Vacation rentals with a kayak in Santa Rosa Island

Condo in Fort Walton Beach

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, 211 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, 159 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.

4.98 out of 5 average rating, 171 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* Hot Tub, SanDestin

Airy 1st floor 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. Relax on the patio’s Bali bed & listen to the waves. WiFi & 55” smart TV. Kitchen w/coffee cart. 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

A two-story beach cottage is displayed with light-colored siding and multiple balconies. The porch extends across the front, supported by white columns. The outdoor area features paved stones, with nearby plants providing a natural touch. Nearby structures are visible in a coastal setting.

4.97 out of 5 average rating, 115 reviews

4 BR 3 BA | Pool | Gym | Pets | 0.7 mi to beach

Gorgeous 4-bedroom 3-bath beach cottage along popular Scenic Hwy 30A. Located in the quaint coastal community of Blue Mountain Beach, this beautifully designed home is a short distance to the picturesque emerald-green waters and sugar-white sand beaches of the Emerald Coast. Our stunning home is a 13-minute walk or a 4-minute bike ride to the beach and walking distance to local restaurants and shops. You will enjoy a fully stocked kitchen, comfortable bedrooms, community pool access & more.

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.

4.96 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.

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, 111 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

4.96 out of 5 average rating, 45 reviews

A clear view of a private pool is framed by swaying palm trees, with the bay visible in the background. Two lounge chairs are positioned near the water's edge, inviting relaxation by the shimmering pool under a bright blue sky.

Home in Ferry Park

Waterfront Home-Dock, Pool, Kayaks, Dogs Welcome!

Step into our artsy mid-century sanctuary directly on the bay. Walk out to panoramic water views with the famous Crab Island on Choctawhatchee Bay in the distance. Swaying palm trees frame the poolside oasis & sweeping water views on over a 1/2 acre of property. Relax in one of the two hammocks, enjoy the private dock, private pool, ocean kayaks, or grill out among the lush landscape for a true tropical Florida experience. Kick your shoes off…Welcome! Must be 25 or older to stay.

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.

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!

4.92 out of 5 average rating, 106 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!

Sundance is designer 7 bedroom home less than one block from Destin's newest beach access. Pool/spa. Free golf cart. 5 kings with private baths (including two on the first floor), 1 queen with private bath, and 1 bunk room create many options for multiple families or groups. Includes free 6 seater golf cart, 2 paddleboards and a full-sized (seasonally heated) pool/spa. Central to Destin’s best shopping, dining, and entertainment

Condo 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.

4.94 out of 5 average rating, 112 reviews

An aerial view of a lagoon-style pool surrounded by lush palm trees and tropical landscaping. The pool features winding pathways, small bridges, and water slides, creating a serene outdoor oasis. Sun loungers are positioned throughout the area, offering relaxation spots under the sun.

Condo in Destin

21115 Amazing 2 Bdrm Heated Pool ~ Special Nov 11

Penthouse with beautiful gulf views in this Luxury upscale vacation home. Large Balcony with pool and gulf views. 2 large bdrms w/ luxury King beds, both bdrms have balcony access. Relax at Destin's Largest Lagoon Pool. Enjoy the heated pool, hot tub, waterfalls, Bistro restaurant and coffee shop. Tiki bar and pool side service! Tennis courts, pickle ball, kids play area, and gym. New Charcoal Grills added onsite!

Popular amenities for Santa Rosa Island kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

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.

4.97 out of 5 average rating, 69 reviews

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

5 out of 5 average rating, 13 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, 23 reviews

Home in Destin

Destin Harbor Condo: Fall Stays/Snowbirds Welcome

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 private balcony is shown with comfortable woven seating, overlooking a vibrant sunset that showcases hues of orange and pink. Lush palm trees are visible in the foreground, while the scenic community pool is partially seen below, enhancing the peaceful coastal ambiance.

5 out of 5 average rating, 19 reviews

Sunrises and Sunsets

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.

4.78 out of 5 average rating, 41 reviews

Brand New Luxury Beach Home!

Superhost

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.

4.88 out of 5 average rating, 8 reviews

Cozy Up on Choctawhatchee Bay

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!

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

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

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, 24 reviews

Cozy Beach Cottage With Private 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!

Other vacation rentals with a kayak

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, 21 reviews

The Ancker Boat House • Waterfront on the Bayou

4.86 out of 5 average rating, 29 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

5 out of 5 average rating, 12 reviews

Condo in Destin

Sandpiper Cove–Snowbird Beach Retreat–Boat Slips

4.92 out of 5 average rating, 12 reviews

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.

Condo in Destin

Pelican Beach Top Floor Beachfront with Best Views

4.95 out of 5 average rating, 60 reviews

A large, inviting lakeside deck overlooks a tranquil water view with trees reflecting in the water. Inside, a brightly colored arcade room features three arcade games and cozy sleeping quarters with a spacious bed. The living area is furnished with comfortable seating and ample natural light.

Home in Sandestin

GolfCart*SanDestin*Pool*Arcade*Disc 4NT+

5 out of 5 average rating, 24 reviews

4BR, Pool, Golf Cart, HotTub, 9Bikes-close Beaches

4.8 out of 5 average rating, 131 reviews

Waterfront! Sleeps 14 & TWO Story Waterslide Fun!!

Superhost