Holiday houses in St. Johns County

Enchanted Oaks Estate-Weddings -Carriage House

1920 Carriage House on lush private estate. Renovated and charming! Situated on secluded, majestic 6 acre riverfront property on the St. John’s River. Enjoy park like grounds filled with azaleas, ancient oak and hickory trees, dripping in Spanish moss. Sit back and watch and listen to hawks and bald eagles overhead! Wake up to a magical sunrise each day! See the manatees lazily grazing! Bass Pro Shop shot their Spring Catalogue here! Owners home is on the property and they are always available

Private & Secluded Oceanfront Home w/ Large Deck

Welcome to a serene beachfront retreat in Ponte Vedra Beach. This home offers direct private beach access, a spacious open layout, and a huge deck with breathtaking ocean views. Plus, there are no houses behind—just a peaceful nature preserve, ensuring a quiet and relaxing stay. If you are a large group, you can book Sandy Shores II (next door) to accommodate up to 16 guests—perfect for family reunions, large gatherings, and special celebrations. LONG STAY DISCOUNTS Jan-Feb, send us an inquiry!

Walk Historic Downtown! “Blue Heaven”

Stunningly renovated cottage combines modern amenities with vintage charm... * 2 master suites with queen beds * Quiet neighborhood walking distance to explore The Nation's Oldest City * Clawfoot tubs inside and out (along with showers, of course!) * Big screened-in porch with hanging daybed * Off-street paved parking * Fully fenced backyard, Weber grill, gas fire pit * Fast Wi-Fi and Smart TV * 2 blocks to Fish Camp, Ice Plant, LaNuvelle, trolley stop * 10 minute walk to central downtown

St. Augustine Sanctuary 3 Pools Spa & Pickleball!

Escape to this tropical paradise spa-style resort with sparkling pool views and resort-style amenities! Newly renovated spacious studio unit features a wet bar kitchen and overlooks the renowned King and Bear golf course. Whether you're looking to improve your golf game, explore historic St. Augustine, or indulge in a rejuvenating spa day, this condo offers everything you need. Enjoy access to three heated pools, a hot tub, tennis courts, a clubhouse, a full-service spa, and a fitness center!

Loins Bridge 0.5m away, 2 Bedroom, Private Hot Tub

Couples Retreat Near Downtown St. Augustine. 0.5 miles from the Bridge of Lions. Enjoy a secluded courtyard, relaxing water fountain, and new 4-person hot tub. Wine down and watch the sunset in a peaceful setting after a exploring. Off-street parking is included. Restaurants, bars, coffee shops, and local favorites are only steps away. Perfect for a romantic getaway, weekend escape, or special occasion. Special requests and accommodations are available to help make your stay unforgettable.

St Augustine Entire Home, King Bed, Pet Friendly

Casita Luxe Retreat Near Historic St. Augustine – Pet-Friendly Haven! Discover this luxurious 3-bedroom, 2-bath retreat! Designed with a modern luxe aesthetic, it features custom wood paneling, a fully equipped kitchen with a chic island, and a king-size plush mattress. Enjoy the large, fenced yard, fire pit, outdoor shower, and fun family games. Pet-friendly, with Wi-Fi, smart TVs, and parking included this home offers comfort and style in an up-and-coming neighborhood. Book now!

The Waddle Inn

Peaceful modern farmhouse 2-bed, 1-bath private 2nd-floor suite on our 2-acre creekfront mini farm. Built in 2023, it offers high-quality linens, smart TVs, and Wi-Fi. Meet our two rescue draft horses, friendly chickens and curious turkey; guests are welcome to help feed treats. Enjoy pool, firepit and on-site kayak rentals on the creek to the St. Johns River. 30–35 minutes to beaches, NAS JAX, TPC Sawgrass and historic St. Augustine. Perfect for couples, families and remote work.

The Shire on 1 acre marshfront with dock and Spa

One of a kind 1930s historic home, newly renovated and transformed into a beautiful secluded getaway. new luxury finishes, while holding its traditional charm. No Events allowed. Rooftop deck, sunrise views of the Atlantic ocean, Downtown, and sunsets over the river. The new dock with covered roof hosts a national geographic like eco system. It’s short walk to the beach and 3 miles to downtown St George street. Follow along @carcabaroad for weekly content of the home.

Luxury Cottage with River Access

Enjoy the peaceful ambiance of this brand new luxury cottage on Julington Creek in Saint Johns County. Centrally located -- we're just a 30 minute drive to the beach, downtown Jacksonville, and St. Augustine. Amenities include a king-sized bed, two TV's, and a fully-equipped kitchen. The cottage is located at the front of our 1-acre property. Our own home is situated just across the lawn from the cottage. Guests will walk through the backyard to access the river.

Lagares

Escape to our beautiful private lake retreat! Enjoy fishing right from the property, relax in the jacuzzi, cool off in the pool, and create unforgettable memories with family and friends. Located just 30 minutes from Florida’s beautiful beaches and historic St. Augustine, our home offers the perfect balance of peaceful nature and nearby attractions. Spacious, comfortable, and fully equipped for the perfect getaway.

Cozy River Retreat w/ Hot Tub and an Amazing View

Cozy Waterfront Retreat with Stunning Sunsets Near Downtown St. Augustine Welcome to your perfect getaway! This fully renovated one-bedroom, one-bathroom home offers breathtaking water views and unforgettable sunsets. Perfect for honeymooners, anniversaries, or a quiet couples getaway where time slows down. Located just 20 minutes from the historic charm and vibrant culture of downtown St. Augustine.

Modern Townhouse | Chef Kitchen | Near Beach & DT

Quiet, clean and genuinely well cared for. This townhouse sits in a peaceful St. Augustine neighborhood, 10 minutes from the beach and 15 from historic downtown. Coffee and snacks are waiting when you arrive. The kitchen has real counter space and full appliances. Two bedrooms, one with a queen bed and one with a bunk bed, plus 2.5 bathrooms and a patio to start your mornings right.