Vacation rentals with a kayak in Anastasia Island

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Top-rated kayak rentals in Anastasia Island

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A heated swimming pool is enclosed by a screened lanai, showcasing clear blue water that glistens in the sunlight. Lounge chairs line one side of the pool area, offering a place to relax. The scenic canal is visible beyond the pool, enhancing the tranquil setting.

Home in Palm Coast

4.84 out of 5 average rating, 135 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

Top guest favorite

A sandy beach extends towards the horizon, meeting rolling waves under a clear blue sky. Dune grass sways gently in the foreground, with a wooden boardwalk leading to the shore. Beach chairs and umbrellas are visible in the distance, indicating a welcoming recreational area.

Condo in St. Augustine

4.94 out of 5 average rating, 143 reviews

Pelican Inlet 2 Bedroom Condo Steps from the Beach

Enjoy this newly renovated 2 bedroom 2 bath condo for your dream getaway. This is a ground floor unit in the "B" building which means you are just steps to the beautiful Crescent Beach, Matanzas Inlet, pool, tennis courts, pickleball, and more. Just bring your swimsuit. Condo includes beach towels, chairs, boogie and skim boards, beach toys, 2 kayaks, paddleboard, pickleball paddles and tennis racquets. You'll be just a short drive from historic St. Augustine with it's many attractions.

Top guest favorite

The exterior of the mid-century bungalow is surrounded by lush landscaping and palm trees. An expansive deck is visible, offering a space for outdoor relaxation. The green yard features a variety of shrubs and plants, contributing to a serene, natural atmosphere.

Apartment in St. Augustine

4.97 out of 5 average rating, 118 reviews

*1 Block From the Beach! 5 min Drive to Downtown *

In a quiet Vilano Beach community this mid-century bungalow with expansive deck is a beach lovers paradise. Just a stones throw away from one of the most beautiful and private beaches Florida has to offer, and a short drive or water taxi to historic downtown St Augustine, this is truly a gem of a location. You can walk to Publix, bars, restaurants, coffee shops, pier, water taxi, and more. This guest apartment of a 2 story duplex is on the second floor, which has a private entry and parking.

Guest favorite

Cottage in St. Augustine

4.93 out of 5 average rating, 187 reviews

Coastal Cottage -firepit, pet fence, kayaks, bikes

Located in the historic Lighthouse Park neighborhood, this charming 1940s coastal cottage is easy strolling distance to the Lighthouse, Alligator Farm, mini-golf, cafes & more! It is only a 0.8-mi walk to the Bridge of Lions, where you can walk over the Bay to downtown St. Augustine. You couldn't ask for a better location! It's on Anastasia Island so you're a short walk/bike/car ride from the beach & Ampitheater. It's cozy, pet & kid-friendly with a big backyard. Kayaks & bikes available!

Top guest favorite

A light-filled bedroom features a spacious bed with a colorful decorative throw. A wooden ceiling adds warmth, while white curtains provide softness. Decorative elements include a floral-patterned chair and framed artwork, creating a relaxed and inviting atmosphere.

Bungalow in Flagler Beach

4.96 out of 5 average rating, 125 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

Top guest favorite

The outdoor area features a private saltwater pool with a custom spa, surrounded by lush tropical landscaping. A spacious cabana is included, with comfortable seating beneath flowing white drapes. A shaded umbrella is positioned beside the pool, enhancing the relaxation space.

Home in St. Augustine

4.99 out of 5 average rating, 121 reviews

2023 Lux Home 4bd/3.5ba+HotTub+SaltPool+Walk2Beach

* Built in 2023- luxe coastal furnishings & linens * Featured in 2024 Good Housekeeping Mag🌟 * 2 King Suites (1 on each floor) | 2 Queen Bedrooms | 3.5 Baths * Private Saltwater Pool & Spa/Hot Tub * Poolside Cabana | Outdoor Kitchen | Front Porch * Bikes, Beach Toys, Beach Chairs * Lush Tropical Landscaping * 0.2 miles - gorgeous quiet beach * 5.5 miles- historic downtown St Augustine- The oldest city in the United States! * 0.2 miles - Cap's Restaurant for sunset dinner on the water

Guest favorite

The front exterior of the house is shown, featuring a light blue facade and a neatly manicured lawn. A concrete driveway leads to a single-car garage. Lush green bushes and trees frame the house, contributing to a serene environment.

Home in Palm Coast

4.87 out of 5 average rating, 157 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!

Guest favorite

A wooden dock stretches over the calm, turquoise waters of a canal, surrounded by lush greenery. Outdoor seating is available on the deck, with a table and chairs positioned beneath a sheltered area, offering a peaceful spot to relax and enjoy the scenic views.

Home in St. Augustine

4.76 out of 5 average rating, 110 reviews

On the Canal, by Beach, Kayaks, Dock, Fishing

> Canal front home > One small dog OK *with fee > Walkable to the beach and the intracoastal > Neighborhood beach walkover > Fully equipped and stocked kitchen > Extremely safe neighborhood > Private back porch w BBQ, overlooking the historic Treasure Beach canals > Fishing poles, 2 kayaks w/oars, 1 SUP, some beach gear > Fishing is welcome in the canal behind the house! > Books and games provided > Private parking > Washer Dryer > Keurig > 3 days of supplies (TP, trash bags, etc.)

Top guest favorite

A serene backyard features a large swimming pool surrounded by mature greenery. Comfortable seating options are available, including lounge chairs and a small table with chairs, enhancing the outdoor relaxation area. Sunlight reflects off the pool's clear blue water, inviting refreshing moments.

Apartment in St. Augustine

4.97 out of 5 average rating, 102 reviews

Very Special Apt, St Augustine Historic District

Forget your worries in this spacious and serene apartment. A large, quiet space with a fenced beautiful backyard, large pool (rare for the Historic District) and gardens. Dogs are welcome. Just steps to what the walkable city of St. Augustine has to offer. A 3 minute walk to St. George Street for food, fun and frolic. The Fort, Castillo de San Marcos; the riverfront; Flagler College Tour; St. Augustine Lighthouse, restaurants & attractions close by. The beach is a 12 minute drive.

Guest favorite

A spacious living area features a large 75-inch television mounted on the wall. A stylish leather couch and wooden coffee table provide seating, while a modern kitchen with bar stools offers additional space for dining. Warm lighting from pendant fixtures enhances the inviting atmosphere.

Home in St. Augustine

4.95 out of 5 average rating, 174 reviews

Close to downtown, 3BR,6Beds,Movies, Ping Pong,Fun

Minutes to Downtown St. Augustine! Brand New construction, 75-inch TV with wifi, streaming services, video games and karaoke machine, full size ping pong and basketball game. Xbox1 has blu-ray player, Kinect, and several games. 6 beds with additional air mattress and pack&play. Plenty of toys/games throughout. Grill and camping chairs in the garage. Fully stocked kitchen with plenty of amenities, and local and responsive hosts ready to make your stay a terrific one.

Top guest favorite

Aerial view of a home surrounded by lush greenery near a waterway, featuring a long dock extending into the water. The structure is illuminated, highlighting the inviting exterior against the twilight sky.

Home in St. Augustine

4.99 out of 5 average rating, 120 reviews

Gorgeous Views, Golf cart w/beach access!

Beautiful home with outstanding view & access to the Intracoastal. Watch dolphins play, yachts cruise by or catch the sunset from the dock. If you're feeling adventurous, jump on a kayak or paddle board & explore the quaint islands nearby. If the ocean is calling, take a 2 min ride with the included 6 seater golf cart (must sign waiver) & drive right on to Crescent beach. Grab a surf or boogie board for some extra excitement!

Guest favorite

A wooden pier extends into the water, silhouetted against a vibrant sunset. The sun's orange and yellow hues reflect on the water's surface, while gentle waves lap at the shore. Soft clouds are visible in the sky, adding to the serene atmosphere.

Townhouse in St. Augustine

4.91 out of 5 average rating, 109 reviews

Coastal Cottage Vilano Beach St.Augustine

Awake to a Gorgeous Sunrise on the Beach and Unwind on the Intercoastal for an Extraordinary sunset. Downtown St. Augustine is just across the bridge for Dining, Fun attractions, and shopping. Fresh Bath Towels, Beach Towels, 2 Kayaks, Boogie Boards, Beach Chairs, Coolers, Beach Cart, and Fun Family Games. Golf Cart $200/stay, extended stay $300. Pet Friendly $175/pet/stay, Extended stay $300. Beach is walking distance.