
Holiday rentals with a kayak in Anastasia Island
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Top-rated rentals with kayak in Anastasia Island
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

Stunning family canal home with heated pool
Enjoy this charming newly remodelled 1880 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 twins beds. 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

CLUB MED•Family Paradise Retreat-Bring the Dogs
This beautiful home (2000sqft) is just a few blocks from the ocean which has easy beach access,including a play ground for children. Then a street over is the river which has boat ramp! You can also enjoy a local neighborhood restaurant just down the street with a water front view where the sunsets are mesmerizing! The home has been completely remodeled and has a gated back yard with a big pool for you and your family to enjoy. It is also a short drive to the historical down town St.Augustine.

*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.

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!

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

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

NEW Modern Bungalow Close to Downtown! Fenced Yard
- If you are seeking a more affordable vacation rental that is close to all the attractions in downtown St. Augustine, our home is for you! - Private corner lot with a fully fenced in yard for you and your pets - Brand new furniture and appliances - New 55” 4K Roku TV where you can stream all your favorite shows - Superfast 400+ Mbps Wi-Fi speeds - Kitchen includes large pantry and is fully stocked with cooking supplies - 15-20 minutes to St. Augustine Beach & 10 minutes to Vilano Beach

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.

Bring the boat! 2 Bedroom Steps from the Beach
Newly renovated 2 bedroom 2 bath condo for your dream getaway. Boat storage and ramp available. This is a 2nd floor unit just steps to the beautiful Crescent Beach, Matanzas Inlet, pool, tennis and pickleball courts. Enjoy the sunset from the balcony with a peek view of the inlet. Just bring your swimsuit. Condo includes beach towels, chairs, boogie and skim boards, pickeball and tennis rackets,. You'll be just a short drive from historic St. Augustine with it's many attractions.

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 table. 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.

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!

The Turtle Nest, a delightful Oceanfront getaway
Welcome to the Turtle Nest. This Oceanfront 2 bedroom is a delightful getaway for 2 or 3 people. Come and enjoy the gorgeous sunrise and moonrise views over the ocean from this charming and newly renovated hideaway. Five minutes from the heart of historic St Augustine and with direct access over the dune to the peaceful Vilano Beach, its hard to wait to get a cool drink in hand and one's toes in the sand.
Popular amenities for kayak rentals in Anastasia Island
House rentals with a kayak

Midcentury Bungalow w/hot tub-walk to amphitheater

Palmetto House, Lighthouse Park- w/ Bikes & Kayaks

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

The Mangrove House

Dolphins and Dream Water Views, Dock Your Boat!

Walk To Beach•Hot Tub•Large Backyard•Outdoor Games

Brisas del Mar

Family & Pet Retreat w/ Fenced Yard · Walk to Park
Other holiday rentals with a kayak

GameRoom | Canal | Large Dock | Pool | 6 beds

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

Waterfront Zen-Private Dock, Paddleboards, Jacuzzi

Admiral Suite.

Our Four Palms - Waterfront Home w/ Floating Dock

Canal Front! Heated Pool, Tiki Hut & Floating Dock

Palm Paradise - DT just1 Block Stroll & Beach 3 Mi

History By Day, Heaven By Night. Waterfront Oasis
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- Daytona International Speedway
- EverBank Stadium
- Daytona Boardwalk Amusements
- Summer Haven st. Augustine FL
- Lightner Museum
- St Augustine Amphitheatre
- Daytona Lagoon
- Fountain of Youth Archaeological Park
- Kathryn Abbey Hanna Park
- VyStar Veterans Memorial Arena
- Adventure Landing Jacksonville Beach
- Ravine Gardens State Park
- St Johns Town Center
- Saint Augustine Town Plan Historic District
- Ocean Center
- TPC Sawgrass
- St. Augustine Alligator Farm Zoological Park
- University of North Florida
- Daytona Beach Bandshell
- Ocean Walk Shops
- Embry Riddle Aeronautical University
- Vilano Beach Fishing Pier
- Anastasia State Park
- Memorial Park




