Holiday rentals with a kayak in Santa Rosa Island

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.

4.99 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.

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, 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

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.

A modern living area is depicted with a wooden coffee table at the center. Two blue sofas provide seating, complemented by a flat-screen TV mounted on the wall. Large sliding glass doors offer unobstructed views of the Gulf of Mexico, with outdoor seating visible on the balcony.

4.96 out of 5 average rating, 157 reviews

Beachfront 6th Floor 1BR at Pelican, Amazing Views

Completely renovated 6th floor, Pelican Beach condo is right on the beach with unobstructed views of the Gulf of Mexico. It has 1 bedroom, 2 full bathrooms, full kitchen, custom bunks and sleeps 6. Located in the heart of Destin in popular Pelican Beach Resort, you will enjoy the beach, the view, brand new appliances, furniture, and updated kitchen. Linens and towels are among the amenities included. High quality mattresses even for the pullout bed. We follow highest cleaning standards.

A tranquil lagoon pool meanders through lush tropical landscaping, with palm trees lining the perimeter. Clear blue water reflects the sky, inviting relaxation. Pathways connect various seating areas and greenery, enhancing the serene resort atmosphere.

4.91 out of 5 average rating, 128 reviews

21017 Gorgeous Gulf Views ~ 3 Bdrm ~ Book Nov 28th

Gorgeous Panoramic Gulf Views from this 10th floor Luxury Penthouse! Large Balcony, Seating for 8, & 2 Large chairs & 2 rockers. New living room sofa sleeper, Lagoon Pool and gulf views from nearly every corner, 3 Brdms: 2 King Beds, 1 Queen Bed and a Sofa Sleeper All Bdrms have balcony access, and gulf views! 5 Star Resort with Lagoon Pool, heated pool, hot tub, Sports Lounge/restaurant and coffee shop. Tiki bar, Free shuttle, Tennis, pickle ball, basketball, gym & New grills.

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

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!

4.86 out of 5 average rating, 122 reviews

A vibrant blue coastal home with multiple stories is showcased, featuring large windows and balconies. A six-seater golf cart is parked in front of the house, with the pristine beach visible in the background, enhancing the inviting atmosphere of this ocean view property.

Home in Destin

Sunkissed! Oceanview! Pool! Golf Cart! 6 Bedrooms

Sunkissed is an updated, ocean view home that is only a 1/2 block stroll to Destin’s sugar sand beaches. Includes 6 seater golf cart, and 2 paddleboards. Features a full-sized (seasonally heated Oct.-April) pool, grilling area and relaxing outdoor living space. 5 king suites (including a 1st floor king suite) and separate pool house to accommodate your group’s needs. Central to Destin’s best shopping, dining, and entertainment!

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.

Home in Fort Walton Beach

A classic waterfront home is shown from the outside, featuring a large front porch with white railings. Colorful kayaks and paddleboards are displayed on a wooden rack beside a grassy yard, surrounded by lush greenery. Ceiling fans hang above, providing comfort.

4.94 out of 5 average rating, 80 reviews

3 Br Waterfront Florida Classic on the Bayou

Enjoy the comfort and beauty of classic old Florida at this beautiful waterfront home. Moments away from white sand beaches and downtown, you are in an oasis of relaxation here at the Florida Classic on the Bayou. This home was thoughtfully designed and cherished by a prominent local family and features rich Florida history and details. It is our pleasure to share this oasis with you.

Popular amenities for kayak rentals in Santa Rosa Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

Superhost

A spacious living area features a large sectional sofa with decorative cushions. Light wood accents are present in the coffee table and dining area, which is set against a backdrop of creamy walls and large windows. A ceiling fan adds a functional touch to the room.

Home in Destin

4.71 out of 5 average rating, 24 reviews

Private Beach | Gulf Views | Comm Pool | Elevator

4.96 out of 5 average rating, 23 reviews

The exterior of the waterfront home features a spacious deck connected by a wooden walkway. Surrounding palm trees and lush greenery create a tropical ambiance. A sandy area can be seen by the water's edge, inviting outdoor activities and relaxation.

Home in Niceville

Waterfront Haven - Perfect for Family Vacations

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

4.99 out of 5 average rating, 76 reviews

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.

Home in Santa Rosa Beach

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

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.

Home in Santa Rosa Beach

4.88 out of 5 average rating, 8 reviews

Cozy Up on Choctawhatchee Bay

Superhost

Home in Santa Rosa Beach

5 out of 5 average rating, 3 reviews

The Retreat in Santa Rosa Beach- Bungalow E

4.92 out of 5 average rating, 65 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, 52 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

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, 25 reviews

Luxury 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 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

Apartment in The Village of Baytowne Wharf

A cozy studio features a queen bed dressed in soft linens, flanked by bedside tables with lamps. A comfortable sofa is positioned nearby, complemented by a decorative coffee table. Art depicting sea life adorns the walls, and a stylish chandelier adds character to the space.

4.95 out of 5 average rating, 88 reviews

“Sea La Vie” (the Sea is Life) Lasata-Baytowne

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

The living area features a spacious layout with a large sectional sofa and a comfortable armchair. A 65-inch curved TV is mounted on a decorative cabinet. Floor-to-ceiling windows provide views of the Gulf, and a dining area is visible in the background.

4.8 out of 5 average rating, 76 reviews

IRC 604: Gulf Front Luxury (2 Bed / 2 Bath)

Apartment in Miramar Beach

4.99 out of 5 average rating, 88 reviews

Contact for Snowbird rates! Stunning Gulf and Bay

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.

Apartment in Fort Walton Beach

4.96 out of 5 average rating, 67 reviews

Pink Flamingo Okaloosa Island