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Holiday rentals with a kayak in Pensacola Bay

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Top-rated Accommodation with a Kayak in Pensacola Bay

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

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Guest favourite
The welcoming entrance features a navy blue front door surrounded by light green siding. A decorative wreath adorns the door. A small table and chairs are positioned nearby, with potted plants adding a touch of greenery. Concrete steps lead up to the entryway.
Home in Downtown Pensacola

Jackson Street Retreat - Highly Acclaimed Digs!

This newly renovated, charming 1926 shotgun house is located in the historic Belmont-Devilliers district in downtown Pensacola. The home is a short walk or bike ride to Blue Wahoos stadium, Joe Patti's Seafood, and Palafox Street. The home has every convenience; new HVAC, appliances & fully equipped kitchen with Keurig/coffee, smart TVs, and Wi-Fi. Additionally, the full bath has a standard whirlpool tub/shower and the backyard has a playhouse for the kiddos. Come enjoy your home away from home.

4.98 out of 5 average rating, 127 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
Top Guest favourite
Houseboat in Gulf Breeze

Delightful 1-bedroom houseboat with free parking.

Please read listing carefully. No pets allowed and no smoking. This is where your glamping adventures begin. You won’t forget your time at this peaceful and quiet place. Our houseboat is docked on the canal with a beautiful view. We make every effort to provide a safe and fun experience. Some amenities include a shower, bathroom sink, kitchenette, microwave, fridge, A/C and gas grill. Since this is a green houseboat, a porta-potty is located about 50 ft. from the boat and the private parking.

4.9 out of 5 average rating, 175 reviews
Guest favourite
Condo 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.
Apartment 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
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
Cottage in Elberta

Hammock Hideaway - waterfront cabin

Backyard oasis on a deep water creek. If you are coming for travel ball, love kayaking and/or just hanging out right on the water, you will appreciate this special hideaway. A fisherman’s/nature lovers dream and truly unique rental experience at this creekside cottage with water frontage on deepwater Hammock Creek. Close to the beach but out of the congestion. We have a multi level backyard with gazebo with swing, fire pit and huge deck. Fully enjoy the wildlife and outdoor activities.

4.98 out of 5 average rating, 124 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, 107 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
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

Enjoy beautiful views of the bayou in our carefully cleaned bungalow. Scenic walking/biking path along the bayou right outside your front door! Distances: Downtown 5 mi, Pensacola Beach 14 mi, Perdido Beach 20 mi, Pensacola NAS front gate 1.5 mi, public boat launch 0.2 mi. Fun fact: The Blue Angels home base is Pensacola, and you can see them practicing from our front porch. See photos for copy/paste of the 2022 practice schedule.

4.98 out of 5 average rating, 200 reviews

Popular amenities for Pensacola Bay kayak rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Holiday House Rentals with a Kayak

Top Guest favourite
Home in Pensacola Beach

Kokomo Key - 2 minutes to Beach - Private Pool

4.97 out of 5 average rating, 135 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
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

4.99 out of 5 average rating, 112 reviews
Top Guest favourite
Four blue beach chairs are arranged in the sand beneath a large umbrella, providing shade. A white building is visible in the background, suggesting a connection to the beach setting. The open sky and coastal environment enhance the relaxation space.
Home in Navarre

Navarre|BEACH| Gulf minutes away| Walk to water

4.98 out of 5 average rating, 101 reviews
Top Guest favourite
The spacious master bedroom features a California king bed covered with a patterned quilt. A reading nook is situated by a window with natural light filtering through sheer curtains. A cozy chair complements a bookshelf filled with various books, adding character to the room.
Home in Elberta

🏖Save $ while still being located near everything!

4.98 out of 5 average rating, 163 reviews
Top Guest favourite
A private sandy beach is visible with a row of blue adirondack chairs facing the water. Lush green grass leads to palm trees situated along the shoreline, while the tranquil bay is seen in the background under a softly lit sky.
Home in Sanders Beach

BAY HOUSE-Private Beach & Sunsets on Pensacola Bay

4.97 out of 5 average rating, 32 reviews
Guest favourite
Home in Milton

Explorer’s Landing–BayouSunsets Waterfront Escape

4.88 out of 5 average rating, 8 reviews
Top Guest favourite
Home in Gulf Breeze

Cozy Cottage on the Bay - Swim, Fish, Play, Relax

5.0 out of 5 average rating, 23 reviews

Cottages with a kayak

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
Guest favourite
Cottage in Pensacola

Perdido Point Hide-A-Way

4.95 out of 5 average rating, 44 reviews
Superhost
A scenic view of a cottage situated by a calm body of water, surrounded by greenery and tall trees. A wooden dock extends over the water, complemented by a gazebo-style roof. The clear blue sky reflects in the tranquil water, enhancing the natural beauty of the setting.
Cottage in Gulf Shores

Lakeside Three Bedroom Cottage - Accessible

A serene sunset over the water is captured, with warm hues of orange and yellow blending into the soft blue sky. Gentle waves are visible along the shoreline, where footprints are marked in the sandy beach, creating a tranquil atmosphere as day transitions to night.
Cottage in Pensacola

Sandy beachfront home on Perdido Bay

4.58 out of 5 average rating, 38 reviews
Cottage in Pensacola

Blue Lagoon Cottage

4.75 out of 5 average rating, 153 reviews

Other holiday rentals with a kayak

Top Guest favourite
A peaceful sunset over calm waters creates a vibrant display of orange and purple hues. A wooden dock extends into the water, reflecting the colorful sky, while silhouettes of trees line the distant shore. The scene evokes tranquility and natural beauty.
Apartment in Gulf Breeze

Redfish Loft, private waterfront Apt. on East Bay

4.96 out of 5 average rating, 244 reviews
Guest favourite
Townhouse in East Hill

Townhome A w/Private Hottub, mins to the beach

4.93 out of 5 average rating, 387 reviews
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 bright waterfront scene is captured, featuring Little Sabine Bay with reflections shimmering on the water's surface. The view includes marinas with sailboats and yachts, framed by palm trees and gardens, with a pool visible in the foreground.
Condo in Pensacola Beach

Stay at Sunshine Daydream on Pensacola Beach

5.0 out of 5 average rating, 164 reviews
Guest favourite
The exterior of the cottage showcases a welcoming entrance with a decorative wreath adorning the door. A paved driveway leads up to the home, surrounded by well-maintained landscaping featuring shrubs and trees. The backdrop includes a clear blue sky highlighting the peaceful neighborhood.
Guesthouse in Pensacola

Private Guesthouse- 2 mi. downtown & 5 mi. Beach

4.97 out of 5 average rating, 225 reviews
Guest favourite
A wooden pier extends over calm waters, reflecting soft pastel hues of a sunset sky. A medium-sized dog stands on the pier, looking toward the camera. In the distance, a small boat is moored near a covered dock.
Guest suite in Pensacola

Waterfront Escape to Gulf Beach Getaway!

4.9 out of 5 average rating, 230 reviews
Top Guest favourite
Guesthouse in Pensacola

Waterfront Haven | King Studio | Hot Tub | UWF I10

4.97 out of 5 average rating, 89 reviews
Top Guest favourite
A cozy sleeping area features a spacious bed with a colorful patterned quilt and decorative pillows. Two blue armchairs and poufs are arranged nearby, and a wall-mounted television is positioned for viewing. Natural light enters through sheer curtains, illuminating the inviting space.
Treehouse in East Hill

The Feathered Nest

4.94 out of 5 average rating, 70 reviews

Destinations to explore