Vacation rentals with a kayak in Anastasia Island

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Top-rated accommodations with a kayak in Anastasia Island

Guests agree: these accommodations with a kayak are highly rated for location, cleanliness, and more.

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Guest favourite

Home in St. Augustine

4.95 out of 5 average rating, 41 reviews

Treasure Beach House on the saltwater canal

Between the sunrise view on the ocean side and sunset over the intracoastal… This charming, fully furnished beach house is minutes from the St. Augustine Historic Downtown. Our private community beach access leads the way to an amazing beach area! The house is located on one of the rare saltwater canals in St Augustine. Directly on the water, with a dock right in the backyard. The canal is connected to the river, where you can boat, fish, kayak, SUP and even jump in the water at the high tide!

Sep. 30 – Oct. 7

$267 CAD per night

Guest favourite

Home in St. Augustine

4.95 out of 5 average rating, 19 reviews

3 min Walk to Beach, Heated Pool/HotTub, Game Rm

You’ve found the perfect beach-vacation gathering spot for your large group and a pet or 2! Your group will love the sparkling heated saltwater pool + hot tub, game room & more. Located in the beautiful Crescent Beach area, the tri-level “After Hours” offers a brand new design and furnishings. Best of all, it’s a 3-minute walk to beach – with beach accessories + beach wagon supplied and a 2 minute walk to the intracoastal waterway with public boat ramp. 15 minutes to downtown St. Augustine too!

Jan. 21 – 28

$1,007 CAD per night

Guest favourite

Apartment in St. Augustine

4.98 out of 5 average rating, 42 reviews

St. Augustine Retreat Near Beach & Downtown

Welcome to your cozy retreat in the heart of St. Augustine! This charming 1 bedroom, 1 bath apartment is perfect for couples or solo travelers looking to experience the best of this historic city. The apartment features a comfortable bedroom with a king-sized bed, a fully equipped kitchen, and a cozy living area where you can relax after a day of exploring. Whether you're here for the weekend or an extended stay, this apartment is the perfect home base for you! We can't wait to welcome you!

May 3 – 10

$273 CAD per night

Guest favourite

Apartment in St. Augustine

5.0 out of 5 average rating, 44 reviews

— • Resort Style Retreat • —

Anastasia Island/Saint Augustine • 10-12 min drive to Downtown St.Augustine • 7-9 min drive to Saint Augustine Beach • 6 min drive to Univ of St.Augustine Welcome to our cozy 1 bedroom, 1 bathroom apartment in the beautiful coastal town of Saint Augustine Beach. This charming, comfy, stylish and relaxing space offers a comfortable and inviting living space, perfect for individuals or couples seeking a peaceful retreat by the intercoastal waterway with one of the best views from our balcony.

Mar. 14 – 21

$245 CAD per night

Guest favourite

Condo in St. Augustine

4.95 out of 5 average rating, 79 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.

Apr. 7 – 14

$308 CAD per night

Guest favourite

Townhouse in St. Augustine

5.0 out of 5 average rating, 31 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.

Nov. 20 – 27

$356 CAD per night

Guest favourite

Cottage in St. Augustine

4.94 out of 5 average rating, 128 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!

Oct. 9 – 16

$320 CAD per night

Guest favourite

Home in St. Augustine

4.98 out of 5 average rating, 43 reviews

Beachfront | Game Room | Kayaks + Toys | Sunrises

Your private beachfront retreat! This 4-bed, 2-bath home offers direct ocean access, beach toys, and kayaks for endless fun. Stay connected with fast WiFi and a dedicated workspace, with Publix just across the street. Downtown historic St. Augustine is a short 10-minute drive away, promising rich culture and dining experiences. After a day of sun and surf, rinse off in the outdoor shower, then relax and listen to the waves with a drink in your hand. Your perfect family getaway begins here!

Jan. 8 – 15

$1,317 CAD per night

Guest favourite

Apartment in St. Augustine

5.0 out of 5 average rating, 42 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.

Jun. 23 – 30

$297 CAD per night

Guest favourite

Guesthouse in East Palatka

5.0 out of 5 average rating, 17 reviews

Charming Rustic Boathouse

Come stay at our rustic boathouse along the serene river. Its weathered, wooden, exterior exudes charm, adorned with unique decor. The sunlight reflects the water, casting shimmering light against the boathouse. Surrounding it, is lush greenery and trees that create a picturesque backdrop. Inside, the boathouse is cozy and inviting, with simple furnishings and the gentle scent of wood. It's a haven where one can escape the bustle of everyday life and embrace the countryside.

Dec. 15 – 20

$158 CAD per night

Guest favourite

Home in St. Augustine

4.98 out of 5 average rating, 41 reviews

2023 Lux Home+Heated Spa+SaltPool+Walk2Beach+4/3.5

* New construction styled with luxe coastal furnishings * 2 King Suites (1 on each floor) | 2 Queen Bedrooms | 3.5 Baths * Private Saltwater Pool * Heated Spa | Poolside Cabana | Outdoor Kitchen * Fenced Lush Backyard Oasis | Bikes, Kayak, Surfboard, Beach Chairs * 5 min walk to gorgeous quiet beach | 10 min drive to historic downtown St Augustine * 5 min walk to Cap's Restaurant for sunset dinner on the water * Amenities abound, no expense spared.

Oct. 30 – Nov. 6

$975 CAD per night

Guest favourite

Home in St. Augustine

5.0 out of 5 average rating, 80 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!

Apr. 5 – 12

$852 CAD per night