Holiday rentals with a kayak in Okaloosa County

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.

Outdoor spaces · Location · Getting around

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!

Value · Outdoor spaces · TV

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!

Value · Location · Bathroom

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.

Location · Value · Parks

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.

Location · Outdoor spaces · Beach

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.

Outdoor spaces · Value · Kitchen

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.

Value · Location · Getting around

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.

Location · Value · Kitchen

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 spaces · Kitchen · Check-in

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.

Location · Outdoor spaces · Family

2705 Gulf Views ~ Book Sept 8th ~ Pools ~ Hot Tub

Blue Water Diamonds is the perfect Oasis to create your family vacation memories! With a pool facing balcony and Gulf Views, you have found your place to relax. The Balcony is perfect for morning sun with coffee overlooking the largest lagoon pool, a secondary pool, splash pad area, Our home Sleeps 6 and is thoughtfully designed with your comfort in Mind, Plenty of seating, Kitchen wares and comfy beds. Charcoal BBQ grills, On-site dining, and Bar.

Value · Location · Condition

Newly remodeled cottage with Shoal River access

Take it easy at this unique and tranquil getaway. Recently rebuilt cottage with modern touches amidst open spaces on wooded acreage. Tranquil deck and fire pit. Access to kayaking and walking trail on owner's nearby property on the Shoal River. Conveniently located 10 minutes from shops and restaurants, but peaceful and serene. Master suite has a king bed (with massage feature), second bedroom has a full sized bed.

Outdoor spaces · Location · Sleep quality