Holiday rentals with a kayak in Destin

Cottage in Long Point Park

A scenic view of a wooden dock extending into the calm water, bordered by lush greenery. A lounge chair sits on the grass nearby, complemented by a potted plant. The tranquil blue sky reflects off the water, enhancing the serene outdoor setting.

4.95 out of 5 average rating, 132 reviews

Water front amazing views and private beach

Cute and cozy 550 sq ft bungalow perfect for couples. Located directly on the bay. Boat ramp 1/4 mile away. Boat dock with slips in your backyard! Work from the kitchen table and watch boats go by. This duplex offers breathtaking views. Fish from your backyard or off the newly built dock. PCB is a 30 min. drive. Mexico Beach is 18 mi. Large back deck, amazing sunsets. Fishing charter option available. Complementary paddle board and kayaks! Quiet and a great place to reset, relax and reconnect!

Apartment in Fort Walton Beach

A bright studio room features a spacious bed with decorative pillows and a cozy blanket. A comfortable sofa is positioned nearby, and a small dining area is visible. Large sliding glass doors open to a balcony, allowing natural light to fill the space.

5 out of 5 average rating, 114 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, 212 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.

4.97 out of 5 average rating, 147 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* 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

4.89 out of 5 average rating, 141 reviews

A pool area features a large, inviting swimming pool adorned with lounge chairs under a bright blue sky. Nearby, beach loungers with an umbrella are visible on a sandy beach, providing a relaxing spot for sunbathing.

Apartment in Sunnyside

Fins Up Carillon/Snowbirds welcome/Lakefront 30a

Welcome to Fins Up @Carillon. Minutes to Rosemary, Seaside, Pier Park, St Andrew’s Park. Newly renovated studio with full kitchen,king bed, pullout sofa & twin air mattress. Perfect location mins to 30A activities/ 15 mins to Pier Park. 5 pools onsite (1 heated), hot tub, playground, tennis/pickleball/basketball courts, 8 beach access points. General store onsite with bike rentals. Condo backs to Lake with a 5-7 minute walk to beach. No traffic here, private beach. Snowbirds welcome

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.

4.96 out of 5 average rating, 134 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. Golf cart available - please 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.

The image showcases a sprawling lagoon pool surrounded by lush palm trees and tropical landscaping. A playful water slide is visible, alongside winding pathways and sun loungers, creating an inviting outdoor space for relaxation and recreation.

4.95 out of 5 average rating, 147 reviews

3107 Amazing Pools ~ Super Special ~ Book Nov 13th

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

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.

4.95 out of 5 average rating, 112 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

Superhost

A bright living and dining area is visible, featuring a large table with a marble top surrounded by white chairs. Large glass windows provide expansive views of the Gulf and beach, while comfortable seating is arranged near a wall-mounted television.

4.9 out of 5 average rating, 157 reviews

2B/2BA Beachfront Corner, Gulf Views East & South

12th-floor 2Br/2B/WD corner unit. Panoramic Gulf views east and south from the living room, and stunning beach views from the master bedroom! Fully renovated, professionally decorated in a coastal theme, and fully stocked for comfort. True beachfront building—no streets to cross. Enjoy many family-friendly resort amenities: indoor/outdoor pools, jacuzzi, fitness center, onsite restaurant, seasonal tiki bar, private beach, and easy access to top Destin attractions.

4.88 out of 5 average rating, 100 reviews

A light-filled living area features a comfortable sofa with patterned upholstery and a large round coffee table. Floor-to-ceiling windows offer views of the ocean, while nautical-themed decor, including an oar and ship wheel, enhances the coastal ambiance.

Flat in Destin

Nautical Dunes - Ocean Front View!

Enjoy breathtaking views of the beach from your private balcony or take a short walk to the sparkling emerald waters and sugar-white sands. The spacious and elegantly decorated condo offers the perfect oasis for relaxation and fun. Soak in the sun by one of the pools, challenge your friends to a game of tennis, or simply unwind in the hot tubs. Bring your family and friends to create unforgettable memories at "Nautical Dunes" on your next beach vacation!

4.89 out of 5 average rating, 105 reviews

Illuminated palm trees frame a serene lakeside setting at night. A covered cabana sits nearby, featuring seating arrangements. Soft lighting gently highlights the landscape, reflecting on the water, while a grassy area offers space for relaxation.

Cabin in Panama City

Cabin on Private Beach with Tiki Bar & Cabana

3 Queen beds, 2 bedrooms, queen futon sofa. Lake front, tiki bar with swings, covered cabana. Gated property for privacy. 20 minutes from Panama City Beach. Ten minutes from Ecofina Springs. Stone tiki kitchen with fireplace, pizza oven, open fire Argentine grill and smoker. Full bathroom on the beach equipped with a shower for easy shower. Beach side cabana with privacy shades, 10 inch mattress, 43 inch smart TV, wood fireplace.

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, 110 reviews

Island Princess 618 | Gulf Views & Beach Service

Experience the ultimate beach getaway at our renovated condo on stunning Okaloosa Island. This beachfront retreat features two spacious bedrooms, two modern bathrooms, and a rare oversized balcony perfect for soaking in the breathtaking views. Relax on the sugar-white sands and take in the emerald-green waters of the Gulf with complimentary beach service, including two chairs and an umbrella, provided from March 1st to October 31st.

Popular amenities for kayak rentals in Destin

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.93 out of 5 average rating, 74 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

Blue Palm Beach House|Heated Pool|Hot Tub

5 out of 5 average rating, 68 reviews

A serene backyard is highlighted by a wooden gazebo and a hot tub, surrounded by well-manicured landscaping. White lounge chairs are arranged on a stone pathway, with decorative pebbles lining the edges, offering a tranquil space for relaxation.

Home in Sunnyside

Jewel of the Sea - Golf Cart, HotTub, EV charger

5 out of 5 average rating, 23 reviews

Home in Destin

Destin Harbor Condo: Fall Stays/Snowbirds Welcome

4.98 out of 5 average rating, 142 reviews

An open-concept kitchen features a glossy black countertop complemented by clear bar stools. A vibrant mural of tropical leaves in bright colors adorns one wall, adding a lively touch to the space. Pendant lights hang above, illuminating the inviting kitchen area.

Home in Sunnyside

Mini Golf, West End, 0.5 to Beach, By 30A, Backyar

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, 16 reviews

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

Superhost

The exterior showcases a modern coastal home with a charming gabled roof and a spacious front porch. Symmetrical large windows are complemented by landscaping featuring small bushes and trees. A concrete driveway leads to the entrance, surrounded by gravel and grass.

Home in Santa Rosa Beach

4.78 out of 5 average rating, 41 reviews

Brand New Luxury Beach Home!

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, 31 reviews

Sleeps 12* Private POOL * Backyard * Ranch Home

4.93 out of 5 average rating, 87 reviews

A relaxing living area showcases comfortable seating with a light-colored sofa and armchair, arranged around a round, black metal coffee table. Large glass doors provide a view of the beach, while natural light fills the space. A decorative fish sculpture adds a coastal touch.

Home in Panama City

Beachfront home directly on the sand *Drift Away*

Cottage rentals with a kayak

Cottage in Laguna Beach on the Gulf of Mexico

Gulf front Laguna Place~Sea-renity Cottage

An intricate fire pit is showcased, featuring the engraved word 'Choctaw.' Flames dance atop the burning logs, surrounded by a stone patio. Nearby, a basket filled with pine cones adds a rustic touch to the natural setting of tall trees and greenery.

Cottage in Ponce de Leon

5 out of 5 average rating, 13 reviews

Choctaw Lodge Retreat

5 out of 5 average rating, 13 reviews

A serene canal view is captured under a clear blue sky, showcasing calm waters reflecting the surroundings. Wooden docks line the canal, leading to several boats moored along the edges. The distant structures provide a backdrop to the tranquil setting.

Cottage in Destin

Boat,Beach &view! Boat slip/walk to the beach

4.84 out of 5 average rating, 155 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, 25 reviews

Luxury Beach Cottage With Private Beach

4.86 out of 5 average rating, 106 reviews

A light-filled bedroom features a cozy bed with a textured white coverlet. French doors open to a sitting porch with two comfortable chairs and festive wreaths. A decorative area rug and a vintage dresser add warmth and charm to the space.

Cottage in Freeport

Waterfront Private Suite, Keyless, mins to beach

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

4.93 out of 5 average rating, 41 reviews

The cottage features a large wrap-around porch supported by light blue columns. Rocking chairs and a swing are positioned for seating. Lush greenery surrounds the home, and multiple windows provide natural light, contributing to a spacious and inviting exterior.

Cottage in Panama City

Cozy 2 bdrm cottage with sunny wrap around porch

Other holiday rentals with a kayak

Apartment in Santa Rosa Beach

A modern kitchen is presented with white cabinetry, a central island topped with light-colored stone, and bar stools. Pendant lights with woven shades hang above the island. Appliances, including a stainless-steel refrigerator and a stove, complete the open layout that connects to a living area with ample natural light.

5 out of 5 average rating, 11 reviews

Steps to Beach w/ View, Pool + Tennis | Sea La Vie

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, 68 reviews

Beach Cottage • Private Beach • Gated •Heated Pool

A balcony features two blue chairs and a small table, offering a direct view of the beach and the shimmering gulf waters. The sandy shore is visible below, lined with beach umbrellas, while the vibrant blue sky enhances the scenic coastal horizon.

4.92 out of 5 average rating, 13 reviews

Pelican Beach Top Floor Beachfront with Best Views

Superhost

Apartment in Panama City Beach

5 out of 5 average rating, 4 reviews

BeachFront- 5 Pools, Starbucks, Movies @ Majestic

Apartment in Destin Harbor

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.

4.94 out of 5 average rating, 64 reviews

Perrydise @ Emerald Grande

Apartment in Fort Walton Beach

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, 14 reviews

DW Sandpiper L03 ~ Walk Out Lanai ~ Lazy River!

Apartment in Miramar Beach

4.99 out of 5 average rating, 88 reviews

Contact for Snowbird rates! Stunning Gulf and Bay