Holiday rentals with a kayak in Santa Rosa Island

4.91 out of 5 average rating, 236 reviews

The exterior of the cottage features a stone facade and a covered carport. A well-maintained path leads to the entrance, surrounded by established shrubs and greenery. A gravel driveway provides access, with a fenced yard visible in the background.

Cabin in Mary Esther

Safe Harbor Cottage on Santa Rosa Sound - Pets ok!

Well furnished private one bedroom cottage with sunroom, patio, and carport. Full kitchen with bar counter. Has washer/dryer! There's a fenced yard with small deck, perfect for dog owners. The home is situated under shady oak trees with access to waterfront on Santa Rosa Sound. You can enjoy playing with the pooch, swimming, boating, kayaking, fishing, and viewing beautiful sunsets. It's a perfect location for visits to Hurlburt AFB, or vacationers seeking easy access to Ft. Walton and Navarre.

4.92 out of 5 average rating, 157 reviews

Townhouse in Destin

Harbor-front Oasis| Steps to the Beach

LOCATION, LOCATION, LOCATION! 5-min walk to the beach. 5-7 minute short drive to exciting Harbor Walk Village or Henderson State Park, what more could you ask for? The unit is conveniently situated in a very quiet, safe neighborhood. One of Destin’s most desirable locations. Open, spacious floor plan, dual balconies, water views, activity space in the garage and extra comfortable bedrooms await you. Arrange for a water taxi to pick you up directly from your boat slip-just outside of your condo!

4.99 out of 5 average rating, 172 reviews

A wooden dock extends into Poquito Bayou, featuring a green umbrella providing shade over a seating area. The clear blue water reflects the sky, while the shoreline is lined with lush greenery. Nearby, a flag is visible, indicating a peaceful outdoor setting.

Apartment in Shalimar

Sylvia's Suite Dreams-kayak & paddleboard free

Live like a local on beautiful Poquito Bayou in Shalimar, FL. This detached guest house will give you access to a gorgeous dock complete with private parking and located less than 20 minutes, by boat or car, from world class beaches and Destin. Our property can accommodate a 2-axle boat trailer. Wake up in the morning and watch the dolphin jump off the dock, fish, go for a swim, paddleboard, kayak or just relax with a cup of coffee. We will work with ALL DOD and DOD contractors and personnel.

4.97 out of 5 average rating, 207 reviews

An aerial view captures the beachfront studio’s location within the Sandestin Resort. The image showcases the pristine white sand and turquoise waters, with pools visible nearby and lush greenery surrounding the buildings, emphasizing the resort’s spacious coastal setting.

Condo in Sandestin

Light &Airy ON Beach | Golfcart*| Oceanview | Pool

Sleek airy 1st floor studio ON BEACH. Sandestin Resort between Destin & 30A. Beach/Pool/HotTub 1 min from patio. Golf Cart w/4+ nts. Pottery Barn King bed with beachfront view. Step off your private patio to the beach or relax on the patio Bali bed. WiFi, 55” smart TV, Kitchen, Washer/dryer. Enjoy free gym, tram, beach, trails, golf, dining, shopping & entertainment all without leaving resort! Perfect honeymoon, baby moon, romantic getaway, girls trip, solo travel or lil’ fam vacay! *NO animals

4.97 out of 5 average rating, 106 reviews

A cozy studio features a queen bed dressed in soft linens, flanked by bedside tables with lamps. A comfortable sofa is positioned nearby, complemented by a decorative coffee table. Art depicting sea life adorns the walls, and a stylish chandelier adds character to the space.

Condo in Sandestin

“Sea La Vie” (the Sea is Life) Lasata-Baytowne

BAYTOWNE STUDIO CONDO WITH BALCONY - Lasata #3307 "Sea La Vie" (the Sea is Life)…We welcome you to our cozy and quaint get away on the Bay side/the Village. From the sand to the very sound of the waves, the Sea is the Life we all crave. Come and enjoy the restful pleasures of Baytowne and all it has to offer. There is plenty of restaurants, shopping and beach access across the Hwy (Sandestin Hilton entrance) only a 5 minute drive. After a stay in Sandestin, life will become more manageable.

Townhouse in Santa Rosa Island

An outdoor dining area features a white circular table surrounded by six adirondack chairs. A partial view of the ocean and sandy beach is visible in the background, under a clear blue sky with few clouds.

4.99 out of 5 average rating, 75 reviews

Luxury Beachfront Home, Sleeps 12, Kayaks, SUPs

🏖 Luxury Beachfront Home for multi-family stays with everything included! Sleeps 12, 3 BR/3.5 BA + 4 Parking spots. On the beach! Unlike most beachfront rentals, this home includes full beach setup and toddler gear—no rentals needed. 🛏 Sleeps up to 12 comfortably 🛌 Beds 1 King, 3 Queens (1 pullout) & 2 sets of bunks 🛁 3 full baths + 1/2 bath 🚗 Parking for 4 cars 📶 Fast Wi-Fi + computer monitor 📺 4 Smart TVs 🚣‍♂️ 3 Kayaks, 2 SUPs, beach chairs, umbrellas, boogie boards, beach toys!

The image displays a large lagoon-style pool surrounded by palm trees and tropical landscaping. Lounge chairs in blue and white are positioned along the poolside. A shallow entry area can be seen, along with a bridge leading to a shaded structure in the distance.

4.94 out of 5 average rating, 154 reviews

3107 Poolside Villa ~ Pools ~ Bar ~ Book Aug 1st

One of only 14 Exclusive Poolside Villas! Welcome to the Villa Cabana Royale! 1450 sq ft of open concept space, with a walk in/ walk out setup, double sliding doors to bring the outdoors in. This poolside villa cabana sleeps 6 and is the perfect location, with an outdoor dining and patio experience in the tropical gardens alongside the gorgeous lagoon pool. The Villa Cabana Royale has 2 huge bedrooms, 2 King Beds, single chair bed, queen sofa sleeper. 4 beds in total. 65" Inch Smart TVs

The living area features a light-colored sofa and a patterned armchair, positioned around a glass coffee table. Large sliding doors reveal direct views of the beach, allowing natural light to brighten the space. A flat-screen TV is situated on a media console across from the seating.

4.95 out of 5 average rating, 111 reviews

Beachfront at Pelican Beach, Stunning Ocean View

Pelican Beach Resort 306 - 3rd floor 1 Bedroom 2 Bathroom 873 sq.ft. condo with Wifi, Free Parking, Smart/Cable TVs, Beach Chairs and Umbrella aiming best class service is right on the beach with great views of Gulf Coast from the balcony. No road crossings, just go down and enjoy our private beach. Pelican Beach offers the dream vacation with BEST views, sand and sea in the area at 5 minute drive from heart of Destin, Harborwalk Village and across Big Kahuna Water & Adventure Park.

4.81 out of 5 average rating, 140 reviews

Home in Santa Rosa Beach

Waterfront! Sleeps 14 & TWO Story Waterslide Fun!!

This family fun home has a 2 story super fast custom water slide, large pool, (extra charge to heat pool) swim up bar, outdoor tiki hut bar with sink and gas grill, charcoal grill, fire pit, sandy beach, dock, boat slip, (no boat lift) paddle boards. Private suite with kitchen & bathroom on lower level with private access leading out to bay. bring your own fishing gear if you like to fish. Home is a labor of love and has brought so much joy to our family & hopefully to yours.

Townhouse in Miramar Beach

4.88 out of 5 average rating, 129 reviews

Gulf Walk * House with Pool & Golf Cart

1 Block to the Beach! Enjoy a beach equipped garage with golf cart, backyard pool, and plenty of space for families or groups — all in one of Miramar Beach’s most desirable locations. This beautifully designed 2BR / 2.5BA townhouse is located in the popular Gulf Walk comm just a short 5-minute walk or 1-minute golf cart ride to Private Beach. With custom coastal-modern design, high-end furnishings, and thoughtful details throughout, this home is the perfect beach getaway.

5 out of 5 average rating, 18 reviews

WaterScape Now Booking 2026! Beach/resort/pool/spa

Stylish 3BR at WaterScape Resort #A225—just steps to pools, splash park, and the sugar-white sands of Fort Walton Beach. Two King suites with memory foam beds, a private bunkroom with 2 TVs, full kitchen with quartz & stainless, pull-out sofa, smart TVs, washer/dryer, tile floors, plus a fun milkshake bar and coffee bar. Also a selfie wall for those picture perfect shots! Complimentary beach service included. One of Expedia’s Top 10 global destinations!

A bright living area is showcased with large windows offering panoramic views of the Gulf of Mexico. Comfortable seating is arranged around a coffee table, with a wall-mounted TV in view. Soft curtains frame the windows, enhancing the coastal ambiance.

4.86 out of 5 average rating, 136 reviews

Beachfront, 2 BR, 16th Floor, Spectacular Views

In the heart of Destin, FL. Step out of the building to the spectacular white sand beaches of Destin. Fully renovated unit with breath taking panoramic views of Gulf of Mexico. Large master suite with private bathroom, and Gulf views. 2nd bedroom with comfortable beds, and guest bath. Fully stocked kitchen and all new appliances. Washer and dryer in the unit. Enjoy complimentary Cable, High Speed WiFi. Beach chairs and umbrella included in the unit.

Popular amenities for Santa Rosa Island kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.89 out of 5 average rating, 114 reviews

The exterior of the designer home features a two-story structure with a white façade, surrounded by green grass and palm trees. A spacious covered porch includes black rocking chairs and leads to a pool area. The property is enclosed by a white fence, enhancing privacy.

Home in Destin

Sundance: Sleeps 18! 1 Block to Beach! Pool & spa!

Home in Fort Walton Beach

A waterfront property featuring a private pool surrounded by a spacious yard. A large dock extends into the water, offering areas for seating and easy access for fishing or boating. Lush greenery and palm trees frame the picturesque setting, enhancing the overall outdoor appeal.

4.95 out of 5 average rating, 77 reviews

Waterfront~Retreat ~Pool & Deep Dock~Boats welcome

5 out of 5 average rating, 16 reviews

An aerial view highlights the serene location of the property, surrounded by lush greenery and water. Nearby access points to the lake and beach are marked, showcasing the proximity to the coastal features of the area.

Home in Santa Rosa Beach

167 Oyster Lake Dr Private pool & Easy Beach Walk

5 out of 5 average rating, 31 reviews

Home in Destin Harbor

Destin Condo: Pool, Private Beach, Beach Cart

Home in Fort Walton Beach

A spacious backyard features a private pool surrounded by a grassy area, with lounge chairs positioned for relaxation. A covered patio offers seating for guests, while a large tree provides shade. The home structure is positioned nearby, enhancing the outdoor retreat.

4.84 out of 5 average rating, 50 reviews

Sleeps 12* Private POOL * Backyard * Ranch Home

Home in Fort Walton Beach

A serene waterfront scene is presented at sunset, showcasing a wooden dock extending into calm waters. Six chairs are arranged on the dock, while a boat is docked nearby. The sky is filled with soft hues of purple and pink, reflected on the water.

5 out of 5 average rating, 21 reviews

Boater/fisherman’s paradise with on-site launch!

4.89 out of 5 average rating, 74 reviews

A dining area is presented with a wooden table and matching bench, surrounded by light blue chairs. A large octopus-themed artwork adorns the wall, while a vase with white flowers sits as a centerpiece. Natural light enters through a glass door, enhancing the space.

Home in Mary Esther

Beach house 2 min from the Boat Ramp and Dog Beach

5 out of 5 average rating, 6 reviews

Home in Mary Esther

Private Water Access | Heated Pool | Kayaks

Cottages with a kayak

A serene waterway reflects the soft colors of sunset, with trees lining the banks and tall grasses swaying gently at the water's edge. The landscape showcases a blend of greens and browns, creating a calm and tranquil atmosphere.

Cottage in Freeport

4.87 out of 5 average rating, 46 reviews

2 bedroom cottage with hot tub

4.83 out of 5 average rating, 167 reviews

A welcoming entrance features a covered porch adorned with vibrant pink flowers and a birdhouse. Two white chairs are positioned beside a small table, inviting guests to enjoy the serene setting. A decorative wind chime adds a touch of charm to the doorway.

Cottage in Mary Esther

Nature's Nest Cottage on the Sound - Pets Welcome!

Cottage in Fort Walton Beach

Two lounge chairs are positioned on a wooden dock, facing tranquil green waters under a bright blue sky. The expansive waterway is visible, with a distant pier extending into the horizon, inviting relaxation and enjoyment of the coastal scenery.

5 out of 5 average rating, 33 reviews

Waterfront Bliss Beach Cottage

4.92 out of 5 average rating, 65 reviews

Cottage in Freeport

Bayview Cottage | Dog Friendly | 15 Min to Beach

Other holiday rentals with a kayak

4.87 out of 5 average rating, 31 reviews

A spacious outdoor deck features a large wooden table surrounded by matching chairs, all shaded by a large umbrella. The view overlooks the marina with boats docked, palm trees lining the area, and buildings in the distance, creating a serene waterfront atmosphere.

Townhouse in Destin

Waterfront Townhome near Destin Harbor Boat Slip

4.93 out of 5 average rating, 14 reviews

Reef Retreat 153 @ El Matador - Gulf front resort

5 out of 5 average rating, 5 reviews

Destin 9216 Sandpiper Cove 1 Bedroom with Bunks

5 out of 5 average rating, 59 reviews

The covered outdoor space is equipped with a spacious sectional sofa adorned with decorative cushions. A wooden coffee table sits at the center. The area features a high ceiling with wood paneling, and large sliding doors open to a sun deck with seating.

Townhouse in Destin

Canalfront, Boat slip, Hot Tub, SUPs, Dogs, Beach

4.95 out of 5 average rating, 79 reviews

A sweeping view from the balcony showcases the resort's multiple swimming pools, surrounded by lounge chairs. The ocean sparkles under clear skies, with boats visible in the marina and a scenic shoreline in the distance.

Condo in Destin Harbor

Perrydise@ Emerald Grande 3BR Harbor & Gulf Views!

The living area features a spacious layout with a large sectional sofa and a comfortable armchair. A 65-inch curved TV is mounted on a decorative cabinet. Floor-to-ceiling windows provide views of the Gulf, and a dining area is visible in the background.

4.81 out of 5 average rating, 81 reviews

IRC 604: Gulf Front Luxury (2 Bed / 2 Bath)

A lush tropical landscape is featured, with tall palm trees surrounding a winding lazy river. Colorful inflatable floats are visible in the water, while lounge chairs and umbrellas provide shaded seating areas. The beach and resort buildings are seen in the background, enhancing the relaxing atmosphere.

5 out of 5 average rating, 19 reviews

DW Sandpiper L03 ~ Walk Out Lanai ~ Lazy River!

An aerial view captures the expansive Waterscape Resort, featuring multiple engaging pool amenities surrounded by lush palm trees. The ocean's vibrant blue water is visible in the background, with clusters of nearby buildings housing vacation rentals.