Holiday rentals with a pool in Anastasia Island

Apartment in St. Augustine Beach

A private balcony offers unobstructed views of the ocean and nearby sandy beach. Two white bar-style chairs are positioned at a small table, inviting relaxation while enjoying the scenery. Lush greenery can be seen in the foreground, complementing the coastal setting.

5 out of 5 average rating, 149 reviews

Ocean Front Escape- Top Floor

Top floor, direct oceanfront 2 bedroom, 2 bathroom condo with elevator and unobstructed beach views from the private balcony, master bedroom, living room, dining room and kitchen. Located in beautiful St. Augustine Ocean & Racquet Resort. We also rent out the corner unit immediately next door, Ocean Front Gem, which is great for those traveling with friends: https://www.airbnb.com/h/saint-augustine-oceanfrontgem Our checkin and checkout process are contact free. We use a Nest lock on the door.

4.99 out of 5 average rating, 435 reviews

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.

Home in St. Augustine

Your Home Away From Home

1,800 SF, 2 bedrooms, 2 1/2 bathrooms, on a secluded 5 acre lot just minutes from Historic Downtown and St. Augustine Beach. The home is 100% HANDICAPPED ACCESSIBLE! Convenient shopping and close by restaurants. Full kitchen, spacious living area, large bedrooms (1 with TWINKLE mattress) ceiling fans. Pet friendly! (Some restrictions apply, advance notice required!) Base rate covers up to 4 guests and there's a small upcharge for 5 or more. Motorcycle friendly! We also do live on the property!

An open living area features a light-toned laminate floor and a spacious dark sofa facing a wall-mounted TV. A white coffee table sits in front of the sofa, while two wooden stools are positioned nearby. The kitchen is visible in the background, with natural light coming through the window.

4.86 out of 5 average rating, 286 reviews

Oceanside complex B17 1 Bed 1 Bath w/Heated Pool

1 Bedroom interior Condo in Oceanfront Complex (no view of the ocean) King Bed, Queen Sleeper Sofa, TV's in Living Room and Bedroom, 1st Floor unit with screened patio, Fully Equipped Kitchen, Dishwasher, Washer/Dryer, WiFi, Cable TV, Clubhouse, Fitness Room, Tennis Courts, 2 Swimming Pools (1 heated) Shuffleboard Courts, Picnic Area & Private Beach Walkway. Dog Friendly (1 DOG ONLY) with a $100 pet fee due on Check In. Restricted Breeds: Rottweiler, Pit bull, Doberman, Chow, German Shepherd.

4.92 out of 5 average rating, 153 reviews

2 King Beds - Walk to Beach

Experience the ultimate getaway at our charming beach retreat, just a short stroll to the beach. Perfect for families, friends, or couples looking to relax and unwind, the perfect blend of comfort and convenience Enjoy a restful night's sleep in two luxurious king-size beds, designed for comfort and relaxation Stay connected with fast, reliable Wi-Fi throughout the property, ensuring you never miss a beat Enjoy the convenience of instant hot water, you never have to worry about running out

Guest house in St. Augustine

A tranquil outdoor space features a well-maintained heated pool surrounded by lush greenery and colorful flowers. Seating areas with black Adirondack chairs are positioned around the pool, offering a peaceful setting. A covered patio stands in the background, complementing the inviting atmosphere.

4.95 out of 5 average rating, 193 reviews

Heated Pool Beach Bungalow Steps to the Ocean

Beautiful brand new in 2022 en-suite Bungalow beach side! Perfect for a romantic get a way or just one person, just 600 steps to the beach. Five minutes to the St Augustine pier and 10 minutes to the oldest city in the US, Historic Downtown St Augustine. Not only do you have the most comfortable bed to fall into, a 50" TV, recliners and an amazing heated pool. Beautiful beach sunrises, fishing, hiking, Concerts at the Amphitheater. For your safety you have an electronic keyless entry.

Townhouse in St. Augustine

The entrance to St. Augustine Beach and Tennis Resort is showcased, featuring a prominent sign with the resort's name. Lush greenery surrounds the gated entrance, providing a welcoming and shaded look. The paved road leads into the community, flanked by well-maintained landscaping.

4.89 out of 5 average rating, 279 reviews

St. Augustine Beach - A Townhouse Oasis!

Guests will discover a warm, inviting townhouse that aims to meet the needs of your vacation getaway. See for yourself why many of the same families rent this townhouse year after year for its quality and value. As hosts, we maintain and provide an up to date, comfortable, and convenient location to all the sites in the greater St. Augustine area; including a convenient 5-6 minute walk to the beach. ALSO, IF YOU LIKE YOUR PRIVACY you will enjoy our screened-in roof-covered lanai.

A light and airy living area features a comfortable gray sofa, a wooden coffee table, and a blue accent chair. A large flat-screen television is mounted on the wall opposite, while sliding glass doors provide access to a balcony area with outdoor seating.

4.97 out of 5 average rating, 187 reviews

Beach Condo, Pools, Bikes, Short Walk to Beach

Relax and unwind at our beautiful beach getaway. This one bedroom condo is located close to all St. Augustine has to offer. You can walk to the beach or take a quick drive to historic downtown. Ocean Village Club is a gated complex that has private beach access just a seven minute walk from your door, two swimming pools, tennis courts, grilling area, and free parking. This second floor unit is light and airy, immaculate, and beautifully decorated. We are family owned and operated.

Apartment 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, 172 reviews

Newly renovated! Steps to BEACH & POOL!

Our little slice of paradise is situated in the heart of St. Augustine Beach right on A1A Beach Blvd. Our unit, recently renovated, is just steps from the beach and closest building to the pool! 2 outdoor pools (1 heated in winter), 5 hot tubs & tennis courts. Perfect location to enjoy our beautiful beaches & all that Anastasia Island has to offer! Historic St. Augustine is less than 7 miles away. Unit is equipped with everything you need for a perfect beach vacation!

4.92 out of 5 average rating, 206 reviews

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.

Flat in St. Augustine

Beach Life in Oceanview Condo

The balcony faces one of Florida's most beautiful beaches - Crescent Beach. Just 3 minutes walk from the beach, enjoy incredible sunrises and sunsets every day, heated pool, outdoor barbecue, free parking available. 15 minutes from downtown St. Augustine, surrounded by all the amenities, start your holiday on this beautiful, ancient beach. We offer short term and long term rentals hoping to provide you and your family with a relaxing, comfortable and quiet holiday resort.

A comfortable living area is showcased with a light-colored sofa and armchair. Natural light flows in through sliding glass doors. A flat-screen TV is mounted on the wall, and a coffee table rests on a wooden floor, surrounded by decorative items.

4.94 out of 5 average rating, 155 reviews

Beautiful ocean, St Augustine beach

Close to shopping and restaurants. 15 min drive to historic downtown. Perfect for families, couples, friends, or solo travelers. Enjoy having no stairs to climb! Family friendly vacation. New king bed. Fully equipped kitchen, free WiFi, 2 pools (one heated), full size washer/dryer in unit, Smart TV, pet friendly 1 Dog Only, requires $50 (cash) registration fee upon check in. There is also a flat $15 Pet Fee for guests bringing a dog. **Strictly NON-SMOKING unit**

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, 130 reviews

Family Beach Condo - Steps To The Sand Or Pool

Our beach condo on Crescent Beach has been our family’s haven for years, and we’re excited to share it with you! The breathtaking ocean views from our living room and balcony are just the start—enjoy a renovated kitchen, comfy bedrooms, and family-friendly touches that make this place truly special. Whether you’re here to relax, explore historic St. Augustine, or enjoy the natural beauty of Anastasia State Park, we hope you’ll create lasting memories like we have!

A bright living room features an open layout illuminated by natural light. Neutral-toned furniture is paired with colorful accent pillows. A natural jute rug lies beneath a low coffee table, while a ceiling fan enhances airflow. Large glass doors open to an outdoor area.