Holiday rentals with a kayak in Okaloosa County

A large swimming pool is visible, surrounded by lounge chairs and palm trees. Clear blue skies reflect on the water's surface, while a bright orange building is seen in the background. The area is designed for relaxation and recreation.

4.94 out of 5 average rating, 54 reviews

Spacious Lakefront 2BR • 3 Pools • Minutes-2-Beach

DESTINation Vacation offers 2 Bedrooms, Large Jack & Jill Bath, 3 Beds + queen sleeper, pack n’ play, accessible workspace, & large picture windows. This ground floor condo is steps from 1 of the 3 amenity pools; a 7 minute walk to the beach & it’s in the heart of Destin, Florida. You’ll be just a few minutes away from: 🏄‍♂️Henderson Park State Beach🏄‍♂️ ⚽️Morgan sports complex ☀️Big Kahuna’s Waterpark 🏎️The Track Family Fun Park 🛍️Destin Commons 🏝️HarborWalk 🎣Charter Fishing 🐚Silver Sands Outlets & more

4.95 out of 5 average rating, 100 reviews

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.

Apartment in Fort Walton Beach

5 out of 5 average rating, 118 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, 226 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.

4.91 out of 5 average rating, 143 reviews

A balcony table is set for breakfast, featuring two white cups, a plate with blueberries, and a muffin. A pink orchid adds a pop of color. The background showcases a pastel sunset over water and buildings.

Townhouse in Destin

Snowbird favorite! | Heart of Destin | Waterfront

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.

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.

Guest house in Mary Esther

4.79 out of 5 average rating, 53 reviews

Coastal Retreat - Dock, Dolphins & Majestic Oaks

The Gulf Coast Guest House (sleeps 4 guests) is a unique hideaway nestled in between the old oak trees and your own private beach & dock located on the Santa Rosa Sound/Intercoastal Waterway next to the Gulf of Mexico. Enjoy your leisure time by the fire pit, rocking & fishing on the dock or swimming on the zero gravity entry, private sandy beach! Centrally located to a myriad of attractions and adventures from Pensacola to Navarre Beach to Destin and outdoor fun on the Blackwater River!

Aerial view of a lagoon-style pool area, featuring winding blue waters surrounded by lush palm trees. Bridges connect various sections, with a water slide visible in the background. Relaxation areas and poolside loungers are scattered throughout the sunlit space.

4.87 out of 5 average rating, 125 reviews

3102 Stunning 2 Bdrm ~ Heated Pool ~ Book Mar 11th

One of only 14 Exclusive Poolside Villas! Welcome to the Grand Villa Cabana, 1473 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 8 and is the perfect location, with an outdoor dining and patio experience in the tropical gardens alongside the gorgeous lagoon pool. The Grand Villa Cabana has 2 huge bedrooms, 1 King Bed, 1 Queen Bed, Full over Full Bunk Bed and 1 queen sofa sleeper. 5 beds in total.

A cozy living space is presented with a light, neutral palette. A plush sofa and an armchair create a comfortable seating area, while a round coffee table features a decorative woven design. Natural light enters through the window, enhancing the inviting ambiance.

5 out of 5 average rating, 8 reviews

Sandpiper Cove 4201 FREE Beach Service Destin, FL

Step inside to find a beautifully decorated living space with an open floor plan that allows for easy flow from room to room. The living room features a plush sofa and 2 chairs, perfect for lounging and watching TV on the flat-screen. Enjoy a home cooked meal in the fully equipped kitchen, complete with all the necessary appliances and utensils. This are the beach chairs and umbrella service on the beach! This means you don't have to haul chairs and umbrellas back and forth to the beach!

Superhost

Apartment in Fort Walton Beach

4.92 out of 5 average rating, 36 reviews

112 | Free Beach Svc + Heated Pool + Pickleball

Cozy mornings, golden sunsets, and the sound of the surf — “Happy Hours” is your laid-back beach retreat on beautiful Okaloosa Island. Enjoy coffee or cocktails on the spacious balcony, where the gentle sea breeze and distant Gulf views set the tone for a perfect day. Step outside to heated pools, tennis and pickleball courts, and walk to some of the area’s best local restaurants and beach bars. Whether it’s your morning cup or your evening toast, every hour feels a little happier here.

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, 109 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.