
Vacation rentals with a kayak in Santa Rosa Island
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Top-rated kayak rentals in Santa Rosa Island
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House rentals with a kayak

*Private Waterfront Retreat: Kid & Pet Friendly*
Our stay was great! The house looked as depicted in the photos - everything was clean and inviting. It was great for our family vacation! The neighborhood was peaceful and quiet. We especially liked the swings at the dock - we spent time there every morning looking out over the water! Sarah was communicative and flexible about our check in time as well!

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.

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

Lagoon & Beach! Private Pool, Sleeps 12, Location
Great location to the beach, quiet neighborhood, great outdoor space, beautiful views of the lagoon, comfortable beds!

The getaway spot
John’s home is a perfect place to stay in Pensacola. It’s in a safe neighborhood and is centrally located. We were in town over Memorial Day weekend for a funeral and did not have much traffic to deal with despite the house being close to the naval base and beaches. Everything we needed was available and check- in was super easy. I highly recommend this house for a stay in Pensacola.

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!

Kayaks & Paddle boards/Private Patios Water Views
We had a fantastic stay during our girls’ trip! The townhome is perfectly situated in a quiet neighborhood, with serene bay views on one side and just a short five-minute walk to the beach on the other. Kayaking on the peaceful bay was a definite highlight. The home was spotless and well-equipped with everything we needed for a comfortable and relaxing beach week. We made great use of the kayaks, beach gear, and spent plenty of time unwinding on the balconies. The location was also ideal—just a quick drive to great restaurants, shopping, and downtown Pensacola. Lauren and Reid were exceptional hosts—friendly, responsive, and thoughtful. Thank you for making our trip so memorable. We’re already looking forward to coming back!
Cottage rentals with a kayak

Hammock Hideaway - waterfront cabin
We had a great trip.! Extremely accommodating for our family of four. We came for a fishing trip. They have kayaks we all enjoyed taking out to the bay. Caught several different types of fish, and even seen some dolphins one evening. Far enough away for a peaceful vacation, yet close enough to drive to the beach for the other fishing we did. Great stay.! Fantastic hosts.!

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!

Pool/Lagoon/Beach Views/Paddle Boards/Kayaks 4/4!
Absolutely loved this stay! The pictures do not do it justice, it was beautiful! The house smelled and looked great right when we stepped in. Meredith was such a great host! Super responsive before and throughout our stay! She went above and beyond for our stay this weekend! I would 100% book again! This stay was amazing and I was so sad to leave. Book here if you are thinking about it!!

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.

Retro Cottage by the Bay:15 Mins 2 Beach/Pets
Nice place to stay with family and friends…. We was in 4 adults and 3 kids, and it was perfect, the fact of just have one bath may take us little tight, but the rest of house was really spacious…. Great outside space, to parking and/or play with kids. view of Sea from the house is spectacular. We could stay for a lot off days, the house is very comfy and welcoming…… They also have one side gate that work well to come in with boat/jetski or trailer……If I could describe this property in one word it would be: AMAZING.

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-
Wendye was super responsive and proactive as our host. We planned to bring our two goldendoodles and typically use a playpen instead of a crate. Since the house rules say a crate must be used, I ran the playpen by Wendye for approval and she was very understanding and accommodated us by allowing the use of it instead of crates. Overall the stay was exactly as expected and we were very happy to have chosen this host and property! Thank you!
Cabin rentals with a kayak

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
We really enjoyed our stay! The place was great. So peaceful! Joseph did well at communicating as well! We hope to go back again!

Dat Lakehouse Retreat w/private dock & more!
Absolutely loved the place! Look forward to staying here again soon! Perfect place to relax and enjoy the old Florida feel while still being just down the road from everything everyone loves about PCB!

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!

Blessed
Such a cute little cabin we had a nice weekend. Everything was just as described would go back.
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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
- Walton Dunes Beach Access
- Wayside Park, Okaloosa Island