
Vacation rentals with a kayak in Santa Rosa Island
Find and book unique kayak rentals on Airbnb
Quick stats about vacation rentals with a kayak in Santa Rosa Island

Total vacation rentals
Explore 20 vacation rentals in Santa Rosa Island

Nightly prices starting at
Santa Rosa Island vacation rentals start at $223 CAD per night before taxes and fees

Verified guest reviews
Over 890 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities

Vacation 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 vacation 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
Top-rated accommodations with a kayak in Santa Rosa Island
Guests agree: these accommodations with a kayak are highly rated for location, cleanliness, and more.

Sandestin Resort Studio, Spectacular Bay Views
Our Bayside Studio offers spectacular panoramic views of Choctawhatchee Bay. Located in Sandestin Resort on a quite enclave framed by Florida pines and the fairways of The Links Course, your own personal balcony on the third floor serves as the perfect viewpoint of the Bay. Guests and children will enjoy our relatively low nightly rates but also have access to all the amenities Sandestin has to offer (Beach, golf, tennis, water-sports, spa, nature trails, many kids activities, dining, shopping).

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!

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.

Zen Retreat ON Beach~Golfcart*~Oceanview~Pool
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

Waterfront~Retreat ~Pool & Deep Dock~Boats welcome
Luxury Waterfront escape w/ Pool , Deep-Water Dock & Sunset Views🌴 Bring your boat or jet skis and enjoy direct access to the intercoastal bay—just minutes from Crab Island. Relax poolside, unwind on the water, and enjoy peaceful sunset views while still being only 10 minutes from the beach, dining, and downtown Fort Walton Beach. 🚤 Private deep-water dock (boat & jet ski ready) 💦 Heated pool for year-round use 🌅 Waterfront views + outdoor living 🏖️ Quick drive to beaches & attractions

Luxury Beachfront Home, Sleeps 12, Kayaks, SUPs
🏖 Luxury Beachfront Home for multi-family stays with everything included! Sleeps 12, 3 BR/3.5 BA + 4 Parking spots. On the beach! Unlike most beachfront rentals, this home includes full beach setup and toddler gear—no rentals needed. 🛏 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!

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.

Waterfront! Sleeps 14 & TWO Story Waterslide Fun!!
This family fun home has a 2 story super fast custom water slide, large pool, (extra charge to heat pool) swim up bar, outdoor tiki hut bar with sink and gas grill, charcoal grill, fire pit, sandy beach, dock, boat slip, (no boat lift) paddle boards. Private suite with kitchen & bathroom on lower level with private access leading out to bay. bring your own fishing gear if you like to fish. Home is a labor of love and has brought so much joy to our family & hopefully to yours.

Gulf Walk * House with Pool & Golf Cart
1 Block to the Beach! Enjoy a beach equipped garage with 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.

Jet Ski Adventure - Family Getaway
780 On The Bay Experience the best of the Emerald Coast at 780 On The Bay. Our property offers a stunning Bay Front vacation Rental in the heart of Miramar Beach. Our property offers a unique, serene waterfront setting on the Choctawhatchee Bay, perfectly positioned for both relaxation and adventure. Located just a 5-minute drive or a scenic 15-minute walk to the world famous white sand beaches, you can enjoy the peace of the bay with easy access to the Gulf of America.

21017 Gorgeous Views ~ Pools ~ Gym ~ Book Aug 10th
Gorgeous Panoramic Gulf Views from this 10th floor, 3 bedrooms end unit, all bedrooms have access to the 100 ft extra large balcony with gulf views. Seating for 8. Resort Lagoon Pool and second Heated pool, 2 King Beds, 1 Queen Bed and a Queen Sofa Sleeper All the comforts of home, easy walk to the beach, or free Shuttle. 5 Star Resort, onsite Restaurant, coffee shop and pool side Tiki bar, Tennis, pickle ball, basketball, state of the art gym & BBQ grill area

Boater/fisherman’s paradise with on-site launch!
Villa with waterfront views! Wake up to stunning views of the bayou from every room in the house! Bring your own boat and launch on-site (plenty of trailer parking available), fish off the dock with a cleaning station , or watch dolphins play as you sip your morning coffee on the back porch. Located near tennis/pickleball courts, golf course, and just a short drive to the beach or boat ride to Crab Island …adventure and relaxation await!
Popular amenities for Santa Rosa Island kayak rentals
House rentals with a kayak

Waterfront Haven - Perfect for Family Vacations

Destiny West|Heated Pool|Golf Cart|Gym

Destin Condo: Pool, Private Beach, Beach Cart

Sleeps 12* Private POOL * Backyard * Ranch Home

Luxury Beach Estate 5200 SqFt Pool 2 Golf Carts

Massive Waterfront Wonder w/8 beds & Boat Dock

Beach house 2 min from the Boat Ramp and Dog Beach

Take it Breezy | Golf Cart & FREE Excursions
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 vacation rentals with a kayak

Reef Retreat 153 @ El Matador - Gulf front resort

Canalfront, Boat slip, Hot Tub, SUPs, Dogs, Beach

Perrydise@ Emerald Grande 3BR Harbor & Gulf Views!

Destin Beach House•Sleep12•Hot Tub•Pool•RoofDeck B

DW Sandpiper L03 ~ Walk Out Lanai ~ Lazy River!

WaterScape Guest Favorite | Beachfront | Resort

8th floor Beachfront at Pelican Stunning Views

Stunning beach views *Not your grandma’s condo*
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 | $290 CAD | $273 CAD | $333 CAD | $292 CAD | $364 CAD | $535 CAD | $556 CAD | $369 CAD | $305 CAD | $320 CAD | $252 CAD | $315 CAD |
| 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 |
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- Rentals with a kayak Okaloosa County
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- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- Opal Beach
- Pier Park
- Henderson Beach State Park
- Village of Baytowne Wharf
- Seacrest Beach
- Frank Brown Park
- Navarre Beach Fishing Pier
- Aqua Resort
- Johnson's Beach, Gulf Islands National Seashore
- HarborWalk Village
- Topsail Hill Preserve State Park
- Grayton Beach State Park
- Gulf Breeze Zoo
- Fort Walton Beach Landing
- Jade East Towers
- Shipwreck Island Waterpark
- The Boardwalk on Okaloosa Island
- Morrison Springs
- Pensacola Bay Center
- Destiny East
- Camp Helen State Park





