Holiday rentals with a kayak in Santa Rosa Island

Townhouse in Miramar Beach

4.87 out of 5 average rating, 127 reviews

Gulf Walk * Beach House wh Pool and Golf Cart

1 min to Private Beach! Enjoy a beach equipped garage with opt budget friendly golf cart, backyard pool, and plenty of space for families or groups — all in one of Miramar Beach’s most desirable locations. This beautifully designed 2BR / 2.5BA townhouse is located in the popular Gulf Walk comm just a short 5-minute walk or 1-minute golf cart ride to Private Beach. With custom coastal-modern design, high-end furnishings, and thoughtful details throughout, this home is the perfect beach getaway.

4.97 out of 5 average rating, 194 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 OceanView SanDestin

Sleek airy 1st floor studio ON BEACH. 🛺 Golf cart w/4+ nts. In Sandestin Resort between Destin & 30A. NEW Pool & Hot Tub! Pottery Barn King bed with beachfront view. Step right off our private patio to the beach or relax on the patio round Bali bed. WiFi, 55” smart TV, Kitchen, Washer/dryer. Enjoy free gym, tram, beach, trails, golf, dining, shopping & entertainment all without leaving resort! Perfect honeymoon, baby moon, romantic getaway, girls trip, solo travel or lil’ fam vacay! *NO animals

Condo 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, 127 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, 149 reviews

Townhouse in Destin

Harbor-front Oasis| Steps to the Beach

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, 161 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.

4.93 out of 5 average rating, 148 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. Optional Golf cart available - 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.

4.93 out of 5 average rating, 14 reviews

A wooden dock extends over calm waters, with two gray deck chairs positioned for relaxation. Lush green trees line the shoreline, and a few houses are visible in the distance under a bright blue sky with scattered clouds.

Home in Ferry Park

On the water! 7 minutes to the beach!

Bring your boat and your RV. Relax with the whole family in this private water front cottage. 7 minutes to the white sands of Okaloosa Island and 6 miles by boat to Crab Island or just walk out back and paddle the bay. There are 3 public boat ramps with in 2 miles of the property. The waterway will accommodate a draft of 24”. Ferry Street Park and Uptown Station are just minutes away. Everything in the house is brand new and kept perfectly clean and organized so you and yours can relax .

A dining area features a round table surrounded by woven chairs. A cozy sofa and a decorative console table are positioned nearby. Large sliding glass doors provide unobstructed views of the beach, while soft natural light fills the space, enhancing the coastal decor.

4.9 out of 5 average rating, 291 reviews

Beachfront 8th Fl. 1 BR at Pelican, Stunning Views

Completely renovated 8th floor condo right on the beach with unobstructed views of the Gulf and the beach. Located in the heart of Destin in popular Pelican Beach Resort, you will enjoy the private beach, multiple outdoor pools, an indoor pool, hottubs and more. Our beachfront condo has been professionally renovated with brand new cabinets, AC, floors, appliances, furniture, kitchen and more. All mattresses are brand new, cool-gel memory foam for a cool night's sleep. Fully stacked kitchen.

The image displays a large lagoon-style pool surrounded by palm trees and tropical landscaping. Lounge chairs in blue and white are positioned along the poolside. A shallow entry area can be seen, along with a bridge leading to a shaded structure in the distance.

4.94 out of 5 average rating, 152 reviews

3107 HOT Poolside Villa ~ Pools ~ Book May 6th

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

Apartment in Fort Walton Beach

5 out of 5 average rating, 4 reviews

Newly renovated gulf-front condo on 1st floor

Enjoy your beach getaway in this spacious 2BR/2BA Gulf-front condo! This first-floor unit sleeps 8 with private patio to experience sunrise views over gulf, updated kitchen w/ quartz countertops, renovated baths w/ walk-in shower in the primary, and in-unit laundry. Relax w/ beachfront access, beach chair service (march-oct), pool, fitness center, tennis court, grill, volleyball net, picnic area, kayak, books, games, & dry bar w/ beverage cooler. Close to shopping, dining & attractions!

A bright living space features a cozy sofa, armchair, and a dining table. Large windows provide expansive views of the beach and ocean. Light-colored walls and neutral decor create a relaxed ambiance, while a flat-screen TV and artwork add character to the room.

4.95 out of 5 average rating, 110 reviews

Renovated Beachfront at Pelican, Stunning Views

Pelican Beach Resort 302 - 3rd floor 1 Bedroom 2 Bathroom 873 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.

4.83 out of 5 average rating, 106 reviews

Home in Destin

Beach+Pool+Hot Tub | Golf Cart(incl) + Game Room

Welcome to Destin Beach House — a spacious, FULLY RENOVATED (March 2026) Crystal Beach retreat just steps from Destin’s famous white-sand beaches. You'll love the open Kitchen, private pool (optional heating), hot tub, Outdoor TV, game room, and FREE 6-passenger golf cart, making it easy to cruise around. Perfect for family vacations and group getaways, with open living spaces and a private backyard oasis designed for relaxing after a day on the Emerald Coast.

Popular amenities for Santa Rosa Island kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

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.

4.91 out of 5 average rating, 81 reviews

Santa Rosa Beach|Heated Pool|Pet Friendly|Hot Tub

5 out of 5 average rating, 55 reviews

The open-concept kitchen features sleek cabinetry, modern appliances, and a large island, providing an inviting space for meal preparation. In the lower section, a dock area showcases a boat lift and lush greenery along the water's edge, emphasizing the waterfront setting.

Home in Destin

Waterfront, Boat dock, Bikes, BEACH, HOT TUB

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.

4.95 out of 5 average rating, 75 reviews

Waterfront~Retreat ~Pool & Deep Dock~Boats welcome

4.91 out of 5 average rating, 11 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

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 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.

4.91 out of 5 average rating, 11 reviews

Cozy Up on Choctawhatchee Bay

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.

4.88 out of 5 average rating, 43 reviews

Sleeps 12* Private POOL * Backyard * Ranch Home

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, 17 reviews

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

Other holiday rentals with a kayak

Condo 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.

4.97 out of 5 average rating, 97 reviews

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

4.93 out of 5 average rating, 92 reviews

A spacious living area is highlighted by large windows offering views of the beachfront. Light blue seating arrangements complement the neutral decor. A dining table for four is positioned beside artwork featuring herons. Direct access to the outdoor patio is visible.

Condo in Miramar Beach

B105 | Beachfront with Beach Service, Pool, & WiFi

A private balcony offers stunning gulf views, featuring two lounge chairs and a dining table. The ocean sparkles under sunlight, creating a serene backdrop for relaxation. The balcony extends from the living area, allowing easy access to enjoy the fresh sea breeze.

4.93 out of 5 average rating, 15 reviews

Gulfgate 1005 2BD/2BA Destination

The large outdoor pool is surrounded by palm trees, creating a serene environment. Lounge chairs are arranged around the pool, and glowing lights reflect off the water. The beach and ocean are visible in the background, enhancing the coastal ambiance.

4.93 out of 5 average rating, 15 reviews

Beachfront Condo | Resort Pool | Sleeps 6

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.

4.88 out of 5 average rating, 69 reviews

Waterfront Beach Retreat - 4bdrm

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, 77 reviews

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

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.

4.98 out of 5 average rating, 56 reviews

Pelican Beach 19th Floor 1 Br - on the Beach