Vacation rentals with a kayak in Santa Rosa Island

Condo in Fort Walton Beach

5 out of 5 average rating, 132 reviews

Waterfront cozy condo with king bed & resort pool

Welcome to The Salty Pirate, your waterfront vacation paradise! Kick back & relax in our calm, stylish condo featuring a king size bed, luxury bathroom & kitchenette. Relax in bed, enjoy the boats cruise by or watch the 65 inch TV. The waterfront balcony entices you to read & relax. Enjoy the resort style pool or reserve the 2-seater kayak (when available) provided for you to explore the waterway. Downtown restaurants & bars are walking distance & the white sugar sand beaches are 2 miles away!

4.92 out of 5 average rating, 154 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, 165 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, 200 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. 🛺 Golf cart w/4+ nts. In Sandestin Resort between Destin & 30A. Beach/Pool/HotTub 1 min walk. Pottery Barn King bed with beachfront view. Step off our 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

A wooden dock extends over calm waters, with two gray deck chairs positioned for relaxation. Lush green trees line the shoreline, and a few houses are visible in the distance under a bright blue sky with scattered clouds.

4.94 out of 5 average rating, 17 reviews

On the water! 7 minutes to the beach!

Bring your boat and your RV. Relax with the whole family in this private water front cottage. 7 minutes to the white sands of Okaloosa Island and 6 miles by boat to Crab Island or just walk out back and paddle the bay. There are 3 public boat ramps with in 2 miles of the property. The waterway will accommodate a draft of 24”. Ferry Street Park and Uptown Station are just minutes away. Everything in the house is brand new and kept perfectly clean and organized so you and yours can relax .

4.97 out of 5 average rating, 101 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.

4.9 out of 5 average rating, 294 reviews

A dining area features a round table surrounded by woven chairs. A cozy sofa and a decorative console table are positioned nearby. Large sliding glass doors provide unobstructed views of the beach, while soft natural light fills the space, enhancing the coastal decor.

Condo in Destin

Beachfront 8th Fl. 1 BR at Pelican, Stunning Views

Completely renovated 8th floor condo right on the beach with unobstructed views of the Gulf and the beach. Located in the heart of Destin in popular Pelican Beach Resort, you will enjoy the private beach, multiple outdoor pools, an indoor pool, hottubs and more. Our beachfront condo has been professionally renovated with brand new cabinets, AC, floors, appliances, furniture, kitchen and more. All mattresses are brand new, cool-gel memory foam for a cool night's sleep. Fully stacked kitchen.

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, 74 reviews

Sea Turtle House-On Beach-Townhome-Kayaks/SUP

🏖 Steps from the Ocean | 3BR/3.5BA Townhome w/ Views + Kayaks & SUPs! Relax in this spacious 3-story townhome—literally steps from the beach! Enjoy breathtaking ocean views, modern comforts, and everything you need for fun in the sun. 🛏 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!

4.87 out of 5 average rating, 108 reviews

Condo in Miramar Beach

Alerio D202: Gulf Beach Escape

This beautiful condo is a 3 bed/2 bath perfect Destin vacation rental with spacious accommodations for up to 7! It’s located in a newly developed area just across the road from the beach. Enjoy a short walk to the beach or open your windows and smell the fresh ocean air from the patio Everything within this space is updated with a modern feel including brand new living room furniture, USB lamps throughout, hardwood flooring, granite countertops and a large balcony that faces Scenic Drive

Apartment in Santa Rosa Island

5 out of 5 average rating, 9 reviews

Newly renovated gulf-front condo on 1st floor

Enjoy your beach getaway in this spacious 2BR/2BA Gulf-front condo! This first-floor unit sleeps 8 with private patio to experience sunrise views over gulf, updated kitchen w/ quartz countertops, renovated baths w/ walk-in shower in the primary, and in-unit laundry. Relax w/ beachfront access, beach chair service (march-oct), pool, fitness center, tennis court, grill, volleyball net, picnic area, kayak, books, games, & dry bar w/ beverage cooler. Close to shopping, dining & attractions!

4.95 out of 5 average rating, 110 reviews

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.

Condo in Destin

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.

Townhouse in Miramar Beach

4.88 out of 5 average rating, 130 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.

Popular amenities for Santa Rosa Island kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.89 out of 5 average rating, 84 reviews

A heated pool features clear blue water surrounded by lush greenery. A hot tub is positioned nearby, and seating areas include a lounge chair with an umbrella and a cozy hanging chair. The outdoor space is enhanced by a wooden decking that leads to the pool.

Home in Santa Rosa Beach

Santa Rosa Beach|Heated Pool|Pet Friendly|Hot Tub

5 out of 5 average rating, 60 reviews

The open-concept kitchen features sleek cabinetry, modern appliances, and a large island, providing an inviting space for meal preparation. In the lower section, a dock area showcases a boat lift and lush greenery along the water's edge, emphasizing the waterfront setting.

Home in Destin

Waterfront, Boat dock, Bikes, BEACH, HOT TUB

4.89 out of 5 average rating, 113 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!

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, 76 reviews

Waterfront~Retreat ~Pool & Deep Dock~Boats welcome

5 out of 5 average rating, 28 reviews

Home in Destin Harbor

Destin Condo: Pool, Private Beach, Beach Cart

An open living area features a cozy seating arrangement with a blue sofa and natural light filtering through bamboo blinds. A flat-screen television is mounted on the wall, and a dining area with four cushioned stools is visible, accompanied by a wooden coffee table and artwork.

4.89 out of 5 average rating, 36 reviews

The Pink Cottage

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, 17 reviews

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

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.

4.87 out of 5 average rating, 47 reviews

Sleeps 12* Private POOL * Backyard * Ranch Home

Cottage rentals 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

4.86 out of 5 average rating, 44 reviews

2 bedroom cottage with hot tub

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, 31 reviews

Waterfront Bliss Beach Cottage

4.83 out of 5 average rating, 166 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!

4.92 out of 5 average rating, 62 reviews

Cottage in Freeport

Bayview Cottage | Dog Friendly | 15 Min to Beach

Other vacation rentals with a kayak

4.87 out of 5 average rating, 30 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

4.97 out of 5 average rating, 30 reviews

The exterior of the waterfront home features a spacious deck connected by a wooden walkway. Surrounding palm trees and lush greenery create a tropical ambiance. A sandy area can be seen by the water's edge, inviting outdoor activities and relaxation.

Home in Niceville

Waterfront Haven - Perfect for Family Vacations

4.96 out of 5 average rating, 26 reviews

A cozy dining area within the Airstream features a white table set for two, accompanied by patterned cushions. A vase of fresh flowers rests at the center, while large windows provide a view of the water and surrounding landscape.

Camper/RV in Niceville

Waterfront Airstream with Fishing, Boat Rental

4.94 out of 5 average rating, 17 reviews

A private balcony offers stunning gulf views, featuring two lounge chairs and a dining table. The ocean sparkles under sunlight, creating a serene backdrop for relaxation. The balcony extends from the living area, allowing easy access to enjoy the fresh sea breeze.

Condo in Destin

Gulfgate 1005 2BD/2BA Destination

4.91 out of 5 average rating, 47 reviews

Townhouse in Destin

Destin Beach House•Sleep12•Hot Tub•Pool•RoofDeck B

4.95 out of 5 average rating, 76 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!

Condo in Santa Rosa Island

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!