53 vacation homes  

$249-1,799/night

28 Rollins Dunes Dr

4 Bedrooms • 4 Baths (3 full, 1 half) • Sleeps 1-10
Allows pets Accessible Internet Firewood Provided Oceanfront Private Pool
Breezy.Bold.Beachfront.
This stylish oceanfront escape is your front-row seat to sun, surf, and serious relaxation. With panoramic views, a private pool, sleek interiors, and beach access just steps away, it’s the perfect blend of coastal cool and everyday luxury—dog welcome, of course.

Photos Details Inquire


$90-377/night

Bay Breeze Bungalow

3 Bedrooms • 2 Baths • Sleeps 1-8
Allows pets Internet Near Ocean Downtown
Location Location Location! Nestled in a serene residential street on the beautiful Anastasia Island, our charming bungalow offers the perfect blend of tranquility and convenience. This centrally located gem is just a mile from the iconic Bridge of Lions, the gateway to the historic old town of St. Augustine, and within reach of all the island's exciting attractions.

Photos Details Inquire


2 Bedrooms • 2 Baths • Sleeps 1-6
Allows pets Internet Hot Tub

Stay beachside and soak up the sun at this beautiful coastal condo! Just a short walking distance to the ocean w/ beach, community pool, hot tub, and tennis court access. After a fun filled day in the sun, retreat to this costal haven and sit on the balcony to watch the sunset or take a short drive to Downton St. Augustine and explore what the oldest city in America has to offer. Discover rich history at the fort Castillo de San Marcos and the Lighthouse or indulge in some local cuisine.


Photos Details Inquire


1 Bedroom • 1 Bath • Sleeps 1-4
Allows pets Internet Oceanfront
Enjoy long-range sunset views from your balcony! Be the first in the ocean every day, soak up the sun, or lounge by the oceanfront pool with soothing waves crashing in the background. Retreat every night to your stylish condo w/ coastal decor, an open concept living area, king size bed and ensuite bathroom. Smell the crisp ocean air from the 6th floor balcony while you reflect on a relaxing, fun day. Located near top attractions and unit has view of river

Photos Details Inquire


3 Bedrooms • 4 Baths (3 full, 1 half) • Sleeps 1-8
Allows pets Internet Oceanfront
Nestled gracefully along the sandy shores, this three-story coastal retreat stands as a beacon of luxurious seaside living. Positioned mere steps from the lapping waves, it offers an unparalleled connection to the rhythm of the ocean. With three bedrooms, each boasting its own ensuite bathroom, this property epitomizes comfort, elegance, and convenience. When you open the sliders to your private balcony and feel the ocean mist on your face, you'll know your vacation has begun!

Photos Details Inquire


5 Bedrooms • 4 Baths • Sleeps 1-14
Internet Ocean View Private Pool Hot Tub
Gather friends and family at your Vilano Beach Paradise! Private beach access, new pool swim spa and hot tub, lighthouse themed game room & theater, colorful coastal bedrooms, EPIC bunkbed with tube slide, firepit, and mini-golf! Most fun in St Augustine! 5 bedrooms for 14 guests. Savor cocktails at the kitchen island, enjoy FL themed loft Nintendo Switch, kayaks, and paddleboards. Smart TVs and speedy Wi-Fi. 6 minutes to Historic St. Augustine. A short walk to Publix, restaurants, & shops.

Photos Details Inquire


2 Bedrooms • 2 Baths (1 full, 1 half) • Sleeps 1-5
Allows pets Accessible Internet Near Ocean

The home features a private, enclosed back patio where you can relax with your favorite beverage and delicious snacks and soak up the Florida sunshine after a splendid day at the beach. Spread out comfortably on the sectional and binge-watch a favorite series on the smart TV. Or gather around the dining table for some board game action. The kitchen is fully equipped with all the essentials needed to prepare meals. Both bedrooms are located upstairs. Located .6 miles from public beach access.


Photos Details Inquire


4 Bedrooms • 2 Baths • Sleeps 1-8
Lakefront
Escape to this stylish canal-front retreat with a private screened pool, designer kitchen, and peaceful vibes! Just minutes from beaches, parks, and the vibrant European Village, this 3BR getaway is perfect for relaxing, fishing, or soaking up the Florida sun in total comfort.

Photos Details Inquire


4 Bedrooms • 2 Baths • Sleeps 1-9
Allows pets Internet
Designed with large groups in mind, ‘Casa Nueve’ is the ideal vacation rental for St. Augustine travelers who desire comfort and privacy. The 4-bedroom, 2-bathroom interior boasts modern accents, custom artwork, and pops of bold Spanish decor, while the fenced backyard offers a spot to enjoy meals fresh off the grill. Stay less than 4-miles from the robust Historic District, home to Ponce de Leon's Fountain of Youth, Old Jail, ghost tours, and the Castillo de San Marcos National Monument!

Photos Details Inquire


1 Bedroom • 1 Bath • Sleeps 1-4
Allows pets Internet Near Ocean Downtown
This charming one-bedroom, one-bath condo is perfectly situated within walking distance to a variety of restaurants and the iconic Conch House Marina. The living room sofa is also a sleeper for additional guests. If location tops your priority list, this property is an ideal choice and is perfect for people on the go who want their home base to be in the best location!
PET RULES: There is a $200pet fee for 1 dog.
At no time may pets be on any furniture or beds. If pet hair is found on furniture, additional cleaning fees may apply.
You must pick up after your dog. If pet waste is found in the backyard, a $50 pet waste fee will be added to your stay.
There are no breed restrictions at this property 🙂Unattended pets must be crated. No cats allowed

Photos Details Inquire


3 Bedrooms • 3 Baths (2 full, 1 half) • Sleeps 1-10
Allows pets Internet Downtown
All of St. Augustine will be at your fingertips with a stay at this spacious 3-bedroom, 2.5-bathroom vacation rental! This charming home comes complete with 2 living spaces, a fully equipped kitchen, and a dedicated dining area. Spend quality time in the Florida sunshine, whether you lounge on the sands of Surfside Park Beach, journey through time by exploring the streets of Historic Downtown St. Augustine, or stay at home for a barbecue on the private patio and fenced in backyard.



Photos Details Inquire


3 Bedrooms • 2 Baths • Sleeps 1-6
Allows pets Internet Fireplace
Welcome to this inviting canal-front home, a serene escape designed for relaxation and waterfront enjoymen with its own boat lift and private dock. With three spacious bedrooms and two well-appointed bathrooms, this coastal-inspired property blends charm and functionality. Step into an open-concept living area that seamlessly integrates the kitchen and living room, creating the perfect space for entertaining and everyday living.

Photos Details Inquire

1 – 12 of 53 places to stay