Holiday rentals with a kayak in Key Largo

4.87 out of 5 average rating, 181 reviews

A serene sunset view showcases a circle of white Adirondack chairs positioned around a fire pit. The calm waters reflect vibrant hues of orange and purple from the sky, creating a peaceful atmosphere.

Townhouse in Key Largo

Sunrise Escape - Ocean Front Villa - Sleeps 10

Wake up to the sunrise over the ocean and unwind with sunset views from your private jetty. This marina-front, ocean-view townhouse in Kawama Yacht Club puts you steps from kayaking, snorkeling, and the best of the Keys. Spacious, stylish, and designed for unforgettable family and friend getaways. Breathtaking sunrises from one of two private terraces, coffee in hand, overlooking the marina and the Atlantic Ocean. Located in an exclusive, quiet section of Kawama Yacht Club, this beautifully po

LocationValueAir conditioning

A collage showcases four images: A serene sunrise over water, a cozy bedroom with a flat-screen TV, an open-concept living area with a kitchen and dining space, and a tranquil view of the evening sun reflected on the bay, complete with a kayak along the shoreline.

4.91 out of 5 average rating, 207 reviews

Tiny Home on Waterfront | Bay Views | Deck | Pool

Down by the waters of Manatee Bay, you’ll find this idyllic tiny home for 6. With a full kitchen, three comfy beds,and access to a community pool, this is a prime location to enjoy the best of Key Largo. Sit on the deck and dip your toes in the water or explore the bay using the available kayaks and paddle boards. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

ValueLocationPets

A stunning aerial view captures the waterfront homes bathed in warm sunset hues, with a tranquil canal lined by lush mangroves. Several boats are visible at the dock, while palm trees provide a tropical ambiance to the serene scene.

4.95 out of 5 average rating, 111 reviews

Tropical Waterfront, Boat Dock, Sunset View, Kayak

Waterfront home in gated community & upscale area. For tropical island scenic views, boating, fishing, kayaking for 5, sun & water sports you've found the place! Only 1 hour from Miami airport. On a canal only a few houses in from the bay. 80 ft of dock space. Rent a boat or bring your own. Parking available for an RV, boat trailer & covered parking for your car. Watch boats go by, iguanas sun & manatee sightings without leaving home. Fish cleaning table, gated community, overlooking mangroves.

ValueOutdoor spacesDecor

Holiday home in Key Largo

Ocean Shores Villa 3 with pool and boat slip

This centrally located boater's paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill downstairs. With only 4 units in the building the guests have half an acre of waterfront entertainment (boat slip, Kayaks, Bikes, Hammock and Pool). 32ft Dock Slip and Trailer Parking are included in the rental. Relaxing Balcony that looks down the Ocean Canal is the perfect place to have your morning coffee. Conveniently located near Sandbars, State parks and many attractions.

LocationOutdoor spacesAccuracy

4.95 out of 5 average rating, 162 reviews

4.96 out of 5 average rating, 213 reviews

A serene waterfront view is framed by palm trees, with two green chaise lounges positioned for relaxation. The setting sun casts warm hues across the sky, reflecting on the water's surface. A Tiki structure adds charm, creating an inviting outdoor space.

Tiny home in Key Largo

Oceanfront Lookout Point w/two Kayaks & Deck

Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

Outdoor spacesValueNearby

A serene canal view is framed by a tiki hut, with seashell decorations hanging gently. Clear water reflects the blue sky, while surrounding palm trees and thatched roofs add a tropical touch, creating a peaceful atmosphere. A boat dock is visible along the waterway.

4.97 out of 5 average rating, 188 reviews

Key Largo Waterfront: Tiki, Dock, Kayak & Pool

Waterfront retreat perfect for couples, families, or boaters looking to explore the best of the Keys. Dock your boat. Snorkel right from your door. Fish from the dock. (poles etc. provided). Paddle through mangroves with the tandem kayak, or relax with a drink while the sun sets over the canal. Steps from two heated pools, a playground, a sandy beach. 0.3 miles from groceries & restaurants. Fishing, diving famous reefs, or just unwinding under the tiki, this puts paradise at your doorstep.

LocationOutdoor spacesRiver

4.97 out of 5 average rating, 236 reviews

A sunset view is captured from a covered outdoor seating area, showcasing a tranquil waterway. Silhouettes of kayaks and a table are visible, while the setting sun creates a warm glow across the horizon. Natural textures are evident in the thatched roof above.

Tiny home in Key Largo

My Little Oasis2 Waterfront Retreat, Key Largo

Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

LocationValueDecor

4.9 out of 5 average rating, 197 reviews

Apartment in Key Largo

Tropical Getaway

This light, airy two bedroom condo is located in the community of Kawama. Overlooks a small lake, where people swim, kayak and paddleboard. The condo community features two pools, tennis courts, playground, fishing, beach and marina. A long jetty extends out in the ocean where you can watch the beautiful sunrises or sunsets in the afternoons. Centrally located in Key Largo near restaurants, shopping and attractions. Come down and enjoy the peaceful atmosphere of our tropical area.

LocationValueFamily

4.93 out of 5 average rating, 394 reviews

A solar and wind powered houseboat is moored on calm waters, featuring bright yellow shutters and a roof deck. Wind turbines and an American flag adorn the top, contrasting with the soothing blue sky and fluffy clouds in the background.

Boat in Islamorada

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.

Outdoor spacesLocationView

4.98 out of 5 average rating, 118 reviews

Townhouse in Key Largo

Fun the Keys! Pool, Marina, Clubhouse, Fishing & m

Escape to Sunset Corner on exclusive Holiday Isle! Enjoy 2 bedrooms, 2 full bathrooms, walkout access to a sprawling green lawn, beach gear included, and top-tier amenities: 2 resort pools (one seasonally heated), 2 hot tubs, private beach access, lighted tennis and pickleball courts, basketball hoop, shuffleboard, fitness center, and a BBQ pavilion. Perfectly situated just steps from the beach and minutes from HarborWalk Village’s dining and entertainment!

Outdoor spacesValueBiking

A waterfront patio is shown with comfortable seating, overlooking a calm body of water. The sun sets in the distance, casting warm light over the scene. Tropical vegetation can be seen, adding to the serene atmosphere.

4.9 out of 5 average rating, 174 reviews

The Paradise 2

Relax with the whole family at this peaceful place to stay. Our home is located right by the water. Modern spacious and spotless with private parking, fast Wi-Fi, cold AC plus cozy beds and pillows in every bed. Relax on the waterfront patio chairs, swim in our newly renovated pool, go kayaking out in the bay, watch the manatees and dolphins swim by and go fishing from our backyard dock anytime. We are sure you will absolutely love our Tiny Home!

Outdoor spacesValueBack garden

4.97 out of 5 average rating, 133 reviews

The living area features a spacious blue sectional sofa with decorative pillows and throws. A round coffee table sits at its center. Natural light fills the room, illuminating two framed beach-themed artworks on the wall, and the open kitchen and dining area are visible in the background.

Townhouse in Key Largo

Kawama K1 Beautiful Lagoon View free bikes & kayak

Escape to paradise at Kawama Yacht Club, a private community featuring 24-hour security and an array of exclusive amenities: Salt water lagoon, 2 heated pools, Kids playground, Tennis courts, Marina boat ramp, boat parking, Jetty & Fire pits. We also provide kayaks and bikes so you can fully immerse yourself in the beauty of the surrounding area. Don't miss out on the ultimate Florida Keys getaway, book your stay at Kawama Yacht Club now.

Outdoor spacesValueGrill

Popular amenities for kayak rentals in Key Largo

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.9 out of 5 average rating, 115 reviews

NEW! Casa Palma - Golf Cart, 2 King, Pool, Kayaks

LocationOutdoor spacesComfort

4.96 out of 5 average rating, 204 reviews

A serene lakeside view features lounge chairs placed on sandy shores, framed by palm trees. A kayak rests nearby, with the crystal clear water reflecting shades of blue and aqua. The peaceful scene invites relaxation under the bright sky.

Home in Miami

Modern Beach Lake-Front House in Miami !

LocationOutdoor spacesIndoor spaces

4.95 out of 5 average rating, 152 reviews

Home in Marathon

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

Outdoor spacesLocationWalkability

A two-story waterfront home is shown, featuring a screened patio on the lower level and large windows that enhance natural light. Surrounding palm trees and tropical plants add to the outdoor ambiance. A dock is visible, along with kayaks positioned nearby.

4.94 out of 5 average rating, 62 reviews

Keys Paradise 3/3 Waterfront, Jacuzzi, Kayaks+More

Outdoor spacesLocationNearby

A two-story home with a light blue exterior is complemented by a heated pool surrounded by a lounging area. Lush greenery and a palm tree frame the space, providing a serene atmosphere. The patio below is equipped with ample outdoor seating for relaxation.

4.85 out of 5 average rating, 41 reviews

Waterfront Key Largo Home - Tropical Paradise

Outdoor spacesValueDecor

5.0 out of 5 average rating, 22 reviews

Home in Islamorada

OceanView 2/2.5 w Beach Pool & Marina Islamorada

LocationOutdoor spacesFamily

4.94 out of 5 average rating, 33 reviews

Waterfront 4BDR Key Largo | Heated Pool + 60’ Dock

LocationValueWifi

Two individuals are seated in blue chairs on a sandy waterfront, overlooking a serene bay during sunset. The sky is decorated with a blend of orange, pink, and purple hues, while boats are gently floating in the water, reflecting the vibrant colors.

4.78 out of 5 average rating, 86 reviews

Deckhouse

LocationOutdoor spacesBathroom

Cottage rentals with a kayak

5.0 out of 5 average rating, 111 reviews

My Little Paradise North Key Largo

Outdoor spacesValueQuiet

4.95 out of 5 average rating, 106 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 bed & pool

LocationOutdoor spacesPool

A charming coastal rental is depicted, featuring blue and beige siding with large windows. The setting is by the water, offering a serene view. Outdoor seating options are visible nearby, along with palm trees and decorative plants enhancing the inviting exterior.

4.85 out of 5 average rating, 40 reviews

Waterfront Keys Cottage w/Sleeping Loft Sleeps 6

Outdoor spacesLocationPets

An open living area features warm wooden beams on the ceiling and large windows allowing ample natural light. A rustic coffee table is centered on a patterned rug, with a comfortable sofa positioned nearby. Barstools line a counter, creating a casual dining space.

Cottage in Islamorada

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

ValueOutdoor spacesBeach

4.76 out of 5 average rating, 185 reviews

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.

Keys Waterfront Oasis • Tiki • Private Pool • Dock

Outdoor spacesLocationCondition

5.0 out of 5 average rating, 15 reviews

Private room in Key Largo

A guest room features a queen-sized bed adorned with a floral comforter. Two wooden nightstands with lamps flank the bed. French doors open to the outdoor garden, while light-colored curtains soften the sunlight filtering in from the windows.

Cottage Sunroom Waterfront Retreat 2 ppl

LocationOutdoor spacesLaundry

4.58 out of 5 average rating, 807 reviews

A waterfront Tiki space features a thatched roof providing shade over comfortable seating. Two kayaks rest on the dock, and a serene canal view reflects the vibrant blue sky. The tiny home is visible in the background, showcasing large windows and a charming exterior.

4.87 out of 5 average rating, 150 reviews

Waterfront Getaway | Kayaks, Private Dock & BBQ

LocationValueBeach

An outdoor lounge area features comfortable seating arrangements with cushioned chairs and a sectional. A striped rug covers the deck, while a thatched roof provides shade. The adjacent waterway is visible, lined with boats and marina structures in the background.

4.93 out of 5 average rating, 118 reviews

THE PARADISE

Outdoor spacesLocationSleep quality

Cabin rentals with a kayak

4.55 out of 5 average rating, 282 reviews

Cabin in Key Largo

2 BR/2 BA Oasis Kayaks, Pool, Beach & Dock Rental

Outdoor spacesValueGetting around