Vacation rentals with a kayak in Okaloosa Island

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.

Summer is HERE! | 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!

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.

Sea Turtle House-On Beach-Townhome-Kayaks/SUP

🏖 Steps from the Ocean | 3BR/3.5BA Townhome w/ Views + Kayaks & SUP! Relax in this spacious 3-story townhome—literally steps from the beach! Enjoy breathtaking ocean views, modern comforts, and everything you need for fun in the sun. 🛏 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 🚣‍♂️ Kayaks, SUP, beach chairs, umbrellas, boogie boards, beach toys included!

Pink Flamingo Okaloosa Island

Sitting DIRECTLY ON THE BEACH look out from your private balcony looking over the white sand and Emerald Green water. One bedroom, one bath. The condo is on the 3rd floor middle unit. Newly renovated and decorated beach retro with a pink flamingo twist. Your stay includes keyless entry, private patio, 55" Smart TV, Wi-Fi, and record player with vinyl collection. Note: The couch is not pullout, but two twin rollout mattresses are provided upon request. No pets. Sorry. THERE IS A 2 ADULT LIMIT.

Lovely Waterfront Home-Pool-Boat Dock-Pets Welcome

Step into our artsy mid-century sanctuary directly on the bay. Walk out to panoramic water views with the famous Crab Island on Choctawhatchee Bay in the distance. Swaying palm trees frame the poolside oasis & sweeping water views on over a half acre of property. Relax in one of the two double hammocks, enjoy the private dock, private pool, ocean kayaks, or grill out among the lush landscape for a true tropical Florida experience. Serenity by the Sea. Kick your shoes off… Welcome, your home!

3107 Amazing Pools ~ Hot Savings ~ Book Aug 8th

One of only 14 Exclusive Poolside Villas! Welcome to the Villa Cabana Royale! 1450 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 6 and is the perfect location, with an outdoor dining and patio experience in the tropical gardens along side the gorgeous lagoon pool. The Villa Cabana Royale has 2 huge bedrooms, 2 King Beds, single chair bed, queen sofa sleeper. 4 beds in total. 65" Inch Smart TVs

2B/2BA Beachfront Corner, Gulf Views East & South

12th-floor 2Br/2B/WD corner unit. Panoramic Gulf views east and south from the living room, and stunning beach views from the master bedroom! Fully renovated, professionally decorated in a coastal theme, and fully stocked for comfort. True beachfront building—no streets to cross. Enjoy many family-friendly resort amenities: indoor/outdoor pools, jacuzzi, fitness center, onsite restaurant, seasonal tiki bar, private beach, and easy access to top Destin attractions.

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.