Family-friendly holiday rentals in St. Augustine

5.0 out of 5 average rating, 155 reviews

Private oasis, heated pool, exceeds expectations

Private retreat on 2 acres of gated land, just 20 minutes to historic downtown St. Augustine and 25 minutes to the beach. This fenced property offers a perfect blend of relaxation, fun, and comfort. Enjoy your private pool, or let the kids enjoy their own space in the pool house, featuring TV, games, and a cozy hangout area. Start your day with fresh eggs from our happy hens- an experience that feels both farm-fresh and uniquely memorable. This home is designed to make your stay unforgettable.

Indoor spacesKitchenGrill

Superhost

A three-tiered fountain is situated in a lush tropical garden, surrounded by various palm and fern plants. Water flows gently from the top tier and cascades down to the basin below, creating a peaceful ambiance in this serene outdoor space.

Treehouse in St. Augustine

4.91 out of 5 average rating, 668 reviews

courtyardtreehouseinthehistoricdistrict

You have found your cozy oasis tucked in a (Real) Treehouse lodged in Ancient Oak. Set in a lush tropical garden in the historic district. It’s a minimalist’s dream, exemplifying the appeal of tiny living: compact, clean, efficient and 2 1/2 blocks to the historic districts shopping and restaurants. Relax on the Sun Deck, Rain Deck or in the Courtyard’s Tropical Garden The day time peaceful beauty is only eclipsed by the the nighttime display of laser lights projected onto the oaks canopy.

Indoor spacesKitchenComfort

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, 231 reviews

Downtown • Historic Whitney House • Luxury Baths!

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.

KitchenFamilyWifi

5.0 out of 5 average rating, 274 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

FamilyIndoor spacesValue

Villa in St. Augustine Beach

A spacious living area features a light gray sectional sofa with a chaise, positioned on a natural fiber rug. A round mirror enhances the sense of space, while a dining area is visible in the background, complete with wooden chairs and a table.

5.0 out of 5 average rating, 127 reviews

VILLA One

The Villas are designed for short stays, long weekends or for a unique styled location for brands to shoot their products. The space features warm tones, natural finishes and local art for an effortless vibe that allows visitors to relax the second they walk in the door. Complete with two bedrooms, two bathrooms and a backyard complete with tropical landscaping, lounge area, dining and outdoor shower. One of 4 Villas located in St. Augustine Beach. Not pet friendly. @staugustinebeachvillas

FamilyIndoor spacesOutdoor spaces

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, 166 reviews

2023 Lux Home 4bd/3.5ba+HotTub+SaltPool+Walk2Beach

🌴 Featured in Good Housekeeping & Designed by HGTV-featured Builders ✨ 🏡 New 2023 Luxury Coastal Home 🛏️ 2 King Suites + 2 Queen Bedrooms 🛁 3.5 Bathrooms 💦 Private Saltwater Pool + Heated Spa/Hot Tub 🍹 Poolside Cabana & Outdoor Kitchen 🚲 Bikes, Beach chairs, Cooler & Toys included 🌿 Tropical Backyard Oasis w/ Mature Palms, Lounge Chairs, Outdoor Shower & Turf 👣 Walk 0.2 miles to the beach 🌅 Stroll 0.2 miles to Cap’s for Waterfront Sunset Dinner 🏰 10 min to Historic St. Augustine

KitchenIndoor spacesLaundry

4.96 out of 5 average rating, 138 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.

Indoor spacesFamilyCondition

4.98 out of 5 average rating, 343 reviews

A private hot tub is set in a serene outdoor area surrounded by greenery and wood paneling. The tub is equipped with a cover and nearby is a container holding spa towels, providing a relaxing space for guests.

Villa in St. Augustine

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.

Indoor spacesKitchenGetting around

A private saltwater pool is centrally located within a spacious patio area, surrounded by well-maintained grassy lawns. Lounge chairs are positioned alongside the pool, while tables and chairs can be seen in the background. The home features sliding glass doors providing access to the pool area.

4.97 out of 5 average rating, 106 reviews

Music on Marilyn- Steps from the Amp! •Jacuzzi•

Nights of Lights & mere seconds from the St. Augustine Amphitheater— a short bike ride to the beach and downtown, this modern escape is 3 beds and 2 baths. Welcome to Music on Marilyn! This is the quintessential St. Augustine experience. Nestled on a quiet street that dead ends to the intracoastal, walking distance to the St. Augustine Amphitheater, Lighthouse, Anastasia Park, Alligator Farm and much more! St. Augustine Beach and historic downtown are just a short bike ride away.

FamilyIndoor spacesCondition

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 Vilano Beach

4.9 out of 5 average rating, 177 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.

Indoor spacesKitchenSleep quality

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, 118 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!

KitchenIndoor spacesLaundry

A dining area is featured with a blue table at its center, surrounded by four wooden chairs with woven seats. Natural light filters through bamboo shades on the windows, highlighting a wooden sideboard displaying beach-themed decor.

4.97 out of 5 average rating, 156 reviews

Perfect One Bedroom Cottage in Lighthouse Park

One bedroom one bath cozy cottage vibe! Perfect couples retreat. This is one half of a duplex. The second half is currently vacant. Excellent location. 5 blocks to the lighthouse. 1 mile to historic downtown. 1.3 miles to the Amphitheater. 0.8 miles to Anastasia State park. 3 miles to the St. Augustine Beach Pier. Walking distance to many great restaurants and bars, mini golf, and boutique shops! Walk or bike to downtown!

KitchenFamilyDecor

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

4.99 out of 5 average rating, 158 reviews

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.

Home in Butler Beach

Driftmark Cabin - RV friendly, Pool + Beach!

Indoor spacesFamilyParking

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.

4.99 out of 5 average rating, 124 reviews

Heated Pool/Hot Tub 1 mile to dwntn/beach

Indoor spacesKitchenComfort

4.99 out of 5 average rating, 646 reviews

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.

Flat in St. Augustine

Villa Tizoc

KitchenIndoor spacesDecor

4.99 out of 5 average rating, 107 reviews

A wooden dock extends over calm water, leading towards a vibrant sunset. Tree silhouettes frame the scene, while soft, warm colors reflect off the water's surface, creating a serene atmosphere that enhances the natural beauty of the waterfront.

Cottage in St. Augustine

Cozy River Retreat w/ Hot Tub and an Amazing View

KitchenIndoor spacesWalkability

4.92 out of 5 average rating, 155 reviews

Flat in St. Augustine

Cozy Garden - Sleeps 4- hottub/outdoor shower!

FamilyIndoor spacesCheckout

4.95 out of 5 average rating, 198 reviews

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.

Flat in Vilano Beach

Charming Vintage Intracoastal Apartment

KitchenFamilyAccess

4.91 out of 5 average rating, 123 reviews

Kid & Dog Haven: Poolside Fun in St. Augustine

FamilyKitchenDecor

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.

5.0 out of 5 average rating, 200 reviews

Don’t You Wanna? Heated Pool & SPA 4Bed & 3Bath

KitchenIndoor spacesHospitality

Family- and pet-friendly home rentals

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.

4.97 out of 5 average rating, 128 reviews

St Augustine Entire Home, King Bed, Pet Friendly

FamilyIndoor spacesBeach

An outdoor pool area is framed by palm trees, showcasing a large heated pool surrounded by a spacious patio. Colorful Adirondack chairs are arranged invitingly along the edge, offering a perfect spot for relaxation. The atmosphere is bright and sunny, with clear blue skies overhead.

4.9 out of 5 average rating, 176 reviews

Coastal Retreat w/Pool, Walk to beach, restaurants

FamilyKitchenOutdoor spaces

4.98 out of 5 average rating, 126 reviews

A living area features a modern, light-toned sofa paired with a round coffee table. Natural light filters through large windows adorned with red curtains. The open floor plan leads to a dining area, highlighting a connection between spaces with exposed wooden beams.

Home in Lincolnville

Historic Lincolnville Retreat!

FamilyKitchenCheckout

4.91 out of 5 average rating, 104 reviews

The Secret Garden On Locust!

FamilyKitchenDecor

A comfortable living area features a large sectional sofa adorned with yellow and grey cushions. A flat-screen television hangs above a decorative fireplace. A coffee table with a small plant is centered on a textured area rug, and natural light filters through the nearby windows.

4.91 out of 5 average rating, 333 reviews

SaraCasa - First Floor House 2Br/1.5Bath

FamilyKitchenPets

Apartment in St. Augustine

A spacious living area features wood-paneled walls and large glass doors, offering views of the ocean. A chandelier hangs from the ceiling. The seating area includes a comfortable couch and a dark coffee table, while a television with vibrant display adds a touch of modernity.

4.92 out of 5 average rating, 117 reviews

Treehouse Artist Haven Direct Oceanfront 2br

KitchenFamilyBathroom

A charming coastal bungalow is set amidst lush green grass, surrounded by palm trees and nature. The driveway leads to the front entrance, featuring a single-car garage. The home is framed by a clear blue sky dotted with clouds, highlighting its welcoming facade.

4.94 out of 5 average rating, 230 reviews

Surfside House

FamilyKitchenGetting around

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, 133 reviews

Casa Coquina Walk to Downtown Clean Quiet Spacious

FamilyIndoor spacesLaundry

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 140 reviews

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

FamilyIndoor spacesAccuracy

The exterior of a two-story vacation home is showcased, featuring a welcoming porch with wooden railings and steps leading up to the entrance. The surrounding landscape includes a spacious paved driveway, lush greenery, and various trees, creating a serene atmosphere.

4.9 out of 5 average rating, 106 reviews

Vilano Beach Home, 3 Bed, 2 Masters, Heated Pool

FamilyIndoor spacesDecor

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, 193 reviews

Pool home oasis steps to ocean

Indoor spacesKitchenDecor

A spacious screened-in pool area features a large blue swimming pool surrounded by patio tiles. Comfortable seating arrangements with multiple chairs and a table are visible nearby, providing a relaxed space for leisure. Natural light streams in through the screened enclosure.

4.93 out of 5 average rating, 195 reviews

Heated Pool, Beach, Patio Lounge, Near Downtown

Indoor spacesKitchenHospitality

A private pool area is showcased, featuring a large, clear swimming pool surrounded by a spacious patio. Lush greenery and palm trees create a serene atmosphere. Sliding glass doors provide access to the home, while a shaded pergola adds an inviting touch to the outdoor space.

4.95 out of 5 average rating, 99 reviews

Poolside Oasis ~ walking distance to Downtown

KitchenIndoor spacesDecor

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, 103 reviews

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

Indoor spacesFamilySleep quality

Superhost

Home in St. Augustine Beach

5.0 out of 5 average rating, 4 reviews

Luxury Beach Retreat, Pool Spa Sauna Yoga Studio

KitchenFamilyHot tub