
Holiday rentals with a kayak in Pensacola
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Top-rated Accommodation with a Kayak in Pensacola
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Holiday House Rentals with a Kayak

Spacious & Bright 3BR/2B near DWTN & Beach
We absolutely loved our stay. The house was clean, comfortable, and Rose-Marie was very kind + helpful to us! We were given a list of local recommendations which was nice to have when planning our days. The house layout is very nice for spending time together, but the bedrooms are private. Everything was very clean & we did not have any encounters with the local outside crawlers. I could not recommend this stay more!!

Cozy Home on a Lake - 8 Miles to the Beach!
This place is not only in a great neighborhood that feels welcome and secure, but it being 8 min from some of the most laid back and beautiful beaches in the area is so undersold. I went to the beach at sunrise and sunset daily while working remote for 3 weeks. I barely went to the more popular ones in the area because this local one is so great, and if you like scuba diving the best dive shop, dive pros, and boat charters are only 10 min away. Also has very quick and easy access to Orange Beach and Gulf Shores Alabama, which in my opinion is the best parts of the local area.

BAY HOUSE-Private Beach & Sunsets on Pensacola Bay
My family and I celebrated a long vacation here the week of Memorial Day and Donna’s home was a perfect stay. We enjoyed the large clean rooms, the amazing porch, the private beach, and the access to kayaks, bikes, and the fully stocked kitchen. The neighborhood was cute and close to a large pier, downtown, and small roads perfect for a morning bike ride. It was incredibly peaceful and the most amazing way to spend the week. We are really grateful for the opportunity to stay here! We hope to return soon!

Steps away from the calm.
Brittney’s place was very lovely and we already have plans to be back! Such a lovely home perfect for a family. We had a 6 month old who a pack and play was provided for. A 4 year old who had a cute bedroom with toys and extras that she enjoyed. She even slept in her big girl bed for once because of how enticing this childrens bedroom was. I personally enjoyed the master bedroom with the private balcony. Perfect for a couple. My grandparents enjoyed the 3rd bedroom on the second floor. My husbands personal favorite was the closet outside filled with goodies like floaties, life vests, toys and so so many fun things to use on the beautiful cove just steps from the home.

Relax on Blackwater River
Second time staying here. Very cute place, extremely well kept and comfortable. Great family time. Love Blackwater River!!! Thank you Adam and Alisa

Close to Beach Pool with Canal View
Alex's home is in the perfect location between amenities and the beach. This beautiful home is located less than 20 minutes from watching the Blue Angles on the beach or having a coffee in downtown. The backyard offers a nice break from crowds on the beach and let's you play in the water and still see the ocean. Saw some fish jumping as well so I imagine there is some good fishing just steps away from your bedroom.

Kayaks & Paddle boards/Private Patios Water Views
Located just between the beach and the inlet with views of both from the front and back of the condo. Had everything you needed for your trip to the beach, bikes to ride, kayaks, and a paddle board. Beach access was a short walk and not as busy as closer to the boardwalk. It is 3 floors with balconies on each floor. We loved our stay and would stay here again.

Vintage Beach Bungalow
We LOVED our time here! The home was cozy, clean, conveniently located. We SUPER enjoyed the porch and yard. The proximity to the bay was so lovely— my daughter and I fed the fish and crab hunted every evening! Loved the master bed & shower! All the decor was SO cute & funky.
Cottages with a kayak

Hammock Hideaway - waterfront cabin
This home is exceptional. Very comfortable living area, well equipped kitchen, and bedrooms conducive to restful nights! Our favorite spot was the screened-in porch for morning coffee and quiet evenings where herons and turtles appeared to entertain us! Also Donna, the host, was very attentive checking in to see if anything was needed! We look forward to staying there again when back in Alabama! We give this house a 5+!

Coastal Country Living
Such a cute cozy place! My boyfriend and I loved the decor and it was so clean!! Kimberly was in top of everything she’s such a great host. Definitely book here so worth it. The beds are so comfy too you will sleep like a baby!

Octopus Cottage
If I could give Vincent 1000 stars I would! Honestly one of the best hosts I’ve had through Airbnb. Very accommodating, friendly, responsive, and inviting. He was flexible with our check in & prompt with responses. We arrived and were gifted a bowl of fruits and goodies.. I always find that to be such a thoughtful gesture from hosts ❤️ He let us borrow beach chairs, a boogie board and an umbrella which made our trips to the beach so much comfier. We brought my senior basset hound and he had a whole thing out together for my pup (another super thoughtful gesture to fellow pet owners) Truly a 10/10 stay with this host. Thank you so much again Vincent!!

Nature's Nest Cottage on the Sound - Pets Welcome!
We’re repeat visitors and our stay this time was just as lovely as the last. The Nest offers a cozy place to hang out, bed down, and base from. We love spending time kayaking the sound and watching for wildlife. Beaches, seafood, and all the Ft.Walton/Destin vacation fun is close by, but the Nest is homey and easily fit our family of four. Very grateful for laundry to wash bathing suits in between beach days!

Luxury Beach Cottage With Private Beach
When you visit Annie’s place, enjoy a glass of wine or cozy cup of coffee with their stunning view of the bay only a few footsteps out the back doors. Immaculate gardens and lawn greet you upon arrival. This is the most well stocked home I have ever rented. Tons of activities indoor and outdoor to keep kiddos of all ages entertained. Luxury indoor and outdoor entertainment spaces. This place is lovely whether you want to relax or play. Communication with the hostess was prompt and thoughtful. We never wanted to leave! Thanks again Annie.

Spanish Moss House on Wolf Bay w/Pier + Boat Slip
We love the cottage. With a boat lift and dock for our boat it’s the perfect location. The large trees and peaceful setting are perfect for time away from jobs.

Blue Lagoon Cottage
Good location, not far from beaches and local restaurants.

Perdido Coastal Cottage- pets ok w/ fee-
Very cute, clean, and cozy space! The outdoor space was fully-fenced and was a great place for my dogs to hang out!
Cabin rentals with a kayak

Waterfront Pensacola Paradise with Boat Slips!
Stayed here while evacuating from Hurricane Milton. Check-In process was super straight forward, the hosts were very understanding of our situation and allowed us to check in early after we drove 8 hours from the Tampa area! The cabin was charming and relaxing. Good internet and environment to get some work done. Plenty of activities to do on-site. Great views of the water! We were even able to use the kayaks at the stay. The fishing was great too, we were able to catch over 45 fish in the 3 days we were there. While there was plenty of stuff to do on-site, everything you need is within 5-10. The beach and great restaurants are super close. Definitely will be coming back under different circumstances!

Riverfront Milton Cabin w/ Boat Ramp & Dock!
We had a wonderful time here! Having plenty of paddle boards and kayaks was a plus as well as the dock with swings. The house was comfortable and spacious and the fur babies had the best time in the water! Everything was exactly as described.

Creekside Fishcamp
Joesph’s place was beautiful, and peaceful. We had the best stay. He was such a friendly host and made sure we were comfortable and didn’t need anything. His house was sparkling clean, and such a hidden gem, the sun room was everything. We will be back!

Waterfront tiny Cabin/ Glamping
Our stay was beyond what we imagined. The cabin was just perfect.. we had just enough space for our 2 adults and 2 kids. The kids had so much fun sleeping in the loft (they were old enough to do so)… the Murphy bed was super comfy, and everything was very clean!! The location was incredibly beautiful and peaceful. We enjoyed seeing dolphins right off the dock every day.. watching beautiful sunsets… and loved getting to use the kayaks. The only problem was that we couldn’t stay longer!! We will be back again for sure!!
Quick stats about holiday rentals with a kayak in Pensacola
Total rentals
20 properties
Nightly prices starting at
$116 NZD before taxes and fees
Total number of reviews
2.4K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
10 properties include access to Wi-Fi
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- Gulf State Park
- Gulf Shores Public Beach
- Alabama Point Beach
- Destin Harbor Boardwalk
- Romar Lakes
- Crab Island
- Princess Beach
- OWA Parks & Resort
- James Lee Beach
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Waterville USA/Escape House
- Langdon Beach
- Perdido Key Beach
- Pensacola Dog Beach
- Branyon Beach
- Tiger Point Golf Club
- Steelwood Country Club
- Pensacola Beach Crosswalk
- Surfside Shores Beach
- Gulfarium Marine Adventure Park
- Eglin Beach Park
- Gulf Shores Shrimp Fest
- Adventure Island