscaping, showcasing a large, clear swimming pool. Sun loungers are arranged around the pool, providing places to relax. A tiki hut offers shaded seating options, enhancing the outdoor living experience with serene water views.

4.84 out of 5 average rating, 50 reviews

Waterfront Keys Home | Pool, Hot Tub & 35’ Dock

5.0 out of 5 average rating, 18 reviews

Home in Key Colony Beach

Fall discounts! Best Location in Marathon & KCB!

A crystal-clear swimming pool is framed by a sunlit patio, featuring a TIKI HUT with a shaded seating area in the background. The vibrant yellow house is visible, along with several boats docked along the water's edge, under a clear blue sky.

5.0 out of 5 average rating, 67 reviews

Best Marathon House - Heated Pool and Spa - Canal

4.93 out of 5 average rating, 81 reviews

Beach House, Private Pool, Dock, Gulf View Sunsets