Family-friendly holiday rentals in Historic District, St. Augustine

The historic home features a grand façade with elegant columns and a decorative balcony. A wrought iron gate opens to a brick pathway leading to the entrance. Large windows allow for ample natural light, framed by soft garden landscaping against a vibrant sunset backdrop.

4.97 out of 5 average rating, 442 reviews

Genovar Mansion Rose Garden Suite Private Entrance

The direct view of a gorgeous live oak canopy on Magnoila Avenue and incredible architecture make this historic home a memorable place to stay. This romantic ground floor suite is perfect for couples with a private entrance, queen poster bed, living room, spacious bathroom, individual climate control, heirloom antiques and reserved driveway parking spot. The home is located within the historic district, close to trolley stops and within easy walking distance to downtown. 6 minutes to the beach.

A spacious living room features a light-colored sofa adorned with decorative pillows and a glass coffee table. Two elegant armchairs with floral patterns are placed beside the sofa, and natural light streams through large windows adorned with wooden shutters. A cozy area rug anchors the seating area.

4.95 out of 5 average rating, 207 reviews

Downtown HistoricLuxury • Designer Kitchen & 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.

A dining area is showcased with a wooden table surrounded by six chairs, featuring vibrant floral upholstery. A woven pendant light hangs above, illuminating the space. An ocean-themed mural adorns the wall, complemented by potted plants positioned nearby.

4.92 out of 5 average rating, 149 reviews

Charming Old-Florida Apartment

This darling Uptown apartment is in the thick of it! Next door to fabulous uptown shops and eateries -- including our own bodega and taproom. Walkable to bustling historic downtown, the fort, the Bridge of Lions, and the Matanzas River. Bikeable to Vilano Beach and Anastasia State Park. And a short drive to additional beaches on Anastasia Island or in Vilano. Enjoy a slice of Saint Augustine typically only enjoyed by the locals, and relax in the friendly historic Abbott Tract neighborhood.

Place to stay in St. Augustine

A stone fountain stands at the center of a lush courtyard, surrounded by vibrant green ferns and tropical plants. A wooden bench is positioned nearby, offering a tranquil space for relaxation amid the serene sounds of cascading water.

4.91 out of 5 average rating, 976 reviews

Moon Over the Courtyard in the Historic District

You have found your cozy oasis tucked under an ancient Oak tree in a private, lush tropical Courtyard in the Historic District of St Augustine. Sit by the fountain, feed the roaming tortoises day or enjoy the fire and the 1000's of tiny lights reflected on the tree canopy by night. This small studio and exemplifies the appeal of tiny living: compact, clean, efficient, and convenient. The Courtyard is a short walk from all of the Historic Districts Shops, Restaurants and Attractions.

The exterior of the home features a two-story structure with a welcoming porch. Potted plants hang from the posts, and a decorative sign is positioned near the entrance. Lush greenery and various plants are arranged along the pathway leading to the front steps.

4.99 out of 5 average rating, 213 reviews

Historic St. Augustine 2/2 Duplex & Pool

About this space: Welcome to this 2 unit home located in Historic St. Augustine. This home is close and within walking distance to all the fun downtown has to offer. It is also a short drive to the beaches! This home has 2 bedrooms and 2 full bathrooms, a living room, kitchen, den and direct pool access. This space: This home is a 2 unit house Guest access: There is a lockbox on the door with a key inside Other things to note: Please keep in mind that the pool is a shared space :)

A serene outdoor space is surrounded by lush green palm trees and various potted plants. Soft gravel covers the ground, with pathways leading to a green door, enhancing the natural ambiance of the area.

4.96 out of 5 average rating, 108 reviews

Luxe Lemon Lower in Historic Downtown St Aug.

Stay in the heart of Historic Downtown St Augustine in this 100yr old 2BR/1B completely renovated in 2023! Only a 7 min walk to Downtown a 12 min drive to the beach, you'll love this charming home! Guests should be adults or older children. 1 parking space available. Note: The loft atop this unit is also rentable, w/ connected or disconnected private entrance, & sleeps 2. Ask us or search "AirBNB Lemon LOFT" or "AirBNB Lemon WHOLE" to rent loft or the whole house.

Bungalow in St. Augustine

A cozy living area features a blue sofa adorned with several pillows. A coffee table rests on a patterned rug, and light streams through large window blinds that brighten the space. Decorative wall art adds character to the neutrally painted walls.

4.92 out of 5 average rating, 387 reviews

Uptown Classic Bungalow Comfy Walk Everywhere

The Uptown Bungalow is located on a quiet street only a block away from all the action in the heart of the nation's oldest city. Built in 1910 the unit has been renovated, is tastefully decorated ,and is equipped with everything you will need to make your stay in St. Augustine a great experience. Dine in the kitchen or an outdoor patio set on the screened in porch where the guests can enjoy a café & scones in the AM or in the evenings cocktail & Hors d'oeuvres.

A cozy living area features a comfortable sofa paired with a light-colored armchair and a round coffee table. Natural light flows through multiple windows, illuminating the space. The full kitchen is visible, showcasing modern appliances and blue cabinetry, complemented by woven wall decor.

4.96 out of 5 average rating, 226 reviews

Charming 1 Bedroom apt, Historic St Augustine

You will love this newly remodeled one bedroom apartment in Historic St. Augustine. Originally built in 1910 and completely updated in 2023. Just two blocks from St. George St, walking distance to Flagler and all of downtown St Augustine. This apartment offers one bedroom with king size bed, full kitchen and private patio. Free off street parking, so you are able to park, walk around and enjoy everything downtown has to offer.

A bright bedroom features a four-poster bed dressed in white linens. Two bedside lamps offer gentle illumination, while large windows allow natural light to fill the space. The light-colored walls and flooring create a serene atmosphere.

4.95 out of 5 average rating, 244 reviews

Lemon Street Studio (Very Walkable + Free Parking)

Located just a few blocks from all that downtown has to offer, the Lemon Street Studio is the perfect way to enjoy your trip to St Augustine. Less than a 10 minute walk to St George Street, the Castillo de San Marcos, the Bayfront, and Flagler College. The one bedroom apartment welcomes you with free off-street parking, a private entrance, and a stylish space to relax after hitting the town.

A modern kitchen features white cabinetry and stainless steel appliances. A central island with two stools provides additional seating. Natural light floods the space through multiple windows, highlighting the quartz countertop and decorative vase of flowers on the counter.

4.95 out of 5 average rating, 379 reviews

Apt A - Comfort of Home in Historic St Augustine

Charming old world apartment in the historic district (AND a short 3-4 miles from multiple beaches) with a completely updated bathroom and kitchen. The kitchen has all new appliances, cupboards and quartz countertop. My favorite part of this apartment is the porch where you can relax, enjoy your morning and evening beverages, watch horse drawn carriages and mingle with our neighbors...

5 out of 5 average rating, 130 reviews

The cottage exterior features a welcoming white facade with a covered porch and steps leading to the front door. Lush greenery and a stone wall border the pathway, while trees provide shade, creating a serene atmosphere near the entrance.

Cottage in St. Augustine

1900s Cottage in Heart of Town-walk everywhere!

Welcome to Groveside Cottage on the historic street of St. Augustine! In 1920s Grove Avenue was the home of several families of cigar makers and two cigar manufacturing companies. This charming cottage is a great mix of vintage and modern; you will be amused! We allow 1 dog, please message us - approval required before booking. Thank you!

4.96 out of 5 average rating, 254 reviews

Tree Top View 2

Our 600 sq ft apartment offers a private balcony shaded by centuries-old live oaks, alive with birds and squirrels. The view also includes a touch of our neighbor’s eclectic backyard, adding local character. Inside, enjoy a king bed, separate living area, and kitchen. A short 1/2 mile walk brings you to historic downtown St. Augustine.

Popular amenities for Historic District, St. Augustine family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A well-lit outdoor living space features a heated pool surrounded by smooth pavers. Several adirondack chairs are positioned nearby for seating, and a dining table is set for outdoor meals. String lights illuminate the area, creating a cozy ambiance.

4.97 out of 5 average rating, 121 reviews

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

4.89 out of 5 average rating, 193 reviews

Beachy Condo| Steps to Beach | Pools | Hot Tubs

Guesthouse in St. Augustine

An outdoor seating area features multiple blue Adirondack chairs arranged around a circular stone patio, complemented by a small green table. A lamp post stands nearby, and a flag flutters gently in the breeze, surrounded by lush greenery and tall palm trees.

4.91 out of 5 average rating, 604 reviews

Captain's Quarters Tiny House

Condo in St. Augustine Beach

A cozy living area features soft beige furnishings and decorative blue pillows. A wooden coffee table occupies the center, while a stone fireplace adds warmth. Large sliding doors provide natural light and reveal views of the outdoors, framed by sheer curtains.

4.93 out of 5 average rating, 134 reviews

Cozy Beach Townhome - Bikes, Garage & Pickle Ball!

Condo in St. Augustine Beach

The living area features comfortable seating, including a soft blue sofa and an armchair, arranged around a white coffee table. Light-colored décor and subtle greenery create a relaxed ambiance. The space is illuminated by a contemporary chandelier, with a view of the kitchen and dining area in the background.

4.95 out of 5 average rating, 166 reviews

Newly renovated! Steps to BEACH & POOL!

4.98 out of 5 average rating, 312 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

Perfect location 2 Bedroom Private Hot Tub

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, 137 reviews

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

A sunlit indoor pool area features large glass doors that open to an outdoor pool surrounded by palm trees. Comfortable lounge chairs are positioned around the poolside, creating a relaxing space for guests. A hot tub is visible in the foreground, enhancing the inviting atmosphere.

5 out of 5 average rating, 269 reviews

Ocean Gallery 1/1, 2 pools

Family- and pet-friendly home rentals

A charming white cottage showcases a welcoming porch adorned with hanging planters. An American flag flutters by the entrance, while a gravel pathway leads up to the home, surrounded by manicured greenery and shaded by large trees, creating a serene exterior setting.

5 out of 5 average rating, 108 reviews

Palo Haus 1918 Cottage in Downtown St. Augustine

A cozy living area features a dark sofa with accent pillows and a classic wooden rocking chair. Natural light flows through the window, illuminating the rich wooden flooring. An open doorway reveals a dining space with a stylish light fixture and a set of wooden dining chairs.

4.93 out of 5 average rating, 380 reviews

Downtown Lodge - Clean-Pet Friendly-Free Parking

A cozy sleeping area features a spacious bed adorned with a patterned bedspread and accented by a decorative pillow. A bedside table holds a small lamp, while a dark cabinet provides additional storage. Light filters in through a window dressed with textured blinds.

4.96 out of 5 average rating, 199 reviews

Traveler’s Nest of uptown St. Augustine with pool!

Tiny home in St. Augustine

A scenic view of the Bridge of Lions at sunset, featuring vibrant orange and pink hues in the sky. The bridge's lights are illuminated, reflecting in the calm water below, creating a serene atmosphere. Silhouettes of birds are seen in the distance.

4.88 out of 5 average rating, 247 reviews

Cheerful Studio by LionsBridge,short🚶‍♀️to downtown.

Holiday home in St. Augustine

An aerial view captures the charming neighborhood surrounding Hope & Glory, with tree-lined streets and various homes. The picturesque landscape features glimpses of the nearby water and distant landmarks, including the prominent cross, symbolizing the area's historical significance.

5 out of 5 average rating, 170 reviews

Walk Historic Downtown! "Hope & Glory"

4.89 out of 5 average rating, 634 reviews

The living area features soft turquoise walls and light hardwood flooring. A spacious white sofa is complemented by green accent pillows. A wall-mounted television and decorative surfboards add character to the space. Natural light fills the room through the window, creating a bright atmosphere.

Bungalow in Lincolnville

The Hideaway

Guest suite in St. Augustine

A spacious studio features a king bed with a patterned blanket, complemented by a cozy sofa and armchair. A kitchenette is visible in the background, along with a modern ceiling fan overhead. Large windows allow natural light to fill the room.

4.98 out of 5 average rating, 378 reviews

Cozy studio 15 mins to beaches & historic downtown

A spacious backyard is highlighted by a private round pool, surrounded by lush greenery and palm trees. An outdoor cabana features a bar area, while a well-maintained lawn adds to the inviting atmosphere. The charming pink structure complements the serene setting.

5 out of 5 average rating, 114 reviews

Pink Palms *Heated Pool* Walk to Downtown

Family-friendly home rentals with a pool

A screened-in balcony offers views of the lush greenery and marshlands beyond. Colorful cushions adorn a comfortable seating area, while a small wooden table sits centrally. Natural light fills the space, creating a peaceful atmosphere for relaxation.

4.99 out of 5 average rating, 120 reviews

Riverfront direct views-Get it ALL in St Augustine

The exterior of a single-story house is displayed, featuring a sloped roof and an inviting entryway. Green grass surrounds the home, complemented by mature trees and landscaped bushes. A concrete driveway leads up to the entrance, providing accessible access.

4.99 out of 5 average rating, 433 reviews

Your Home Away From Home

4.92 out of 5 average rating, 168 reviews

Covered seating is arranged around a sleek coffee table on a patio with a view of a large heated pool, accented by palm trees and umbrellas. A dining area with a table and chairs is visible, offering ample space for relaxation and enjoyment.

Condo in Lincolnville

F1, Downtown, POOL, beaches, porch, parking!

5 out of 5 average rating, 115 reviews

Lush greenery frames a wooden pathway leading to a sandy beach, with palm trees and residential buildings visible in the background. The sky is illuminated by soft hues of sunset, creating a serene backdrop for the coastal environment.

Condo in Treasure Beach

Boutique Beachside condo with easy access to beach

A bright living area features large floor-to-ceiling windows that provide sweeping ocean views. Comfortable seating is arranged around a central coffee table adorned with decorative items. A Smart TV is positioned for easy viewing, while a ceiling fan adds a cooling breeze.

4.97 out of 5 average rating, 127 reviews

Family Beach Condo - Steps To The Sand Or Pool

A serene outdoor pool area is framed by palm trees and lounge chairs. The stylish building showcases multiple stories with large windows. The sky transitions to a blend of colors at sunset, creating a peaceful ambiance around the pool, which features inviting turquoise water.

4.97 out of 5 average rating, 107 reviews

>•< Resort Style Retreat >•<Pool>•<Kayaks >•<

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, 165 reviews

Heated Pool, Beach, Patio Lounge, Near Downtown

A bright and airy living area is depicted, featuring a round dining table surrounded by four white chairs. A sectional sofa with light grey upholstery is positioned nearby, complemented by decorative pillows. A well-equipped kitchen area is visible, with modern appliances and cabinetry, providing a functional space.