Vacation rentals with a kayak in Stock Island

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, 179 reviews

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

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.

ValueOutdoor spacesPool

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, 320 reviews

AUG/SEPT. Save$ Oceanfront 4 BIKE/2 Kayak KING Bed

*PERFECT LOCATION! * 35' Seawall *AWESOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. At MM# 23 only 25min to Key West. In a gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C *Fully equipped kitchen *Includes grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library. Too much to list! WE WILL NEED YOUR EMAIL WHEN YOU CONFIRM THE BOOKING IN ORDER TO SEND YOU THE REGISTRATION FORMS AND THE RULE PACKET.

Outdoor spacesValueWalkability

5 out of 5 average rating, 4 reviews

Houseboat in Key West

*Aug/Sept Low Rates!* Go Your Own Wave Houseboat

Welcome to your private floating retreat anchored in the shallow, crystal-clear waters of Cow Key Channel, Key West. This newly renovated, coastal-themed cozy houseboat was designed for couples who want more than just a place to sleep. Float above turquoise water, sip coffee on the expansive front deck, and watch Key West sunsets from your private rooftop deck. Our houseboat designated for outdoorsy couples seeking a little bit more of adventure on the water! It's your own wave! Book now :)

Outdoor spacesLocationAir conditioning

4.76 out of 5 average rating, 21 reviews

Boat in Key West

3BR In Resort Village, Pools, Free Kayak & Shuttle

Experience the ultimate KEY WEST VIBE aboard our 3BR/2BA sailboat Located at the luxury Perry Hotel, you’ll enjoy on water living, palm trees, and salty air. Free Perks: Kayak, pools, parking, & free shuttle to Old Town! Full Resort Access: 2 pools & hammock park, 3 restaurants, ice cream shop, private bathhouse & Views of million-dollar yachts Plz read everything below before booking. I want you to be completely informed about staying on the water. We look forward to hosting you! 🌊💙⚓

Outdoor spacesLocationGetting around

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.

4.82 out of 5 average rating, 117 reviews

OCEANIA... water front cottage retreat ~

OCEANIA... water front cottage retreat ~ Completely remodeled, direct cannal-front cottage offers everything you'll need for the perfect getaway. Boat dock (35ft), HD Smart TVs, washer & dryer, S/S appliances! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

ValueLocationGrill

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.

4.89 out of 5 average rating, 157 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!

Outdoor spacesLocationFamily

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, 126 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***

LocationValueDecor

4.96 out of 5 average rating, 55 reviews

Tiki Time in Cudjoe Key 136

Open water, upscale Oceanfront Retreat! This waterfront gem offers amazing views of the Atlantic Ocean and is the perfect getaway for your next vacation in Paradise. This 2 bedroom, 2 bathroom vacation home is equipped with everything you need to unwind and relax. Offering a high end kitchen, stainless appliances, three smart tv's and a 54-foot seawall to dock your boat. VO COMMUNITY REGISTRATION FEE OF $125.00 IS DUE UPON ARRIVAL IN CASH OR CREDIT CARD ONLY.

LocationOutdoor spacesHospitality

Tiny home in Summerland Key

A bright blue bungalow is displayed next to neighboring structures, featuring a set of patio table seating for four on the concrete patio. Surrounding palm trees and gravel landscaping provide a tropical ambiance.

4.81 out of 5 average rating, 98 reviews

Lakefront Bungalow

Welcome to our King Bed Bungalows — your bright little island retreat designed for pure relaxation🌿✨ Each bungalow features a king-size bed, coffee station, mini fridge, toaster, and the couch includes a convenient pull-out bed, ideal for kids or additional guests. Open layout room windows invite in beautiful natural light. Please note: our bungalows do not include a kitchen — just the essentials for comfort, connection, and carefree island living.🌴

LocationOutdoor spacesCheckout

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, 133 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.

ValueOutdoor spacesCleanliness

4.93 out of 5 average rating, 230 reviews

The houseboat is anchored in the Cow Key Channel, featuring a sunlit exterior with a white finish. A deck extends from the entrance, complemented by a hammock and kayaks nearby. Clear blue skies and calm waters create a peaceful setting.

Houseboat in Key West

Beautiful Houseboat in Key West

Enjoy a unique and peaceful stay on our cozy houseboat in Key West. Perfect for couples or small families who want a relaxing water experience close to town. Comfortable sleeping area, deck space, and beautiful sunset views. Check-in is by appointment with personal captain meet-and-greet and boat transfer from the marina. A memorable island stay surrounded by nature and ocean air.

LocationOutdoor spacesCondition

A serene outdoor space features palm trees swaying gently by the water's edge, with a small floating dock visible. Loungers are arranged by the pool, surrounded by pebbled landscaping and lush greenery, all under a clear blue sky.

4.9 out of 5 average rating, 39 reviews

White House - Receive $400 towards a Boat Rental!

Receive a $400 gift certificate towards a boat rental. When you reserve a week for any of the dates and house below. When you book a full week at one of our homes staying between the dates of Sept 1, 2026 through Dec 19, 2026 Except for Nov 21-28, 2026 Please reach out before booking for boat availability. Kayaks come with the rental. Small floating dock for your boat.

LocationOutdoor spacesCondition

Popular amenities for Stock Island kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

A serene scene is captured featuring a sparkling blue pool surrounded by white lounge chairs. A tall palm tree sways gently in the background, with clear water visible beyond the pool, creating a relaxing atmosphere by the water’s edge.

Home in Key West

4.82 out of 5 average rating, 11 reviews

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Outdoor spacesValueHospitality

A calm canal is visible, featuring turquoise waters and surrounded by tropical vegetation. Palm trees and lush greenery line the water's edge, while several boats are docked nearby, providing easy access to the canal. The atmosphere reflects a serene coastal environment.

Home in Summerland Key

Living In Beautiful Paradise

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, 185 reviews

Ocean Front Home in Great Location

ValueOutdoor spacesAccuracy

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.

4.97 out of 5 average rating, 33 reviews

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

Outdoor spacesLocationPool

4.86 out of 5 average rating, 7 reviews

Ocean Breeze Retreat w/ Dock| Keys Escape

LocationConditionKitchen

4.93 out of 5 average rating, 96 reviews

Oceanfront w/ Dock, Swimming pool, Hot Tub, Kayaks

LocationOutdoor spacesGetting around

A vibrant view of the water showcases a serene marina. Palm trees sway gently in the breeze, and thatched-roof structures line the shore. Clear blue skies enhance the tranquil atmosphere, reflecting off the water's surface.

4.78 out of 5 average rating, 74 reviews

Waterfront FL Keys Cottage @ Venture Out

LocationOutdoor spacesAccess

4.8 out of 5 average rating, 10 reviews

Florida Keys Getaway - Ocean Views, Kayaks!

ValueOutdoor spacesAccess

Cottage rentals with a kayak

4.82 out of 5 average rating, 117 reviews

OCEANIA... water front cottage retreat ~

Outdoor spacesLocationParks

4.83 out of 5 average rating, 42 reviews

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

LocationValueDecor

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.

4.74 out of 5 average rating, 189 reviews

Calypso Cottage

ValueOutdoor spacesPool

4.94 out of 5 average rating, 179 reviews

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

ValueOutdoor spacesCondition

A tranquil pool is set against a backdrop of palm trees and a vibrant sunset. The water reflects the hues of the sky, creating a calming scene. Loungers are positioned along the poolside, offering a inviting space to relax.

4.84 out of 5 average rating, 32 reviews

2Bd/1Ba Waterfront Retreat w/35’ Dock

LocationOutdoor spacesAccess

Other vacation rentals with a kayak

4.43 out of 5 average rating, 7 reviews

Boat in Key West

Dream Catamaran

ValueGetting aroundCleanliness

A serene bedroom is depicted, featuring a colorful bedspread and decorative pillows. A wicker basket with neatly rolled towels is positioned on the bed. Additionally, a bright living area showcases soft seating, a dining space, and sliding glass doors leading to an outdoor view.

Home in Big Pine Key

4.67 out of 5 average rating, 3 reviews

Ocean Mist

LocationKitchenBathroom

4.95 out of 5 average rating, 20 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.

Condo in Key West

Coconut Mallory. Waterfront & Key West charm.

LocationValueComfort

A modern travel trailer is positioned beside a sandy area, featuring a tan thatched roof for shade. Large windows allow for natural light while the exterior showcases a sleek design in black and white. The setting highlights the nearby waterfront and tropical environment.

Camper/RV in Geiger Key

4.68 out of 5 average rating, 37 reviews

Waterfront RV that sleeps 5 "Wahoo"

Outdoor spacesLocationCheckout

Boat in Key West

4.91 out of 5 average rating, 22 reviews

Super-Cozy boat in Key West!

LocationViewCheckout

A spacious living room features two sofas, one of which is a fold-out bed, and a coffee table centered on a patterned area rug. Large windows with wooden blinds allow light to fill the room, highlighting the full kitchen area and breakfast bar in the background.

Houseboat in Key West

4.77 out of 5 average rating, 366 reviews

Key West Houseboat Paradise

LocationOutdoor spacesIndoor spaces

The image captures a panoramic view of the waterway between Key West and Stock Island, with lush greenery lining the shore. Boats can be seen gently navigating the calm waters, while the bright blue sky complements the tranquil scene.

Condo in Key West

5 out of 5 average rating, 8 reviews

Superb 2 BR 2 bath condo in waterfront resort

LocationValueGetting around

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.