Holiday rentals with a kayak in Santa Rosa Island

Townhouse in Miramar Beach

4.87 out of 5 average rating, 126 reviews

Gulf Walk * Beach House wh Pool and Golf Cart

1 min to Private Beach! Enjoy a beach equipped garage with opt budget friendly 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.

4.83 out of 5 average rating, 105 reviews

Home in Destin

Beach+Pool+Hot Tub | Golf Cart(incl) + Game Room

Welcome to Destin Beach House — a spacious, FULLY RENOVATED (March 2026) 5-bedroom Crystal Beach retreat just steps from Destin’s famous white-sand beaches. Guests love the open Kitchen, private pool (optional heating), hot tub, Outdoor TV, game room, and 6-passenger golf cart, making it easy to cruise to the beach, Destin Commons, and local restaurants. Perfect for family vacations and group getaways, with open living spaces and a private backyard oasis designed for relaxing after a day on th

Apartment in Fort Walton Beach

A spacious resort-style pool is featured in the foreground, surrounded by a landscaped area with palm trees. The curved building in the background consists of multiple balconies, offering a view of the pool and the surrounding area. A clear blue sky complements the scene.

5 out of 5 average rating, 124 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!

4.91 out of 5 average rating, 143 reviews

Townhouse in Destin

Snowbird favorite! | Heart of Destin | Waterfront

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, 161 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.

Flat 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, 169 reviews

An open studio layout is presented with a spacious king-size bed and a comfortable sofa. A round table sits nearby, while large glass doors lead to a balcony with ocean views. Soft, neutral tones are used throughout, enhancing the serene atmosphere.

Apartment in Sandestin

Zen Retreat ON Beach, Golfcart*Oceanview SanDestin

8th fl. stylish open studio w/stunning VIEW, beachfront in Sandestin Resort between Destin & 30A. 🛺 Golf cart with 5+ nts. NEW Pool & Hot Tub. West Elm furniture & King size bed w/ocean view. Sleek Kitchen w/dishwasher & Keurig. WiFi, 55” smart TV. Washer/dryer. Huge balcony to gaze @ the sea. Enjoy the beach, dining, shopping, trails, golf & entertainment all without leaving the resort. Tram pass & Gym. Perfect for honeymoon, baby moon, girls trip, solo travel or lil family vacay *NO animals

4.93 out of 5 average rating, 15 reviews

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.

Home in Ferry Park

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 .

A spacious lagoon pool is surrounded by tropical palm trees and lush landscaping. Bright blue lounge chairs are positioned around the pool area on light-colored stone flooring, inviting relaxation. An expansive view of the pool extends towards a building with a blue roof, under a clear blue sky.

4.89 out of 5 average rating, 124 reviews

2901 Gorgeous 2bdrm ~ HOT Discount ~ Book Apr 14th

Welcome to Pretty in Paradise, this gorgeous gulf view condo has been renovated with sea inspired decor. Large Balcony w/ pool and Gulf views. 2 Extra Large Bdrms w/ 2 Luxury King Beds, both Bdrms have balconies! Second Bdrm has an additional balcony. Relax at Destin's Largest Lagoon Pool, enjoy a heated pool, hot tub, waterfalls, a poolside bar, Bistro restaurant, Sports lounge and coffee shop. Tiki bar and pool side service! Tennis Courts, pickle ball, basketball, kids play area, gym.

Superhost

Flat in Fort Walton Beach

5 out of 5 average rating, 3 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!

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.

4.94 out of 5 average rating, 109 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.

Apartment in Fort Walton Beach

5 out of 5 average rating, 11 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!

Apartment in Fort Walton Beach

A panoramic view of the beach showcases soft white sands meeting the tranquil turquoise waters of the Gulf. Beach umbrellas and chairs line the shore, with a clear blue sky above enhancing the serene coastal landscape.

4.98 out of 5 average rating, 113 reviews

Island Princess 618 | Beach Service Included

Experience the perfect beach escape in our beautifully renovated beachfront condo on stunning Okaloosa Island. This inviting retreat offers two spacious bedrooms, two modern bathrooms, and a rare oversized balcony—ideal for relaxing while taking in breathtaking Gulf views. Step onto the sugar-white sands and enjoy the emerald-green waters with complimentary beach service, including two chairs and an umbrella, provided from March 1 through October 31.

Popular amenities for kayak rentals in Santa Rosa Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5 out of 5 average rating, 52 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

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.

5 out of 5 average rating, 13 reviews

167 Oyster Lake Dr Private pool & Easy Beach Walk

Home in Fort Walton Beach

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.

4.88 out of 5 average rating, 32 reviews

The Pink Cottage

A serene view of Choctawhatchee Bay is captured at sunset, showcasing vibrant hues in the sky. A wooden dock extends over the water, leading to a covered area, bordered by lush greenery and trees. Small boats are visible along the shore, completing the tranquil setting.

4.91 out of 5 average rating, 11 reviews

Cozy Up on Choctawhatchee Bay

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, 17 reviews

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

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.

4.9 out of 5 average rating, 41 reviews

Sleeps 12* Private POOL * Backyard * Ranch Home

4.93 out of 5 average rating, 68 reviews

A wooden dock extends into clear water, leading to a vibrant green landscape. Lush trees and grasses frame the scene, while a large house is visible in the background, set among the greenery. Bright blue skies provide a serene backdrop.

Home in Mary Esther

Massive Waterfront Wonder w/8 beds & Boat Dock

4.94 out of 5 average rating, 65 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

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, 42 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, 28 reviews

Waterfront Bliss Beach Cottage

Superhost

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

4.82 out of 5 average rating, 163 reviews

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

4.98 out of 5 average rating, 60 reviews

Cottage in Freeport

Bayview Cottage | Dog Friendly | 15 Min to Beach

Other holiday rentals with a kayak

A serene beach view features gentle waves lapping at the soft, white sand. The clear blue water transitions from a lighter shade near the shore to a deeper turquoise further out, under a bright, cloudless sky.

4.94 out of 5 average rating, 77 reviews

Beach Cottage • Private Beach • Gated •Heated Pool

4.96 out of 5 average rating, 71 reviews

A vibrant living area features an orange accent wall and a circular coffee table on a decorative rug. A comfortable beige sofa adorned with colorful cushions invites relaxation, while a vintage-style lamp hangs above. A mirrored console table displays decorative items and warm lighting.

Flat in Santa Rosa Beach

Charming On-the-Bayou come paddleboard or kayak

Superhost

4.8 out of 5 average rating, 5 reviews

NEW Listing! Beachfront 1st Floor w/Amazing Views!

A large swimming pool is visible, surrounded by lounge chairs and palm trees. Clear blue skies reflect on the water's surface, while a bright orange building is seen in the background. The area is designed for relaxation and recreation.

4.95 out of 5 average rating, 58 reviews

Spacious Lakefront 2BR • 3 Pools • Minutes-2-Beach

The large outdoor pool is surrounded by palm trees, creating a serene environment. Lounge chairs are arranged around the pool, and glowing lights reflect off the water. The beach and ocean are visible in the background, enhancing the coastal ambiance.

4.93 out of 5 average rating, 15 reviews

Beachfront Condo | Resort Pool | Sleeps 6

5 out of 5 average rating, 25 reviews

Home in Destin

Destin Condo: Pool, Private Beach, Gear Included

Waves gently lap at a sandy beach, reflecting the soft hues of a sunset. The sky is filled with clouds, creating dynamic patterns above. The coastline stretches into the distance, bordered by greenery and beachside structures.

4.99 out of 5 average rating, 77 reviews

The Seahorse 30A! Golf cart included! Sleeps 10!