
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!

New Heated Pool & Interior/Walk to Private beach!
Aimee’s home has 5 stars for a good reason! From the minute we started to plan the trip to the time we left Aimee was extremely helpful! The home was so clean and in a quiet area. My kids loved swimming in the pool in the morning. If there were any questions or issues Aimee was so responsive and quick to help in whatever way she could. We loved how close it was to the beach. We were able to ride bikes to almost everywhere. The beach bungalow is in a great location. We would absolutely stay here again.

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.

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

Beach FRONT| Deep Fishing Pier |Pet Friendly
Great stay. We enjoyed all the equipment, fishing equipment, paddle boards, beach chairs, etc

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

Beach, Kayaks, and Water Access!
Very ecstatic with Airbnb. Eric and Katie were like working with family members. Had a life changing event in our family and thought we were going to have to change our dates I had originally reserved. Eric was very helpful during that period. We love this area. We have family about 50 miles from the Emerald Coast. We were able to check out the two peers going to Destin and Pensacola for activities. Also were able to get into Baker for the Strawberry Fields, and Samuel‘s steakhouse in Crestview. Don’t forget to use the National Seashore to go into Pensacola. All a very easy approximately 30 minute drive. It was just the two of us with our two small dogs 🐶 🐶 Thanks again. Would love to reserve your place next year. The weather was very cooperative Mar. 14-24

Close to Beach Pool with Canal View
Family of 4 plus one small pup all enjoyed a wonderful staycation with a beautiful pool, yard, house, and location. Beautiful space with lots of lights. Very clean, easy to location, host communicated very quick, and would be willing to stay again in the future. Thank you so much for hosting my family and allowing us to call your space home for a few days!
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
From the moment we arrived, we knew we had found somewhere special. Our hostess was the best we’ve ever encountered, genuinely kind, attentive, and clearly passionate about creating a beautiful experience for her guests. The cottage was absolutely enchanting with original doors, creaky floors that tell a story, and antiques that give the space so much character and history. It felt like stepping into another time, in the best possible way!! The private beach on the bay was pure magic. Quiet, peaceful, and breathtaking. The hostess had an amazing selection of beach gear available in the storage area, which made beach days even easier and more fun! Just a short walk from the cottage was a lovely park that was perfect for our kids to run and play. It made the stay even more family-friendly and convenient. We can’t wait to return. This place has our hearts!

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
This place is so cute! From the roosters crowing in the morning to the tree frogs singing in the evening; we loved it. The property is filled with charm having beautiful gardens & a variety of Annie's antique treasures around the cottage... vintage, quirky ,rustic... It all takes you back to a simpler time and gives you that true southern, "old florida" vibe. Annie is so personable and sweet..and knows all the hot spots around town for shopping, food and adventure.... and its just a short drive to the beautiful white sandy beaches on the Gulf. Wonderful place!

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!
The house was in great shape. the outdoors were peaceful. I enjoyed having coffee on the dock at the water every morning during our stay.

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
I booked Stephen’s place for my parents for their honeymoon and they loved it! They enjoyed the privacy, simplicity and peacefulness of the cabin and they loved sitting on the dock. Stephen was also super helpful and accommodating with checkout.

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!
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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
- Langdon Beach
- Grayton Beach State Park
- Blue Mountain Beach
- Perdido Key Beach
- Pensacola Dog Beach
- Tiger Point Golf Club
- Pensacola Beach Crosswalk
- Camp Helen State Park
- Pensacola Dog Beach West
- San Carlos Beach
- Raven Golf Club
- Eglin Beach Park
- Gulfarium Marine Adventure Park
- Fort Walton Beach Golf Course
- Seacrest Beach
- Wayside Park, Okaloosa Island
- Walton Dunes Beach Access