Vacation rentals with a kayak in Santa Rosa County

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Top-rated kayak rentals in Santa Rosa County

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Guest favorite

Townhouse in Milton

4.93 out of 5 average rating, 114 reviews

Fins Left - 30 mins to Beaches on Blackwater River

Relax & take it Easy, You're on River Time in this Cozy, Private Unit of a Riverfront Duplex located on a Quiet Basin along the Blackwater River. This 2 bedroom, 1 bath unit has a Comfortable living room, Full Kitchen & Covered Back Porch with Outdoor Dining & with Great Views. Enjoy breathtaking Sunsets, Kayaking, Fishing & more. Peaceful & Only 30 minutes to Pensacola Beach, Navarre Beach or Downtown Pensacola. Close to bike trails, hiking & Canoeing. Near Wedding Venues & Weber's Skate World.

Feb 4 – 11

G$26,118 GYD per night

Guest favorite

Apartment in Gulf Breeze

4.97 out of 5 average rating, 145 reviews

Redfish Loft, private waterfront Apt. on East Bay

Light airy open floor plan " pet friendly " loft style apartment with private bedroom. Watch the blue herons & dolphins, sit on one of two private decks sipping coffee as you watch the sunrise on the Bay. Paddle the clear waters in our kayaks or bring your SUP. Cook your fresh catch on your private grill or visit a local seafood restaurant. Private, secluded, quiet neighborhood. Join us @ Fire pit that is usually going on the weekends. East Bay is known for it's Red fish and calm waters.

Oct 20 – 27

G$29,371 GYD per night

Guest favorite

Camper/RV in Navarre

4.92 out of 5 average rating, 110 reviews

The Camper Retreat with kayaks and nature trail

The best of both worlds. Our 11-acre waterfront family’s retreat is the ideal getaway for outdoor enthusiasts and beach lovers. With RVs on the front of the property and the occasional tent camper dispersed through out the acreage, you’ll enjoy time away from the crowds walking the mulched trail to the water or using the two kayaks provided for guest use. We offer additional experiences. Outdoor brunch for two/group, afternoon teatime, boho picnic, s’mores bundles, etc. Message with interest.

Nov 28 – Dec 5

G$29,581 GYD per night

Guest favorite

Home in Navarre

4.96 out of 5 average rating, 116 reviews

East Bay Hideaway - Sun. Swim. Sunset. Stargaze.

Nestled between the world's most beautiful beaches, this bayfront retreat has it all. Enjoy captivating views from the kitchen, living & den spaces. Views continue as you step out on the screened lanai w/room for all to gather poolside. Need a warmer, invigorating quiet time? Stroll across the patio & find a privately situated hot tub. Finally, wander down the dock to fish, swim, connect or star gaze over the glassy waters of East Bay. Unbelievable sunsets await, book before this seasons fills!

Oct 22 – 29

G$125,366 GYD per night

Guest favorite

Guesthouse in Milton

4.99 out of 5 average rating, 113 reviews

Charming Bayou Bungalow - walk to downtown Milton!

Enjoy visiting historic Milton while staying in our comfortable cottage, which is close to everything making it easy to plan your visit. Walk to downtown Milton for live music, festivals, breweries, restaurants. Ride on site bikes on Blackwater Heritage Trail. Explore Marquis Bayou and Blackwater River in on site kayaks. Pick blueberries in season. 40 mins to Navarre Beach. 30 mins to Pensacola. Kitchen w/fridge/micro/toaster oven/dbl burner cooktop New Queen bed with comfy Serta mattress.

Mar 20 – 27

G$20,924 GYD per night

Guest favorite

Cabin in Century

4.95 out of 5 average rating, 127 reviews

Absolute Tranquility

Private and secluded retreat! Only a short 35 mins from Pensacola. Unplug at this gorgeous getaway retreat in a country setting. This cozy 2BR/1BA lakefront cabin resides on 25 acres of serenity. Step into the raised sunroom and take in the panoramic views of the spring fed lake and the rolling pastures. Enjoy the shade relaxing in the hammock, or soak in the brand new 4 person hot tub on the lower deck. Deer are out most mornings and evenings. This well stocked lake is great for fishing too!

Aug 5 – 12

G$33,672 GYD per night

Guest favorite

Condo in Pensacola Beach

5.0 out of 5 average rating, 112 reviews

Stay at Sunshine Daydream on Pensacola Beach

Come experience vacation paradise at "Sunshine Daydream" Located in the heart of Pensacola Beach. Perfect beaches, fantastic restaurants/bars, and shopping are only steps away. Enjoy pristine views of Little Sabine Bay from all over this magnificently renovated condo. Unwind on the 300 sq ft covered balcony and watch the sunset from the best location on the island! The complex hosts a large heated swimming pool, private beach, exercise room, dock, elevators, and a full time cleaning staff.

Aug 4 – 11

G$62,362 GYD per night

Guest favorite

Condo in Pensacola

4.96 out of 5 average rating, 148 reviews

Comfy Bayou Cottage - just steps from the water

Are you looking for a comfortable, clean place to relax in an established and desirable area of town while visiting beautiful Pensacola? Then look no further. The Bayou Cottage is located just steps from the water along Bayou Texar and only minutes from the downtown entertainment district and our pristine beaches. Enjoy a morning walk along the waters edge under the oak trees, check out the neighborhood beach or let this location serve as your hub while enjoying all Pensacola has to offer!

Jan 12 – 19

G$27,069 GYD per night

Guest favorite

Bungalow in Pensacola

4.96 out of 5 average rating, 117 reviews

May and June! Red Door Bungalow Downtown Sleeps 6!

Ready for Summer Vacation in Pensacola! Love the charm of an older home, but require the comforts of a modern one? Welcome to our cozy Red Door Bungalow! This quaint home is half a mile from the center of downtown Pensacola. Local restaurants, Blue Wahoos stadium, shopping, parks, and night life are around the corner. 10 mins from NAS. 15 min to the beach. Park and playground are located right across the street. This home is perfect for that quick getaway or mid-term stay! DM questions

Aug 9 – 16

G$27,202 GYD per night

Guest favorite

Guesthouse in Navarre

4.95 out of 5 average rating, 216 reviews

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

One of the new houses on the beach. Where you have beautiful views of the sunrise over the Gulf from your front deck and the sunset over the Santa Rosa Sound from your back deck. You are just a short walk to amazing shelling, swimming, paddle boarding, kayaking, boogie boarding or just plain relaxing on the "Most Relaxing Place in Florida." All on the sugar white sand beaches of the Emerald Coast. During your stay here you will find yourself in a suite full of amenities.

Jan 5 – 12

G$34,002 GYD per night

Guest favorite

Townhouse in Gulf Breeze

4.95 out of 5 average rating, 111 reviews

Gulf Breeze Your own private resort on the bay!

Best sunset's in Pensacola area. A place where you can watch for dolphins, fish off the dock, pull your boat up, take the kayak out. lay under your own pergola with lounge chair's. Listen to the waves while lying in the hammock watch the pelicans crash land in the bay. grill on the deck . have a picnic. swim off the dock , lay in a raft. Fire Pit , corn hole game in garage,1400 square feet with accommodations for 6. 3 bd/ 2.5 bath 3 mile's to Pensacola beach .

Feb 12 – 19

G$33,797 GYD per night

Superhost

Home in Milton

4.79 out of 5 average rating, 151 reviews

*Waterfront Home w/Boat Dock, & Kayaks!

Read full description before booking! 25-30 minutes to the beach depending on traffic. Bring your boat and dock it in your back yard!! Sit on the porch and enjoy coffee in the morning listening to the birds and frogs nearby. The home is nestled in the quiet community of Escambia Shores. Surrounded by tall pines this relaxing home is perfect for a family vacation or honeymoon. Great fishing in the canal or off the dock! Or Kayak into the bay to fish!

Dec 12 – 19

G$20,575 GYD per night