
Holiday rentals with a kayak in St. Augustine
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in St. Augustine
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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.

DIRECTLY on the ocean. Entire private first floor.
Recently reopened after two months undergoing major renovation! Previously had 110 very favorable reviews while with a different vacation rental company. The only non-five star ratings (a few 4 stars) of the 110 cited the "somewhat outdated" kitchen. That has been totally remedied with keen attention to the highest quality! Everything has been thought of for your enjoyment, even FREE pinball! You need to bring nothing except your enthusiasm for having a relaxing, stress-free and amazing time!!!

Lakefront cottage and dock★Free bikes & paddleboat
Bring your fishing gear or small boat to enjoy a fun getaway at the Captain's Cottage with a dock on Lake Stella. Key-less entry allows for self check-in and welcomes you to this comfortable clean 962 sq. ft. space with two queen size beds, one bathroom, full kitchen, florida room, and a fenced-in backyard. A paddle boat is provided. Three kayaks and 2 bicycles are also available! Or you can bring your boat and go fishing! Enjoy swimming, lovely sunsets and strolls around the beautiful lake.

Surfside House
This special vacation home is close to everything, making it easy to plan your visit. Ideal location across from the beach, just minutes to drive or bike into historic downtown St. Augustine. The 1950's coastal bungalow is set on Vilano Beach's historical Street. The home has been completely remodeled, plenty of parking and is pet friendly. Surfside's pet friendly beach access/parking and North Shore Community Park is 1 block away with tennis/ pickle ball courts, playground and dog park.

*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!

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

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!

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!

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.

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 St. Augustine
House rentals with a kayak

Midcentury Bungalow w/hot tub-walk to amphitheater

Palmetto House, Lighthouse Park- w/ Bikes & Kayaks

Dolphins and Dream Water Views, Dock Your Boat!

Waterfront • Heated Pool • Dock & Game Room

2BD, Pool+Spa, Walk to beach, Putput, Kayaks

Stunning family canal home with heated pool

Newly built, charming cozy and quiet river home

Fishing Capital on the St John’s River
Cottage rentals with a kayak

Lakefront cottage and dock★Free bikes & paddleboat

Cozy River Retreat w/ Hot Tub and an Amazing View

Coastal Cottage -firepit, pet fence, kayaks, bikes

Waterfront home with private dock, walk to beach
Cabin rentals with a kayak

Lake Broward Guest House-BoatDock, Nightly Rentals

Lake Broward Cabin w/ Private Boat Launch & Dock!

Serene Lakefront Retreat - Firepit, Sunset Views

Cabin on Aree Pond
When is the best time to visit St. Augustine?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $303 SGD | $230 SGD | $258 SGD | $226 SGD | $238 SGD | $222 SGD | $230 SGD | $220 SGD | $222 SGD | $267 SGD | $269 SGD | $311 SGD |
| Avg. temp | 13°C | 15°C | 17°C | 20°C | 24°C | 27°C | 28°C | 28°C | 26°C | 22°C | 17°C | 14°C |
Quick stats about holiday rentals with a kayak in St. Augustine

Total holiday rentals
Explore 40 holiday rentals in St. Augustine

Nightly prices starting at
St. Augustine holiday rentals start at $129 SGD per night before taxes and fees

Verified guest reviews
Over 2,400 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
40 of St. Augustine holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across St. Augustine rentals

4.9 Average rating
St. Augustine stays are highly rated by guests – averaging 4.9 out of 5!

Nearby attractions
St. Augustine’s top spots include St. Augustine Distillery, St. Augustine Alligator Farm Zoological Park and Lightner Museum
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- Ocean Center
- Daytona Beach Bandshell
- EverBank Stadium
- Daytona Boardwalk Amusements
- St Augustine Amphitheatre
- Summer Haven st. Augustine FL
- Lightner Museum
- Kathryn Abbey Hanna Park
- VyStar Veterans Memorial Arena
- Daytona Lagoon
- Fountain of Youth Archaeological Park
- Saint Augustine Town Plan Historic District
- Adventure Landing Jacksonville Beach
- St Johns Town Center
- Ravine Gardens State Park
- TPC Sawgrass
- University of North Florida
- St. Augustine Alligator Farm Zoological Park
- Memorial Park
- Vilano Beach Fishing Pier
- Little Talbot
- Anastasia State Park
- Ocean Walk Shops
- Guana Reserve Middle Beach
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