Holiday rentals with a kayak in Okaloosa County

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Top-rated rentals with kayak in Okaloosa County

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

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Top guest favourite

Apartment in Fort Walton Beach

5 out of 5 average rating, 115 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!

Guest favourite

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

4.91 out of 5 average rating, 143 reviews

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!

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.

Flat in Shalimar

4.99 out of 5 average rating, 160 reviews

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.

Top guest favourite

An outdoor dining area features a white circular table surrounded by six adirondack chairs. A partial view of the ocean and sandy beach is visible in the background, under a clear blue sky with few clouds.

Townhouse in Okaloosa Island

4.99 out of 5 average rating, 67 reviews

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

🏖 Steps from the Ocean | 3BR/3.5BA Townhome w/ Views + Kayaks & SUPs! 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 🚣‍♂️ 3 Kayaks, 2 SUPs, beach chairs, umbrellas, boogie boards, beach toys!

Guest favourite

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.

Apartment in Destin

4.87 out of 5 average rating, 123 reviews

3102 Poolside Heated Pool ~ 2 Bdrm ~ Book Jan 6th

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.

Guest favourite

A houseboat is docked on a covered pier, surrounded by calm water. White chairs are positioned on the deck, offering a relaxing view of the bayou. Lush greenery frames the setting, while the dock's wooden surface provides easy access.

Houseboat in Fort Walton Beach

4.95 out of 5 average rating, 114 reviews

Unique water front stay Houseboat Destin/FWB

Seas the Day, center on Ft. Walton Beach,quiet bayou connected to bay and gulf on private 1 acre residence. We are 1 of only 3 HB for 50 miles in area. Paddle boards, kayaks , fishing poles and outdoor fire pit. Car needed to get to white sand beaches (4 miles). Shopping close by. A comfy futon in for a second bed. Boat has AC and heat. Unit is to stay docked.Recently renovated inside and out . Larger deck area with loungers . New lighting and ceiling this past spring! Rare find

Top guest favourite

A spacious game room features a billiards table with a vibrant blue felt surface and a shuffleboard table nearby. Natural light fills the room through multiple windows, illuminating the white shiplap walls and dark wood accents overhead. Green pendant lights add a modern touch.

Home in Destin

5 out of 5 average rating, 14 reviews

Across Str+GOLF CART+Chair Srvc+priv pool+6 KINGS

+GOLF CART effective 3/1/26 "Chill Pill"+Get some group R&R at "CHILL PILL" +NO SHARING BATHROOMS +6 King suites, all attached baths plus a big bunk room, 7.5 baths! +Across street to beach FREE chair srvc (seasonal) for 6 +TONS of beach supplies +SUP/kayak. Shoot pool/shuffleboard in spacious living area, never feels crowded. Heat private pool (fee). LOCATION: blocks from Bass Pro Shop corner! *Sleeps 24 in beds>MAX 12 adults> only 12 & under in bunks. Parking for 6 per City.

Top guest favourite

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.

Apartment in Fort Walton Beach

4.98 out of 5 average rating, 110 reviews

Island Princess 618 | Gulf Views & Beach Service

Experience the perfect beach escape in our beautifully renovated beachfront condo on stunning Okaloosa Island. This inviting retreat offers two spacious bedrooms, two modern bathrooms, and a rare oversized balcony—ideal for relaxing while taking in breathtaking Gulf views. Step onto the sugar-white sands and enjoy the emerald-green waters with complimentary beach service, including two chairs and an umbrella, provided from March 1 through October 31.

Guest favourite

A vibrant blue coastal home with multiple stories is showcased, featuring large windows and balconies. A six-seater golf cart is parked in front of the house, with the pristine beach visible in the background, enhancing the inviting atmosphere of this ocean view property.

Home in Destin

4.86 out of 5 average rating, 122 reviews

Sunkissed! Oceanview! Pool! Golf Cart! 6 Bedrooms

Sunkissed is an updated, ocean view home that is only a 1/2 block stroll to Destin’s sugar sand beaches. Includes 6 seater golf cart, and 2 paddleboards. Features a full-sized (seasonally heated Oct.-April) pool, grilling area and relaxing outdoor living space. 5 king suites (including a 1st floor king suite) and separate pool house to accommodate your group’s needs. Central to Destin’s best shopping, dining, and entertainment!

Guest favourite

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

4.84 out of 5 average rating, 159 reviews

Nature's Nest Cottage on the Sound - Pets Welcome!

Come spend a magical vacation with us and enjoy our comfortable cottage on Santa Rosa Sound. Close enough to town, shopping, and beaches, but off the beaten track away from the heavy tourist traffic. Our nest is a private home with a shallow beach and small dock where you can relax along Santa Rosa Sound. The cottage has a complete kitchen, laundry, covered parking, fenced yard, grill, and patio. Life is easy at the ShipAhoy Nest!

Superhost

Apartment in Destin

4.75 out of 5 average rating, 4 reviews

Pet-Friendly 1BR Retreat with FREE Beach Service!

Welcome to Kitzi’s Corner – Pet-Friendly 1BR Retreat with FREE Beach Service! Discover the charm of old Florida with all the modern comforts at Kitzi’s Corner, a first-floor one-bedroom condo nestled in the heart of Sandpiper Cove in Destin, FL. This peaceful retreat is pet-friendly and includes complimentary beach service (seasonal) – so all you need to bring is your swimsuit and a sense of relaxation.

Guest favourite

A bright living area features a comfortable sofa and a coffee table, with a dining table set for four. Large sliding glass doors open to the balcony, offering unobstructed views of the Gulf of Mexico. Soft natural light filters through sheer curtains.

Apartment in Destin

4.91 out of 5 average rating, 173 reviews

Beachfront, 7th Flr at Pelican, Breathtaking Views

Spacious one bedroom two bathroom unit with unobstructed spectacular views of the Gulf of Mexico. Recently renovated and decorated professionally, guests will enjoy a new kitchen with granite counter-tops, stylish cabinets, and stainless steel appliances. Kitchen is fully equipped for a family or group of 6. Our guests just step out to the white sand beach from the resort, no streets to cross.