Vacation rentals with a kayak in Anastasia Island

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Popular amenities for Anastasia Island kayak rentals

House rentals with a kayak

Top guest favorite
A shaded seating area features colorful, adirondack-style chairs arranged around a small green table. An umbrella provides protection from the sun, overlooking a serene freshwater canal surrounded by lush greenery and vibrant kayaks visible in the water.
Home in Palm Coast
5 out of 5 average rating, 30 reviews

The Flamingo Nest

SavannahRating, 5 stars1 week ago
As soon as we entered the flamingo nest we felt right at home! Patty is an exceptional host, she gave us some of the best tips on places to go! She also had so many extras and just things in the house that made the stay that much more enjoyable! She even had extra flip flops in different sizes! The back yard was our favorite place to hang out and watch all the wildlife! It’s so peaceful and just the right distance from town and the beach! We will definitely be coming back to the flamingo nest!
Top guest favorite
Home in Palm Coast
5 out of 5 average rating, 63 reviews

Laguna Paradiso-Waterfront Pool Spa Games Firepit

StaceyRating, 5 stars2 days ago
What a gem of a place! We had a wonderful stay and enjoyed the house SO MUCH. The house was spotless, had tons of natural light, and was stocked with everything we needed for a great stay. The kids absolutely loved the hot tub and pool. How amazing that it overlooked the water... it almost felt like an infinity pool! The game room was a hit with my 9 year old and he played pool for the first time! This was surely a vacation to remember and we would gladly stay here again in a heartbeat.
Guest favorite
A light-filled living area features a comfortable leather sofa and a circular wooden coffee table atop a textured rug. A pair of windows offers natural light, while a wall clock adds a functional element. A dining table with wooden chairs is visible leading into the kitchen area.
Home in St. Augustine
4.93 out of 5 average rating, 46 reviews

Grand Oak 1/4 mile Stroll to DT & 3 Miles to Beach

Bahig Rating, 5 stars3 weeks ago
Linda I would like to thank you for hosting me in your place. It is truly a number one place that deserves thanks. It is the best place in all aspects. The attention to the smallest details is such that your guest finds everything he needs and more. As for cleanliness, arrangement and location, they are the best.
Guest favorite
The three-story property features a modern architectural design with multiple balconies that offer outdoor seating. Palm trees surround the home, and a spacious driveway leads to the garage. The sunset casts a warm glow over the exterior, enhancing the inviting atmosphere.
Home in St. Augustine
4.95 out of 5 average rating, 21 reviews

Oceanscape - Ocean Views/Heated Pool/Golf Cart

KailaRating, 5 stars1 month ago
I cannot say enough great things about this beautiful home! The ocean views were incredible, plenty of things to do around the area, pool and fenced in back yard was great for the kiddos and there was plenty of space for 3 different families. We are looking forward to coming back!
Guest favorite
A heated pool with a protective screen cage is surrounded by tropical plants and seating areas. Outdoor furniture, including a dining table and chairs, is positioned adjacent to the pool, creating a comfortable space for relaxation and enjoyment.
Home in St. Augustine
4.96 out of 5 average rating, 69 reviews

Huge pool, beach PacMan mins to everything, pet ok

BrentneyRating, 5 stars1 week ago
This was our second year staying here and we loved it. Extremely clean, responsive host, and close to everything. We will be staying again next year!
Top guest favorite
A wooden dock extends into a calm canal, featuring two colorful kayaks in red and blue. Two Adirondack chairs provide seating for relaxation while enjoying the view of the water and nearby greenery. The sky is dotted with fluffy white clouds.
Home in Palm Coast
4.97 out of 5 average rating, 64 reviews

*Waterfront*Pool*Hot Tub*Dock*Game Room*

AutumnRating, 5 stars2 weeks ago
We had an amazing experience staying at Matthew’s ’s place! The space was spotless, beautifully decorated, and exactly as pictured. Every detail was thoughtfully considered, including the fully stocked kitchen. The location was ideal—close to everything, yet peaceful and quiet for a good night’s sleep. Check-in was seamless and communication with Matthew was excellent. He was incredibly friendly and responsive. We didn’t want to leave and would absolutely stay here again without hesitation. Highly recommend to anyone visiting the area. Thank you for making our trip so special!
Top guest favorite
A spacious backyard features a volleyball net set on lush green grass, surrounded by tropical foliage and palm trees. The two-story house is visible in the background, with a cozy seating area and hot tub indicated on the patio below.
Home in St. Augustine
5 out of 5 average rating, 37 reviews

Sun•Soak•S'mores | Hot Tub•Fire Pit•Steps To Beach

LucindaRating, 5 stars1 month ago
We had a wonderful stay at this property! Property is clean and well maintained. Our family really enjoyed our stay and we will book at this location again! Property was just as described, with easy access to the beach and overall a very comfortable place to stay with our adult children and grandchild. The "beach supplies" that are available were just what we needed to have a good time at the beach without packing/purchasing all the needed things! The back yard with a large hot tub, patio and firepit area was a nice place to hang out in the evenings. Host Seth was awesome and very responsive!
Top guest favorite
An illuminated putting green is featured in the foreground, with a golf flag positioned at the hole. Soft, colorful lighting highlights the nearby dock and seating area, creating a welcoming atmosphere for evening relaxation by the water.
Home in St. Augustine
5 out of 5 average rating, 40 reviews

Brisas del Mar

PeytonRating, 5 stars5 days ago
This was the perfect location near St. Augustine for a large group. The Airbnb was set up perfect with lots of activities in the space. She had everything you could possibly need from extra blankets and pillows to Tupperware and serving platters in the kitchen! It was also very secure and safe. Everything was clean and it felt like home away from home. Couldn’t recommend this place enough!

Cottage rentals with a kayak

Top guest favorite
A comfortable seating area is offered with a light-colored couch adorned with colorful pillows. A plant sits on a side table, while large windows provide a view of Lake Stella. Natural light brightens the space, complemented by a patterned rug and stylish cabinetry.
Cottage in Crescent City
4.96 out of 5 average rating, 90 reviews

Lakefront cottage and dock★Free bikes & paddleboat

ElizabethRating, 5 stars3 weeks ago
This was mine and my husband’s first time staying in Florida and hands down loved this little home. Missy was amazing. The house was so cute! Was nice and quiet and wasn’t too bad of a drive from the places we wanted to visit.
Guest favorite
A light-filled living area features a cozy white sofa adorned with striped cushions, complemented by a round dining table with four rattan chairs. A vibrant vase with white flowers sits at the center, while turquoise accents enhance the coastal decor. A Smart TV is positioned on a wooden shelf.
Cottage in St. Augustine
4.92 out of 5 average rating, 178 reviews

Coastal Cottage -firepit, pet fence, kayaks, bikes

LibbyRating, 5 stars2 weeks ago
I am a native Florida I've been to St. Augustine many times. I have to say this was my absolute favorite visit! It was wonderful having a fenced-in backyard for our dog to run around in, and it was so nice having the screened in Breezeway to enjoy the evenings free of bug bites. Details in accessing the cottage were impeccable. The location is peaceful and far enough away from the hustle and bustle to be private, but right across the street from a great Putt-Putt spot, of an extremely short drive from the Alligator Farm, Anastasia State Park, and downtown. Parking downtown can be a mess, but for a few $10 Uber rides this entire stay was stress-free! My husband and I packed a ton of activities into a long weekend, and still had a great full kitchen to make a few meals "at home" as well. The garage offered a range of additional activities, loved having the grill, bikes, and kayaks; Anastasia St Park is one of our favorite kayaking spots. So pleased with our stay!
Top guest favorite
An outdoor seating area is arranged around a fire pit, featuring colorful Adirondack chairs in blue, orange, and red. The tranquil canal reflects the sunset, with palm trees framing the scene. A gazebo is visible in the background, enhancing the serene atmosphere.
Cottage in St. Augustine
5 out of 5 average rating, 46 reviews

Waterfront home with private dock, walk to beach

ShawnRating, 5 stars2 weeks ago
We absolutely loved everything about our stay at this charming St. Augustine Airbnb! From the moment we arrived, the hosts made us feel welcome by personally introducing themselves—a thoughtful touch that set the tone for the rest of our stay. You can truly feel the love and care they’ve poured into this cozy rental. The location is perfect, with easy access to all that St. Augustine has to offer. The beds were incredibly comfortable, the shower felt luxurious, and the beautiful backyard with the firepit quickly became one of our favorite spots to unwind. Every detail has been so well thought out—it felt like a home away from home. If I could give it 6 stars, I would! We’re already looking forward to returning and can’t wait to book this lovely house again. Highly recommended!
Top guest favorite
The exterior of the cottage features tall palm trees and lush greenery surrounding the property. A stairway leads to the entrance, which is elevated above ground level. A wooden structure with a trellis is positioned near the house, harmonizing with the natural landscape.
Cottage in Palm Coast
4.95 out of 5 average rating, 21 reviews

Seagrape Cottage- Steps away from the beach

BethanyRating, 5 stars2 weeks ago
This was an absolute beach vacation gem!! In fact, I felt I could live here!! We have visited the Crescent Beach area several times in the past, but we were looking for a place even more quiet and less touristy...and this was it. Even on a holiday weekend (Memorial Day) the area and the beach were quiet and peaceful. The house was just the right size for my husband, daughter, and I. It is often hard to find a house at the beach that isn't too big. It was a quiet neighborhood and so easy to walk just up the street for easy access to the beach. The house had everything we needed and the outdoor deck/patio were perfect for dining outside! Lots of beach amenities, too, including chairs, umbrellas, and a wagon to haul it all! I really can't say enough about Mary's place. Just perfect. We hope to return!!

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