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.

Outdoor spacesLocationHospitality

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, 321 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.

ValueOutdoor spacesCondition

4.78 out of 5 average rating, 23 reviews

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! 🌊💙⚓

LocationOutdoor spacesBathroom

A colorful array of lounge chairs in yellow, green, and blue is positioned by a shared pool area. A thatched-roof cabana is visible, providing shaded seating near the water's edge. The lush surroundings and bright blue sky complement the inviting atmosphere.

4.94 out of 5 average rating, 33 reviews

Oceanside home 109, dock,kayaks,bikes,pool,fishing

This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. This is #109 and I also rent adjacent homes 111 and 107 in case you need more than one. We are 80 feet from the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on the balconies or poolside, where you can sun, fish or boat from the docks. Key West is 17 miles away.

Outdoor spacesLocationSleep quality

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, 118 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!

Outdoor spacesValueFamily

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 spacesLocationBathroom

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, 127 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***

ValueOutdoor spacesKitchen

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, 135 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.

ValueLocationTV

Tiny home in Summerland Key

A well-lit sleeping area features a spacious bed with decorative pillows and a cozy throw. Light wood accents and modern furnishings complement the room. A kitchenette area includes a mini fridge and Keurig coffee maker, with curtains providing separation and natural light from the windows.

4.8 out of 5 average rating, 85 reviews

Bungalow

Pet-friendly glamping in The Keys. Camp in comfort on your next Key West escape in an air-conditioned bungalow. Close to our amenities. Featuring a living room (with sleeper sofa), bathroom with shower, and a king-size bed, this vacation rental getaway sleeps 4. Our bungalows also boast patio table seating for four, Smart streaming TV, Wi-Fi, microwave, mini fridge, Keurig coffee maker, blow dryers, charcoal grill, and steamers.

Outdoor spacesLocationCondition

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.

Outdoor spacesLocationCondition

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 spacesKitchen

A charming waterfront villa is framed by lush palm trees, featuring a spacious sandy area with vibrant landscaping. A boat is docked nearby, with soft clouds drifting across the blue sky, contributing to a serene outdoor environment.

4.97 out of 5 average rating, 29 reviews

Aug. Discount, Waterfront Retreat/Pool/golf cart

Step into your private oasis! This stunning home features a sprawling outdoor space, perfect for boating, fishing or relaxing under the stars. Complete with a beautiful landscaped butterfly garden, park benches and tables. This property is one of a kind compared to space and privacy. Perfect for relaxation and rejuvenation.

LocationOutdoor spacesQuiet

Popular amenities for Stock Island kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.92 out of 5 average rating, 97 reviews

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

Outdoor spacesValueHospitality

4.96 out of 5 average rating, 55 reviews

Tiki Time in Cudjoe Key 136

ValueLocationSleep quality

4.94 out of 5 average rating, 18 reviews

Blue Palms Retreat

LocationOutdoor spacesCheckout

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

Outdoor spacesValueAmenities

A boat is docked at a private marina, showcasing a spacious outdoor area. A fish cleaning station is visible nearby, along with a hose and power source. Colorful buildings line the waterfront, and clear blue skies reflect over the water.

5.0 out of 5 average rating, 20 reviews

35’ dock/Completely Remodeled VO 366

LocationOutdoor spacesFamily

4.8 out of 5 average rating, 10 reviews

Florida Keys Getaway - Ocean Views, Kayaks!

Outdoor spacesValueBiking

5.0 out of 5 average rating, 14 reviews

Waterfront home in florida keys 35’ dock for boat

Outdoor spacesValueParking

Home in Big Pine Key

New place to stay

Big Pine Retreat

Cottage rentals with a kayak

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.

4.82 out of 5 average rating, 33 reviews

2Bd/1Ba Waterfront Retreat w/35’ Dock

ValueOutdoor spacesHospitality

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

LocationOutdoor spacesHot tub

4.83 out of 5 average rating, 42 reviews

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

LocationValueHospitality

4.82 out of 5 average rating, 118 reviews

OCEANIA... water front cottage retreat ~

Outdoor spacesValueAccess

4.94 out of 5 average rating, 179 reviews

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

Outdoor spacesLocationAir conditioning

Other vacation rentals with a kayak

5.0 out of 5 average rating, 4 reviews

Houseboat in Key West

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

LocationOutdoor spacesKitchen

4.97 out of 5 average rating, 35 reviews

A coastal-style home features a light green exterior with a covered porch and white railings. Colorful chairs are arranged on the lower deck, while stairs lead up to the entrance. The property is adjacent to a calm waterway, enhancing its scenic appeal.

Villa in Cudjoe Key

Howard House on the Sea

Outdoor spacesLocationComfort

4.43 out of 5 average rating, 7 reviews

Dream Catamaran

ValueAir conditioningSleep quality

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 spacesCleanliness

4.7 out of 5 average rating, 20 reviews

Resort chic on the water!

LocationCleanlinessKitchen