
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 $154 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
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

Wi-Fi availability
120 of Pensacola Beach holiday rentals include Wi-Fi 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 Accommodation with a Kayak in Pensacola Beach
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

Cozy Bayou Cottage - 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 Cozy Bayou Cottage 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!

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.

Redfish Loft, private waterfront Apt. on East Bay
Boat lift available-extra daily fee- 12k lb " pet friendly with fee " loft apartment with private bedroom. Watch the blue herons & dolphins, sit on one of two private decks sipping coffee as you watch the sunrise on the Bay. Paddle the clear waters in our kayaks or bring your SUP. Cook your fresh catch on private grill or visit a local seafood restaurant. Secluded, neighborhood. Join us @ Fire pit ..is usually going on the weekends. East Bay is known for it's Red fish and calm waters.

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.

Stay at Sunshine Daydream on Pensacola Beach
Come experience vacation paradise at "Sunshine Daydream" Located in the heart of Pensacola Beach. Perfect beaches, fantastic restaurants/bars, and shopping are only steps away. Enjoy pristine views of Little Sabine Bay from all over this magnificently renovated condo. Unwind on the 300 sq ft covered balcony and watch the sunset from the best location on the island! The complex hosts a large heated swimming pool, private beach, exercise room, dock, elevators, and a full time cleaning staff.

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+

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.

Pelican's Paradise~Amazing View, FREE Kayaks,Pool!
Welcome to our home, Pelican's Paradise! Come enjoy beautiful views, coffee on the balconies, & serene waters. This 2 bed/2.5 bath comfortably sleeps 8 and includes a fully stocked kitchen, laundry room, and 2 kayaks! It sits on the cove of Perdido Bay, providing the perfect, secluded place for families to relax, play, and paddle safely. Spend all day here, isolated and tucked away. Or take a short 5 mile drive to the Gulf beaches, parks & dining of Perdido Key! Minutes from Naval Base.

Waterfront Paradise "No Wake Zone" On Perdido Key
Welcome to "No Wake Zone Villa" located on Perdido Key, Florida. Beautiful waterfront condo located on the Intracoastal waterway with a semi-private beach. Perdido Key is a coastal community located between Pensacola, Florida and Orange Beach, Alabama. No more than a few hundred yards wide in most places. Perdido Key stretches some 16 miles, with 60% of it located in federal or state parks-making it one of the last remaining unblemished stretches of wilderness on the Gulf of Mexico.

Kayaks & Paddle boards/Private Patios Water 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.

Waterfront Escape to Gulf Beach Getaway!
Waterfront private guest suite with ensuite bedroom including an ultra comfortable king-sized bed. Walk out of your bedroom’s sliding door to a private deck steps away from our beach and pier where you can enjoy swimming, paddle boarding, kayaking or just enjoy the view! You will have your own private full kitchen. Book a massage with our massage therapist before your stay and enjoy your massage just steps away from your suite. Additional bed and bath available as well.

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.
Popular amenities for Pensacola Beach kayak rentals
Holiday House Rentals with a Kayak

Private Waterfront Retreat: Family & Pet Friendly

*Waterfront Home w/Boat Dock, & Kayaks!

Tidy Bayou Bungalow

Bayfront Bliss | Dock & Sunsets, Spacious Living

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

Private Pool, Steps to the beach, Golf cart

Relax on Blackwater River

Casa Verde: Heated Pool +JET SKI & Pontoon rental
Cottages with a kayak

Hammock Hideaway - waterfront cabin

Coastal Country Living

Riverview Retreat • Hot Tub • Golf Cart • Fire Pit

Octopus Cottage

The Cabin on the River

Waterfront Bliss Beach Cottage

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

Cottage minutes from Fairhope/Foley/Gulf Shores.
Cabin rentals with a kayak

Safe Harbor Cottage on Santa Rosa Sound - Pets ok!

Fish & Relax! Magnolia River Cabin Hideaway

Riverfront Milton Cabin w/ Boat Ramp & Dock!

Creekside Fish Camp | Pier, Kayaks & Skiff

Waterfront Cabin 3 bedroom 2 bath kayaks and boat
Destinations to explore
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- Destin Beach
- Gulf Shores Public Beach
- Crab Island
- Destin Harbor Boardwalk
- Perdido Key Beach
- OWA Parks & Resort
- Opal Beach
- Henderson Beach State Park
- Village of Baytowne Wharf
- Gulf State Park
- Navarre Beach Fishing Pier
- Flora-Bama Lounge
- Johnson's Beach, Gulf Islands National Seashore
- Alabama Point Beach
- The Hangout
- HarborWalk Village
- Gulf Breeze Zoo
- The Wharf Amphitheater
- The Lighthouse Condominiums
- Fort Walton Beach Landing
- Jade East Towers
- The Boardwalk on Okaloosa Island
- Gulfarium Marine Adventure Park
- Destiny East





