Holiday rentals with a kayak in Big Pine Key

4.94 out of 5 average rating, 155 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

Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

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.

4.96 out of 5 average rating, 27 reviews

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

This Key Colony Beach home is a welcoming, modern canal-front duplex home provides a relaxing and comfortable atmosphere for your vacation in the Florida Keys! The home features 2 large bedrooms and 2 bathrooms, a modern kitchen with large island and granite counter tops, a master bedroom with private bathroom and modern, plank flooring tile throughout the home. Enjoy the relaxing 9 X 20 ft porch & comfortable furniture. Outside: Lounge chairs & other seating, a kayak, a 37 foot dock

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, 32 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

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.

4.95 out of 5 average rating, 133 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.

Home in Upper Sugarloaf Key

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.

4.94 out of 5 average rating, 108 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.

The living area features a spacious sectional sofa facing a large window with multiple shutters, allowing natural light to fill the room. A modern coffee table is situated on a soft area rug, complemented by dining stools near the open kitchen with updated appliances.

4.88 out of 5 average rating, 133 reviews

Waterfront Sanctuary in the Keys!

Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

An aerial view captures a vibrant community of stilt homes nestled along the coastline, with clear blue waters stretching in the background. Lush palm trees dot the landscape, while a distinctive red marker indicates a specific location within this scenic setting.

4.84 out of 5 average rating, 114 reviews

Spanish Queen @Venture Out

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

4.66 out of 5 average rating, 29 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

If you are looking to enjoy the natural beauty, and romantic stay in a rear cabin with complete bath and kitchen independent of the main house but with a patio that shares the amenities of games and entertainment of a mini resort our Oceanfront small apartment is the place for you. You and your couple can enjoy the exclusivity this property will give you, like the 5 kayak and fishing rods, volleyball, chess, bowling, carbon and propane BBQ grill, and a fire pit.

A serene view of a waterfront canal is captured from a covered porch. The calm water reflects the sky, with boats docked along the edges. Palm trees gently sway in the breeze, enhancing the coastal setting. Nearby structures suggest a vibrant community atmosphere.

4.81 out of 5 average rating, 296 reviews

Jan. Save $!$ Oceanfront 4 Bikes/2Kayaks. KING bed

*PERFECT LOCATION! * 35' Seawall *AWESOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

4.91 out of 5 average rating, 34 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

4.88 out of 5 average rating, 126 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.

A comfortable outdoor seating area is showcased, with bright blue cushions arranged around a dark table. The view overlooks crystal-clear waters, and decorative lanterns provide soft lighting. A potted flower adds a touch of color beside the seating, enhancing the peaceful ambiance by the water.

4.87 out of 5 average rating, 124 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Popular amenities for kayak rentals in Big Pine Key

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.

4.97 out of 5 average rating, 73 reviews

Sombrero beach vacation paradise, great location

A serene waterway is shown, flanked by palm trees and waterfront homes. A boat is seen navigating the calm waters, with clear skies enhancing the tranquil scene. The reflection of the surroundings is visible on the surface, creating a peaceful atmosphere.

4.64 out of 5 average rating, 175 reviews

Ocean Front Home in Great Location

A tranquil pool is surrounded by lush palm trees, offering a serene atmosphere. The water reflects sunlight, while seating options are provided by the poolside. The design features a curved edge and a spa section, creating an inviting outdoor retreat.

5 out of 5 average rating, 16 reviews

The Roseate House at Grassy Key Lic. #VACA-25-222

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, 60 reviews

Marathon Keys Escape • Pool • Hot Tub • Near Beach

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, 64 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

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, 73 reviews

Blue Ocean Bungalow-May dates now available

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.

4.87 out of 5 average rating, 30 reviews

Golf Coast Oasis near Sombrero Beach

A private pool is bordered by lush palm trees and a thatched Tiki Hut. Lounge chairs are arranged around the pool area, and colorful outdoor decor adds a cheerful touch. Clear blue skies and sunshine illuminate the space, creating an inviting outdoor retreat.

4.92 out of 5 average rating, 26 reviews

Private Pool! Luxury Paradise Pointe, Pet Friendly

Cottage rentals with a kayak

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 ~

4.97 out of 5 average rating, 97 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 beds & pool

A bright window offers views of the canal and vibrant outdoor scenery. Two stools are positioned in front of the window, inviting guests to relax and enjoy the surroundings. Colorful decorations add a charming touch to the space, enhancing the coastal atmosphere.

Cottage in Cudjoe Key

4.69 out of 5 average rating, 169 reviews

Calypso Cottage

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

Other holiday rentals with a kayak

A spacious outdoor area features a large wooden swim spa, framed by vibrant greenery and decorative accents. A sun umbrella provides shade over one side, while light-colored tiles and wooden decking surround the spa, creating a relaxing ambiance. The sky is clear with soft clouds.

5 out of 5 average rating, 13 reviews

3Bed 2Bath~Kayaks~Cabana Club~Swim Spa~Fish Equip

4.9 out of 5 average rating, 31 reviews

Private Dock| 5min beach| Kayak| Sunset view|RV

4.81 out of 5 average rating, 21 reviews

Apartment in Marathon

Feb 16-23 1st Floor, Slip, King Bed, Heated Pool

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.

5 out of 5 average rating, 10 reviews

Discount to Jan 31! Direct to Ocean! Fun Amenities

4.95 out of 5 average rating, 63 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

A light blue oceanfront home is set against a backdrop of palm trees and tropical landscaping. The building features a screened porch and a roof deck, offering expansive views. A sandy beach area leads to calm waters with a floating dock visible nearby.

4.83 out of 5 average rating, 6 reviews

Tropical Paradise

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, 59 reviews

The Mini Coconut

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.