Cottage holiday rentals in St. Augustine

5.0 out of 5 average rating, 278 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

ValueFamilyLong stay

The charming cottage is framed by lush greenery and a pathway leading to a welcoming front porch. The airy porch is adorned with hanging plants and a ceiling fan, inviting relaxation. Gravel landscaping enhances the surrounding gardens, offering a serene first impression.

4.95 out of 5 average rating, 201 reviews

Casa Verde 1885 - Walk to Downtown

Let this gem located in the historic Abbott Tract be your home away from home. Located just 2 blocks from the Downtown area and all it has to offer. This cottage was built in 1885 and retains its old-world charm while featuring modern conveniences. Whether you’re enjoying breezes from Matanzas Bay sitting on the front porch swing, or dining in the resort-like back yard featuring an outdoor bar, built-in eating area, covered porch and lounge chairs, this is an experience not to be missed.

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4.91 out of 5 average rating, 235 reviews

Coastal Cottage -firepit, pet fence, kayaks, bikes

Located in the historic Lighthouse Park neighborhood, this charming 1940s coastal cottage is easy strolling distance to the Lighthouse, Alligator Farm, mini-golf, cafes & more! It is only a 0.8-mi walk to the Bridge of Lions, where you can walk over the Bay to downtown St. Augustine. You couldn't ask for a better location! It's on Anastasia Island so you're a short walk/bike/car ride from the beach & Ampitheater. It's cozy, pet & kid-friendly with a big backyard. Kayaks & bikes available!

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The exterior of a two-story cottage showcases wooden shingle siding and a welcoming front porch. Lush greenery and colorful plants surround the house, with potted flowers placed in the foreground. Sunlight highlights the charming architectural details against a clear blue sky.

4.98 out of 5 average rating, 319 reviews

Charming 2/2 Cottage ~ Walk to Historic Downtown

This St. Augustine home is right in the heart of quaint & historic downtown! The lovely two level cottage has an upstairs full bath and two private bedrooms each with a queen bed. Downstairs is a second full bath, as well as a living room and full kitchen. The space is perfect for 1-4 guests. A short 8-10 minute walk allows visitors to explore the many downtown historic sites, museums & restaurants. One parking spot is available on our lot. Free street parking for additional cars.

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The exterior of the two-story home features a wrap-around porch adorned with hanging plants. Lush greenery surrounds the property, providing a serene backdrop. The structure is painted in light colors, with large windows allowing natural light to illuminate the space.

4.94 out of 5 average rating, 504 reviews

Perfect location- Cottage Retreat in historic area

This charming two story gem with a wrap around front porch is perfect for your stay while visiting historic St. Augustine. Situated within walking distance of the Fountain of Youth and the Old Town Trolley Tours, you can easily explore all the city has to offer! It’s in a perfect location near the city’s downtown area featuring Castillo de San Marcos (1 mile away) and many local shops and restaurants. Check out the featured guidebook which references many nearby points of interest.

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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.

4.91 out of 5 average rating, 179 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.

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5.0 out of 5 average rating, 195 reviews

Cottage in Lincolnville

~Romantic Historic 1888 Cottage~Walk to Downtown

Come live in history! This cottage traces its roots back to humble beginnings and it still stands today as one of Lincolnville's original historic treasures. Nestled in the heart of America's oldest city, this endearing circa 1888 cottage offers an intimate, refined escape with a boutique ambiance. This is the ideal retreat for travelers seeking a romantic getaway or guests who wish to be transported to a more graceful time. Modest in scale but grand in experience.

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A charming cottage is surrounded by lush greenery and tropical plants. The entrance features a shaded outdoor seating area with two chairs and a table, set under a red umbrella. The light-colored house is topped with a metal roof and has multiple windows, inviting natural light.

4.89 out of 5 average rating, 243 reviews

Downtown House near Flagler College & St George st

Enjoy this charming, (originally a carriage house in 1899) adorable cottage, nestled in the heart of historic downtown St Augustine! It's a rare find for its proximity. Walking distance to all of downtown and Flagler College! No driving necessary for a full complete vacation. This amazing little house has a fully stocked kitchen that opens up to a shaded deck. We do require guests be 25+ to book instantly otherwise please inquire. Please read the whole listing.

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An aerial view highlights the charming blue cottage surrounded by lush palm trees and vibrant greenery. The proximity to pristine beach waters is visible, along with neighboring coastal homes. A walkway leads from the yard to the street, emphasizing the inviting outdoor space.

4.98 out of 5 average rating, 114 reviews

Vilano Charmer, Capo’s Cottage, 1/2 block to beach

Charming 3/2 beach cottage located in the historic Surfside Community of Vilano. Once this home belonged to the Capo Family who brought visitors from downtown St Augustine across the Intercoastal on a ferry to the beach in the 1920’s. Today, you can enjoy the vintage vibe, with modern conveniences. Only 2 min walk to Surfside Beach! Under new ownership, formerly an Airbnb for many years. One small dog will be considered.

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4.97 out of 5 average rating, 115 reviews

A light-filled kitchen features modern appliances, including an oven and a large dining table. Windows offer a view of the ocean, while natural light highlights the white cabinetry and rustic decor. The space is complemented by potted plants and hanging light fixtures.

Cottage in Ponte Vedra

Cane Cottage Oceanfront Oasis

Cane Cottage was renovated in 2018-2019 after extensive damage from multiple hurricanes. Our vision was to bring this old Florida beach cottage back to its original charm while also adding new life and modern amenities. From the outdoor entertaining spaces to the lavish interior finishes this AirBnB makes for the perfect beach retreat. Well designed and functional home with many well-thought-out touches.

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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.

4.99 out of 5 average rating, 110 reviews

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.

ValueFamilyComfort

The living area features a comfortable white sofa accompanied by a woven coffee table. A ceiling fan circulates air above, while a wall-mounted TV is positioned for easy viewing. Bright wood flooring and light walls create a spacious ambiance, complemented by a dining area in the background.

4.96 out of 5 average rating, 277 reviews

1920s Coastal Cottage | Walk to Amp & Downtown

Light-filled, historic charm meets modern coastal living. Built in the 1920s, this meticulously updated 2-bedroom, 1-bathroom cottage features original heart pine floors, walls of windows, and a breezy, open feel that instantly makes you feel at home. Nestled in the quiet, historic Lighthouse Park neighborhood, you are right between the beach and historic downtown — 5 minutes to both.

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Popular amenities for cottage rentals in St. Augustine

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A charming cottage is framed by lush palm trees and tropical plants. A white picket fence surrounds the front yard, providing a welcoming entrance. The home's metal roof and light exterior complement the clear blue sky, creating an inviting curb appeal.

4.88 out of 5 average rating, 118 reviews

The Coconut Cottage. Hot Tub. Walk To Beach

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5.0 out of 5 average rating, 26 reviews

Brand New Immaculate Cottage

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4.91 out of 5 average rating, 179 reviews

The Shire on 1 acre marshfront with dock and Spa

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4.99 out of 5 average rating, 110 reviews

Cozy River Retreat w/ Hot Tub and an Amazing View

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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.

4.97 out of 5 average rating, 231 reviews

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

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Pet-friendly cottage rentals

Cottage in St. Augustine Beach

A welcoming porch is framed by lush greenery, including a palm tree and decorative plants. The cheerful yellow exterior is complemented by a bright red door. Comfortable seating is visible, inviting guests to relax in the shade under the roof overhang.

Oceans 11: Steps from the Ocean, Quiet Beach

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4.87 out of 5 average rating, 183 reviews

4.99 out of 5 average rating, 115 reviews

The entrance features a welcoming design with a vibrant pink door, flanked by wooden shutters. A rocking chair sits on the porch beside a potted plant. The doormat displays a cheerful message, inviting guests into the cottage.

Cottage in Lincolnville

Location! Stylish Downtown Cottage Getaway

LocationFamilyCleanliness

4.97 out of 5 average rating, 172 reviews

A serene lakeside view is captured, highlighting calm water that reflects lush greenery and a blue sky. Trees frame the scene, creating a peaceful atmosphere. The shoreline features soft vegetation, inviting opportunities for relaxation and contemplation.

Cottage in Palm Coast

Cheerful lakeside 2/2 cottage with a private pool

ValueLocationOutdoor spaces

4.87 out of 5 average rating, 195 reviews

Pet Friendly Getaway 3 Blocks to Old City-Unit A

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Cottage in St. Augustine Beach

A private courtyard is softly illuminated by string lights, creating a warm ambiance at night. Lush greenery, including large tropical plants, surrounds a rustic wooden dining table set on a patterned stone surface, inviting outdoor gatherings.

Enchanting courtyard, quiet cottage by beach

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4.97 out of 5 average rating, 189 reviews

4.88 out of 5 average rating, 162 reviews

A bright and open living area is highlighted by a natural wood ceiling and decorative hanging light fixtures. A modern dining space features a white table surrounded by chairs. A cozy blue accent chair adds a pop of color, while large windows allow natural light to fill the room.

Cottage in Satsuma

Waterfront Retreat | 2 Docks + River Views

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4.87 out of 5 average rating, 117 reviews

A spacious bed is featured with a stylish black and white patterned duvet and accent pillows. Two bedside tables with decorative lamps sit on either side. A piece of wall art and a storage unit are visible, contributing to an organized and inviting sleeping area.

Cottage in Elkton

Cottage w/pool on horse property, St. Augustine.

ValueFamilyAccess

5.0 out of 5 average rating, 36 reviews

The Anchor & Vine - Historic Uptown St. Augustine

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Private cottage rentals

A bright living area is furnished with a spacious white sofa and a coffee table, complemented by two patterned ottomans. Natural light fills the room through multiple windows, while a large artwork depicting a coastal scene hangs prominently on the wall.

4.93 out of 5 average rating, 106 reviews

Olastay Cottage

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A bright living area combines modern and Boho styles, featuring a yellow sofa and patterned area rug. A wall-mounted television offers entertainment. The open kitchen includes white cabinetry and bar seating, complemented by natural light from nearby windows.

4.96 out of 5 average rating, 327 reviews

Couples Boho Bungalow close to Beach and Downtown

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A charming cottage exterior is framed by a white picket fence and colorful tropical plants. The front door, adorned with a wreath, welcomes guests. Large windows allow natural light to fill the space, while a well-maintained pathway leads to the entrance.

4.97 out of 5 average rating, 315 reviews

Charming Downtown Historic Cottage

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A spacious deck overlooks a clear blue saltwater pool surrounded by lounge chairs and umbrellas. Lush greenery and palm trees frame the view of the water and dock area in the distance, creating a serene outdoor space for relaxation.

4.98 out of 5 average rating, 198 reviews

Fun Waterfront Retreat, Heated Pool, Rooftop Deck

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Cottage in Green Cove Springs

Two charming guest houses are surrounded by well-maintained landscaping filled with colorful azaleas. Mature trees provide shade, and sunlight filters through, creating a serene outdoor space. The residences feature distinct architectural styles, showcasing a harmonious blend with the lush surroundings.

Guest House-Enchanted Oaks Estate-Weddings-Dock

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4.98 out of 5 average rating, 157 reviews

4.89 out of 5 average rating, 113 reviews

The entrance features a solid brown door with modern glass accents, welcoming guests into the cottage. A small decorative mat lies on the porch, and bright blue siding complements the entryway. Light fills the interior through visible open spaces beyond the entrance.

Cottage in Butler Beach

Tones of Blue

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A cozy living area features a floral-patterned sofa, complemented by two decorative lamps and a wooden coffee table. Natural light filters through a window, enhancing the room's inviting atmosphere. A console table and an accent table with a decorative arrangement provide additional charm.

4.89 out of 5 average rating, 388 reviews

Adorable Uptown Cottage

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