Vacation rentals with a kayak in Santa Rosa Island

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Popular amenities for Santa Rosa Island kayak rentals

House rentals with a kayak

Top guest favorite
Home in Navarre
4.99 out of 5 average rating, 67 reviews

*Private Waterfront Retreat: Kid & Pet Friendly*

DanRating, 5 stars3 weeks ago
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!
Top guest favorite
Home in Inlet Beach
4.97 out of 5 average rating, 110 reviews

New Heated Pool & Interior/Walk to Private beach!

HeatherRating, 5 stars1 week ago
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.
Guest favorite
Home in Navarre
4.97 out of 5 average rating, 76 reviews

Beach FRONT| Deep Fishing Pier |Pet Friendly

JoeRating, 5 stars3 weeks ago
Great stay. We enjoyed all the equipment, fishing equipment, paddle boards, beach chairs, etc
Guest favorite
Home in Gulf Shores
4.96 out of 5 average rating, 129 reviews

Lagoon & Beach! Private Pool, Sleeps 12, Location

TomRating, 5 stars1 month ago
Great location to the beach, quiet neighborhood, great outdoor space, beautiful views of the lagoon, comfortable beds!
Guest favorite
Home in Pensacola
4.85 out of 5 average rating, 34 reviews

The getaway spot

KristinRating, 5 stars3 weeks ago
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.
Guest favorite
Home in Navarre
5 out of 5 average rating, 12 reviews

Beach, Kayaks, and Water Access!

LauraRating, 5 stars2 months ago
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
Guest favorite
Home in Gulf Breeze
4.92 out of 5 average rating, 25 reviews

Close to Beach Pool with Canal View

iaRating, 5 stars2 weeks ago
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!
Guest favorite
Home in Pensacola Beach
5 out of 5 average rating, 61 reviews

Kayaks & Paddle boards/Private Patios Water Views

AliceRating, 5 stars6 days ago
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

Top guest favorite
Cottage in Elberta
4.98 out of 5 average rating, 98 reviews

Hammock Hideaway - waterfront cabin

JessicaRating, 5 stars1 week ago
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.!
Top guest favorite
Cottage in Pensacola
4.97 out of 5 average rating, 75 reviews

Coastal Country Living

SloaneRating, 5 stars2 weeks ago
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!
Guest favorite
Cottage in Gulf Shores
4.95 out of 5 average rating, 73 reviews

Pool/Lagoon/Beach Views/Paddle Boards/Kayaks 4/4!

JuliaRating, 5 stars2 months ago
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!!
Top guest favorite
Cottage in Pensacola
4.98 out of 5 average rating, 56 reviews

Octopus Cottage

TeylorRating, 5 starstoday
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!!
Top guest favorite
Cottage in Fort Walton Beach
5 out of 5 average rating, 15 reviews

Luxury Beach Cottage With Private Beach

SarahRating, 5 stars2 days ago
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.
Guest favorite
Cottage in Freeport
4.98 out of 5 average rating, 45 reviews

Retro Cottage by the Bay:15 Mins 2 Beach/Pets

KelvinRating, 5 stars2 weeks ago
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.
Superhost
Cottage in Freeport
4.85 out of 5 average rating, 101 reviews

Waterfront Cottage Unit, Keyless, mins to beach

KristenRating, 5 stars2 weeks ago
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!
Top guest favorite
Cottage in Pensacola
4.99 out of 5 average rating, 155 reviews

Perdido Coastal Cottage- pets ok w/ fee-

MelissaRating, 5 stars2 weeks ago
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

Guest favorite
Cabin in Milton
4.96 out of 5 average rating, 23 reviews

Riverfront Milton Cabin w/ Boat Ramp & Dock!

KayrenRating, 5 stars1 week ago
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.
Top guest favorite
Cabin in Elberta
4.98 out of 5 average rating, 45 reviews

Creekside Fishcamp

MelodyRating, 5 stars2 weeks ago
We really enjoyed our stay! The place was great. So peaceful! Joseph did well at communicating as well! We hope to go back again!
Cabin in Panama City Beach
4.7 out of 5 average rating, 10 reviews

Dat Lakehouse Retreat w/private dock & more!

ChrisRating, 5 stars3 weeks ago
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!
Guest favorite
Cabin in Pensacola
4.85 out of 5 average rating, 13 reviews

Waterfront Pensacola Paradise with Boat Slips!

TimothyRating, 5 stars8 months ago
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!
Cabin in Foley
4.69 out of 5 average rating, 118 reviews

Blessed

TaraRating, 5 stars1 month ago
Such a cute little cabin we had a nice weekend. Everything was just as described would go back.

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