Vacation rentals with a kayak in Santa Rosa County

4.95 out of 5 average rating, 193 reviews

A view from the deck captures a tranquil pathway leading to a private dock, flanked by trees. Lush green grass fills the yard, and the calm waters of the bay are visible in the distance under a clear blue sky.

Apartment in Gulf Breeze

Redfish Loft, private waterfront Apt. on East Bay

PafouaRating, 5 stars1 day ago

Jeff and Mary’s house was perfect for the two of us! Everything was clean and spacious enough for the two of us. I especially loved the use of the dock for fishing and the deck and wrap around balcony for longing around. I would gladly rent it again in a heart beat!

4.88 out of 5 average rating, 144 reviews

Two bright yellow kayaks are positioned on the grassy shore, facing the calm water. Tall trees and sparse vegetation frame the serene view of the waterfront, with a clear blue sky and wispy clouds above. The natural landscape invites exploration and outdoor activities.

Camper/RV in Navarre

Bayfront Forest Camper with kayaks/nature trail

NoahRating, 5 stars1 day ago

We were down for a wedding and decided to stay for one night to enjoy the bay and to kayak. This was the perfect place to be on the last day of our trip. Check in was at 4 but the host was flexible in letting us check in at noon so we could enjoy the day on the land. The host were amazing and very personable and we will be planning a full week in the near future. It was peaceful, clean, and much needed before heading back home!! Memorable stay and beautiful scenery. Very peaceful and serene.

4.93 out of 5 average rating, 150 reviews

A charming orange cabin is set among tall trees, surrounded by a green lawn. A welcoming front porch with white railings is complemented by an American flag. A wooden deck leads to the raised sunroom, creating a connection to the serene natural surroundings.

Cabin in Century

Absolute Tranquility

WilbertoRating, 5 stars4 days ago

We wanted to take a moment to express our heartfelt gratitude for sharing your little slice of private paradise.This cabin was really clean and well stocked. It was an absolute pleasure to spend our 16th anniversary here. The kayaking was a highlight for us, we enjoyed exploring the calm waters, and seeing all the nearby animals. Our dogs were so happy to run around the property. The hot tub was a definite recharge during our relaxation session, surrounded by nature's serenity. We're grateful for the laughter, stories, and memories we created and definitely would love to return someday.

4.99 out of 5 average rating, 140 reviews

Two white kayaks are positioned in the foreground, facing a tranquil waterway covered with lily pads. Surrounding greenery and trees create a serene natural landscape under a partly cloudy sky.

Guesthouse in Milton

Charming Bayou Bungalow - walk to downtown Milton!

NoraRating, 5 stars2 days ago

This was the nicest Air B&B we have stayed in so far. It was just perfect. It was on a beautiful bayou with places to sit out and enjoy. The accommodations were perfect - very clean, nicely decorated, and all amenities that we needed were available. It was just lovely.

4.93 out of 5 average rating, 187 reviews

A view framed by lush greenery showcases the tranquil waters of Pensacola Bay in the distance. Native plants and flowers add vibrant color, and a wooden path leads toward the sandy beach, blending nature with the scenery.

Tiny home in Gulf Breeze

Water-Front tiny home.

EuniceRating, 5 stars1 week ago

Kim was a wonderful host. We stayed in touch the whole time, and even when we arrived, she welcomed us personally and we had a nice chat about the area. The little beachfront house is a wonderful place—I had an amazing birthday weekend there. Waking up and being able to see the blue water right from your door is priceless! The place is located close to everything! The only issue we had for some reason was with the phone signal, and the Wi-Fi in the house didn’t seem to work either. But other than that, it has all the basic comforts of a cozy little place.

4.95 out of 5 average rating, 244 reviews

A private deck showcases four chairs in vibrant colors, two in turquoise and one in white, alongside a round table. A potted pink flower adds a touch of color. Views of the Gulf are visible in the distance, with soft gray skies above.

Guesthouse in Navarre

S.K.I. Beach House (Spending our Kids Inheritance)

ZanetaRating, 5 stars2 weeks ago

We stayed at Linda and Bud's condo for 6 nights on Spring Break. Right when we walked in, the place felt like heaven. The bed was the comfiest bed we ever slept in. Everything was sparkling clean, and the kitchen had everything you need. The deck on both sides was wonderful, and we sat there every morning drinking coffee. The place was only a few steps to the beach, making it a perfect destination spot. I highly recommend! To quote my 10 year old daughter, it was the "best vacay ever!" Thank you so much Linda and Bud for sharing your condo with us. We will definitely be coming back!- Janet, Greg and Alice:)

4.94 out of 5 average rating, 134 reviews

An orange kayak rests on sandy ground near the water, accompanied by two turquoise chairs positioned for relaxation. A grassy area surrounds the kayak, leading to a dock visible in the background, framed by lush trees and a cloudy sky.

Townhouse in Gulf Breeze

Gulf Breeze Your own private resort on the bay!

SarahRating, 5 stars1 month ago

This was a very clean, and peaceful slice of paradise. Everything was immaculate, and honestly felt so homey in a coastal granny kinda way. We regretted only spending 3 nights! We found it easy to cook our own meals with the kitchen supplies provided and loved the fire pit. *don’t miss out on a meal at Shaggys though!*

4.99 out of 5 average rating, 105 reviews

Soundside Paradise

DavidRating, 5 stars6 days ago

This was a beautiful property! It was located directly on the intercostal waterway - which was fantastic for breakfast/coffee mornings and sunset evenings from the back porch. There were plenty of beach chairs/boogie boards and toys for the little ones. No need to pack and bring with you for your trip - which we appreciate. The beach was a stones throw away and we liked to ride our bikes instead of drive/walk. The Kayaks were a hit and wish we would have used them more. I’d like to call out that Robert was super responsive to questions before our trip and was available during our stay. Overall - this trip a true Gem and we look forward to booking again!

4.8 out of 5 average rating, 186 reviews

Home in Milton

*Waterfront Home w/Boat Dock, & Kayaks!

MachelleRating, 5 stars1 month ago

We really enjoyed our stay!! It was a clean, spacious place for the whole family including our four legged friend. We enjoyed the “small town” feel of Milton. Shopping, beaches and restaurants were all very close by. Our host was very friendly and responsive. I would recommend visiting this place.

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What guests are saying

2bedroom with dock, hot tub, pool, & boat charter

4.86 out of 5 average rating, 42 reviews4 weeks ago

Where do I start?! The place was great for my family and dogs. Hal has great communication and super helpful. Hal was going to the store one evening and actually offered to grab us something if we needed. He actually built a stand for the hot tub cover while we were there. Works great! The house has plenty of room. The shower outside was super helpful when we came back from the beach. Thanks Hal!

Villa in Navarre

What guests are saying

Relax on the Sound Side

4.73 out of 5 average rating, 30 reviews7 months ago

Even though it rained every day, porch sitting was great, there is also a covered patio under the porch for grilling and sitting with friends. Access to the beach and ocean was just right there! Perfect location to everything we could want to do. Navarre is now my favorite home away from home!

Condo in Navarre

What guests are saying

Blackwater Bay Bungalow

4.97 out of 5 average rating, 32 reviews2 weeks ago

Steven's home was clean, the master bedroom mattress was extremely comfortable and the view was great. There's a good selection of board games, good Wi-Fi and a smart TV. One thing to note is that there's only one TV in the house and it's in the living room. We had four adults, two children and a Pomeranian and there was plenty of room for all of us. At one point there was no hot water and Steven responded almost immediately. He had a gentleman that promptly arrived and fixed it. The neighbors are very friendly with great dogs. I have no complaints at all and would stay at Steven's again.

Bungalow in Milton

What guests are saying

Sandy Feet Retreat

4.85 out of 5 average rating, 40 reviews3 months ago

Sandy Feet Retreat was quiet and relaxing. The house and kitchen had whatever you could possibly need. Kim thought of EVERYTHING! There is a storage closet with beach chairs, boogie boards, toys, goggles and even sun screen. The kayak was so much fun and there was a carrier that made it easy to walk to the beach with it. Kim was constantly in communication to help make our stay easier. She went above and beyond. We stayed over Christmas and Kim had a Christmas tree set up! She even had some fun gifts under the tree for us when we arrived. I can honestly say she is one of the best air b n b hosts I have ever had the pleasure to deal with. We will definitely stay again if we are at Navarre Beach in the future.

Townhouse in Navarre

What guests are saying

Stay at Sunshine Daydream on Pensacola Beach

5 out of 5 average rating, 131 reviews1 week ago

Condo looked just like the pictures. Was on the second floor of a high-rise condo. Pool was pristine. Nice little beach area on the bay side. Thick concrete walls made for a quiet stay (even during spring break). The best part of this condo is how close it is to the boardwalk, the public beach and many restaurants. You can walk pretty much everywhere you want want to go in Pensacola beach from the location of the condo.

Condo in Pensacola Beach

What guests are saying

CORAL CRAB CONDO-2 Master’s Suites~Pet Friendly

4.79 out of 5 average rating, 243 reviews3 weeks ago

We had an enjoyable stay at the Coral Crab! The townhome was located in a quiet community with an easy walk to the beach and an easy 1.5 mile drive to the nearest dog beach. We brought our pup along to this pet friendly rental and we all enjoyed the space. The kitchen was large enough and well-stocked for frequent cooking. The garage was full of great beach accessories which we took advantage of. Jennifer was a lovely and professional host and we would happily return. :)

Townhouse in Pensacola Beach

What guests are saying

Waterfront Destination - Delightful 2 Bedroom RV

4.77 out of 5 average rating, 39 reviews7 months ago

Clarence and Julie were awesome hosts! The fresh baked bread was especially wonderful. They made us feel like family and the accommodations were extremely comfortable. We enjoyed every minute that we were there and we are so grateful for them and the opportunity to stay.

Camper/RV in Navarre

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Popular amenities for Santa Rosa County kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

Aerial view of the property featuring a spacious one-acre area, the 450-foot dock extending over the water, and a private beach. Surrounding greenery highlights the tranquil atmosphere, while a quiet dead-end street offers a serene environment, visible in the background.

4.98 out of 5 average rating, 63 reviews

*Private Waterfront Retreat: Kid & Pet Friendly*

JessicaRating, 5 stars2 weeks ago

Great stay! Loved doing yoga in the mornings on the dock. Very peaceful setting.

4.79 out of 5 average rating, 110 reviews

The living area is furnished with a large sectional sofa and a circular wicker chair. A light wooden coffee table centers the space, while a decorative rug adds texture. Natural light flows in through a window adorned with blinds, complemented by a small plant and wall decor.

Home in Pensacola

Spacious & Bright 3BR/2B near DWTN & Beach

AndreaRating, 5 stars2 weeks ago

Such an amazing and literally felt like home. Gave great instructions and activities to do. Cleanliness was excellent and the atmosphere loving and family oriented. Will definitely be visiting again. Thanks for having us and being amazing host.

4.98 out of 5 average rating, 165 reviews

Home in Pensacola

Tidy Bayou Bungalow

JenniferRating, 5 stars3 days ago

This was our 2nd time staying here while visiting our college daughter. Beautiful place. Cozy and great for feeding and hanging out with family and friends. The neighborhood is peaceful. We enjoy taking walks. We caught the Blue Angels practicing and some dolphins swimming by!

5 out of 5 average rating, 9 reviews

The open-concept kitchen features a large island with bar seating for four, equipped with modern appliances. Bright blue walls are adorned with nautical decor, while warm wood cabinetry adds contrast. Natural light fills the space, highlighting the inviting interior and providing a welcoming atmosphere.

Home in Mary Esther

Tropic Like It's Hot

AbbieRating, 5 stars3 months ago

This place is amazing! Clean and feels like home. So much space and room for so things to do. The house is secluded but not at the same time. The small “beach” at the house is a major bonus. Kids could easily go play and we could watch from the porch. We seen all kinds of wildlife from eagles, cranes and even a fox. This was the first family vacation we have had in years and it was over Christmas. Dillon did awesome with a Christmas tree and lights on the house and even supplied a gingerbread house for us to build. We definitely plan on being back in the warmer weather so we can enjoy the outside much more.

Two kayaks in vibrant green are positioned on a grassy area near a sandy beach, with life jackets placed nearby. A community pier extends toward the water, and the distant skyline is visible under a clear blue sky.

5 out of 5 average rating, 10 reviews

Large Beach Front| Wedding Venue | Family Reunions

NicoleRating, 5 stars13 months ago

Great place to stay! We booked both condos as we were traveling with 8 adults and 7 kids. Great for a large group. We had small kids and the beach area was great place for them to play as the ocean was calm and shallow. There was also a sand pad away from the ocean. The space was great . She really thought through all amenities. We enjoyed the coffee bar each morning and drinking pork coffee on the deck or by the beach. She has a great amount of beach toys and kayaks , paddle boards, chairs, bikes , etc for the beach and outside activities as well. Would definitely recommend.

5 out of 5 average rating, 79 reviews

A view from a height captures a manicured yard featuring lush green grass and shaded areas provided by surrounding trees. A fire pit is positioned on a brick patio, while a private dock and colorful kayaks are visible near the Blackwater River.

Home in Milton

Relax on Blackwater River

RayRating, 5 stars2 weeks ago

Amazing place to stay on the river. House is awesome, just like the pictures. We didn't stay long, but the one day we had to really enjoy house on the river was amazing. They have kayaks, paddleboards, and canoes with a private launch. Quiet neighborhood with friendly neighbors. It was awesome. Adam and Alisa responded immediately to any questions we had. Great hosts. I can't recommend this place enough.

5 out of 5 average rating, 12 reviews

Beach, Kayaks, and Water Access!

LauraRating, 5 stars1 month 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

4.94 out of 5 average rating, 18 reviews

Pelican Landing Navarre Beach

AudreyRating, 5 stars1 month ago

We loved Pelican Landing! It was the perfect peaceful beach getaway for our large group of 12 people! Plus it had every beach accessory you could ever need- beach towels, chairs, umbrellas, wagon, cooler, bikes, and more! Janice was very friendly and responsive. We had some A/C issues but she was very prompt to send out multiple HVAC technicians the day of, and even provided a free day of golf cart use for the trouble. We highly recommend this house and host!

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Cottage rentals with a kayak

4.99 out of 5 average rating, 83 reviews

A modern kitchen and living area is described, featuring a spacious granite island with a gas stove and stylish bar stools. A large smart TV is mounted above a decorative fireplace, while cozy seating is arranged around the living space. Soft lighting adds to the welcoming ambiance.

Cottage in Pensacola

Comfortable home & game room, near NAS & downtown

KendraRating, 5 stars3 months ago

We loved staying at this cozy home!Everything was just as listed and everything was so cute! We took advantage of the bikes provided and took a ride in the park along the bayou close by. It was very scenic and we love the neighborhood! It is a perfect location for visiting my son who lives on NAS Pensacola. Katie and Chad were very helpful and responsive when I had questions about the area. We loved our trip and our stay there!

4.98 out of 5 average rating, 49 reviews

The charming cottage features a light blue exterior with decorative flower boxes beneath the windows. A white picket fence encloses the front yard, which is neatly landscaped with green grass. A bright red door serves as a welcoming entryway, framed by lush greenery.

Cottage in Pensacola

Octopus Cottage

RobinRating, 5 stars1 month ago

We were so pleased with our stay. This is the most adorable space! Although we didn’t cook while there, the kitchen was well equipped. We are coffee drinkers and he gad everything we needed for our morning cups. We were able to bring our little dog and he loved the little enclosed area. Last night we were walking in for the night and noticed the lovely lights in the trees. You won’t be disappointed staying here!

4.91 out of 5 average rating, 76 reviews

A wooden gate features a sign that reads 'The Bunkalow' in elegant script. A colorful toucan and a flower are depicted beside the sign, adding a tropical touch to the entrance.

Cottage in Pensacola

The Bunkalow, A Cozy Gulf Coast Getaway

AnnaRating, 5 stars1 month ago

D’anna and her family are amazing hosts! Stayed four days during spring break and it was the best airbnb i’ve ever stayed in! Truly a great experience would recommend it 1000%!!