Holiday rentals with a kayak in Big Pine Key

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.

4.94 out of 5 average rating, 142 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

4.96 out of 5 average rating, 156 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.

4.95 out of 5 average rating, 126 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.

4.95 out of 5 average rating, 131 reviews

A spacious living area features a comfortable futon adorned with a decorative pillow. Large windows provide views of the tranquil water, allowing natural light to brighten the space. The walls are designed in a soft, neutral tone, enhancing the overall welcoming feel.

Houseboat in Key West

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Garrison Bight Marina in Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

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.

4.87 out of 5 average rating, 118 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!

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, 105 reviews

Lighthouse - Beach Houses Key West

If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. Our amazing Lighthouse is a 2 bed 1 bath Loft Bungalow sitting just a few feet from our private beach. The master bedroom loft is accessed by a spiral stair, and has a beautiful bird’s eye view of the Atlantic Ocean. Our nautical inspired living room leads outside to an exterior deck facing the beach perfect for peaceful mornings.

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.

4.87 out of 5 average rating, 106 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***

5 out of 5 average rating, 8 reviews

Home in Little Torch Key

Beautiful Keys Home w/ Open Water Views & 90' Dock

Gorgeous 3BR 2.5BA home with 2000 sq ft for up to 8 guests. Crystal clear canal with multiple open water views. Completely furnished kitchen, dining room, living room, bathrooms, & TV room with large screen TV. Screened in porch, free parking, CAC, WIFI, 3 TVs, 90' of dock for your boat, air compressor, 2 work stations, Tiki bar, outside fridge, one car garage & one car port, dog friendly under 40 pounds, 3 kayaks, corn hole board, 4 bikes, and yoga mats & weights.

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.

4.82 out of 5 average rating, 283 reviews

Nov. & Dec. 50% off! Oceanfront, 4 Bikes 2 Kayaks

*PERFECT LOCATION! * 35' Seawall *AWWSOME 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!

4.89 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.

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.

4.89 out of 5 average rating, 118 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.

4.95 out of 5 average rating, 139 reviews

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

Perfect for families, couples, groups, or solo travelers, this spacious home offers 5 bedrooms, 3 bathrooms, an open living room, and a fully stocked kitchen. Easy to reach and simple to access, it’s set in a peaceful neighborhood close to island fun and water adventures. Just a short walk to Sweet Savannah’s Ice Cream & Sweets Parlor, this retreat is ideal for relaxing or exploring. We look forward to hosting you!

Popular amenities for kayak rentals in Big Pine Key

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

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

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, 9 reviews

Discount to Jan 31! Direct to Ocean! Fun Amenities

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, 42 reviews

Yellowtail Getaway with Boat Dock and Pool 2

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.

5 out of 5 average rating, 40 reviews

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

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, 71 reviews

Blue Ocean Bungalow NOV/DEC discounts, AVAIL DATES

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, 33 reviews

COZY Family Home- 5 minutes from sombrero beach

4.95 out of 5 average rating, 58 reviews

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

Sea Glass Beach Bungalow in Key Colony Beach!

A sandy beachfront is framed by palm trees, with the glistening Atlantic ocean in the background. A volleyball net is set up on the sand, along with multiple seating areas for relaxation, inviting guests to enjoy the tranquil environment and scenic views.

4.9 out of 5 average rating, 39 reviews

Viamarhe House-Private beach, Kayak, yard games

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.

4.81 out of 5 average rating, 102 reviews

OCEANIA... water front cottage retreat ~

4.97 out of 5 average rating, 91 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

A coastal view features multiple white houses with balconies situated along the waterfront. Palm trees sway gently in the breeze, and clear blue skies create a serene backdrop. Vehicles are parked in the driveways, emphasizing accessibility to the beachfront.

4.93 out of 5 average rating, 15 reviews

Ocean Breeze @ VO - Kayaks, Bikes, 30 Min from KW

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.

4.72 out of 5 average rating, 159 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 modern two-story home features a clean white exterior with navy blue accents. A set of black stairs leads to a covered balcony adorned with potted plants. Large windows allow natural light to enter, while a gravel driveway provides ample space in front.

5 out of 5 average rating, 43 reviews

Waterfront Escape -VACA-23-408

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.

5 out of 5 average rating, 21 reviews

Seaside Sunrise. Newly remodeled waterfront

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.

4.88 out of 5 average rating, 82 reviews

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

A spacious outdoor dining area features a glass-top table with several red chairs, set against a vibrant backdrop of greenery and water. The view of the calm sea and fluffy clouds can be seen in the distance, enhancing the tranquil setting.

4.84 out of 5 average rating, 32 reviews

Yellow Home - Receive $400 towards a Boat Rental!

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

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!

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, 57 reviews

The Mini Coconut

A serene canal view reveals a concrete dock bordered by sun loungers. Two boats are docked alongside, gently floating on the water, while the scene is framed by lush palm trees and quaint waterfront homes in the background.