Holiday rentals with a pool in Anastasia Island

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Top-rated rentals with a pool in Anastasia Island

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Guest favourite
A private balcony features two light-colored chairs and a round table, providing views of the ocean and a nearby pool. The scenery includes lush greenery and a clear sky, while birds can be seen flying in the distance.
Apartment in St. Augustine
4.85 out of 5 average rating, 286 reviews

Direct Oceanfront ~ Fantastic Views!

Only 50 steps to the ocean, with the pool in between! Unit 202 at Beacher’s Lodge Condos offers stunning ocean views and overlooks a heated Olympic-sized pool. This modern one-bedroom, one-bathroom condo, with a king-size bed and sofa sleeper, has a fantastic view from the living room, kitchen, and private balcony. Its conveniently located near the beach, oceanfront pool, and local amenities, including restaurants and a convenience store. Free dedicated Wi-Fi is also available during your stay.

Top guest favourite
An expansive backyard features a refreshing saltwater pool and a hot tub, surrounded by lush turf landscaping. A two-story building with a wooden staircase overlooks the serene outdoor space, framed by palm trees and vibrant plants. Lounge chairs are positioned nearby for relaxation.
Home in St. Augustine
4.98 out of 5 average rating, 117 reviews

Driftmark Cabin - RV friendly, Pool + Beach!

Experience the ultimate beachside getaway at our fully renovated Airbnb, just steps away from the sun-kissed sands. This luxurious retreat offers modern comfort with a private pool and inviting hot tub, allowing you to unwind in style. The recently upgraded interior boasts premium amenities, ensuring a relaxing stay. Outside, lush turf landscaping surrounds the pool, creating an oasis of comfort. Whether you're lounging by the pool, or enjoying the beach a stone's throw away, Driftmark delivers.

Top guest favourite
A vibrant swimming pool reflects the evening sky, surrounded by well-maintained landscaping. Poolside seating includes colorful lounge chairs and a dining set, while a floating flamingo adds a playful touch. Soft lighting from string lights enhances the serene atmosphere as dusk approaches.
Home in St. Augustine
4.99 out of 5 average rating, 105 reviews

Designer•As Seen on HGTV•Pool•Luxury Kitchen&Baths

No Cleaning Fee! 3 Min Drive/ 15 Min Walk to Historic Downtown 2 Min Drive to the St Augustine Amphitheater 2 Min Drive to the Anastasia State Park Beach 1 Min. Drive to Anastasia Fitness Club/Suana-Steam Rm/Pool. Looking to get away from the hustle & bustle of the city? This designer home with an amazing pool is the perfect place to recharge. Downtown & the scenic beaches in Anastasia State Park are just a minutes away. With spacious living & modern amenities, the Home offers maximum comfort

Guest favourite
An expansive view of a serene beach is captured, featuring soft sand and gently lapping waves. Sparse vehicles are seen along the shoreline, with stretches of greenery and dunes adding texture to the landscape. The horizon showcases a clear blue sky, merging with the ocean.
Apartment in St. Augustine
4.91 out of 5 average rating, 217 reviews

St Augustine Beach, comfy condo

Relax on the beach or unwind at the pools. Close to shopping and restaurants. 15 min drive to historic downtown. Perfect for families, couples, friends, solo travelers. You're an 8 minute walk on property to beach with beach chairs, umbrella, and a beach mat. Fully equipped kitchen, free WiFi, 2 pools (one heated), fitness room, full size washer/dryer in unit, Smart TV, pet friendly 1 Dog Only, $50 cash reg fee plus a flat $15 Pet Fee for those bringing a dog **Strictly NON-SMOKING**

Top guest favourite
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.
Apartment in St. Augustine
4.98 out of 5 average rating, 107 reviews

Family Beach Condo - Steps To The Sand Or Pool

Please note: The "20 min walk to the beach" shown above in the listing is some AI generated nonsense from AirBNB and incorrect—our condo is right on Crescent Beach! Our beach condo has been our family’s haven for years, and we’re excited to share it with you! Enjoy stunning ocean views, a renovated kitchen, comfy bedrooms, and family-friendly touches. Whether you’re relaxing, exploring St. Augustine, or enjoying Anastasia State Park, we hope you’ll create lasting memories, just like we have!

Top guest favourite
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.
Cottage in St. Augustine
4.98 out of 5 average rating, 188 reviews

Fun Waterfront Retreat, Heated Pool, Rooftop Deck

You've found your waterfront oasis tucked under the White Birds of Paradise! This spacious retreat was formerly a commercial art gallery. Two queen beds, one full bathroom & full kitchen make for comfortable living! You have a fenced path leading you down to the beautiful waters of Salt Run where a rooftop deck & salt water in-ground pool invites you to relax and slow down. Less than a mile to downtown St. Augustine, a little over a mile to the Amphitheater and about 3 miles to the beach.

Top guest favourite
A balcony table is set for two, featuring white plates and cups, with expansive ocean views. Lush greenery and sandy beach can be seen in the distance under a clear blue sky, creating a serene and inviting outdoor space.
Apartment in St. Augustine Beach
4.97 out of 5 average rating, 233 reviews

Ocean Front Gem: Top Floor Corner Unit

Top floor, direct ocean front, corner unit with elevator and beautiful unobstructed views of the beach from both bedrooms, living room, dining room, kitchen and private balcony. We have upgraded the condo and believe it to be the best condo in St Augustine Ocean and Racquet Resort. We also offer the condo immediately next door for rent, Ocean Front Escape: https://www.airbnb.com/h/saint-augustine-oceanfrontescape. Our checkin process is contact free. We use a Nest lock on the front door.

Top guest favourite
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.
Guest house in St. Augustine
4.94 out of 5 average rating, 175 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.

Top guest favourite
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.
Apartment in St. Augustine
4.98 out of 5 average rating, 170 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.

Top guest favourite
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.
Apartment in St. Augustine Beach
4.95 out of 5 average rating, 152 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!

Guest favourite
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
4.93 out of 5 average rating, 175 reviews

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.

Top guest favourite
Lush greenery frames a wooden pathway leading to a sandy beach, with palm trees and residential buildings visible in the background. The sky is illuminated by soft hues of sunset, creating a serene backdrop for the coastal environment.
Apartment in St. Augustine
5 out of 5 average rating, 109 reviews

Boutique Beachside condo with easy access to beach

Skipper’s Hideaway is a charming beachside retreat that sleeps up to six, with a king bed, queen sofa pull-out, and twin daybed with trundle. Located on the ground floor for easy access, the condo offers a partial Atlantic Ocean view from the living room window. Just steps from Crescent Beach, this peaceful spot is perfect for relaxing. For more excitement, the shops, restaurants, and nightlife of downtown St. Augustine are only a 15-minute drive away.

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