Holiday rentals with breakfast in Anastasia Island

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.

5 out of 5 average rating, 69 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

Home in Ponte Vedra Beach

A spacious deck features two yoga mats positioned for relaxation, with fresh towels and bottled water placed on each mat. Hammocks are visible in the background, alongside a bench, while the serene oceanfront stretches beyond, showcasing golden sand and gentle waves under bright blue skies.

5 out of 5 average rating, 43 reviews

Beachfront Private HOME 11 steps to sand! BIG LOT

⭐️Serenity Shores is FIVE STAR, GUEST FAVORITE beachfront home! Reconnect and rest at DIRECT beachfront home in prestigious PV Beach, miles from public access, just steps to sand🤩Hospitality is our passion! FREE welcome gift, breakfast starters, waters! Relax to soothing waves in hammocks close to spas, golf, Guana Park, museums, dining, St. Augustine & TPC golf. Get FLEX bedrooms-with 2 weeks notice. FAST WiFi & workspace, FREE parking & amenities, HUGE deck & beach supplies! coffee/tea bar🐬

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.

5 out of 5 average rating, 24 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.

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.

4.98 out of 5 average rating, 46 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

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.

4.78 out of 5 average rating, 27 reviews

Little Castillo on Prince Road

Relax and enjoy Little Castillo, my 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 is receiving baby-proofing . From Carrera marble in the foyer to spa like bathrooms and 7 chandeliers, you are welcomed. Brand new water filtration (‘24) and living room furniture (‘25) because we listen to you, our guests. So…Relax. Enjoy. Be well. Mi casa es su casa.

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, 278 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.

Townhouse in St. Augustine Beach

4.84 out of 5 average rating, 51 reviews

seawinds

"Beautifully newly decorated & upgraded beachside 2 bedrooms 2.5bath townhouse/condo with a garage . 5 min from ocean,pool ,jakuzzi. very quiet,relaxing.beach towels &items provided. best beach in Florida. Ancient city, many trails and things to do. across is supermarket. Lenai overlooks great place for morning coffee or discussions. Ancient city provides restaurants, and view of 17th century. 10 min to path leading to S Aug. park and jungle path leading to 17th century quarry.

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.

4.83 out of 5 average rating, 244 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, 27 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. The Oceanview Cottage is part of the Bayfront Marin House range of lodging options.

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.

4.96 out of 5 average rating, 28 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.

A modern home with a light exterior and a metal roof is featured. A front porch with wooden rocking chairs provides a welcoming touch. The driveway is spacious, leading to a fenced yard with greenery visible around the property.

4.98 out of 5 average rating, 91 reviews

Coastal St. Augustine Retreat, Quiet Neighborhood

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 Anastasia Island

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 spacious pool area is enclosed by a screened lanai, featuring a large in-ground pool surrounded by patio pavers. Sun loungers are positioned nearby, with a view of the lush green landscaping and trees beyond the pool area.

4.86 out of 5 average rating, 14 reviews

Canal Front Pool Home in Palm Coast

Private room in Palm Coast

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, 47 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!

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.

5 out of 5 average rating, 72 reviews

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

New place to stay

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, 272 reviews

High Tide - breezes galore!

Private room in St. Augustine

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

Private room in St. Augustine

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, 196 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

Private room in Palm Coast

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, 347 reviews

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

Private room in St. Augustine

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 light-filled room features a king bed with colorful decorative pillows. A small wooden desk and two black chairs are present, alongside bedside tables with lamps. A large mirror adorns the wall, while natural light enters through a window dressed with blue curtains.

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!