
Holiday rentals with a kayak in Santa Rosa Island
Find and book unique kayak rentals on Airbnb
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 $272 NZD per night before taxes and fees

Verified guest reviews
Over 890 verified reviews to help you choose

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

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Santa Rosa Island holiday rentals include Wi-Fi 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 Accommodation with a Kayak in Santa Rosa Island
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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.

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!

The Retreat in Santa Rosa Beach- Bungalow C
Welcome to your dream coastal escape in Santa Rosa Beach, Florida! Our newly renovated bungalow offers a blend of relaxation & adventure. Bungalow C sleeps 8 & offers 4 spacious bedrooms, a fully equipped kitchen & living room. Just steps away, enjoy the resort-style pool & our boat dock that is included for all renters to dock your boat. It’s the perfect spot to kayak or paddle board as well. The Retreat is close to the beaches and restaurants, but also offers a nice, peaceful oasis to unwind

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

Beachfront 8th Fl. 1 BR at Pelican, Stunning Views
Completely renovated 8th floor condo right on the beach with unobstructed views of the Gulf and the beach. Located in the heart of Destin in popular Pelican Beach Resort, you will enjoy the private beach, multiple outdoor pools, an indoor pool, hottubs and more. Our beachfront condo has been professionally renovated with brand new cabinets, AC, floors, appliances, furniture, kitchen and more. All mattresses are brand new, cool-gel memory foam for a cool night's sleep. Fully stacked kitchen.

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.

WaterScape Guest Favorite | Beachfront | Resort
Escape to our beautifully renovated condo at WaterScape Resort, just steps from the heated pools, lazy river, splash pad, and the sugar-white sands of Fort Walton Beach. Enjoy two King suites with memory foam mattresses, a private bunkroom with a TV in each, a fully equipped kitchen, Smart TVs, in-suite laundry, a Coffee Bar, Milkshake Bar, Selfie Wall, and complimentary beach service with two chairs and an umbrella included.—all in one of Expedia's Top 10 beach destinations in the world!

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.

2705 Gulf & Pool View ~ Book Aug 11 ~ Resort Pools
Blue Water Diamonds is the perfect Oasis to create your family vacation memories! With a pool facing balcony and Gulf Views, you have found your place to relax. The Balcony is perfect for morning sun with coffee overlooking the largest lagoon pool, a secondary pool, splash pad area, Our home Sleeps 6 and is thoughtfully designed with your comfort in Mind, Plenty of seating, Kitchen wares and comfy beds. Charcoal BBQ grills, On-site dining, and Bar.

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
Holiday House Rentals with a Kayak

4 BR 3 BA | Pool | Gym | Pets | 0.7 mi to beach

Sleeps 12* Private POOL * Backyard * Ranch Home

Private Water Access | Heated Pool | Kayaks

Beach house 2 min from the Boat Ramp and Dog Beach

Destin Condo: Pool, Private Beach, Beach Cart

Massive Waterfront Wonder w/8 beds & Boat Dock

GolfCart Pool 9 Bikes HotT 3 Kayaks Beach Toys BBQ

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

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

Waterfront Bliss Beach Cottage

Bayview Cottage | Dog Friendly | 15 Min to Beach

2 bedroom cottage with hot tub
Other holiday rentals with a kayak

Reef Retreat 153 @ El Matador - Gulf front resort

Perrydise@ Emerald Grande 3BR Harbor & Gulf Views!

Newly renovated gulf-front condo on 1st floor

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

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

Waterfront Sound Tri-level TH

Stunning beach views *Not your grandma’s condo*

Guest Home of Eden House Mansion
When is the best time to visit Santa Rosa Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $354 NZD | $333 NZD | $407 NZD | $357 NZD | $444 NZD | $653 NZD | $679 NZD | $451 NZD | $373 NZD | $391 NZD | $308 NZD | $384 NZD |
| 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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- Rentals with a kayak United States
- 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





