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Vacation rentals with a kayak in Vaca Key

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Top-rated kayak rentals in Vaca Key

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Top guest favorite
Home in Marathon
5 out of 5 average rating, 63 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

Top guest favorite
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.
Home in Marathon
5 out of 5 average rating, 43 reviews

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

Experience the relaxing setting of this 4BR 4.5Bath home, ideally situated in the picturesque waterfront neighborhood of Marathon, FL. Discover the area's scenic beauty and a diverse selection of water activities, attractions, and landmarks. After a day of exploring, return to our home for a rejuvenating stay. ✔ 4 Comfy BRs ✔ Open Design Living ✔ Full Kitchen ✔ Balcony ✔ Backyard (Pool, Games, BBQ, Lounges, Dining) ✔ 73-Foot Dock ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

Top guest favorite
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
4.96 out of 5 average rating, 160 reviews

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.

Top guest favorite
An aerial view captures the canal-front neighborhood, showcasing tree-lined streets and houses with turquoise roofs. The winding canal leads toward the open turquoise waters in the distance, emphasizing the area's coastal charm and accessibility to boating activities.
Home in Marathon
4.93 out of 5 average rating, 40 reviews

Oasis Canal-Front Home: Pool, Dock, BBQ, and more!

Oasis Florida Keys Welcome to our charming canal-front home, the perfect oasis for your next vacation getaway! Nestled in a highly central area, our home promises an unforgettable stay with a wide range of amenities that cater to both relaxation and adventure. Our spacious and inviting home is ideal for families or friends seeking a memorable retreat. With its open-concept design and stylish decor, the home is perfect for bonding, relaxing, or simply unwinding after a day of exploration.

Top guest favorite
Home in Marathon
5 out of 5 average rating, 28 reviews

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

Welcome to your dream Serenity Oasis! 🌊🌺 This 3 BR sanctuary in the heart of the Florida Keys has been redesigned so every detail lets you indulge in the ultimate getaway in Paradise🌴. Enjoy evening swims under the stars in your private heated pool✨, morning kayak adventures or bike rides 🚲, foosball or cornhole games, popcorn-filled movie nights 🍿, and unwind after a long day in your spa-like bathroom. At Serenity Oasis, every corner is made for joy, laughter, and relaxation 🍹☀️

Top guest favorite
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.
Home in Marathon
5 out of 5 average rating, 56 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

Top guest favorite
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
4.95 out of 5 average rating, 130 reviews

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.

Top guest favorite
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
4.93 out of 5 average rating, 361 reviews

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.

Guest favorite
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
4.86 out of 5 average rating, 22 reviews

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.

Guest favorite
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.
Home in Marathon
4.93 out of 5 average rating, 44 reviews

Waterfront w/pool and hot tub

Professionally decorated, spacious, canal view keys home located in Key Colony Beach, the “Gem” of the Florida Keys. Featuring 2BR 2BA accommodating up to 6 ppl in a large & open living room & backyard, provided w/2 bikes, 2kayaks, grill, and 2 minutes walk to Sunset park, it is the perfect Florida Keys getaway for your family. This location is in the heart of the Florida Keys only 45 minutes from Key West and 35 minutes to Islamorada.

Guest favorite
A large pool surrounded by lush greenery and palm trees is visible, offering hammocks for relaxation. The modern house, featuring a shaded outdoor dining area and lounge chairs, provides a resort-style ambiance. Clear blue skies enhance the inviting atmosphere of the backyard.
Home in Marathon
4.89 out of 5 average rating, 36 reviews

Marathon pool house 5 min walk to sombrero beach

Very nice and private house located walking distance from Sombrero beach, this house has room for a boat on a wide canal, house has very large pool with a resort style back yard.. Kids and adults will love the Pool, pingpong table, bbq, good kayaking, fishing, biking, swimming, dining, great shopping, close to everything, 5 beds total. Enjoy yourself in this beautiful resort style home and you won't leave disappointed...

Popular amenities for Vaca Key kayak rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a kayak

Guest favorite
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
4.96 out of 5 average rating, 90 reviews

Key Colony Paradise

Guest favorite
A hot tub is set under a blue canopy, inviting relaxation. Adjacent, outdoor seating with colorful chairs is positioned near the water, framed by palm trees and an American flag. The calm canal reflects the vibrant surroundings, enhancing the tranquil atmosphere.
Home in Marathon
4.96 out of 5 average rating, 51 reviews

Experience the Ultimate Florida Keys Getaway.

Superhost
An aerial view showcases a vibrant waterfront community with colorful homes lining the canal. A serene blue pool is visible in front of one residence, while boats can be seen docked along the waterfront. The tranquil ocean extends into the horizon, under clear blue skies.
Home in Marathon
5 out of 5 average rating, 9 reviews

Discount to Jan 31! Direct to Ocean! Fun Amenities

Guest favorite
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.
Home in Marathon
5 out of 5 average rating, 43 reviews

Yellowtail Getaway with Boat Dock and Pool 2

Guest favorite
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.
Home in Marathon
4.94 out of 5 average rating, 62 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

Top guest favorite
A light-filled living area features a comfortable seating arrangement with leather sofas and a large area rug. A television is housed within a white entertainment unit, flanked by decorative glass vases. Expansive sliding glass doors open to the outside, providing an airy ambiance.
Home in Key Colony Beach
4.95 out of 5 average rating, 59 reviews

Sea Glass Beach Bungalow in Key Colony Beach!

Guest favorite
A spacious pool area is surrounded by patio tiles, featuring two green lounge chairs and multiple seating options for relaxation. Palm trees and a canal are visible in the background, enhancing the outdoor ambiance. The clear blue sky reflects a pleasant atmosphere.
Home in Marathon
4.97 out of 5 average rating, 61 reviews

Paradise Ocean Front 4/3Home Heated Pool

Guest favorite
The outdoor area features a private free-form pool surrounded by a spacious patio. Vibrant blue lounge chairs and relaxing seating areas, including two tiki huts, are situated under swaying palm trees, creating a welcoming space for outdoor relaxation.
Home in Marathon
5 out of 5 average rating, 5 reviews

Reel Knotty ~ Waterfront Pool Home, 35' Dock

Other vacation rentals with a kayak

Guest favorite
A modern beach house is presented with a light-colored exterior, surrounded by a pebbled landscape. Palm trees are visible, providing a tropical feel. The building features large windows and a distinct entryway, enhancing its architectural appeal.
Home in Marathon
5 out of 5 average rating, 22 reviews

Seaside Sunrise. Newly remodeled waterfront

Superhost
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.
Home in Marathon
4.88 out of 5 average rating, 83 reviews

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

Guest favorite
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
4.97 out of 5 average rating, 93 reviews

Islamorada bungalow 2 bed & pool

Guest favorite
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.
Home in Marathon
4.97 out of 5 average rating, 72 reviews

Sombrero beach vacation paradise, great location

Guest favorite
A sandy shoreline is bordered by swaying palm trees, providing a peaceful oceanfront view. A yellow kayak rests on the beach, while a hammock is visible nearby, adding to the tranquil setting. The distant jetty extends into the calm sea, enhancing the serene atmosphere.
Guesthouse in Marathon
4.95 out of 5 average rating, 22 reviews

The Pink Dolphin House.

Top guest favorite
A serene waterfront view captures the modern multi-story building surrounded by lush greenery. The calm water reflects the clear blue sky, while a private wooden dock extends into the water, providing an inviting entrance to the property.
Townhouse in Islamorada
4.92 out of 5 average rating, 13 reviews

NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom

Top guest favorite
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
5 out of 5 average rating, 14 reviews

Oceanfront 3-Story Luxury, Dockage, Gameroom

Guest favorite
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.
Home in Marathon
4.96 out of 5 average rating, 27 reviews

Get Hooked private pool and dock, ample parking

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Vaca Key
  6. Rentals with a kayak