Family-friendly holiday rentals in St. Augustine

4.98 out of 5 average rating, 114 reviews

HtdPool w/Arcade, Fire, GolfCart Access, 1.2 mi DT

ISLE BE BACK 🌴— brand NEW modern home! **Golf Cart Access for an additional fee Please inquire if interested!** Welcome to your ultimate St. Augustine getaway! Just 5 mins from downtown, this fun-filled retreat is perfect for families, friends, or anyone looking to relax and play. Swim in the pool, compete on the putting green, roast s'mores by the fire pit, or challenge your crew on the retro Pac-Man machine—all without leaving the house! ✔Sleeps 8 comfortably ✔Self check-in & free parking

A spacious waterfront deck offers lounge seating with blue cushions, set against a vibrant sunset sky filled with pink and orange hues. A hammock is positioned nearby, with palm trees framing the stunning view of the water and docks in the background.

5 out of 5 average rating, 147 reviews

Fan Fave Waterfront: Lion’s Bridge & Old Town View

Our reviews set us apart. WE'D LOVE TO HOST YOU! Walk across the Bridge of Lions to downtown St. Augustine with amazing restaurants and attractions. A short walk to historic downtown, less than 1 mile to Castillo de San Marcos fort. Anastasia State Park Beach, the Alligator Farm and lighthouse are less than two miles away. Several restaurants and bars only a few blocks away. Whether going to the old fort or Flagler College, our home provides a great base for exploring an amazing part of Florida!

4.97 out of 5 average rating, 128 reviews

Home in Flagler Beach

Walk to Beach | Pool, Spa & Private Dock

This isn’t just a beach house — it’s your private coastal escape. Start your morning with coffee and a short walk to the beach. Spend the day poolside or out on the water, then unwind in the spa as the sun sets over the intracoastal. 👉 A perfect mix of beach days and relaxing waterfront evenings. 📍 Location • Walk to beach • Short drive to Flagler Beach restaurants & shops • Quiet, private neighborhood Centrally located between St. Augustine and Daytona Beach -35 minutes LBTR #37009

5 out of 5 average rating, 260 reviews

A charming two-story cottage is seen behind an ornate wrought-iron gate, framed by vibrant green grass and well-maintained landscaping. Large windows allow natural light to fill the exterior, and a cheerful yellow door adds a welcoming touch.

Cottage in Lincolnville

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

The living room is furnished with two light-colored sofas and a central coffee table, creating a spacious and inviting space. A decorative fireplace is framed by mirrors and artwork, while natural light filters in through shuttered windows and greenery adds a touch of nature.

4.94 out of 5 average rating, 218 reviews

Historic Whitney House •Designer•Steps2Attractions

Off Street Parking for 2 vehicles 2 Min. walk to St George St 5 Min drive to Anastasia State Park Beach 6 Min drive to Fitness Club/Pool High Speed Starlink Internet Luxury Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury baths. Immerse yourself in the rich history and vibrant culture, with its charming streets and local attractions. Whether seeking adventure or relaxation, this retreat offers the perfect base.

A modern home with a distinctive triangular roof stands among lush greenery. A manicured lawn extends in front, bordered by palm trees. The building features a combination of light-colored siding and wooden accents, with a small balcony that adds to its architectural charm.

4.99 out of 5 average rating, 128 reviews

Luxury Modern Home in Prime Location 2BDR-3BTH

Book your Spring Break vacation with us! Our contemporary home offers comfort, elegance, and curated amenities. Explore the historic downtown, climb the lighthouse, enjoy live performances, indulge in local cuisine, and relax on the nearby beach. The Lighthouse Beacon is the perfect retreat for families and friends, catering to all preferences. Experience the magic of Saint Augustine and create cherished memories. Book your stay now and let us be your guiding light in this captivating city.

4.96 out of 5 average rating, 121 reviews

A classic 43-foot Gulf Star yacht is moored in calm waters, exhibiting a spacious deck with a covered seating area. The hull is painted in a crisp white, reflecting sunlight, while nearby masts and boats frame the picturesque marina scene.

Boat in St. Augustine

Funshine - Vacation on a 43' Gulfstar Yacht

A unique, memorable place, anything but ordinary. Try living the boating lifestyle on a classic and quaint vintage 43 foot Gulf Star yacht. Only 1.2 miles to the historical St. Augustine Bayfront and less than 10 miles to many of our gorgeous beaches. This 2-bedroom 1.5 bath beauty allows you to experience a life on a live-a-board. You will vacation within a reasonable walking distance to many of the attractions in St Augustine, a winery, distillery, several museums, many restaurants.

The outdoor area features a private saltwater pool with a custom spa, surrounded by lush tropical landscaping. A spacious cabana is included, with comfortable seating beneath flowing white drapes. A shaded umbrella is positioned beside the pool, enhancing the relaxation space.

4.99 out of 5 average rating, 150 reviews

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

The outdoor area features a heated pool surrounded by comfortable lounge chairs and shaded umbrellas. A spacious patio includes additional seating and a tranquil atmosphere, enhanced by palm trees and bright blue skies.

4.99 out of 5 average rating, 181 reviews

4Bed, 3Bath-Heated Pool & SPA-Don't You Wanna?

Don't You Wanna...4 Bedroom, 3 Bath with HEATED POOL, SPA, and Outdoor Shower located in the heart of Vilano Beach of historic St. Augustine, FL. Our conveniently located home allows you to bring family and friends to share memories with a nice sunset or sunrise just down the street at the third street beach access point. Want to have a nice dinner at one of the most popular restaurants in all of St. Augustine? Walk around the corner to Cap's On The Water for great dining.

Superhost

A newly renovated historic home is set against a serene natural backdrop, featuring a large deck accessible via a wooden walkway. The exterior showcases multiple arched windows and a modern roof deck, surrounded by lush vegetation and reflected in the calm waters of the marsh.

Cottage in St. Augustine

4.91 out of 5 average rating, 171 reviews

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.

A tranquil backyard area is featured, showcasing a heated pool surrounded by lush greenery. Two black chairs are positioned on the stone patio, offering a comfortable spot for relaxation. The space is enclosed by vibrant tropical plants, enhancing the private atmosphere.

4.96 out of 5 average rating, 181 reviews

Pool home oasis steps to ocean

Cottage style home with comfortable porches to enjoy sound of ocean waves breaking on the front and back porches. Pool in the back yard (heated by request for $50 per day) cookshed, fenced with lush trees and woods to the east. The inside looks large with high wood ceilings and multiple windows and glass doors to the beautiful pool area. Located on a dead end street in a family neighborhood with 5 star restaurants nearby. Fifteen minute drive to downtown St. Augustine.

The living room features a light-colored sofa adorned with blue pillows, accompanied by two armchairs. A round mirror hangs on the wall, and natural light floods the space through multiple windows. A decorative plant stands near the entrance, and a minimalist coffee table is centered in the room.

4.99 out of 5 average rating, 103 reviews

Charming Home in historic downtown, walk to it all

Our home, Casita Uva de Playa, is the perfect centrally-located home in the Historic Region of Downtown St Augustine. You can walk less than 1/2 mile into the city for a perfect breakfast biscuit, taste amazing cuban food, take in all the history, or enjoy a martini. You can also take a short 10 minute car ride to the beach. Or just relax in our quiet cottage. Your comfort and relaxation while on vacation is our priority. Come stay with us!

Popular amenities for St. Augustine family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 215 reviews

The cottage features a charming front porch with white railings and decorative trim. Lush green plants are arranged along the pathway, enhancing the welcoming entrance. A well-maintained lawn and a paved driveway lead to the home's exterior, which is adorned by vibrant blue siding.

Cottage in St. Augustine

3BR/2 Bath/Outdoor Kitchen/Hot Tub/Ocean 3 blocks

A large heated saltwater pool presents a curved design with a spa area seamlessly integrated. The pool area is surrounded by pavers and features vibrant turquoise lounge chairs. Lush greenery and decorative planters enhance the tranquil outdoor setting, enclosed by a white privacy fence.

5 out of 5 average rating, 111 reviews

Heated Pool/Hot Tub 1 mile to dwntn/beach

4.97 out of 5 average rating, 129 reviews

Luxury pool & spa home steps to beach & 2 masters!

Camper van/Motorhome in St. Augustine

A comfortable seating area features a yellow couch adorned with decorative throw pillows inspired by The Beatles. The large windows allow ample natural light, while soft gray curtains frame the view. A small side table complements the space, enhancing the cozy atmosphere.

4.87 out of 5 average rating, 198 reviews

Yellow Submarine II

A charming two-story apartment stands above a pool area framed by lush greenery. The balcony offers a view of the pool, while the surrounding landscape features vibrant foliage and mature oak trees. The pool is bordered by textured paving stones and a patio set in the background.

4.99 out of 5 average rating, 628 reviews

Villa Tizoc

A comfortable living area is showcased with a gray sofa adorned with decorative pillows. A glass coffee table sits in front, accented by a floral arrangement. Two windows provide natural light, and stylish curtains frame the view. A small bookshelf stands against the wall.

4.95 out of 5 average rating, 183 reviews

Charming Vintage Intracoastal Apartment

The image captures a spacious outdoor pool surrounded by palm trees and lounge chairs. The clear blue water reflects the sky, adding to the serene atmosphere. The condominium's architecture is visible in the background, providing a picturesque setting for relaxation.

4.96 out of 5 average rating, 103 reviews

Condo near Downtown St Augustine/beach/golf

An expansive backyard features a refreshing saltwater pool and a hot tub, surrounded by lush turf landscaping. A two-story building with a wooden staircase overlooks the serene outdoor space, framed by palm trees and vibrant plants. Lounge chairs are positioned nearby for relaxation.

4.99 out of 5 average rating, 143 reviews

Driftmark Cabin - RV friendly, Pool + Beach!

Family- and pet-friendly home rentals

An aerial view captures the colorful buildings and lush landscaping of the property, with the iconic Bridge of Lions visible across the water. Boats can be seen docked along the Intracoastal, while the vibrant greenery frames the scene, creating a serene setting.

4.94 out of 5 average rating, 109 reviews

LIONS VIEW | Waterfront | 5-min walk to Downtown

The exterior of Casa Coquina is presented, featuring a charming façade with rounded archways. A light blue garage door complements the neutral-colored walls. Lush greenery, including palm trees and decorative plants, enhances the inviting entryway, while a driveway leads to the garage.

4.99 out of 5 average rating, 123 reviews

Casa Coquina Walk to Downtown Clean Quiet Spacious

4.87 out of 5 average rating, 223 reviews

St. Aug Oceanfront Home w/ Heated Pool & Firepit

A private saltwater pool is surrounded by a spacious deck and lush greenery. Palm trees frame the area, offering a shielded retreat. A patio space is visible, providing comfortable seating options and direct access to the home.

4.95 out of 5 average rating, 152 reviews

Peaceful Oasis Pet Friendly heated Pool & Gameroom

4.92 out of 5 average rating, 220 reviews

Cottage in St. Augustine

Coastal Cottage -firepit, pet fence, kayaks, bikes

The living area features a modern design with custom wood paneling on one wall. A leather sofa is positioned in the foreground, while a decorative coffee table and a small workstation with a chair are visible. Soft lighting highlights a piece of scenic artwork above the table.

4.96 out of 5 average rating, 108 reviews

St Augustine Entire Home, King Bed, Pet Friendly

Two blue patio chairs are positioned on a wooden deck, facing the ocean. The expansive beach and gentle waves are visible in the background, under a clear blue sky dotted with soft clouds.

4.88 out of 5 average rating, 150 reviews

Oceanfront Barefoot Beach Retreat

Holiday home in St. Augustine

A single-story beachside home is surrounded by well-maintained lawns and tropical landscaping. The light blue exterior is complemented by palm trees that provide shade. A wide pathway leads to the entrance, with windows and shutters adding architectural interest.

4.9 out of 5 average rating, 108 reviews

Beautiful Beachside Vacation Home W/ Amenities

Family-friendly home rentals with a pool

A cozy outdoor space features a wooden deck surrounding a small pool, complemented by colorful cushions and lounge chairs. Soft lighting from string lights overhead adds a warm ambiance. The area is enclosed by a wooden fence, providing privacy for guests.

4.97 out of 5 average rating, 94 reviews

Top-Rated Stay | Pool, Tiki Bar, Walk to the Beach

Superhost

5 out of 5 average rating, 5 reviews

Pelicans Paradise Pool Home —Steps to Downtown

4.95 out of 5 average rating, 41 reviews

Walk 2 Beach | Salt/Heat Pool | Game Room | EV

4.94 out of 5 average rating, 32 reviews

Ping Pong• Pets• DT 10 mins• BBQ• King• Fast Wifi

4.94 out of 5 average rating, 32 reviews

The Peaceful Puffin - Pool l Hot Tub l 5 min to DT

Superhost

5 out of 5 average rating, 4 reviews

Waterfront Sunrise! Pool, Dock, Kayaks & Game Room

5 out of 5 average rating, 12 reviews

Private Pool/Spa! Walk to Beach & Two Kitchens

A private backyard area features a heated pool amidst a paved patio. A tiki bar with seating and a TV is situated nearby. Sun loungers line the poolside, along with tropical landscaping. Soft evening light enhances the ambiance of the space.