
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.

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.

Zen Retreat ON Beach, Golfcart* Hot Tub, SanDestin
8th fl. stylish open studio w/stunning VIEW, beachfront in Sandestin Resort between Destin & 30A. 🛺 Golf cart with 3+ 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

Sandestin Elation Studio - Baytowne - Golf Cart
Ground-floor studio in Sandestin Golf & Beach Resort with serene golf course and lake views. Steps from Baytowne Wharf’s dining and entertainment. Features a king bed, queen sofa bed, full bath, and kitchenette with microwave and mid-size fridge. Enjoy Wi-Fi, Netflix, resort tram access, and beach gear in garage storage. Golf cart available - please inquire about availability and fee. Perfect for a relaxing escape in the heart of Sandestin. And Yes! you may drive the golf cart to the beach.

Unique water front stay Houseboat Destin/FWB
Seas the Day, center on Ft. Walton Beach,quiet bayou connected to bay and gulf on private 1 acre residence. We are 1 of only 3 HB for 50 miles in area. Paddle boards, kayaks , fishing poles and outdoor fire pit. Car needed to get to white sand beaches (4 miles). Shopping close by. A comfy futon in for a second bed. Boat has AC and heat. Unit is to stay docked.Recently renovated inside and out . Larger deck area with loungers . New lighting and ceiling this past spring! Rare find

Nautical Dunes - Ocean Front View!
Enjoy breathtaking views of the beach from your private balcony or take a short walk to the sparkling emerald waters and sugar-white sands. The spacious and elegantly decorated condo offers the perfect oasis for relaxation and fun. Soak in the sun by one of the pools, challenge your friends to a game of tennis, or simply unwind in the hot tubs. Bring your family and friends to create unforgettable memories at "Nautical Dunes" on your next beach vacation!

Island Princess 618 | Gulf Views & Beach Service
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.

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!

21115 Amazing 2 Bdrm ~ Heated Pool ~ Book Feb 28
Penthouse with beautiful gulf views in this Luxury upscale vacation home. Large Balcony with pool and gulf views. 2 large Bdrms w/ luxury King beds, both Bdrms have balcony access. Relax at Destin's Largest Lagoon Pool. Enjoy the heated pool, hot tub, waterfalls, Bistro restaurant and coffee shop. Tiki bar and pool side service! Tennis courts, pickle ball, kids play area, and gym. New Charcoal Grills added onsite!

C603 | Beachfront with Beach Service, Pool, & WiFi
*** THE POOL IS CURRENTLY CLOSED AND WILL REMAIN CLOSED THROUGH DECEMBER 2025*** Welcome to Beach House Condo C603, your beachfront escape! Wake up to Gulf views from your private patio and enjoy easy beach access plus a host of amenities - Private beachfront balcony - Direct beach access; no roads to cross - Enjoy beach service on us Mar 1 - Oct 31 ONLY - Fully-equipped kitchen & private laundry

Beachfront, 7th Flr at Pelican, Breathtaking Views
Spacious one bedroom two bathroom unit with unobstructed spectacular views of the Gulf of Mexico. Recently renovated and decorated professionally, guests will enjoy a new kitchen with granite counter-tops, stylish cabinets, and stainless steel appliances. Kitchen is fully equipped for a family or group of 6. Our guests just step out to the white sand beach from the resort, no streets to cross.
Popular amenities for kayak rentals in Santa Rosa Island
House rentals with a kayak

Waterfront Haven - Perfect for Family Vacations

Private Beach | Gulf Views | Comm Pool | Elevator

Golf Cart | SanDestin | Pool | Arcade | Lake View

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

The Retreat in Santa Rosa Beach- Bungalow E

GolfChart H/CPool 9 Bikes HotT Beachclose 3 Kajaks

Beach house 2 min from the Boat Ramp and Dog Beach

Take it Breezy | Golf Cart | Free Excursions
Other holiday rentals with a kayak

The Ancker Boat House • Waterfront on the Bayou

Beach Cottage • Private Beach • Gated •Heated Pool

“Sea La Vie” (the Sea is Life) Lasata-Baytowne

Pelican Beach Top Floor Beachfront with Best Views

IRC 604: Gulf Front Luxury (2 Bed / 2 Bath)

Pink Flamingo Okaloosa Island

Summit at Topsail #1011

NEW 8th floor Beachfront at Pelican Stunning Views
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 | £137 | £130 | £189 | £168 | £212 | £286 | £296 | £197 | £163 | £179 | £159 | £169 |
| 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 £82 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
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- Point Washington State Forest
- Aqua Resort
- Crab Island
- Destin Harbor Boardwalk
- WonderWorks Panama City Beach
- Opal Beach
- Pensacola Beach
- Frank Brown Park
- MB Miller County Pier
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Blue Mountain Beach
- Grayton Beach State Park
- Gulfarium Marine Adventure Park
- The Track - Destin
- Camp Helen State Park
- Gulf Breeze Zoo
- Shipwreck Island Waterpark
- Gulf World Marine Park
- Tarkiln Bayou Preserve State Park
- Pensacola Museum of Art
- Pensacola Beach Boardwalk
- Johnson Beach
- Pensacola Lighthouse and Museum




