Vacation rentals with a kayak in Santa Rosa Island

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!

4.99 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.

4.98 out of 5 average rating, 178 reviews

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

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!

Condo in The Village of Baytowne Wharf

A light-filled living area features a cozy sofa and ceiling fan. A large TV hangs on the wall, with views of a private balcony visible through sliding glass doors. A dining table, adorned with decorative items, offers a space for meals and gatherings.

4.91 out of 5 average rating, 123 reviews

Grand Sandestin 4th flr 1 b.room-Steps to Baytowne

Elegant 1BR retreat with 4th-floor views from large balcony, steps from the Village of Baytowne Wharf. Just a 5–10 min TRAM ride to Sandestin pristine private beaches. Features a king bed, queen sofa sleeper, full kitchen, in-unit washer/dryer, and refined décor. Stay connected with high-speed Wi-Fi, unwind with Netflix, and enjoy use of beach chairs and an umbrella stored in our private garage-level storage. Perfect for couples or small families looking to relax and explore Sandestin.

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, 105 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!

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 perfect beach escape in our beautifully renovated beachfront condo on stunning Okaloosa Island. This inviting retreat offers two spacious bedrooms, two modern bathrooms, and a rare oversized balcony—ideal for relaxing while taking in breathtaking Gulf views. Step onto the sugar-white sands and enjoy the emerald-green waters with complimentary beach service, including two chairs and an umbrella, provided from March 1 through October 31.

A sand dollar pendant is displayed on a textured wooden surface. The soft, natural colors of the pendant contrast with the blurred blue and green background, evoking a coastal ambiance. The pendant is attached to a simple rope, enhancing its beach-inspired aesthetic.

4.87 out of 5 average rating, 150 reviews

2615 Gorgeous 2 Bdrm ~ Heated Pool ~ Book Jan 3rd

Gorgeous Gulf views in this luxury upscale vacation home with sea inspired decor. Large Balcony with high top Table and 6 seats, 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 heated pool, hot tub, waterfalls, a poolside bar, Bistro restaurant and coffee shop. Tiki bar and pool side service! Tennis Courts, pickle ball, basketball, kids play area, gym.

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!

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!

Come spend a magical vacation with us and enjoy our comfortable cottage on Santa Rosa Sound. Close enough to town, shopping, and beaches, but off the beaten track away from the heavy tourist traffic. Our nest is a private home with a shallow beach and small dock where you can relax along Santa Rosa Sound. The cottage has a complete kitchen, laundry, covered parking, fenced yard, grill, and patio. Life is easy at the ShipAhoy Nest!

A bright living area features a comfortable sofa and a coffee table, with a dining table set for four. Large sliding glass doors open to the balcony, offering unobstructed views of the Gulf of Mexico. Soft natural light filters through sheer curtains.

4.91 out of 5 average rating, 173 reviews

Beachfront, 7th Flr at Pelican, Breathtaking Views

Spacious one bedroom two bathroom unit with unobstructed spectacular views of the Gulf of Mexico. Recently renovated and decorated professionally, guests will enjoy a new kitchen with granite counter-tops, stylish cabinets, and stainless steel appliances. Kitchen is fully equipped for a family or group of 6. Our guests just step out to the white sand beach from the resort, no streets to cross.

Popular amenities for Santa Rosa Island kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.96 out of 5 average rating, 25 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

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

4.94 out of 5 average rating, 64 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

Golf Cart | SanDestin | Pool | Arcade | Lake View

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

5 out of 5 average rating, 25 reviews

A planter filled with vibrant pink flowers stands in the foreground, while two lounge chairs are positioned on a grassy lawn. The backdrop features a serene view of the bay under a colorful sky at dawn, with palm trees gently framing the scene.

Home in Freeport

Eden House: Mansion and Guest House on the Bay

5 out of 5 average rating, 13 reviews

Luxury Pet Friendly Beach Home with Golf Cart

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.

4.99 out of 5 average rating, 76 reviews

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

Superhost

5 out of 5 average rating, 3 reviews

The Retreat in Santa Rosa Beach- Bungalow E

Other vacation rentals with a kayak

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.

4.93 out of 5 average rating, 14 reviews

Pelican Beach Top Floor Beachfront with Best 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.

4.94 out of 5 average rating, 53 reviews

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

4.99 out of 5 average rating, 89 reviews

Condo in Miramar Beach

Contact for Snowbird rates! Stunning Gulf and Bay

Townhouse in Santa Rosa Beach

A wooden serving tray holds a wine bottle and two glasses filled with a light beverage, set on a balcony table. The backdrop features lush greenery and the shimmering Gulf of Mexico, complementing the serene coastal ambiance.

4.97 out of 5 average rating, 61 reviews

Beautiful Gulf Views,South of 30A,Pool + Hot tub,

Condo in Fort Walton 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, 72 reviews

Pink Flamingo Okaloosa Island

Superhost

An open-concept living area features a bright kitchen equipped with stainless appliances and quartz countertops. A spacious living room with a light-colored sofa and accent chairs offers views through sliding glass doors. Natural light fills the space, complemented by modern decor.

Condo in Sandestin

5 out of 5 average rating, 9 reviews

1-bdrm, Sleeps 4

4.8 out of 5 average rating, 132 reviews

Waterfront! Sleeps 14 & TWO Story Waterslide Fun!!

A balcony table with four wooden chairs is positioned overlooking the Gulf. The horizon merges the tranquil blue sea and sky, reflecting sunlight. The unobstructed view enhances the outdoor space, inviting relaxation while watching the waves below.