Holiday rentals with a kayak in Stock Island

4.92 out of 5 average rating, 13 reviews

A large outdoor pool area is surrounded by lounge chairs with cushioned blue fabric. Lush palm trees and greenery create a relaxed atmosphere. The pool is clear and inviting, under a bright blue sky, with a shallow section and a diving area visible.

Apartment in Key West

Coconut Mallory. Waterfront & Key West charm.

The Coconut Mallory Resort and Marina offers island-style relaxation set amidst lush greenery and scenic waters. Enjoy spacious accommodations featuring a fully equipped kitchen, comfortable living area, and private balcony. Relax at the outdoor pools, hot tub, or enjoy libations at Gumbos, the on-site bar with marina views (currently closed). Marina usage is available. Easily explore all Key West has to offer. Located just 2 miles from Smathers Beach, 3 miles from Duval Street, and 4 miles from

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, 147 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, 136 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.

4.88 out of 5 average rating, 122 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.

4.85 out of 5 average rating, 109 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***

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, 288 reviews

December Save 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!

4.85 out of 5 average rating, 20 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

4.89 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.

4.88 out of 5 average rating, 121 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.

5 out of 5 average rating, 9 reviews

Home in Key West

Poolside Paradise

The whole group will enjoy easy access to everything from this centrally located two bedroom/2bath home with a private heated pool. Poolside Paradise is only 1/2 block from world famous Duval Street, walkable to almost everything you may want to do in Key West.

4.93 out of 5 average rating, 166 reviews

A serene pool area is visible in the foreground, bordered by lush greenery and ocean views. Tall palm trees sway gently along the shoreline, where the calm water reflects the sky. A distant pier can be seen, enhancing the coastal atmosphere.

Apartment in Key West

Beach Club Ocean Front 2BR Condo

Come fall in love with Key West in our luxurious ocean front condo. The Key West Beach Club is located directly on the Atlantic in a quiet residential secured building. It is a 2BR, 2 1/2 Bath located in Mid-Town.

Popular amenities for kayak rentals in Stock Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

The image showcases a modern two-story home with a light blue exterior, surrounded by lush landscaping. A heated pool is visible in the foreground, alongside kayaks and paddle boards. The ocean view offers clear, open water, enhancing the tranquil setting of 'The 7-Mile Villa.'

5 out of 5 average rating, 23 reviews

Seagrass-Free • New 5BR Pool Home w/ Ocean View

Two pelicans are perched on a wooden dock, surrounded by rippling water. The dock is supported by green posts, providing a serene setting in a tropical landscape. Subtle foliage in the foreground enhances the natural ambiance of the scene.

5 out of 5 average rating, 19 reviews

Oceanside home 111, dock,kayaks,bikes,pool,fishing

4.78 out of 5 average rating, 9 reviews

An inviting living area features a cozy sectional sofa adorned with patterned pillows. Large windows provide ample natural light, while a TV stands on a wooden console. A dining area with a light fixture and a view of the balcony is visible in the background.

Home in Summerland Key

Sailfish Dream on Cudjoe Key-28 day minimum

5 out of 5 average rating, 3 reviews

Blue Mind #225, 35' Seawall Venture Out

4.95 out of 5 average rating, 74 reviews

Amazing Ocean views, Atlantic access, 35’ boatslip

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

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

Aerial view of the Venture Out community showcases a large swimming pool adjacent to the sandy beach. Palm trees surround the area, with calm turquoise waters extending into the distance. Amenities include a tiki structure and a spacious lounging area, ideal for relaxation and outdoor activities.

4.78 out of 5 average rating, 50 reviews

Waterfront FL Keys Cottage @ Venture Out

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 ~

4.94 out of 5 average rating, 147 reviews

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

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.

4.94 out of 5 average rating, 18 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.

4.71 out of 5 average rating, 163 reviews

Calypso Cottage

Other holiday rentals with a kayak

A circular garden bed surrounds a palm tree, featuring a variety of green plants and a whimsical figure. The area is bordered by a low stone wall, with well-maintained grass providing a lush backdrop.

Home in Naval Air Station Key West

Quiet Little Place

A private swimming pool is surrounded by a concrete patio, overlooking the water. Tropical plants and lounge chairs offer seating options, while a small table is positioned nearby. The calm waters in the background reflect clear blue skies, creating a serene setting.

Townhouse in Marathon

4.55 out of 5 average rating, 11 reviews

Keys Waterfront- Spectacular Gulf View, Dock, Pool

A bright, airy living space is illuminated by natural light, featuring a comfortable sofa adorned with decorative pillows. A coffee table sits in front of the sofa, while textured wall art adds visual interest. The dining area is visible, showcasing a modern table with white chairs.

4.6 out of 5 average rating, 10 reviews

Salty Air Retreat. 2/1 Half Duplex. Dockside.

The living area features a light gray sofa and a cozy recliner, arranged around a wooden coffee table. Accents include a decorative basket and a blue rug, while natural light filters through white blinds, creating a welcoming atmosphere.

4.95 out of 5 average rating, 21 reviews

Sea Turtle Cove

The waterfront property is shown from across the water, highlighting its spacious exterior and proximity to neighboring homes. The serene blue water reflects the clear sky, while palm trees are visible in the background, suggesting a tropical setting.

Holiday home in Cudjoe Key

4.75 out of 5 average rating, 36 reviews

Waterfront Home Casa Del Sol 2/2 sleeps 6

The image captures a lagoon-shaped pool featuring a gentle entry ramp. Sunlight reflects off the clear water, surrounded by palm trees and colorful landscaping. Comfortable lounge chairs with umbrellas provide shaded seating, enhancing the inviting outdoor space of the Hyatt Beach House.

Apartment in Key West

Waterfront Resort, Private Beach, 7 Nights, Hyatt

A sleek Airstream trailer is positioned under a wide awning, providing shade on a sunny day. The polished exterior reflects sunlight, and palm trees can be seen in the background, enhancing the tropical setting.

Campervan/Motorhome in Geiger Key

4.55 out of 5 average rating, 33 reviews

Waterfront Airstream sleeps 3 "Tarpon"

The exterior of a two-story home is framed by tall palm trees, with shaded parking underneath. A picnic table and a grill are positioned on the ground level, while a balcony overlooks the lush surroundings.