
Holiday rentals with a kayak in Santa Rosa Island
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Top-rated rentals with kayak in Santa Rosa Island
Guests agree: these rentals with 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).

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!

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 Townhome near Destin Harbor Boat Slip
Welcome to our beach getaway in Holiday Isle. Our place has a King size bed w/private shower, 5 minute walk to beach & a boat slip. There is beach access to 4 different beaches, a 30-foot boat slip, & a 300-pound ice machine. We have a kayak & life jackets for your pleasure. This 4 bedroom 2 bath townhouse overlooks the Destin Harbor with a Panoramic view of Destin Harbor from the deck. The Destin water taxi will pick you up at our dock & take you to your destination in the Destin Harbor.

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 .

“Sea La Vie” (the Sea is Life) Lasata-Baytowne
BAYTOWNE STUDIO CONDO WITH BALCONY - Lasata #3307 "Sea La Vie" (the Sea is Life)…We welcome you to our cozy and quaint get away on the Bay side/the Village. From the sand to the very sound of the waves, the Sea is the Life we all crave. Come and enjoy the restful pleasures of Baytowne and all it has to offer. There is plenty of restaurants, shopping and beach access across the Hwy (Sandestin Hilton entrance) only a 5 minute drive. After a stay in Sandestin, life will become more manageable.

Sea Turtle House-On Beach-Townhome-Kayaks/SUP
🏖 Steps from the Ocean | 3BR/3.5BA Townhome w/ Views + Kayaks & SUPs! Relax in this spacious 3-story townhome—literally steps from the beach! Enjoy breathtaking ocean views, modern comforts, and everything you need for fun in the sun. 🛏 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!

Gulf Walk * House with Pool & Golf Cart included
Golf cart included in 7 nights stay! 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.

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

3107 Poolside Villa ~ Pools ~ Gym ~ Book June 19th
One of only 14 Exclusive Poolside Villas! Welcome to the Villa Cabana Royale! 1450 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 6 and is the perfect location, with an outdoor dining and patio experience in the tropical gardens alongside the gorgeous lagoon pool. The Villa Cabana Royale has 2 huge bedrooms, 2 King Beds, single chair bed, queen sofa sleeper. 4 beds in total. 65" Inch Smart TVs
Popular amenities for kayak rentals in Santa Rosa Island
House rentals with a kayak

Waterfront, Boat dock, Bikes, BEACH, HOT TUB

Sundance: Sleeps 18! 1 Block to Beach! Pool & spa!

Waterfront~Retreat ~Pool & Deep Dock~Boats welcome

Destin Condo: Pool, Private Beach, Beach Cart

The Pink Cottage

Sleeps 12* Private POOL * Backyard * Ranch Home

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

Home on Bay-Private Pool-Boat Access-Kayaks-Fish!
Other holiday rentals with a kayak

Reef Retreat 153 @ El Matador - Gulf front resort

Ground Floor Condo at Sanctuary at Redfish

Jet Ski Adventure - Family Getaway

Beachfront Condo | Resort Pool | Sleeps 6

Pelican Beach 19th Floor 1 Br - on the Beach

Cozy Up on Choctawhatchee Bay

Stunning beach views *Not your grandma’s condo*

*SALE 190N June 8-13 Ariel Dunesll OceanViewPools
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 | £155 | £146 | £178 | £168 | £213 | £287 | £297 | £197 | £163 | £171 | £135 | £168 |
| 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 £112 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
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- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- Aqua Resort
- Seacrest Beach
- Opal Beach
- Frank Brown Park
- Navarre Beach Fishing Pier
- Village of Baytowne Wharf
- Johnson's Beach, Gulf Islands National Seashore
- Blue Mountain Beach
- Grayton Beach State Park
- Gulf Breeze Zoo
- HarborWalk Village
- Fort Walton Beach Landing
- Henderson Beach State Park
- The Boardwalk on Okaloosa Island
- Shipwreck Island Waterpark
- Topsail Hill Preserve State Park
- Camp Helen State Park
- Gulfarium Marine Adventure Park
- Pier Park
- Gulf World Marine Park
- Jade East Towers





