Holiday rentals with breakfast in St. Augustine

5 out of 5 average rating, 75 reviews

A vibrant outdoor space features a heated pool surrounded by a textured deck. Lounge chairs are positioned for relaxation under a large umbrella. A mural with tropical foliage and pink flamingos adds a colorful backdrop, complemented by cabanas and palm trees in the area.

Home in Butler Beach

Resort-Style Pool, Walk to Beach, 3 Kings, Games

Dive into your tropical getaway! Relax in the heated pool surrounded by cabanas & lush palms, breathe in the ocean air, dine al fresco & park your boat out front! ★ Private POOL heated (free), hot outdoor shower, OCEAN BREEZES ★ WALK TO BEACH ~ Drive onto beach ~ Beachfront parking ★ WFH: 330+ mbps wifi, 3 desks, coffee/espresso bar, charging ports ★ Casper K/Q BEDS ~ Roku TVs ★ Fusbol, Ms. Pac-Man, Poker, Games ★ Firepit, Gas BBQ, Hammock, Cornhole, Jenga ★ Keyless entry, Fully Fenced backyard

Apartment in St. Augustine Beach

The exterior of a two-story building is shown, featuring a textured yellow facade and a brown roof. Windows are present on both levels, with landscaping that includes green shrubs and palm trees in the foreground, set against a clear blue sky.

4.91 out of 5 average rating, 274 reviews

High Tide - breezes galore!

High Tide is the upper unit in my Triplex in St.Augustine Beach - SAGE TIDES - on the East side of A1A Beach Blvd (i.e. no street to cross!). Two large bedrooms with a new KING bed and a Queen and a rollaway. Walking distance to everything - bring your flip flops - stay awhile! On a dead end road, two houses from the beach make it a 90sec walk to the sand dunes and ocean! Two decks to catch the breezes, morning & night! The decks are only accessible by your unit. Bonus - Pet friendly!

An outdoor area is depicted, featuring a salt-water pool surrounded by lounge chairs and shaded by a red umbrella. Permanent string lights provide soft illumination. Tropical landscaping and a covered space in the background suggest an inviting environment for relaxation and leisure.

4.94 out of 5 average rating, 32 reviews

Luxury Home with Pool, Pickle Ball and Hot Tub

Your family will be a walk away to downtown Saint Augustine when you stay at this centrally-located place. Everything you need is at the Pelican’s Oasis from the outstanding outdoor area with a salt water pool and covered living area to an elegant indoor entertainment area with bar, ice machine and beer fridge. Covered Pickle Ball court, Hot Tub and 6 seater Golf Cart ( for additional fee). Plenty of room throughout the house to enjoy different seating areas and even a selfie stage with props.

Home in Ponte Vedra Beach

4.98 out of 5 average rating, 44 reviews

Direct Oceanfront Home|Guana Preserve|Steps 2 Sand

🐬Serenity Shores is a Guest Favorite DIRECT oceanfront retreat in prestigious ultra private Ponte Vedra Beach. 🐬Set between Atlantic Ocean & protected Guana Preserve, enjoy rare privacy with miles of undeveloped shoreline just steps from your deck 11 steps to sand. 🐬Relax to waves, spot coastal wildlife, and unwind near world-class golf, spas, dining, historic St. Augustine and TPC Sawgrass. Recreation nearby! 🐬Perfect for couples and small groups seeking a memorable beachfront escape.

4.98 out of 5 average rating, 50 reviews

The exterior of a single-story home is highlighted by a tiled roof and arched windows. A manicured lawn surrounds the entrance, featuring a driveway and a garage. Lush green landscaping adds a welcoming touch to the property.

Home in Palm Coast

Palm Coast Oasis: Near Beach

Dog-friendly home with a beautiful yard, patio & WiFi, close to golf and beaches! This single-level, 3-bedroom Palm Coast home is perfect for beachgoers and golfers alike, with world-class courses nearby and beaches like Varn and Flagler just a short drive away. Enjoy central AC, a sunroom with yard views, and a lovely backyard ideal for BBQs or relaxing on the patio. Inside, you'll find a well-equipped kitchen, multiple TVs, and space to unwind. Perfect for your Florida getaway! LBTR 34693

5 out of 5 average rating, 32 reviews

A sandy path meanders through coastal vegetation, leading toward the Atlantic Ocean. A rustic wooden bench is positioned on one side of the path, inviting relaxation. The ocean stretches into the distance under a partly cloudy sky, enhancing the serene coastal setting.

Cottage in Vilano Beach

Oceanview Cottage at Vilano Beach

The Oceanview Cottage is a raised cottage with great views of the Atlantic Ocean from the front deck and the living room. You're renting the entire house--full kitchen with a breakfast bar, living area, and two separate bedrooms, one King, one Queen. The bathroom has a shower, and there is a half bath in the King bedroom. The Oceanview Cottage is pet friendly, with an additional fee. The Oceanview Cottage is part of the Bayfront Marin House range of lodging options.

Bungalow in St. Augustine

A charming bungalow is framed by lush palm trees, with a welcoming teal front door at its center. A stone pathway leads through gravel landscaping adorned with greenery, creating an inviting approach to the home.

4.98 out of 5 average rating, 281 reviews

"Flagler Shack"- a funky tropical oasis!

"Flagler Shack"- funky, cozy, cool...renovated island bungalow! * 10 min walk to downtown(over Bridge of Lions) * 10 min bike ride to the AMP(farmers market, concerts) * Awesome bars and restaurants literally out your back door...Odd Birds, Blackfly, Sarbez, Llama, Slugs Pub, Gas Fresh Island Market, Osteen’s, Osprey Tacos, Mojos Tacos * 15 Min walk to Conch House Marina and Restaurant * 20 min bike ride to beach at Anastasia State Park * 5 min drive to Saint Augustine Beach

Guest suite in St. Augustine

A tranquil bedroom showcases a queen bed adorned with a leaf-patterned duvet cover. Two bedside lamps cast soft light on either side, while bright blue and green walls create a soothing ambiance. Light filters through shuttered windows, enhancing the warm wooden floor.

4.81 out of 5 average rating, 250 reviews

Historic St. Augustine Gateway

Experience the allure of St. Augustine from our charming private suite. Nestled within a leisurely stroll of the historic heart of St. Augustine and a mere 5-minute drive from its world-renowned beaches. Your sanctuary consists of two distinct areas – a gracefully adorned bedroom featuring a comfortable queen bed, and a cozy den with sofa. Connected to our residence with a separate private entrance and a quaint deck, this suite affords you the utmost privacy and independence.

5 out of 5 average rating, 76 reviews

An outdoor area features a grassy lawn with a corn hole game and an inviting stone fire pit. Adirondack chairs surround the fire pit, and a gazebo with string lights can be seen in the background, enhancing the space's relaxing atmosphere.

Home in Vilano Beach

4 Min Walk To Beach! Hot Tub•Golf Sim•Fully Fenced

Wake up hearing waves, stroll to the beach with coffee, and come home to your own golf simulator, hot tub, and lanai oasis! This is St. Augustine paradise on Vilano Beach. 🩴4 Min Walk To The Beach 👣Walk to Publix, Restaurants & Pier ⛳️ Golf Simulator 🚿Hot Tub 🛁 Rainfall Shower 🔥Propane Grill & Fire Pit 🌴Screened in Lanai 👶Baby/Toddler Friendly 🐶 Dogs Welcome ($140/dog) 🏖️ Beach Gear & Games 🛜1G Wifi Planning Ahead? ❤️ this listing in the top right corner

Home in St. Augustine South

A curving staircase with a black railing leads to an inviting living area. A modern chandelier hangs overhead, casting patterned shadows on the marble floor. Soft natural light filters through windows with striped coverings, illuminating the space beyond.

4.81 out of 5 average rating, 32 reviews

Little Castillo on Prince Road

Gear up or wind down at Little Castillo, my remodeled Florida home. Only minutes to - beaches, historic district, great eateries. Fenced pet friendly property boasts a hot tub, fire pit, screened smoking porch, ample parking and we will kit you out for the beach. From Carrera marble in the foyer to spa like bathrooms and 7 chandeliers, you are welcomed. New water filtration (‘24) and living room furniture (‘25) because we listen. So…Relax. Enjoy. Be well.

4.97 out of 5 average rating, 102 reviews

The bedroom features a king-size bed with a quilted bedspread and decorative pillows. A bedside lamp sits on a dark wooden nightstand. Large windows with drapes allow natural light into the space, creating a serene environment. A comfortable chair is positioned near the window.

Condo in St. Augustine

Luxury Golf & Spa condo in Beautiful St. Augustine

Beautiful 1 bedroom pristine condo unit has it all. Comfortable king size bed, privacy, full bathroom with roman bathtub, washer/dryer, full kitchen with all the utensils you will need, two flat screen tv's, fast free wifi, private balcony overlooking lush gardens with a fountain. The Laterra resort boasts a plethora of amenities right outside your doorstep. Heated pool, pool with waterfall feature, hot tub, tennis courts, award winning Golf and restaurants nearby!

4.87 out of 5 average rating, 183 reviews

A spacious wooden deck is illuminated by string lights, featuring a seating area with wicker furniture and a designated space for dancing. The tranquil river view and the sunset create a serene backdrop, with Spanish moss hanging from nearby oak trees.

Cabin in St. Augustine

ROMANTIC RIVERFRONT CABIN~ BRING BOAT ~ SLEEPS 2

Relax with your sweetheart while watching the fish jump from your own private deck. The cabin has been open for 3 years and has 92 reviews and has 4.89 STARS out of 5! "The View is absolutely beautiful, especially the sunsets! & You can see this amazing view right from the bed!" Alex April 2022/ We've replaced the microwave with an air fryer. Everything you need to have a wonderful vacation is right here! Including Breakfast foods!

Popular amenities for St. Augustine Holiday Accommodation with Breakfast

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with breakfast

A bright red single-story house is surrounded by trees, with large windows providing natural light. A covered porch with a white railing enhances the welcoming appearance. A spacious driveway leads to the entrance, facilitating easy access.

5 out of 5 average rating, 3 reviews

Havana Hideaway | Private Pool | Dedicated Office

A heated pool and spa are showcased within a screened lanai, surrounded by lush greenery and colorful plants. Sunlight reflects off the clear water, while a waterfall feature adds a tranquil touch. The outdoor space is designed for relaxation and enjoyment throughout the year.

5 out of 5 average rating, 62 reviews

Oasis! 1 Queen Suite (pvt bath, Heated Pool/Spa)

5 out of 5 average rating, 48 reviews

Home in Palm Coast

Luxury Palmasis Oasis - 1 Of a Kind Pool+Theatre

Home in Green Cove Springs

A welcoming living area is presented with two light blue sofas arranged around a wooden coffee table. A decorative plant sits at the center of the table, which is set on a patterned area rug. Soft natural light enters through sheer curtains, enhancing the cozy atmosphere.

4.93 out of 5 average rating, 40 reviews

NEW! LARGE 4BR home in Golf Community with POOL

4.97 out of 5 average rating, 38 reviews

A spacious outdoor area features a heated in-ground pool surrounded by a screened enclosure. Comfortable seating is arranged around a coffee table, with a modern fan mounted on the wood ceiling. An inviting hot tub is positioned next to the pool, enhancing the relaxation space.

Home in Palm Coast

Luxury 5-Bedroom Retreat with Pool

5 out of 5 average rating, 6 reviews

St Augustine’s Gem Modern Furnished New Home

Private room in Pomona Park

A serene sunset reflects off the calm surface of the lake, creating a warm golden hue. Silhouetted trees line the horizon, while subtle ripples disturb the water, enhancing the peaceful atmosphere of the natural setting.

5 out of 5 average rating, 17 reviews

Best Bass Fishing - Private Lake Como

The kitchen features wooden ceiling beams and a combination of white cabinetry and dark countertops. A central island with seating is highlighted, while modern appliances are neatly arranged. Natural light enters through multiple windows, enhancing the airy feel of the space.

4.65 out of 5 average rating, 37 reviews

Cozy Beach House Of Your Dreams

Apartment rentals with breakfast

Apartment in St. Augustine Beach

4.91 out of 5 average rating, 274 reviews

High Tide - breezes galore!

Apartment in St. Augustine Beach

A shaded outdoor area features a hammock with striped fabric, inviting relaxation. Stone pavers lead to a landscaped garden area with green foliage and seating. A patio setting is visible in the background, complete with table and chairs for outdoor dining.

4.88 out of 5 average rating, 283 reviews

Low Tide - Beach Bungalow

A cozy seating area features a plush armchair and a modern light fixture. Black French doors open to reveal a bright bedroom with a light-colored bed and decorative pillows. A bowl of oranges sits on a granite countertop, enhancing the inviting environment.

4.83 out of 5 average rating, 12 reviews

Downtown Apartment in the Middle of it All

A comfortable living area is displayed, featuring two patterned armchairs and a side table. Natural light fills the space from a window, complemented by a television mounted on the wall. A glimpse of the adjoining kitchen area with blue cabinets is visible in the background.

4.86 out of 5 average rating, 14 reviews

Ambrose's Retreat - Historic B&B Downtown

Apartment in St. Augustine

A cozy dining area is depicted with a round black table and two wooden chairs. A bottle of water rests on the table, while light enters through a glass door leading outside. The entrance to a bedroom is visible in the background.

4.96 out of 5 average rating, 199 reviews

Charming Sanchez 2 ~ 5min drive to downtown/Bikes

Bed and breakfast rentals with breakfast

A screened lanai features a spacious pool surrounded by colorful umbrellas and lounge chairs. Inflatable pool floats are seen in the water, while a shaded seating area provides a comfortable space for relaxation. Lush greenery is visible in the background.

4.92 out of 5 average rating, 350 reviews

Queen*Low cost*No shower*Pool*Hot Tub*Bkfst*1/2 ba

A themed room features a spacious bed with an ocean-inspired coverlet, complemented by two sets of bunk beds. A compass mural adorns one wall, and floral curtains frame a window. Soft lighting is provided by bedside lamps on either side of the bed.

4.86 out of 5 average rating, 51 reviews

King&3 bunks-Priv Bath, low cleaning fee

4.9 out of 5 average rating, 130 reviews

Chef Taylor's Zen Inspired Retreat (1 bedroom)

The exterior of a traditional Victorian inn is framed by tropical greenery and colorful flower beds. The inviting entrance features a spacious porch adorned with string lights, a sign indicating the property as a bed and breakfast, and steps leading to the entrance.

4.9 out of 5 average rating, 145 reviews

Downtown"Grace Darling"Old Powder House Inn-B'fast

An outdoor area features a solar-heated pool surrounded by a screen enclosure. Several colorful umbrellas provide shade over lounging chairs and a dining space. Pool floats and deck chairs are visible, creating an inviting atmosphere for relaxation and enjoyment.

4.92 out of 5 average rating, 358 reviews

King Bed*Heated Pool*Hot Tub*Brkfst*Joel and Kathy

A screened-in pool area features a variety of seating options, including colorful umbrellas and lounge chairs. Floating inflatables accompany the rounded pool, which is surrounded by greenery. Nearby, a hot tub is visible, adding to the relaxing atmosphere.