
Holiday rentals with a kayak in Santa Rosa Island
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Top-rated Accommodation with a Kayak in Santa Rosa Island
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Holiday House Rentals with a Kayak

Romantic Seagrove Palmetto Bungalow 30A Lakefront
We LOVE the Bungalow. Could not recommend it more to couples visiting 30A. We really enjoyed the outdoor space - morning, afternoon, and night. The inside was clean, comfortable, and had everything you need. Felicia is a great host!

Beach FRONT| Deep Fishing Pier |Pet Friendly
We had such a fun vacation. The view was breathtaking and fishing off of the pier was a blast! We hope to rent this place again next year!

Spectacular golf course home 15 min to beach
This was a great home to stay in.

Perfect Executive Getaway!
John was a wonderful host!!! I would definitely stay again. The house is very nice and has everything you need. The neighborhood is upscale and quiet!! All the neighbors were very friendly and spoke passing by on their boats as well as when we passed by on ours!! They even recommended places to fish and that was very helpful.

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

6 mi to beach Pickleball Pool Hot tub Paddle Brds
This was truly a home away from home for us on our family vacation! We felt so comfortable here and everything was pristine upon arrival. We all loved our bedrooms and the beds were very comfortable which is a big deal for a vacation rental. The biggest plus of this house for a family with four kids was the POOL!!! There were so many pool toys and we spent most of our time swimming! The backyard was super fun and our kids were in heaven. There were bikes to ride, a basketball hoop, a treehouse with a slide and swings, a hot tub, and an outside tv, couch, and dining table. It was very quick for us to get out to the beach from the house and we were able to use all the beach stuff from the garage including chairs, buckets, shovels, boogie boards, etc. The neighborhood is quiet and so beautiful with all of the trees. We would definitely recommend this house to anyone, especially families! We had a great experience.

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.

Kokomo Key on Navarre Beach - Private Pool
Our large family gets together every year at the beach. Everyone agreed this was our best trip yet - and we’ve had great ones in the past. The house had more than enough room for all of us, the kitchen had everything we needed, the pool and 2 beaches gave us lots of fun options. The kids rode bikes, relaxed n the hammocks, used the kayak and paddle board, and enjoyed the pool. It was wonderful to have an outdoor shower to keep tracking sand to a minimum. If 10 stars had been an option, we would rate it as 11!
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!!

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.

Retro Cottage by the Bay:15 Mins 2 Beach/Pets
This beautiful home exceeded all expectations! The view of the sea is absolutely stunning — you can enjoy it from the living room, kitchen, and even while relaxing outside. Every detail of the house is thoughtfully designed, and it comes with all the amenities you could need. From the cozy, well-furnished rooms to the fully equipped kitchen, it truly felt like a home away from home. Whether you’re looking for a peaceful retreat or a comfortable space for family or friends, this place is perfect. I can’t wait to come back!

Waterfront Cottage Unit, Keyless, mins to beach
Had the best time here! Beautiful marsh area and so fun to explore with canoe and kayak. Such a peaceful and relaxing space.

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

Safe Harbor Cottage on Santa Rosa Sound - Pets ok!
These are some of the best hosts we have ever had! From the moment we arrived with a tire issue, Steve was immediately friendly and helpful with multiple local repair shops to try and suit our needs. In the following days he had lots of local restaurants, dive locations and dog park recs. Their place has all the necessities you'd need on your vacation. The kitchen allowed us to cook breakfast, and prepare leftovers any day we needed. All other rooms were stocked, clean and well kept. The dogs loved to fetch n cool off in the Sound on their frequent swims. Lush foliage was a surprise as it contributed to wildlife, birds and shady temps! It is definitely the place to privately slow down, sit back an watch the sun rise on the dock as boats travel by slow and unbusily. Topping it all off was the spacious porch/yard with water hose. It spoiled us as we are usually unable to fully rinse and dry out all of our dive gear before returning home. Come and visit their oasis, you won't regret it!!

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!!

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!
Destinations to explore
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- Alabama Point Beach
- Destin Harbor Boardwalk
- Crab Island
- Princess Beach
- James Lee Beach
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Blue Mountain Beach
- Grayton Beach State Park
- Langdon Beach
- Perdido Key Beach
- Pensacola Dog Beach
- Tiger Point Golf Club
- Pensacola Beach Crosswalk
- Gulfarium Marine Adventure Park
- Eglin Beach Park
- Raven Golf Club
- Camp Helen State Park
- San Carlos Beach
- Pensacola Dog Beach West
- Seacrest Beach
- Fort Walton Beach Golf Course
- The Track - Destin
- Wayside Park, Okaloosa Island