Holiday rentals with breakfast in St. Augustine

A heated private pool is surrounded by tropical murals and palm trees. Lounge chairs are positioned under an umbrella, while a cozy seating area with a hanging chair offers a perfect spot for relaxation. The vibrant colors of the sunset create a serene ambiance.

5 out of 5 average rating, 72 reviews

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

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.

4.96 out of 5 average rating, 25 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.

4.98 out of 5 average rating, 48 reviews

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, 29 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 St. Augustine

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, 279 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

Flat 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

LowTide part of Sage Tides Triplex - East of A1A beach Blvd , ground floor, old-Florida (build in 1923!) pet-friendly 2 bedroom, cozy unit (900 sf) with a private yard & patio/garden living space & two hammocks. Located on a dead-end street easy walk (2 houses away) to the beach. Yes, old Tile floors, some with cracks but cool for your feet or pets & easy to sweep. Sleeps 2 comfortably, 3-4 tight . There is one full bath (shower only) new in 2022 and the kitchen is fully equipped.

Guest suite in St. Augustine

A small wooden deck is shown with a railing and steps leading up to a white door. A single outdoor chair is positioned beside the door, and a welcome mat is placed at the entrance. Surrounding greenery adds a natural touch to the exterior.

4.83 out of 5 average rating, 245 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, 73 reviews

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

An outdoor space is enclosed with a screened patio, featuring a clear blue heated pool surrounded by lounge chairs. The home is visible in the background, showcasing large windows that provide natural light to the interior.

4.97 out of 5 average rating, 32 reviews

Luxury 5-Bedroom Retreat with Pool

Step Inside a Stunning Vacation Retreat. - Beautifully renovated 5-bedroom, 3-bathroom home. - Luxurious finishes and thoughtful details create a welcoming atmosphere. - Large heated in-ground pool and separate heated spa. - Cozy family room with a 75" Smart TV and electric fireplace. - Game room with pool, foosball, and tennis tables. - Outdoor area with seating for 10, fire pit, and landscaped yard. - Conveniently located near biking trails and stunning beaches.

Apartment in St. Augustine

A swimming pool is centrally located, featuring a fountain with surrounding seating areas. Lush green palm trees provide shade, while manicured grass lawns frame the patio. The inviting pool area is designed for relaxation, with sun loungers positioned around the water.

4.97 out of 5 average rating, 102 reviews

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, 180 reviews

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!

The welcoming front porch features two rocking chairs, softly illuminated by hanging lights. A fenced yard surrounds the home, while vibrant greenery offers a pleasant view. The house is newly built with a bright exterior, inviting a sense of comfort and relaxation.

4.98 out of 5 average rating, 93 reviews

Family & Group Coastal Cottage on a quiet street

Family Amenity tailored experience on a quiet street with a comfortable front porch and back deck relaxing setting and only minutes to most major attractions! Only 7 minutes drive to downtown St. Augustine and minutes to the beach. - New home built in 2023, all new appliances and fresh interior - Corn Hole Set - Back porch string lights - 55 inch Smart TV - King Bed, Queen Bed, and 2 Twin Beds

Popular amenities for rentals with breakfast in St. Augustine

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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.

Havana Hideaway | Private Pool | Dedicated Office

A bright and inviting living area features a ceiling fan and a large flat-screen television mounted above a modern fireplace. Two comfortable chairs and a neutral-toned sofa are arranged around a wooden coffee table, set on a light-colored area rug with subtle stripes.

4.84 out of 5 average rating, 49 reviews

Beach House w/hot tub &firepit-1 block from beach!

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, 54 reviews

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

5 out of 5 average rating, 48 reviews

Luxury Palmasis Oasis - 1 Of a Kind Pool+Theatre

The exterior features a welcoming front porch with two blue chairs, surrounded by landscaped greenery. A cheerful sign is positioned near flower decorations, adding a touch of color. The entrance is framed by light gray siding and complemented by a bright green door.

Beautiful Home All to Yourself!

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.

4.92 out of 5 average rating, 38 reviews

NEW! LARGE 4BR home in Golf Community with POOL

Home in Ponte Vedra Beach

A well-lit bedroom is equipped with a spacious bed adorned with soft linens. Large windows offer a direct view of the ocean waves and sandy beach. A cozy seating area is visible on the deck outside, enhancing the room's peaceful ambiance.

5 out of 5 average rating, 43 reviews

Chic Private Beachfront Escape - 11 Steps to Sand

5 out of 5 average rating, 4 reviews

St Augustine’s Gem Modern Furnished New Home

Apartment rentals with breakfast

Flat in St. Augustine Beach

4.88 out of 5 average rating, 283 reviews

Low Tide - Beach Bungalow

Flat 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, 273 reviews

High Tide - breezes galore!

Superhost

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

Superhost

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

4.96 out of 5 average rating, 197 reviews

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.

Flat in St. Augustine

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, 349 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, 50 reviews

King&3 bunks-Priv Bath, low cleaning fee

Hotel room in St. Augustine

A charming two-story building is framed by tall palm trees adorned with lights. The exterior features two levels of covered porches with white railings, with warm light glowing from the windows. American and Florida state flags are displayed, contributing to the welcoming appearance.

4.88 out of 5 average rating, 8 reviews

Vintage 1920's Inn! 100 Steps to St. George Street! The "Magnolia" room has a king bed private bath with shower and features easy access to our lovely rear porch with serene courtyard views!

Superhost

5 out of 5 average rating, 9 reviews

Lookout Suite at Vilano Beach

4.9 out of 5 average rating, 128 reviews

Chef Taylor's Zen Inspired Retreat (1 bedroom)

The exterior of a traditional Victorian house is displayed, featuring large windows framed in burgundy. Lush greenery surrounds the entrance, complemented by potted plants and a well-maintained walkway. The structure's architectural details are highlighted by the wraparound porch and second-floor balcony.

4.9 out of 5 average rating, 144 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, 357 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.