
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.

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.

Light&Airy ON Beach/*GolfCart/OceanView/@SanDestin
Sleek airy 1st floor studio ON BEACH. 🛺 Golf cart w/4+ nts. In Sandestin Resort between Destin & 30A. NEW Pool & Hot Tub! Pottery Barn King bed with beachfront view. Step right off our private patio to the beach or relax on the patio round Bali bed. WiFi, 55” smart TV, Kitchen, Washer/dryer. Enjoy free gym, tram, beach, trails, golf, dining, shopping & entertainment all without leaving resort! Perfect honeymoon, baby moon, romantic getaway, girls trip, solo travel or lil’ fam vacay! *NO animals

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!

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!

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.

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 .

3102 Gorgeous 2 Bdrm ~ Heated Pool ~ Book Apr 13th
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.

Alerio D202: Gulf Beach Escape
This beautiful condo is a 3 bed/2 bath perfect Destin vacation rental with spacious accommodations for up to 7! It’s located in a newly developed area just across the road from the beach. Enjoy a short walk to the beach or open your windows and smell the fresh ocean air from the patio Everything within this space is updated with a modern feel including brand new living room furniture, USB lamps throughout, hardwood flooring, granite countertops and a large balcony that faces Scenic Drive

Grand Sandestin 4th flr 1 b.room-Steps to Baytowne
Elegant 1BR retreat with 4th-floor views from large balcony, steps from the Village of Baytowne Wharf. Just a 5–10 min TRAM ride to Sandestin pristine private beaches. Features a king bed, queen sofa sleeper, full kitchen, in-unit washer/dryer, and refined décor. Stay connected with high-speed Wi-Fi, unwind with Netflix, and enjoy use of beach chairs and an umbrella stored in our private garage-level storage. Perfect for couples or small families looking to relax and explore Sandestin.

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.

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!

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
House rentals with a kayak

Waterfront, Boat dock, Bikes, BEACH, HOT TUB

Waterfront ~Home~ Private ~Pool & Deep dock~ boats

The Pink Cottage

Cozy Up on Choctawhatchee Bay

The Retreat in Santa Rosa Beach- Bungalow E

Boater/fisherman’s paradise with on-site launch!

Sleeps 12* Private POOL * Backyard * Ranch Home

Massive Waterfront Wonder w/8 beds & Boat Dock
Cottage rentals with a kayak

2 bedroom cottage with hot tub

Waterfront Bliss Beach Cottage

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

Bayview Cottage | Dog Friendly | 15 Min to Beach
Other holiday rentals with a kayak

Beach Cottage • Private Beach • Gated •Heated Pool

NEW Listing! Beachfront 1st Floor w/Amazing Views!

Sola Azul | Gulf-Front Luxe + Beach Service

Destin Condo: Pool, Private Beach, Gear Included

Relaxing 3 Bedroom Condo with Beach Access

Waterfront! Sleeps 14 & TWO Story Waterslide Fun!!

The Seahorse 30A! Golf cart included! Sleeps 10!

GolfChart H/CPool 9 Bikes HotT Beachclose 3 Kajaks
When is the best time to visit Santa Rosa Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £140 | £133 | £193 | £171 | £217 | £292 | £303 | £201 | £166 | £174 | £137 | £171 |
| Avg. temp | 12°C | 14°C | 17°C | 20°C | 24°C | 28°C | 29°C | 28°C | 27°C | 22°C | 16°C | 13°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 £83 per night before taxes and fees

Verified guest reviews
Over 880 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

Rentals with dedicated workspaces
10 properties have a dedicated workspace

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
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- Rentals with a kayak Okaloosa County
- Rentals with a kayak Florida
- Rentals with a kayak United States
- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- Pensacola Beach
- Opal Beach
- Frank Brown Park
- Johnson's Beach, Gulf Islands National Seashore
- Navarre Beach Fishing Pier
- Blue Mountain Beach
- Grayton Beach State Park
- Gulf Breeze Zoo
- Village of Baytowne Wharf
- Henderson Beach State Park
- Camp Helen State Park
- Shipwreck Island Waterpark
- Gulfarium Marine Adventure Park
- The Track - Destin
- HarborWalk Village
- Gulf World Marine Park
- Topsail Hill Preserve State Park
- The Boardwalk on Okaloosa Island
- Aqua Resort
- Destiny East
- Jade East Towers




