Holiday rentals with a kayak in Santa Rosa Island

Find and book unique kayak rentals on Airbnb

Top-rated rentals with kayak in Santa Rosa Island

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

%{current} / %{total}1 / 1
Guest favourite
Townhouse in Miramar Beach
4.87 out of 5 average rating, 126 reviews

Gulf Walk * Beach House wh Pool and Golf Cart

1 min to Private Beach! Enjoy a beach equipped garage with opt budget friendly golf cart, backyard pool, and plenty of space for families or groups — all in one of Miramar Beach’s most desirable locations. This beautifully designed 2BR / 2.5BA townhouse is located in the popular Gulf Walk comm just a short 5-minute walk or 1-minute golf cart ride to Private Beach. With custom coastal-modern design, high-end furnishings, and thoughtful details throughout, this home is the perfect beach getaway.

Guest favourite
Home in Destin
4.83 out of 5 average rating, 105 reviews

Beach+Pool+Hot Tub | Golf Cart(incl) + Game Room

Welcome to Destin Beach House — a spacious, FULLY RENOVATED (March 2026) 5-bedroom Crystal Beach retreat just steps from Destin’s famous white-sand beaches. Guests love the open Kitchen, private pool (optional heating), hot tub, Outdoor TV, game room, and 6-passenger golf cart, making it easy to cruise to the beach, Destin Commons, and local restaurants. Perfect for family vacations and group getaways, with open living spaces and a private backyard oasis designed for relaxing after a day on th

Top guest favourite
A spacious resort-style pool is featured in the foreground, surrounded by a landscaped area with palm trees. The curved building in the background consists of multiple balconies, offering a view of the pool and the surrounding area. A clear blue sky complements the scene.
Apartment in Fort Walton Beach
5 out of 5 average rating, 124 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
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, 161 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 open studio layout is presented with a spacious king-size bed and a comfortable sofa. A round table sits nearby, while large glass doors lead to a balcony with ocean views. Soft, neutral tones are used throughout, enhancing the serene atmosphere.
Apartment in Sandestin
4.97 out of 5 average rating, 169 reviews

Zen Retreat ON Beach, Golfcart*Oceanview SanDestin

8th fl. stylish open studio w/stunning VIEW, beachfront in Sandestin Resort between Destin & 30A. 🛺 Golf cart with 5+ nts. NEW Pool & Hot Tub. West Elm furniture & King size bed w/ocean view. Sleek Kitchen w/dishwasher & Keurig. WiFi, 55” smart TV. Washer/dryer. Huge balcony to gaze @ the sea. Enjoy the beach, dining, shopping, trails, golf & entertainment all without leaving the resort. Tram pass & Gym. Perfect for honeymoon, baby moon, girls trip, solo travel or lil family vacay *NO animals

Guest favourite
A wooden dock extends over calm waters, with two gray deck chairs positioned for relaxation. Lush green trees line the shoreline, and a few houses are visible in the distance under a bright blue sky with scattered clouds.
Home in Ferry Park
4.93 out of 5 average rating, 15 reviews

On the water! 7 minutes to the beach!

Bring your boat and your RV. Relax with the whole family in this private water front cottage. 7 minutes to the white sands of Okaloosa Island and 6 miles by boat to Crab Island or just walk out back and paddle the bay. There are 3 public boat ramps with in 2 miles of the property. The waterway will accommodate a draft of 24”. Ferry Street Park and Uptown Station are just minutes away. Everything in the house is brand new and kept perfectly clean and organized so you and yours can relax .

Guest favourite
A spacious lagoon pool is surrounded by tropical palm trees and lush landscaping. Bright blue lounge chairs are positioned around the pool area on light-colored stone flooring, inviting relaxation. An expansive view of the pool extends towards a building with a blue roof, under a clear blue sky.
Apartment in Destin
4.89 out of 5 average rating, 124 reviews

2901 Gorgeous 2bdrm ~ HOT Discount ~ Book Apr 14th

Welcome to Pretty in Paradise, this gorgeous gulf view condo has been renovated with sea inspired decor. Large Balcony w/ pool and Gulf views. 2 Extra Large Bdrms w/ 2 Luxury King Beds, both Bdrms have balconies! Second Bdrm has an additional balcony. Relax at Destin's Largest Lagoon Pool, enjoy a heated pool, hot tub, waterfalls, a poolside bar, Bistro restaurant, Sports lounge and coffee shop. Tiki bar and pool side service! Tennis Courts, pickle ball, basketball, kids play area, gym.

Superhost
Flat in Fort Walton Beach
5 out of 5 average rating, 3 reviews

Newly renovated gulf-front condo on 1st floor

Enjoy your beach getaway in this spacious 2BR/2BA Gulf-front condo! This first-floor unit sleeps 8 with private patio to experience sunrise views over gulf, updated kitchen w/ quartz countertops, renovated baths w/ walk-in shower in the primary, and in-unit laundry. Relax w/ beachfront access, beach chair service (march-oct), pool, fitness center, tennis court, grill, volleyball net, picnic area, kayak, books, games, & dry bar w/ beverage cooler. Close to shopping, dining & attractions!

Guest favourite
The living area features a light-colored sofa and a patterned armchair, positioned around a glass coffee table. Large sliding doors reveal direct views of the beach, allowing natural light to brighten the space. A flat-screen TV is situated on a media console across from the seating.
Apartment in Destin
4.94 out of 5 average rating, 109 reviews

Beachfront at Pelican Beach, Stunning Ocean View

Pelican Beach Resort 306 - 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.

Top guest favourite
Apartment in Fort Walton Beach
5 out of 5 average rating, 11 reviews

WaterScape Now Booking 2026! Beach/resort/pool/spa

Stylish 3BR at WaterScape Resort #A225—just steps to pools, splash park, and the sugar-white sands of Fort Walton Beach. Two King suites with memory foam beds, a private bunkroom with 2 TVs, full kitchen with quartz & stainless, pull-out sofa, smart TVs, washer/dryer, tile floors, plus a fun milkshake bar and coffee bar. Also a selfie wall for those picture perfect shots! Complimentary beach service included. One of Expedia’s Top 10 global destinations!

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, 113 reviews

Island Princess 618 | Beach Service Included

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.

Popular amenities for kayak rentals in Santa Rosa Island

When is the best time to visit Santa Rosa Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price£136£129£188£167£211£285£295£196£162£170£134£167
Avg. temp12°C14°C17°C20°C24°C28°C29°C28°C27°C22°C16°C13°C

Quick stats about holiday rentals with a kayak in Santa Rosa Island

  • Total holiday rentals

    Explore 20 holiday rentals in Santa Rosa Island

  • Nightly prices starting at

    Santa Rosa Island holiday rentals start at £111 per night before taxes and fees

  • Verified guest reviews

    Over 760 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    20 properties feature pools

  • Wifi availability

    20 of Santa Rosa Island holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Santa Rosa Island rentals

  • 4.9 Average rating

    Santa Rosa Island stays are highly rated by guests – averaging 4.9 out of 5!

  • Nearby attractions

    Santa Rosa Island’s top spots include Destin Harbor Boardwalk, Gulfarium Marine Adventure Park and Crab Island

Destinations to explore