Holiday rentals with a kayak in Santa Rosa Island

4.97 out of 5 average rating, 181 reviews

Condo in Sandestin

Light&Airy ON Beach, Golfcart* Hot Tub, SanDestin

Airy 1st fl. Sleek studio ON BEACH. 🛺Golf cart w/3+ nts. In Sandestin Resort between Destin & 30A. NEW Pool & Hot Tub! West Elm furniture & King bed with beachfront view. Step right off back patio to the beach or relax on patio round Bali bed. WiFi, 55” smart TV, Kitchen, Washer/dryer. Enjoy free gym, tram, beach, trails, golf, dining, shopping & entertainment all without leaving gated resort! Perfect honeymoon, baby moon, romantic getaway, girls trip, solo travel or lil’ fam vacay! *NO animals

Condo in Fort Walton Beach

5 out of 5 average rating, 115 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, 222 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.

4.91 out of 5 average rating, 143 reviews

A balcony table is set for breakfast, featuring two white cups, a plate with blueberries, and a muffin. A pink orchid adds a pop of color. The background showcases a pastel sunset over water and buildings.

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, 160 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.

Condo 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, 139 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.

Townhouse in Okaloosa 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, 67 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!

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.

4.88 out of 5 average rating, 118 reviews

2901 Gorgeous 2bdrm ~ Gulf Views ~ Book Feb 21st

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

Condo in Miramar Beach

4.87 out of 5 average rating, 100 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

Superhost

5 out of 5 average rating, 3 reviews

NEW! 16th floor 2BR Beachfront at Pelican, 3 pools

Pelican Beach Resort 1617 - 16th floor 2 Bedroom 2 Bathroom 955 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.

4.95 out of 5 average rating, 114 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

4.89 out of 5 average rating, 108 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.

Apartment 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!

Popular amenities for Santa Rosa Island kayak rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

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.

4.94 out of 5 average rating, 70 reviews

Waterfront ~Home~ Private ~Pool & Deep dock~ boats

5 out of 5 average rating, 14 reviews

A spacious game room features a billiards table with a vibrant blue felt surface and a shuffleboard table nearby. Natural light fills the room through multiple windows, illuminating the white shiplap walls and dark wood accents overhead. Green pendant lights add a modern touch.

Home in Destin

Across Str+GOLF CART+Chair Srvc+priv pool+6 KINGS

5 out of 5 average rating, 13 reviews

167 Oyster Lake Drive

4.9 out of 5 average rating, 10 reviews

A spacious screened-in patio presents a serene view of the waterfront. Comfortable seating arrangements are complemented by a dining table, while natural light illuminates the terracotta floor. The outdoor scenery features lush greenery and a distant dock, enhancing the tranquil atmosphere.

Home in Miramar Beach

Jet Ski Adventure - Family Getaway

Superhost

A charming retreat is showcased against a backdrop of blue skies and tranquil waters, with a wooden boardwalk leading toward the home. Surrounding greenery and distant coastal homes reflect the serene environment. The ocean is visible in the background, enhancing the coastal character.

4.9 out of 5 average rating, 62 reviews

Waterfront Beach Retreat - 4bdrm

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.

4.9 out of 5 average rating, 10 reviews

Cozy Up on Choctawhatchee Bay

An outdoor area features a blue pool and spa under a screened enclosure, with chairs and a natural gas grill nearby. A spacious deck allows for relaxation. An adjacent game area includes a pool table and arcade machine, providing ample entertainment options.

5 out of 5 average rating, 30 reviews

New Luxury Home with Pool & Spa-2 bikes included

4.95 out of 5 average rating, 59 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

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

4.86 out of 5 average rating, 42 reviews

2 bedroom cottage with hot tub

4.84 out of 5 average rating, 159 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, 26 reviews

Luxury Beach Cottage With Private Beach

4.98 out of 5 average rating, 56 reviews

A sunset view from a fire pit area features four yellow Adirondack chairs arranged around a circular fire pit. A vibrant sky is painted in hues of orange and pink, with silhouettes of trees in the background. The open space invites relaxation and connection with nature.

Cottage in Freeport

Bayview Cottage | Pet Friendly | 15 Min to Beach

Other holiday rentals with a kayak

A private pool area features a rectangular pool surrounded by lounge chairs and palm trees. The two-story white mansion stands in the background, showcasing a spiral staircase leading to the rooftop deck. Paved surfaces create a spacious outdoor setting.

Home in Destin

5 out of 5 average rating, 7 reviews

Mansion! Pool, Free Tiki Cruise! | Neptune's Nest

Home in Fort Walton Beach

The spacious backyard is seen from the water, featuring a private dock with a boat slip. The house, framed by lush trees, has ambient lighting illuminating its exterior. A large lawn stretches towards the house, complemented by the twilight sky filled with subtle hues.

5 out of 5 average rating, 28 reviews

The Ancker Boat House • Waterfront on the Bayou

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.

4.93 out of 5 average rating, 70 reviews

Beach Cottage • Private Beach • Gated •Heated Pool

4.84 out of 5 average rating, 70 reviews

A bright living area features a blue sofa and a large glass sliding door, allowing natural light to fill the space. The room includes a media console and decorative items. Nearby, two vibrant tennis courts are visible under a clear sky, with palm trees framing the scene.

Condo in Miramar Beach

Family Resort + Pickleball 2 Pools, Private Beach

A comfortable living area features a light-colored sofa and armchair, complemented by decorative pillows. A round wooden table is in the center. Floor-to-ceiling glass doors open to a balcony with ocean views, while artwork adorns the walls, adding a touch of color.

5 out of 5 average rating, 3 reviews

Jetty East Unit 317A - Beach Front At Jetty East!

Condo in Miramar Beach

4.86 out of 5 average rating, 7 reviews

Majestic Sun 707A-1/1.5 bath condo with gulf views

The exterior of a two-story home is displayed, featuring large windows that allow natural light to illuminate the interior. A spacious deck is furnished with a turquoise umbrella and chairs, set among well-maintained landscaping, creating an inviting outdoor space.

Villa in Sandestin

4.8 out of 5 average rating, 5 reviews

Sandestin - updated, equipped includes golf cart