Holiday rentals with a kayak in Okaloosa County

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Top-rated Accommodation with a Kayak in Okaloosa County

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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Top Guest favourite

A charming two-story brick house is set amidst a landscaped yard featuring lush green bushes and a winding driveway. The home is adorned with symmetrical windows and a welcoming porch, framed by tall trees under a clear blue sky.

Home in Crestview

Safe/Secure efficiency apartment with pond view

Our unique place has a style all its own. Located on five acres there is always something in bloom on our property. This efficiency apartment, located on the ground floor of our home, has its own entrance, a Queen bed, full kitchen, bathroom with a standing shower, living room with tv, community gym, and washer and dryer access, Our pond has bass, so bring your fishing pole, or read a book while sitting by a babbling creek. Enjoy a small fire at the whimsical chiminea located in the patio area.

LocationOutdoor spacesAir conditioning

4.96 out of 5 average rating, 129 reviews

Top Guest favourite

A wooden boardwalk leads from the sandy beach to the beachfront house, surrounded by tall pine trees and palm plants. A shaded lounge area with comfortable seating is visible on the lawn, inviting relaxation by the water's edge.

Home in Mary Esther

Waterfront - Beachfront Home (Destin) w/Hot tub!

Welcome to your ideal beachfront getaway! We are conveniently located in between Destin and Pensacola. Our rental comes with snorkels, kayaks, paddle boards, corn hole, so you can explore the waters at your leisure. We also have a relaxing fire pit and lounge area right by the water. This is the perfect place to unwind and make memories with your loved ones. Located in a sound, so it's shallow water and no crazy waves! We have had many dolphin sightings near our dock so you might see some too!

Outdoor spacesLocationParking

4.95 out of 5 average rating, 62 reviews

Top Guest favourite

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.

Outdoor spacesValueCheck-in

4.99 out of 5 average rating, 179 reviews

Guest favourite

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.

Outdoor spacesLocationQuiet

4.91 out of 5 average rating, 237 reviews

Top Guest favourite

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!

ValueLocationIndoor spaces

4.92 out of 5 average rating, 167 reviews

Top Guest favourite

Condo in Santa Rosa Island

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.

Outdoor spacesLocationBarbecue

4.98 out of 5 average rating, 120 reviews

Guest favourite

A modern living area is depicted with a wooden coffee table at the center. Two blue sofas provide seating, complemented by a flat-screen TV mounted on the wall. Large sliding glass doors offer unobstructed views of the Gulf of Mexico, with outdoor seating visible on the balcony.

Condo in Destin

Beachfront 6th Floor 1BR at Pelican, Amazing Views

Completely renovated 6th floor, Pelican Beach condo is right on the beach with unobstructed views of the Gulf of Mexico. It has 1 bedroom, 2 full bathrooms, full kitchen, custom bunks and sleeps 6. Located in the heart of Destin in popular Pelican Beach Resort, you will enjoy the beach, the view, brand new appliances, furniture, and updated kitchen. Linens and towels are among the amenities included. High quality mattresses even for the pullout bed. We follow highest cleaning standards.

ValueLocationKitchen

4.96 out of 5 average rating, 169 reviews

Guest favourite

Townhouse in Mary Esther

Waterfront Sound Tri-level TH

Airy waterfront home w/ 2 balconies overlooking the Santa Rosa Sound. Enjoy our welcoming sound side beach or if you’re after waves, Okaloosa Island and Navarre Beach are a short drive in either direction. Covered parking for two and keyless entry. Newly renovated kitchen, comfortable beach decor, 3 large bedrooms with their own attached full baths. Quiet, family friendly, safe neighborhood close to the military bases. Pool seasonally closed. Complex newly paved Dec 2022.

Outdoor spacesValueLayout

4.96 out of 5 average rating, 73 reviews

Guest favourite

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.

Outdoor spacesValueBeach

4.84 out of 5 average rating, 115 reviews

Superhost

Home in Mary Esther

Private Water Access | Heated Pool | Kayaks

Welcome to your Villa Rosa - dream coastal getaway — an extraordinary 6-bedroom, 6.5-bathroom, 6,500 sq ft luxury waterfront estate offering, 270 feet of bay access, 180° water views from every window and unbeatable amenities for groups of all sizes. This Santa Rosa Sound retreat is designed for comfort, privacy, and unforgettable memories, featuring three separate wings, a covered pool, a private dock, a game room, and multiple indoor and outdoor living spaces.

Outdoor spacesIndoor spacesLaundry

4.6 out of 5 average rating, 10 reviews

Top Guest favourite

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!

Enjoy a spacious 3-bedroom, 2-bath condo at Emerald Grande with stunning harbor and gulf views. Relax on your balcony, stroll to HarborWalk Village for dining, bars, and shops, or hop on the complimentary shuttle to the private beach with full service including chairs and umbrellas. 2026 exterior improvements mean discounted rates, while your interior experience, amenities, and views remain fully unaffected. Perfect for families, groups, or weekend getaways.

LocationValueGetting around

4.95 out of 5 average rating, 84 reviews

Guest favourite

An aerial view of a lagoon-style pool surrounded by lush palm trees and tropical landscaping. The pool features winding pathways, small bridges, and water slides, creating a serene outdoor oasis. Sun loungers are positioned throughout the area, offering relaxation spots under the sun.

Condo in Destin

21115 Stunning 2 Bdrm ~ HOT Special ~ Book Sept 22

Penthouse with beautiful gulf views in this Luxury upscale vacation home. Large Balcony 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 the heated pool, hot tub, waterfalls, Bistro restaurant and coffee shop. Tiki bar and pool side service! Tennis courts, pickle ball, kids play area, and gym. New Charcoal Grills added onsite!

Outdoor spacesValueComfort

4.94 out of 5 average rating, 142 reviews