Vacation rentals with a kayak in Anastasia Island

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Top-rated kayak rentals in Anastasia Island

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Three kayaks are secured on a wooden dock overlooking the water. Two bright orange kayaks and one vibrant green kayak are positioned adjacent to one another, with the calm water visible in the background, reflecting the clear blue sky and scattered clouds.

Home in Palm Coast

4.87 out of 5 average rating, 119 reviews

Heated pool home w/boat dock, water front & Marina

*Heated Saltwater Extremely Clean Pool home with dock, closest vacation home to to marina, fuel, boat rentals & intercoastal. Bikes & kayaks included. Shopping, restaurants, bars, golf, walking & biking trails 1 mile. 3-2 sleeps eight. Air mattresses available. Pull out sofa beds Ping-pong & Corn Hole to enjoy. Water views from front & backyard. 10 minutes to beach. St. Augustine & Daytona 30 min. Sand Bars 30 min by boat this home has all you could want in a Florida vacation. Boaters Dream!!

Guest favorite

A colorful display of kayaks is arranged on a wooden rack. The foreground features a green and blue kayak, while pink and orange kayaks are visible in the background. The vibrant colors are complemented by a clear blue sky overhead.

Condo in St. Augustine

4.92 out of 5 average rating, 117 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

Townhouse in St. Augustine

4.99 out of 5 average rating, 69 reviews

Waterfront Sanctuary/ plus use of 2 Kayaks FREE!

This perfect location offers access to BOTH Crescent Beach & the Inter Coastal. Unobstructed direct water views with Spectacular Sunsets & the ability to walk & fish off the dock, wave to the boats and watch the dolphins play! A 10 min walk across the street and you're on Crescent Beach. The best of both worlds! Our beautifully renovated home w/ the Riverview pool & 6 Slip Boat Dock. Comfy King beds, quality linens & MBR Coffee Bar. Fully Equipped Kitchen, washer/dryer, Use of 2 Kayaks.

Guest favorite

Cottage in St. Augustine

4.92 out of 5 average rating, 174 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!

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, 141 reviews

Cute home, peaceful and so central !

Minutes to walk to Holland Memorial Park, the free splash park is open !!+ awesome playground, tennis, soccer/basketball/baseball fields, 10 min. drive to the beach over Dune's Bridge. Minutes to walk to Publix, restaurants, ... so central! Lots of essentials included: essentials for the beach, a kayak, dog box, dog tie out and more. You don’t have to spend more money on certain essentials when you stay here. Commercial trucks /trailers are not allowed on the property per code enforcement.

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, 107 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.)

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, 142 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.

Guest favorite

An aerial view captures the sandy beach bordered by a grassy area and a residential road. Several beach houses line the shore, with some positioned directly facing the ocean. Waves gently lap at the shoreline, and a cloudy sky creates a vibrant backdrop.

Bungalow in Flagler Beach

4.96 out of 5 average rating, 116 reviews

Tropical Beach Bungalow Romantic Couples Getaway

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

Superhost

The custom home is elevated on stilts, featuring spacious decks surrounded by lush greenery. Tall trees and palm plants provide natural shade in the yard, while a sandy path leads to the entrance. The open space invites relaxation in a serene outdoor environment.

Home in St. Augustine

4.8 out of 5 average rating, 64 reviews

Downtown Waterfront Home with Dock

Take a holiday at this unique and quirky custom home. Only 1.2 to Historic downtown and 1.3 to the beach...But you may never want to leave! Sunrises, sunsets, water birds and fish are daily sights when you stay here in this truly magical home. Explore the creek off the dock by kayak or paddle board. This stilt home was built to capture all the views and it's just like being in a lodge in the woods. It’s a great open plan perfect for families.

Top guest favorite

A wooden rack supports two kayaks and one paddleboard, each secured with bright red life jackets. Lush green grass surrounds the base, with a view of the water and trees in the background providing a tranquil setting.

Home in St. Augustine

4.99 out of 5 average rating, 109 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, 100 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.

Top guest favorite

A comfortable living area features a beige sofa with decorative pillows positioned opposite a wooden coffee table. A recliner chair is nearby. The kitchen area includes modern appliances and seating at the counter. Palm tree artwork adorns the walls, enhancing the coastal ambiance.

Apartment in St. Augustine

4.98 out of 5 average rating, 102 reviews

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.

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What guests are saying

Resort-Style with King Bed APT, Full Amenities

5 out of 5 average rating, 13 reviews6 days ago

Condo was exactly how the pictures described and even more specious than expected! Bedroom and walk in closet was spacious and comfortable, loved the dock and amenities in the club house that were included! The area is close to everything - 15 minutes to downtown and less than 15 minutes everywhere we wanted to go ! Perfect place to stay for the value and time of year we come 3x a year and will definitely be staying here again. Host was extreamly responsive and helpful with anything we needed as well ! Thank you so much for the stay !

Condo in St. Augustine

What guests are saying

Coastal SeaRenity - Pool & Canal!

4.91 out of 5 average rating, 33 reviews1 week ago

18 relaxing nights. Large screened pool and lanai. Fully stocked kitchen. Split bedroom layout for privacy. Close to Flagler Beach, with many casual seafood restaurants. Even chairs and cooler provided for a visit to the beach. Lauren, the hostess is super fast at answering questions and offering travel advice. Beautiful neighborhood and friendly chats while dog walking.

Home in Palm Coast

What guests are saying

Laguna Paradiso-Waterfront Pool Spa Games Firepit

5 out of 5 average rating, 58 reviews1 week ago

We had a great stay at Evo’s place. He was very accommodating and went out of his way to make sure our stay was enjoyable. The house was great, and the view incredible. We saw dolphin several mornings, various birds and even a sea turtle. We had two young grandchildren staying with us and the house is child safe. I would not hesitate to stay here again and would encourage others to stay here as well.

Home in Palm Coast

What guests are saying

Waterfront home with private dock, walk to beach

5 out of 5 average rating, 41 reviews2 days ago

This place is lovely! The host is wonderful and really went above and beyond! The house is very clean and well equipped! We enjoyed the snacks she left and my husband loved that there were fishing poles available so that he could fish from the dock. We also appreciated her book with recommendations of various restaurants and local attractions! I would definitely stay here again!

Cottage in St. Augustine

What guests are saying

Huge pool, beach PacMan mins to everything, pet ok

4.98 out of 5 average rating, 65 reviews4 weeks ago

Theresa's house was the PERFECT place for our family of 5! It was clean, cozy with plenty of our own space. The house had everything we needed or wanted and then some! We would absolutely stay there again as well as confidently recommend it to others. We are grateful for such a fantastic setting for our family vacation :).

Home in St. Augustine

What guests are saying

New Close to Beach Heated Pool Amenities!

4.86 out of 5 average rating, 28 reviews1 week ago

We felt right at home and this was by far our favorite place we have ever stayed. There was something for everyone. Our kids loved the pool and the game room and having breakfast on the screened in patio felt like eating at a resort each morning. This place far exceeded our expectations, it was clean, beautiful, and was in a great location between St. Augustine and Daytona. Felix was a great host he was very kind and responsive. Even the neighbors were great they told us about a great beach to take our kids. 100 out of 10 would recommend and I’m sure my wife is trying to book this place again for the summer hahaha. Thank you for a great family vacation filled with unforgettable memories and for making us feel at home.

Home in Palm Coast

What guests are saying

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

4.99 out of 5 average rating, 93 reviews4 weeks ago

Our family absolutely enjoyed our stay. The home is stunning, but more importantly functionally designed. The flow of the home feels perfect, from the front porch all the way to the secluded backyard and side yards for storage. We appreciated the 1st floor master bedroom for the grandparents, the open concept for socializing, the wall hooks throughout for towels, spacious bathrooms, adequate seating for lounging, and cabinets stocked with dishware, appliances, coffee, creamers and even laundry detergent! All of which were unnecessary but appreciated! The spa was easy to use and heated up quickly. Our kids spent hours upon hours in between the pool and spa (due to mild weather). We brought scooters for the kids, since the bikes are adult sized. Riding our scooters to Caps for dinner was so perfect, we did it twice! And would have done it again if we'd been able to stay longer.Honestly, this review isn't even doing this place justice. We were obsessed! Comfortable, relaxed and happy.

Home in St. Augustine