Holiday rentals with a kayak in Santa Rosa Island

4.97 out of 5 average rating, 214 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~New Pool

ON BEACH -Sleek airy 1st floor studio. Sandestin Resort between Destin & 30A. Beach/Pool/HotTub 1 min from patio. Golf Cart w/3+ nts. Pottery Barn King bed with beachfront view. Step off your private patio to the beach or relax on the patio 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

ValueLocationAmenities

4.99 out of 5 average rating, 176 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.

ValueOutdoor spacesFamily

4.92 out of 5 average rating, 164 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!

ValueOutdoor spacesLong stay

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, 301 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.

LocationValueCheck-in

4.97 out of 5 average rating, 110 reviews

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.

Condo in Sandestin

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

BAYTOWNE STUDIO CONDO WITH BALCONY - Lasata #3307 "Sea La Vie" (the Sea is Life)…We welcome you to our cozy and quaint get away on the Bay side/the Village. From the sand to the very sound of the waves, the Sea is the Life we all crave. Come and enjoy the restful pleasures of Baytowne and all it has to offer. There is plenty of restaurants, shopping and beach access across the Hwy (Sandestin Hilton entrance) only a 5 minute drive. After a stay in Sandestin, life will become more manageable.

LocationValueIndoor spaces

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, 76 reviews

Luxury Beachfront Home, Sleeps 12, Kayaks, SUPs

🏖 Luxury Beachfront Home for multi-family stays with everything included! Sleeps 12, 3 BR/3.5 BA + 4 Parking spots. On the beach! Unlike most beachfront rentals, this home includes full beach setup and toddler gear—no rentals needed. 🛏 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!

ValueOutdoor spacesCondition

4.98 out of 5 average rating, 119 reviews

115+ Five-Star Reviews | Renovated Gulf View Condo

Relax and unwind in our beautifully renovated Island Princess condo on Okaloosa Island. With 10 years of hosting experience and 115+ five-star reviews, we provide a clean, comfortable vacation home guests return to year after year. Enjoy beautiful Gulf and bay views from our oversized private balcony, comfortable beds, fully equipped kitchen, spacious living area, direct beach access, and complimentary beach service (2 chairs + umbrella) Mar–Oct. Located in Fort Walton Beach, near Destin.

ValueOutdoor spacesFamily

5.0 out of 5 average rating, 25 reviews

WaterScape Guest Favorite | Beachfront | Resort

Escape to our beautifully renovated condo at WaterScape Resort, just steps from the heated pools, lazy river, splash pad, and the sugar-white sands of Fort Walton Beach. Enjoy two King suites with memory foam mattresses, a private bunkroom with a TV in each, a fully equipped kitchen, Smart TVs, in-suite laundry, a Coffee Bar, Milkshake Bar, Selfie Wall, and complimentary beach service with two chairs and an umbrella included.—all in one of Expedia's Top 10 beach destinations in the world!

Outdoor spacesLocationHot tub

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.

4.96 out of 5 average rating, 112 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.

ValueLocationGetting around

4.82 out of 5 average rating, 144 reviews

Home in Santa Rosa Beach

Waterfront! Sleeps 14 & TWO Story Waterslide Fun!!

This family fun home has a 2 story super fast custom water slide, large pool, (extra charge to heat pool) swim up bar, outdoor tiki hut bar with sink and gas grill, charcoal grill, fire pit, sandy beach, dock, boat slip, (no boat lift) paddle boards. Private suite with kitchen & bathroom on lower level with private access leading out to bay. bring your own fishing gear if you like to fish. Home is a labor of love and has brought so much joy to our family & hopefully to yours.

ValueLocationTV

Townhouse in Miramar Beach

4.86 out of 5 average rating, 133 reviews

Gulf Walk * House with Pool & Golf Cart

1 Block to the Beach! Enjoy a beach equipped garage with 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.

ValueOutdoor spacesAir conditioning

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.

4.92 out of 5 average rating, 142 reviews

21017 Stunning Views ~ Pools ~ Gym ~ Book Aug 24th

Gorgeous Panoramic Gulf Views from this 10th floor, 3 bedrooms end unit, all bedrooms have access to the 100 ft extra large balcony with gulf views. Seating for 8. Resort Lagoon Pool and second Heated pool, 2 King Beds, 1 Queen Bed and a Queen Sofa Sleeper All the comforts of home, easy walk to the beach, or free Shuttle. 5 Star Resort, onsite Restaurant, coffee shop and pool side Tiki bar, Tennis, pickle ball, basketball, state of the art gym & BBQ grill area

ValueOutdoor spacesDecor

Popular amenities for Santa Rosa Island kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.9 out of 5 average rating, 115 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!

ValueLocationCheck-in

4.95 out of 5 average rating, 127 reviews

Home in Santa Rosa Beach

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

LocationOutdoor spacesHospitality

5.0 out of 5 average rating, 8 reviews

Home in Santa Rosa Beach

The Retreat in Santa Rosa Beach- Bungalow C

ValueLocationQuiet

Home in Fort Walton Beach

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.

4.85 out of 5 average rating, 52 reviews

Sleeps 12* Private POOL * Backyard * Ranch Home

LocationOutdoor spacesSleep quality

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

LocationOutdoor spacesCleanliness

Home in Fort Walton Beach

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, 82 reviews

Waterfront~Retreat ~Pool & Deep Dock~Boats welcome

Outdoor spacesLocationBarbecue

4.9 out of 5 average rating, 81 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

ValueOutdoor spacesCleanliness

Home in Fort Walton Beach

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.

5.0 out of 5 average rating, 21 reviews

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

Outdoor spacesLocationCheckout

Cottages with a kayak

4.83 out of 5 average rating, 169 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!

LocationOutdoor spacesWalkability

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.

5.0 out of 5 average rating, 37 reviews

Waterfront Bliss Beach Cottage

Outdoor spacesLocationCleanliness

4.93 out of 5 average rating, 67 reviews

Cottage in Freeport

Bayview Cottage | Dog Friendly | 15 Min to Beach

LocationValueWalkability

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

4.88 out of 5 average rating, 50 reviews

2 bedroom cottage with hot tub

ValueOutdoor spacesParking

Other holiday rentals with a kayak

4.97 out of 5 average rating, 72 reviews

The living area features a light-colored sofa with decorative pillows and a patterned area rug. A large flat-screen TV is mounted on the wall above a rustic wooden console. Floor-to-ceiling glass doors open to a private balcony with ocean views and two chairs.

Condo in Miramar Beach

Majestic Sun 6th Floor View of Emerald Waters -New

ValueLocationHot tub

4.94 out of 5 average rating, 16 reviews

Reef Retreat 153 @ El Matador - Gulf front resort

LocationCleanlinessKitchen

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.

4.93 out of 5 average rating, 70 reviews

Pelican Beach 19th Floor 1 Br - on the Beach

LocationValuePool

4.95 out of 5 average rating, 81 reviews

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.

Condo in Destin Harbor

Perrydise@ Emerald Grande 3BR Harbor & Gulf Views!

ValueLocationBeach

5.0 out of 5 average rating, 63 reviews

The covered outdoor space is equipped with a spacious sectional sofa adorned with decorative cushions. A wooden coffee table sits at the center. The area features a high ceiling with wood paneling, and large sliding doors open to a sun deck with seating.

Townhouse in Destin

Canalfront, Boat slip, Hot Tub, SUPs, Dogs, Beach

LocationOutdoor spacesAccess

Apartment in Okaloosa Island

5.0 out of 5 average rating, 17 reviews

Newly renovated gulf-front condo on 1st floor

LocationWalkabilityIndoor spaces

5.0 out of 5 average rating, 4 reviews

Gulfgate Destination 0505 2BD/2BA

LocationAmenitiesNearby

A lush tropical landscape is featured, with tall palm trees surrounding a winding lazy river. Colorful inflatable floats are visible in the water, while lounge chairs and umbrellas provide shaded seating areas. The beach and resort buildings are seen in the background, enhancing the relaxing atmosphere.