Holiday rentals with a kayak in Santa Rosa Island

Townhouse in Miramar Beach

4.87 out of 5 average rating, 123 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.

Apartment in Fort Walton Beach

5 out of 5 average rating, 118 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, 226 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.

4.99 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.

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.

4.97 out of 5 average rating, 163 reviews

Zen Retreat ON Beach, Golfcart* Hot Tub, SanDestin

8th fl. stylish open studio w/stunning VIEW, beachfront in Sandestin Resort between Destin & 30A. 🛺 Golf cart with 3+ 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

4.92 out of 5 average rating, 36 reviews

Gulf Dunes 112 – Happy Hours | Free Beach Service

Top Reasons to Book Gulf Dunes 112 – Happy Hours: * Spacious King Gulf Front Master Suite with Balcony Access * Large Balcony with Bar Height Furniture for Coffee or Sunset Views * Two Private Beach Access Points (One Handicap Accessible) * FREE Seasonal Beach Service – 2 Chairs Plus Umbrella Each Day of Your Stay (March 1 – October 31) * Heated Pool (Seasonally), Outdoor Grills, Tennis/Pickleball Courts, and a Small Fitness Center * Located Close to Beachview Bar/Grill, Stewbys, Mini-Golf/Ice

Apartment in The Village of Baytowne Wharf

This ground floor studio features a spacious bed covered in striped linens. A flat-screen television is mounted on the wall opposite, with a small dining table nearby. A balcony with views of the golf course can be accessed through sliding glass doors, offering natural light.

4.94 out of 5 average rating, 143 reviews

Sandestin Elation Studio - Baytowne - Golf Cart

Ground-floor studio in Sandestin Golf & Beach Resort with serene golf course and lake views. Steps from Baytowne Wharf’s dining and entertainment. Features a king bed, queen sofa bed, full bath, and kitchenette with microwave and mid-size fridge. Enjoy Wi-Fi, Netflix, resort tram access, and beach gear in garage storage. Optional Golf cart available - inquire about availability and fee. Perfect for a relaxing escape in the heart of Sandestin. And Yes! you may drive the golf cart to the beach.

Aerial view of a lagoon-style pool area, featuring winding blue waters surrounded by lush palm trees. Bridges connect various sections, with a water slide visible in the background. Relaxation areas and poolside loungers are scattered throughout the sunlit space.

4.87 out of 5 average rating, 126 reviews

3102 Stunning 2 Bdrm ~ Heated Pool ~ Book Apr 10th

One of only 14 Exclusive Poolside Villas! Welcome to the Grand Villa Cabana, 1473 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 8 and is the perfect location, with an outdoor dining and patio experience in the tropical gardens alongside the gorgeous lagoon pool. The Grand Villa Cabana has 2 huge bedrooms, 1 King Bed, 1 Queen Bed, Full over Full Bunk Bed and 1 queen sofa sleeper. 5 beds in total.

4.87 out of 5 average rating, 102 reviews

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

A bright living space features a cozy sofa, armchair, and a dining table. Large windows provide expansive views of the beach and ocean. Light-colored walls and neutral decor create a relaxed ambiance, while a flat-screen TV and artwork add character to the room.

4.95 out of 5 average rating, 109 reviews

Renovated Beachfront at Pelican, Stunning Views

Pelican Beach Resort 302 - 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.

Houseboat in Fort Walton Beach

A houseboat is docked on a covered pier, surrounded by calm water. White chairs are positioned on the deck, offering a relaxing view of the bayou. Lush greenery frames the setting, while the dock's wooden surface provides easy access.

4.93 out of 5 average rating, 121 reviews

Unique water front stay Houseboat Destin/FWB

Seas the Day, center on Ft. Walton Beach,quiet bayou connected to bay and gulf on private 1 acre residence. We are 1 of only 3 HB for 50 miles in area. Paddle boards, kayaks , fishing poles and outdoor fire pit. Car needed to get to white sand beaches (4 miles). Shopping close by. A comfy futon in for a second bed. Boat has AC and heat. Unit is to stay docked.Recently renovated inside and out . Larger deck area with loungers . New lighting and ceiling this past spring! Rare find

5 out of 5 average rating, 5 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!

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, 48 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

4.91 out of 5 average rating, 109 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

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

4.9 out of 5 average rating, 10 reviews

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.

Home in Santa Rosa Beach

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!

5 out of 5 average rating, 3 reviews

Home in Miramar Beach

The Retreat in Santa Rosa Beach- Bungalow E

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.

4.92 out of 5 average rating, 38 reviews

Sleeps 12* Private POOL * Backyard * Ranch Home

4.95 out of 5 average rating, 61 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

4.83 out of 5 average rating, 162 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 Garniers 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, 26 reviews

Waterfront Bliss Beach Cottage

4.98 out of 5 average rating, 58 reviews

Cottage in Freeport

Bayview Cottage | Pet Friendly | 15 Min to Beach

Other holiday rentals with a kayak

5 out of 5 average rating, 7 reviews

Beautiful Beachfront Condo * Amazing Balcony 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, 55 reviews

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

The living area features a modern design with two soft gray sofas and a round coffee table at the center. A dining bar with teal stools separates the kitchen space, while a wall-mounted artwork depicting flamingos adds a touch of character. Natural light fills the room through large windows.

4.96 out of 5 average rating, 78 reviews

Pink Flamingo Okaloosa Island

4.93 out of 5 average rating, 122 reviews

Sola Azul | Gulf-Front Luxe + Beach Service

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.

4.92 out of 5 average rating, 12 reviews

Beachfront Condo | Resort Pool | Sleeps 6

Home in Santa Rosa Beach

4.8 out of 5 average rating, 132 reviews

Waterfront! Sleeps 14 & TWO Story Waterslide Fun!!

The living room features a light-colored sofa paired with two modern armchairs, creating an inviting seating area. Floor-to-ceiling windows provide unobstructed ocean views. A coffee table and side tables complement the space, while a large wall-mounted TV and tasteful artwork enhance the atmosphere.