Holiday rentals with a kayak in Flagler County

4.83 out of 5 average rating, 133 reviews

Stunning family canal home with heated pool

Enjoy this charming newly remodelled 1800 sq. ft. 3 bed 2 bath home. The King Master Suite with full private bath boasts relaxing views of the pool/canal through the large picture window. The 2nd canal view bedroom features a comfy Queen bed. The third bedroom completes the sleeping arrangements with two twins. Cook up the days catch while watching dolphins play down at the main canal. The 2025 built heated 30 x 15 swimming pool with more water views will entertain guests and kids!! LBTR#13030

4.96 out of 5 average rating, 96 reviews

Cottage in Crescent City

Lakefront cottage and dock★Free bikes & paddleboat

Bring your fishing gear or small boat to enjoy a fun getaway at the Captain's Cottage with a dock on Lake Stella. Key-less entry allows for self check-in and welcomes you to this comfortable clean 962 sq. ft. space with two queen size beds, one bathroom, full kitchen, florida room, and a fenced-in backyard. A paddle boat is provided. Three kayaks and 2 bicycles are also available! Or you can bring your boat and go fishing! Enjoy swimming, lovely sunsets and strolls around the beautiful lake.

5 out of 5 average rating, 40 reviews

The Flamingo Nest

ON Freshwater Canal, Wheelchair, JW grads & Snowbirds for winter message me, Bird Watch year round! 6 Kayaks, 2 person Canoe & SUP boards upon request, minutes to Beach, Fishing, Golfing, Walk & Bike Trails, SPLASH PAD at Holland Park til 10pm! St Aug & Daytona Beach 25 mins . Reviews are real customers, my property treated like Family I live nearby. Question?ask me! 19"w transport chair, bath chair, walker avail! No one stays home! Communication is key to a successful Vacay! LBTR #37518

4.94 out of 5 average rating, 17 reviews

Home in Flagler Beach

Heated Pool/Steps to Private Beach/Fire Pit/Kayaks

Hammock Heaven is an almost beach front coastal retreat offering both sunrise ocean views and sunset Intracoastal views, which is not common in Flagler Beach. Fully loaded with everything you need and want, it features a heated saltwater pool, canal-front dock with a boat lift, fire pit, chef’s kitchen, coffee bar, executive office and tons of space to unwind. With 4 large bedrooms and cozy coastal décor, it’s perfect for relaxation and fun—and did I mention you’re steps away from the beach?

4.92 out of 5 average rating, 50 reviews

Cottage in Ormond Beach

Manatee & kayak friendly waterfront cottage

Relax at this unique tropical canal front house with direct Tomoka River access. Accessible by boat or car with waterway that connects to the Intracoastal. Bring your boat, jet-ski or kayak and dock it at the property. The house is located 10 minutes from Ormond beach and 20 minutes from Daytona Beach. Public boat ramp is within walking distance. This private fully fenced house is located in a quiet neighborhood that explodes with visitors during Daytona bike week with multiple concerts 🌱

Bungalow in Flagler Beach

4.96 out of 5 average rating, 124 reviews

Tropical Beach Bungalow Romantic Couples Getaway

(Early check ins available upon request only) More things to do in this Funky Beach Town than you can imagine! Plenty of Beach Bars and Restaurants . There's an incredible nightlife on the Island as well! Just get away from the world and lay in a hammock on the beach with a fire and a bottle of Champagne on a private Beach Chikee and feel like you're on a Deserted Island Only Steps Away. There's Surfing, Fishing, suntanning, and plenty more to do on the Island. The unit is not Pet-friendly

5 out of 5 average rating, 15 reviews

Fall Special Waterfront|Pets|Pool|Outdoor Kitchen

Experience the perfect blend of luxury, comfort, and adventure at our waterfront retreat. Book now to create unforgettable memories . Begin your day with a breathtaking sunrise over the tranquil lagoon. This sunlit, luxurious home offers all the comforts you desire for a perfect getaway. Our bright and airy home features a Spa-like Bathroom, Fully Equipped Kitchen: Cook with modern appliances, complemented by a dedicated coffee bar for your morning brew. Enjoy al fresco dining pool side.

4.88 out of 5 average rating, 155 reviews

Peaceful Family Retreat • Central • Pet Friendly

Walk to the free splash park, hit the beach, and save big—this hidden gem includes everything you need for a fun, easy, budget-friendly vacation! We’ve got beach chairs, loungers, umbrellas, beach toys...Just bring yourselves. Inside, enjoy much more than the usual kitchen essentials, lots of sports equipment, and plenty of hygiene essentials. Plus, Publix and restaurants are just steps away in the nearby Island Walk plaza. Four legged family members love the large dog park with pond!

4.89 out of 5 average rating, 76 reviews

Manor on the Canal/Luxury Oasis/Pool-Hot Tub-Dock

You will love the bright, open floor plan waiting for you and your group. The large kitchen island is the hub where friends and family gather. The huge “Florida” room has a pool table, large tv for gaming or to watch the big game. Your private screened in lanai boats a huge table, hot tub, solar and electric heated pool, gas fire pit and gas grill. Fish off the new dock with sitting area or relax on the second waterside patio. Restaurants, shopping and beaches are only 10 minutes away.

Apartment in Flagler Beach

4.91 out of 5 average rating, 94 reviews

Calm Creek - Flagler Beach's Hidden Gem!

There is no other place like this in Flagler Beach! Nestled off Bulow Creek and surrounded by majestic oaks, magnolias and palm trees. Your getaway sits on 3 quiet, secluded acres of pristine Florida beauty. Less than 3 miles from the Flagler Pier & the heart of Flagler Beach. We have a kayak, a canoe, fishing gear, and beach supplies all at no extra cost. Hike, sit on the dock or just relax in the sun. We are also a short drive to St. Augustine & Daytona. Will accommodate 2 adults.

4.95 out of 5 average rating, 22 reviews

Waterfront • Heated Pool • Dock • Game Room

Coastal Luxury – Private Dock, Heated Saltwater Pool & Stunning Decor! Escape to this brand-new, beautifully decorated home on a serene saltwater canal, just 10 minutes from the beach! Enjoy the heated saltwater pool, fish from the private dock, or explore the waterways—you may spot dolphins, manatees, and other marine life. Inside, stylish coastal decor and modern amenities offer the perfect family-friendly retreat. Relax, explore, and make unforgettable memories.