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Holiday rentals with a kayak in Pensacola Beach

Find and book unique kayak rentals on Airbnb

Quick stats about holiday rentals with a kayak in Pensacola Beach

  • Total holiday rentals

    Explore 120 holiday rentals in Pensacola Beach

  • Nightly prices starting at

    Pensacola Beach holiday rentals start at £67 per night before taxes and fees

  • Verified guest reviews

    Over 5,250 verified reviews to help you choose

  • Family-friendly holiday rentals

    110 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    120 of Pensacola Beach holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Pensacola Beach rentals

  • 4.9 Average rating

    Pensacola Beach stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated rentals with kayak in Pensacola Beach

Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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Top guest favourite
The image captures a vibrant sunset over calm waters with streaks of pink and orange illuminating the sky. A wooden dock extends into the distance, and sandy shores are visible in the foreground, creating a serene waterfront atmosphere.
Home in Navarre

Private Waterfront Retreat: Family & Pet Friendly

Welcome to your own private waterfront, beach, and retreat destination! Recently renovated, this home is the perfect place to unwind, relax, and soak in the beach life! Tucked away on a dead-end street away from the tourist hustle & bustle. - Panoramic views of the sunset - Private 450ft dock with 2-story deck - Paddle boards/yoga mats - 1 acre of serenity - Complete kitchen - Fenced backyard, outdoor dining, fire pit Location: - 16 mins/10 miles to Navarre Beach - 14 mins/8 miles to grocery

4.99 out of 5 average rating, 112 reviews
Top guest favourite
The outdoor pool is framed by a screened enclosure, providing clear views of the tranquil bay waters. Comfortable lounge chairs are positioned beside the pool, and potted plants add a touch of greenery. A wooden dock extends into the bay, enhancing the serene ambiance.
Home in Navarre

East Bay Hideaway — A Private Waterfront Escape

Nestled between the world's most beautiful beaches, this bayfront retreat has it all. Enjoy captivating views from the kitchen, living & den spaces. Views continue as you step out on the screened lanai w/room for all to gather poolside. Need a warmer, invigorating quiet time? Stroll across the patio & find a privately situated hot tub. Finally, wander down the dock to fish, swim, connect or star gaze over the glassy waters of East Bay. Unbelievable sunsets await, book before this seasons fills.

4.97 out of 5 average rating, 193 reviews
Guest favourite
Apartment in Pensacola

Cozy Bayou Bungalow - just steps from the water

Are you looking for a comfortable, clean place to relax in an established and desirable area of town while visiting beautiful Pensacola? Then look no further! The Bayou Bungalow is located just steps from the water along Bayou Texar and only minutes from the downtown entertainment district and our pristine beaches. Enjoy a morning walk along the waters edge under the oak trees, check out the neighborhood beach and let this location serve as your hub while enjoying all Pensacola has to offer!

4.96 out of 5 average rating, 282 reviews
Top guest favourite
A tranquil sunset illuminates the sky with shades of orange and purple over a calm bay. Silhouetted dock structures gently reflect on the water's surface, enhancing the serene atmosphere of the waterfront setting.
Flat in Pensacola

Serenity on the Bay-Waterfront attached studio

If you're looking for a quiet, get-away directly on the water, and convenient to everything, this is your place! Enjoy beautiful sunrises and gorgeous evening colors in this lovely waterfront studio. You will have a private hot tub steps from your room looking out over the bay. Direct access to a private dock along with two fishing poles and paddle boards upon request. Minutes to historic downtown and 20 minutes to the Gulf of Mexico and Pensacola NAS. this is an adult only property, 21+

4.99 out of 5 average rating, 178 reviews
Top guest favourite
Home in Pensacola Beach

Kokomo Key - 2 minutes to Beach - Private Pool

If you've been searching for Kokomo Key... Here it is—your tropical escape to the islands. White sand, turquoise waters… it’s got all the vibes of a place where time slows down and the only agenda is relaxation. Relax with the whole family at this peaceful beach house with a private pool, hammocks, unobstructed views of Santa Rosa Sound, and a 2-minute walk to the stunning Gulf beaches! We are pet-friendly, but please remember to let us know you are bringing your pets by checking the box!

4.97 out of 5 average rating, 135 reviews
Top guest favourite
An open living space features a comfortable sofa, complemented by a cozy throw blanket and cushions. Large windows allow natural light to fill the room, which includes a kitchen area with modern appliances. A soft area rug anchors the space, creating a welcoming ambiance.
Home in Milton

Blackwater Bay Mae's Cottage

Mae's Cottage is a peaceful little bay house located right off of Interstate 10 in Milton (< 1 mile) and is within steps to the beautiful Blackwater River and Bay. It is approximately 100 yards from water access where you can enjoy fishing, boating, kayaking or just watching the sun set. There is a public boat launch so bring your boat/jet skis/kayaks and fishing gear and head out to the beautiful waters of Blackwater Bay. Relax with the whole family at this peaceful little bungalow.

4.96 out of 5 average rating, 167 reviews
Top guest favourite
Home in Pensacola Beach

Kayaks & Paddle Boards SunRise & SunSet Views

Welcome to SunnySide UP! The serene 2 bedroom 2.5 bath with water view is located on Little Sabine Bay in Pensacola Beach, FL. Relax on the patio as you look out at the tranquil water as you sip your morning coffee or glass of wine in the evenings. The white sandy beaches of the Gulf of Mexico are right across the street, the nearest public access less than a 5 minute walk! You can also easily walk/drive/trolley to the bustling boardwalk with shopping and plenty of great restaurants.

5.0 out of 5 average rating, 108 reviews
Guest favourite
A kayak glides across calm water, reflecting a vibrant sunset. Pine trees line the shore, framing the scene as hues of orange, pink, and purple fill the sky. Fishing poles are positioned close by, adding to the peaceful setting.
Home in Milton

Twin Waterfront Home w/Boat Dock & Kayaks!

Read full description before booking! 25-30 min drive to Pensacola beach. 2 bedroom, 2 bathroom, 1400 sq ft townhome near Escambia Bay and Pensacola. Bring your boat and dock it in the back yard!! Sit on the porch and enjoy coffee in the morning listening to the birds and frogs nearby. The home is nestled in the quiet community of Escambia Shores. Surrounded by tall pines this relaxing home is perfect for a family vacation or honeymoon. Wonderful fishing off the dock!

4.86 out of 5 average rating, 150 reviews
Top guest favourite
Boat in Pensacola

Classic Boatel Yacht

This memorable place is anything but ordinary. Experience a unique getaway aboard our charming 1977 Boatel Yacht, a 47-foot classic docked on a private dock on the Bayou. Perfectly positioned for a serene retreat, the boat offers rustic elegance and craftsmanship, blending modern comfort with timeless style. Enjoy breathtaking views, bird watching and the excitement of watching the Blue Angels practice from the nearby base. Only 15 minute drive to downtown Pensacola.

4.98 out of 5 average rating, 106 reviews
Top guest favourite
The stilt house features a wooden deck with seating options and overlooks the tranquil Blackwater River. Surrounding trees provide a natural setting, while the calm water reflects the structure and landscape. A boat dock is visible, enhancing the waterfront experience.
Home in Milton

Waterfront with kayaks* Blackwater River Shanty

Enjoy nature in this 2 bedroom stilt house on Paradise Island surrounded by the Blackwater River- just a 30 minute drive to Gulf Beaches! Kayak around the island, enjoying the turtles & birdwatching, or boat or drive to downtown Milton to dock and dine at Blackwater Bistro or Boomerang Pizza. There is a boat ramp, boat house, 4 kayaks and life jackets for guest use. Easily visit Navarre Beach, vibrant Downtown Pensacola, Pensacola Beach, or Ponce de Leon Springs.

4.95 out of 5 average rating, 263 reviews
Top guest favourite
A three-story beach house is set against a clear blue sky, featuring a light-colored exterior and large windows. Palm trees line the entrance, leading to a stairway that connects to the main door. A private beach area is visible in the background.
Home in Pensacola Beach

Soundside Paradise

Private waterfront home with boat dock, private beach, community pool and tennis courts. Relax, unwind, and enjoy the views at this private tropical retreat. Paddle or kayak the sound or drop a line in the water to catch and cook some of the best fish Florida has to offer... all right from your backyard! Home features an open floor plan with breathtaking views of the water seen throughout. This one of a kind experience is sure to create lasting memories!

4.98 out of 5 average rating, 167 reviews
Superhost
Home in Gulf Shores

Lagoon Access, Short Walk to Beach, Sleeps 10!

Welcome to Tide Down! This charming cottage offers lagoon access, a 5–10 min paved walk to the beach, plus 2 bikes and 3 kayaks. Sleeps up to 10 with 3 bedrooms, 2.5 baths, bunk beds, queens, and a sleeper sofa. Pet-friendly (max 2). Washer/dryer included. Starter supplies provided. Contactless check-in. Guests must be 22+, some exceptions can be made with $500 deposit, fully refundable pending no damages. Snowbird discounts available.

4.86 out of 5 average rating, 147 reviews

Popular amenities for kayak rentals in Pensacola Beach

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a kayak

Top guest favourite
Home in Gulf Shores

Beach & Lagoon Retreat - Private Beach Access

4.96 out of 5 average rating, 138 reviews
Top guest favourite
A serene view of a private dock extends into the Blackwater River, surrounded by lush trees. The calm water reflects the clear blue sky, while a grassy area leads to the concrete path beside the water, creating a peaceful atmosphere.
Home in Milton

Relax on Blackwater River

5.0 out of 5 average rating, 110 reviews
Guest favourite
An open living area features a large sectional sofa and a decorative rug. A wall-mounted TV is positioned across from the seating arrangement. The space is brightened by natural light from large windows, while a blue accent wall adds a pop of color. Bar stools line a counter leading to the kitchen.
Home in Navarre

Sandsational Staycation 6 min to the beach

4.94 out of 5 average rating, 182 reviews
Top guest favourite
A wooden pier extends over calm waters, leading towards a spacious coastal home. Flanking the pier, two colorful kayaks rest on the sandy shoreline. Lush greenery and beach houses are visible in the background under a clear blue sky.
Home in Gulf Shores

Lagoon waterfront/Private Pier/Fishing/Gulf Views!

4.95 out of 5 average rating, 107 reviews
Top guest favourite
A panoramic view of the waterfront is visible, showcasing a vast expanse of water under a bright blue sky with scattered clouds. A wooden pier extends into the water, leading towards distant city structures, while grassy land and sandy beach area are framed in the foreground.
Home in Navarre

Beach House w/ ALL Gear Included | Walk to Water

4.98 out of 5 average rating, 119 reviews
Top guest favourite
A spacious deck overlooks the tranquil waters, featuring bright blue chairs arranged for relaxation. Palm trees frame the scene, and the setting sun casts soft hues across the sky, enhancing the peaceful ambiance of this waterfront space.
Home in Gulf Shores

10/10 Location | Steps2Beach | LagoonFront |DogsOK

4.96 out of 5 average rating, 145 reviews
Top guest favourite
The entryway features a light-colored floor with a stylish console table displaying decorative items. A large mirror and two lamps provide illumination. A welcoming door opens to the outside, flanked by windows with sheer curtains, creating a bright and inviting space.
Home in Pensacola

Tidy Bayou Bungalow

4.98 out of 5 average rating, 200 reviews
Top guest favourite
The exterior of the three-story beach home is showcased, featuring a large, inviting pool surrounded by lounge chairs. A spacious deck is visible, with the front of the house displaying double gables and multiple balconies. Lush landscaping is present around the pool area.
Home in Pensacola Beach

Private Pool, Steps to the beach, Golf cart

4.97 out of 5 average rating, 32 reviews

Cottage rentals with a kayak

Top guest favourite
Cottage in Elberta

Hammock Hideaway - waterfront cabin

4.98 out of 5 average rating, 124 reviews
Guest favourite
Cottage in Pensacola

Coastal Cottage Retreat | Foosball table | Firepit

4.98 out of 5 average rating, 184 reviews
Top guest favourite
The charming cottage features a light blue exterior with decorative flower boxes beneath the windows. A white picket fence encloses the front yard, which is neatly landscaped with green grass. A bright red door serves as a welcoming entryway, framed by lush greenery.
Cottage in Pensacola

Octopus Cottage

4.98 out of 5 average rating, 95 reviews
Top guest favourite
The exterior entrance of the cottage is shown, featuring a set of wooden steps leading up to a blue door with a screen and decorative light above. Potted plants are positioned on either side of the steps, enhancing the welcoming appeal.
Cottage in Orange Beach

Spanish Moss House on Wolf Bay w/Pier + Boat Slip

5.0 out of 5 average rating, 99 reviews
Top guest favourite
A charming exterior of a small house is presented, featuring light purple siding and white columns supporting the front porch. Steps lead up to a solid door, with windows flanking each side, and a grassy area surrounds the structure, enhancing its connection to nature.
Cottage in Pensacola

Coastal Country Living

4.97 out of 5 average rating, 97 reviews
Top guest favourite
A spacious grassy area extends towards the water's edge, framed by trees. A wooden dock stretches into the calm bay, featuring a covered seating area. Swing benches are available on the shoreline, providing a perfect spot for relaxation while enjoying the scenic view of the water.
Cottage in Fort Walton Beach

Waterfront Bliss Beach Cottage

5.0 out of 5 average rating, 37 reviews
Guest favourite
Cottage in Pensacola

Perdido Point Hide-A-Way

4.95 out of 5 average rating, 44 reviews
Top guest favourite
A tranquil, tree-lined road is surrounded by majestic, canopied oaks draped with Spanish moss. Two individuals can be seen riding bicycles along the path, embodying the serene natural ambiance of the area. Bright sunlight filters through the leaves, creating a peaceful atmosphere.
Cottage in Magnolia Springs

Riverview Retreat • Hot Tub • Golf Cart • Fire Pit

5.0 out of 5 average rating, 71 reviews

Cabin rentals with a kayak

Top guest favourite
The cabin is nestled among shady oak trees, featuring a wooden deck with seating and a hammock for relaxation. A charcoal grill is positioned nearby, and the surrounding area showcases a dirt path leading to a natural, serene environment.
Cabin in Gulf Breeze

Waterfront tiny Cabin/ Glamping

4.91 out of 5 average rating, 576 reviews
Top guest favourite
A serene waterfront view captures still waters reflecting the soft hues of twilight. Lush green grass leads to a wooden dock, surrounded by tall trees. The landscape offers a peaceful setting, perfect for outdoor relaxation and enjoying nature.
Cabin in Elberta

Waterfront Cabin 3 bedroom 2 bath kayaks and boat

4.95 out of 5 average rating, 222 reviews
Guest favourite
The exterior of the cottage features a stone facade and a covered carport. A well-maintained path leads to the entrance, surrounded by established shrubs and greenery. A gravel driveway provides access, with a fenced yard visible in the background.
Cabin in Mary Esther

Safe Harbor Cottage on Santa Rosa Sound - Pets ok!

4.91 out of 5 average rating, 237 reviews
Top guest favourite
The cabin exterior features a large wall of windows, allowing ample natural light. Surrounded by greenery and water, a small seating area with picnic tables is visible in the foreground, complemented by lush plants and tall trees.
Cabin in Elberta

Creekside Fish Camp | Pier, Kayaks & Skiff

4.98 out of 5 average rating, 59 reviews
Guest favourite
An outdoor fire pit is bordered by several colorful chairs in red and blue. Lush greenery surrounds the site, with views of the tranquil river just beyond. A shaded gazebo is visible in the background, enhancing the peaceful riverside setting.
Cabin in Milton

Riverfront Milton Cabin w/ Boat Ramp & Dock!

4.89 out of 5 average rating, 56 reviews

Destinations to explore