Holiday rentals with a kayak in Santa Rosa Island

4.92 out of 5 average rating, 161 reviews

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, 173 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.

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, 80 reviews

Waterfront~Retreat ~Pool & Deep Dock~Boats welcome

Luxury Waterfront escape w/ Pool , Deep-Water Dock & Sunset Views🌴 Bring your boat or jet skis and enjoy direct access to the intercoastal bay—just minutes from Crab Island. Relax poolside, unwind on the water, and enjoy peaceful sunset views while still being only 10 minutes from the beach, dining, and downtown Fort Walton Beach. 🚤 Private deep-water dock (boat & jet ski ready) 💦 Heated pool for year-round use 🌅 Waterfront views + outdoor living 🏖️ Quick drive to beaches & attractions

4.97 out of 5 average rating, 210 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~Pool

Sleek airy 1st fl. studio ON BEACH. 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

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, 299 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 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.

5 out of 5 average rating, 61 reviews

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

🚤🐾 Bring your boats & your pups for the ultimate Destin getaway at Come Sail Away! This fully remodeled, end-unit canal-front townhome features ✌️ TWO boat slips, kayaks, SUPs, a huge hot tub, expansive decks, and tons of space to relax 🌞🌴 Whether you're reeling in fish from the dock 🎣 or sipping drinks at the wet bar 🍹, there's something for everyone here! ☀️🏖️ Private beach - 0.5 mi 🏝️ Crab Island - 1.7 mi (by boat) 🛍️ Destin Harbor Boardwalk - 1 mi (by boat) 3.6 mi (by car)

5 out of 5 average rating, 21 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!

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, 118 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.

The living area features a light-colored sofa and a patterned armchair, positioned around a glass coffee table. Large sliding doors reveal direct views of the beach, allowing natural light to brighten the space. A flat-screen TV is situated on a media console across from the seating.

4.94 out of 5 average rating, 112 reviews

Beachfront at Pelican Beach, Stunning Ocean View

Pelican Beach Resort 306 - 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.

4.82 out of 5 average rating, 142 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.

Townhouse in Miramar Beach

4.88 out of 5 average rating, 132 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.

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, 141 reviews

21017 Gorgeous Views ~ Pools ~ Gym ~ Book Aug 10th

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

Popular amenities for Santa Rosa Island kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.94 out of 5 average rating, 35 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

4.97 out of 5 average rating, 33 reviews

Home in Destin

Destiny West|Heated Pool|Golf Cart|Gym

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

5 out of 5 average rating, 32 reviews

Home in Destin Harbor

Destin Condo: Pool, Private Beach, Beach Cart

4.88 out of 5 average rating, 75 reviews

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.

Home in Santa Rosa Beach

Waterfront Beach Retreat - 4bdrm

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.

4.84 out of 5 average rating, 51 reviews

Sleeps 12* Private POOL * Backyard * Ranch Home

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 out of 5 average rating, 21 reviews

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

4.93 out of 5 average rating, 73 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

Cottages 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

4.88 out of 5 average rating, 48 reviews

2 bedroom cottage with hot tub

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, 36 reviews

Waterfront Bliss Beach Cottage

4.83 out of 5 average rating, 168 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!

4.93 out of 5 average rating, 67 reviews

Cottage in Freeport

Bayview Cottage | Dog Friendly | 15 Min to Beach

Other holiday rentals with a kayak

A spacious outdoor deck features a large wooden table surrounded by matching chairs, all shaded by a large umbrella. The view overlooks the marina with boats docked, palm trees lining the area, and buildings in the distance, creating a serene waterfront atmosphere.

4.81 out of 5 average rating, 32 reviews

Waterfront Townhome near Destin Harbor Boat Slip

4.93 out of 5 average rating, 15 reviews

Reef Retreat 153 @ El Matador - Gulf front resort

4.94 out of 5 average rating, 17 reviews

Villa in Miramar Beach

Sea Escape

5 out of 5 average rating, 5 reviews

Destin 9216 Sandpiper Cove 1 Bedroom with Bunks

4.92 out of 5 average rating, 50 reviews

Destin Beach House•Sleep12•Hot Tub•Pool•RoofDeck B

4.95 out of 5 average rating, 80 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!

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.

5 out of 5 average rating, 19 reviews

DW Sandpiper L03 ~ Walk Out Lanai ~ Lazy River!

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.