Holiday rentals with a kayak in Santa Rosa Island

Apartment in Fort Walton Beach

A scenic view of a resort-style pool surrounded by lush greenery and palm trees. The sparkling water reflects the blue sky, with boats docked nearby. A peaceful atmosphere is suggested by the sun shining brightly over the landscape.

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, 213 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.

4.98 out of 5 average rating, 173 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.

Apartment 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, 116 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.

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.

4.91 out of 5 average rating, 128 reviews

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.

Apartment in Destin

21017 Gulf Views ~ Heated Pool ~ 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, 113 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, 101 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!

4.92 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

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.

4.91 out of 5 average rating, 171 reviews

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.

Apartment in Destin

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 kayak rentals in Santa Rosa Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

A dining area is displayed featuring a white table with natural wood legs, surrounded by four black chairs. A woven centerpiece holds greenery. The kitchen in the background includes white cabinets and modern appliances with a breakfast bar and additional seating. Natural light fills the space.

4.95 out of 5 average rating, 41 reviews

Bungalow by the Bayou

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

4.95 out of 5 average rating, 61 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+

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, 61 reviews

Waterfront Beach Retreat - 4bdrm

4.86 out of 5 average rating, 35 reviews

A spacious living area features comfortable seating options, including a reclining chair and wicker chairs. Natural light fills the room through sliding glass doors, leading to a balcony with harbor views. A coffee table sits on a light rug, enhancing the relaxed setting.

Home in Destin

lovely home in D heart of Destin 4 BR n 40ft slip.

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

Cottage rentals with a kayak

Cottage in Laguna Beach on the Gulf of Mexico

Sea-renity Cottage~ unobstructed Gulf views of PCB

4.86 out of 5 average rating, 106 reviews

A light-filled bedroom features a cozy bed with a textured white coverlet. French doors open to a sitting porch with two comfortable chairs and festive wreaths. A decorative area rug and a vintage dresser add warmth and charm to the space.

Cottage in Freeport

Waterfront Private Suite, Keyless, mins to beach

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

An intricate fire pit is showcased, featuring the engraved word 'Choctaw.' Flames dance atop the burning logs, surrounded by a stone patio. Nearby, a basket filled with pine cones adds a rustic touch to the natural setting of tall trees and greenery.

Cottage in Ponce de Leon

5 out of 5 average rating, 13 reviews

Choctaw Lodge Retreat

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

4.84 out of 5 average rating, 156 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, 25 reviews

Luxury Beach Cottage With Private Beach

Cabin rentals with a kayak

4.91 out of 5 average rating, 213 reviews

Cabin in Mary Esther

Safe Harbor Cottage on Santa Rosa Sound - Pets ok!

4.95 out of 5 average rating, 39 reviews

An outdoor fire pit is bordered by several colorful chairs in red and blue. Lush greenery surrounds the site, with views of the tranquil river just beyond. A shaded gazebo is visible in the background, enhancing the peaceful riverside setting.

Cabin in Milton

Riverfront Milton Cabin w/ Boat Ramp & Dock!

An inviting sunlit area features two wicker chairs with striped cushions positioned around a small table. A vibrant flower arrangement is placed at the center, with large windows offering a clear view of the surrounding trees and Lake Powell.

Cabin in Sunnyside

4.75 out of 5 average rating, 12 reviews

Dat Lakehouse Retreat w/private dock & more!