
Vacation rentals with a kayak in St. Augustine
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Top-rated kayak rentals in St. Augustine
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House rentals with a kayak

Laguna Paradiso-Waterfront Pool Spa Games Firepit
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.

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

Oceanscape - Ocean Views/Heated Pool/Golf Cart
Thoroughly enjoyed this our family vacation. The home is amazing and an easy walk to the beach. The views are spectacular and the house was beautiful, clean and had everything you could possibly want or need. The beds and living room furniture were comfortable and the golf cart was super handy. The stairs up to 2nd and third ( main) floor were a workout and would not be great for anyone with mobility issues, but the elevator helped with bringing in groceries and luggage.

Huge pool, beach PacMan mins to everything, pet ok
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!

Heated Pool/Steps to Private Beach/Fire Pit/Kayaks
We had a fantastic stay! The home was clean, spacious, and had everything we needed for a comfortable stay. The fully equipped kitchen made cooking easy, and the beds were incredibly comfortable. The highlight was definitely the pool it was the perfect way to cool off in the Florida heat! Ben was a super responsive host and made everything smooth from start to finish. Highly recommend!

Fishing Capital on the St John’s River
Dori is an excellent host. I have never had an Airbnb host contact me personally like Dori and make sure we had everything we needed. Her place has a full kitchen, comfortable beds, a soaking tub and a standup shower. Looking for a place to go and bring your boat? The dock is lovely. We’ve stayed here two years now and love it. Thank you Dori!

Waterfront Pool Oasis Kayak,Bike, games walk2beach
Over the years I have stayed at a LOT of Airbnbs and this house was by far the best. The house was pristine, high quality linens and bedding, setup was perfect for a family vacation with a well stocked game room, pool area and access to water toys/fishing/bikes etc. This is the first time after all of these years using rentals that I’ve actually left a review because it was so top notch. The owner, Ginny, was so responsive, thoughtful and proactive to make sure our stay was wonderful!

Waterfront Htd Pool-HotTub-Dock-Kayak-Beaches!
Beautiful clean house, so many recommendations and games to play inside, absolutely perfect!
Cottage rentals with a kayak

Lakefront cottage and dock★Free bikes & paddleboat
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.

Coastal Cottage -firepit, pet fence, kayaks, bikes
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!

Waterfront home with private dock, walk to beach
-Beautiful home in a nice, quiet neighborhood. -Loved the Florida decor. -The canal view was very peaceful. -Really enjoyed watching all the birds on the feeder. -The white lights around porch and on the palms were beautiful and relaxing. -Very informative book of local sights and restaurants. -Home stocked with everything you need, including a great pod selection of coffee, tea and hot chocolate. -Snack basket was a wonderful touch, including everything to make s’mores. -Michele and Kelly were very friendly and helpful and responded quickly to messages. -I loved staying there so much, I didn’t want to leave.

Seagrape Cottage- Steps away from the beach
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!!
Cabin rentals with a kayak

Lake Broward Guest House-BoatDock, Nightly Rentals
Such a beautiful little place!! Stayed the night before and the night of my wedding and it was so nice having such a cozy and peaceful place to fall asleep and wake up in:)

Lake Broward Cabin w/ Private Boat Launch & Dock!
Rare Florida cabin on a lake. Enjoyed jet skiing and watching the seaplanes take off. Had a nice family Thanksgiving week at the cabin. St Augustine and Ocala are about an hour away.

Peaceful lakeside cabin, game room,kayaks, firepit
My family and I had a wonderful weekend in this cabin. The game room was a hit! We would love to come back when weather is cooler. If you come during summer make sure to make reservations ahead at the springs. You will enjoy a peaceful place with nature around… kids were able to see deers and heron birds… simply lovely.

Cabin on Aree Pond
Beautiful little getaway. Perfect for a small family and pets.
Quick stats about vacation rentals with a kayak in St. Augustine
Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ367 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
20 properties have a pool
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- Ponte Vedra Beach
- Summer Haven st. Augustine FL
- TIAA Bank Field
- Old A1A Beach
- Boneyard Beach
- Daytona Lagoon
- Daytona Beach Boardwalk and Pier
- Kathryn Abbey Hanna Park
- Amelia Island State Park
- Butler Beach
- Crescent Beach
- Fountain of Youth Archaeological Park
- Guana Reserve Middle Beach
- North Beach Guana River Preserve
- Lightner Museum
- Palm Harbor Golf Club
- St. Augustine Alligator Farm Zoological Park
- MalaCompra Park
- Matanzas Beach
- Bent Creek Golf Course
- Eagle Landing Golf Club
- Driftwood Beach
- Ravine Gardens State Park
- Neptune Approach
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