Vacation rentals with a kayak in Okaloosa County

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Top-rated kayak rentals in Okaloosa County

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Guest favorite

Home in Mary Esther

4.94 out of 5 average rating, 17 reviews

Waterfront - Beachfront Gulf Coast Home (Destin)!

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!

Guest favorite

Condo in Fort Walton Beach

5 out of 5 average rating, 80 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 favorite

Apartment in Shalimar

4.99 out of 5 average rating, 148 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.

Guest favorite

Townhouse in Destin

4.95 out of 5 average rating, 118 reviews

Book Now for 2025! | Heart of Destin | Waterfront

LOCATION, LOCATION, LOCATION! 5-min walk to the beach. 5-7 minute short drive to exciting HarborWalk 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!

Guest favorite

Condo in Destin

4.96 out of 5 average rating, 124 reviews

3107 Poolside ~New Year Eve 3 Nt Special ~Dec 31

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

Guest favorite

Condo in Mary Esther

4.88 out of 5 average rating, 160 reviews

Waterfront Condo w FREE Kayaks and Fishing Dock

WATERFRONT CONDO 🤗🏝️ *Two Free Ocean Kayaks for guests ($ 200/day value). Stay on the water with amazing views of the Santa Rosa sound and Okaloosa island, the pool is 5 steps away. *Large and airy one bedroom, one living room, kitchen and bath, TV in both the bedroom and living room. Endless relaxation days. *Kayaks are free to use for the entire stay, free life vests, kayak paddles, beach chairs. *We are 4 miles to the Gulf beach on Okaloosa Island and 9 miles to Destin Harbor

Guest favorite

Condo in Destin

4.95 out of 5 average rating, 133 reviews

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.

Guest favorite

Townhouse in Destin

5 out of 5 average rating, 43 reviews

Xmas decor! Boat slip, SUP/Kayaks, Dogs, Beach!

Bring your boats and your dogs for an unforgettable vacation! - Fully remodeled, canal-front townhome with TWO boat slips, SUPs, kayaks, hot tub, grill, & more - 3BR/3BA - Two living spaces, two covered decks, large sun deck, yard, and full wet bar - 10 minutes to Crab Island - Water taxi will pick you up at dock - Fish right off the dock, with a fish cleaning station, ice maker, and dedicated freezer - Dogs under 30lbs welcome (fees apply) - Private beach access only 0.5 miles away

Superhost

Home in Destin

4.84 out of 5 average rating, 112 reviews

Freestyle! 2 blks to beach! Pool! Free golf cart!

Funky, fun furnishings and just two blocks to the Emerald Coast’s sugar sand beaches! Freestyle’s 6 bedroom/16 person sleeping capacity (including 4 king suites with 2 on the first floor) is ready to let the good times roll for your entire family! Includes a free 2021 six seater golf cart, 2 paddleboards, 2 kayaks, and more. Featuring a full-sized pool, decked-out grilling area, and two separate living areas. Central to Destin’s most popular shopping, dining and entertainment.

Guest favorite

Home in Fort Walton Beach

5 out of 5 average rating, 47 reviews

Waterfront, KING bed, Kayaks, Private Dock, Fenced

➔ 2400 sq. ft. single-story house ➔ Wrap-around balcony/porch w/ sweeping water views ➔ Swimming in the back yard -- Jump off the dock into the bayou! ➔ 3 kayaks ➔ 5-ft aluminum fence; does NOT run along the water line (pictures available upon request) ➔ On-site parking for ALL your vehicles and trailer: Bring your boat or RV & tie your boat off at our dock! ➔ Quiet/Safe neighborhood ➔ Just a few blocks to a public boat launch ➔ 10 min. to VPS airport ➔ 10 min. to public beaches!

Guest favorite

Cottage in Mary Esther

4.85 out of 5 average rating, 130 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!

Guest favorite

Home in Fort Walton Beach

4.9 out of 5 average rating, 52 reviews

3 Br Waterfront Florida Classic on the Bayou

Enjoy the comfort and beauty of classic old Florida at this beautiful waterfront home. Moments away from white sand beaches and downtown, you are in an oasis of relaxation here at the Florida Classic on the Bayou. This home was thoughtfully designed and cherished by a prominent local family and features rich Florida history and details. It is our pleasure to share this oasis with you.