
Holiday rentals with a pool in Anastasia Island
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Top-rated rentals with a pool in Anastasia Island
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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.

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!

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.

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

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.

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.

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.

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!

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.

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**

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!

Seaglass Villa, a Sunny Beachside Retreat
Paradise is found at Seaglass Villa! A perfect blend of relaxation and luxury where a short walk through the resort will lead you to white sand beaches. On arrival of our newly renovated two-story condo, you’ll be welcomed by a sparkling clean space, a calming color palette with all the comforts of home including a stocked kitchen, three bedrooms and two full bathrooms with two screened porches. Guests love the happy-go-lucky vibe of the condo and resort.
Popular amenities for Anastasia Island rentals with a pool
House rentals with a pool

Ocean Village Club-First Floor Access.

Heated Pool/Hot Tub 1 mile to dwntn/beach

Historic St. Augustine 2/2 Duplex & Pool

2023 Lux Home 4bd/3.5ba + SaltPool + HotTub + Walk2Beach

Htd Pool/Arcade, FirePit& PuttingGreen 1.2 mi DT

Free Heated Pool, Game Room, Spa, Sleeps 12

The Salty Seashell, Coastal Pool Home, Sleeps 8

Walk to Beach! Heated Pool•Boat Parking•EV Charger
Apartment rentals with a pool

Riverfront direct views-Get it ALL in St Augustine

BEAUTIFUL OCEAN VIEW 2 BEDROOM CONDO WITH POOL

Direct Oceanfront ~ Fantastic Views!

The Salty Suite Resort style condo

Oceanfront 1st Floor End Unit

Steps from the Beach 2 Bedroom 2 Bath Condo

Gorgeous Sea Place Ocean View Condo

Walk to Beach, Heated Pool, Pet Friendly!
Other holiday rentals with a pool

Sunset Palms - Waterfront/Heated Pool/Pet-Friendly

Beacher's Lodge Balcony Suite #316

Palma Beach House

Oceanfront, Pool, Tennis, BBQ, Patio, Free Parking

luxurious oceanfront condo amazing views! King bed

Beachfront St. Augustine Condo • Pool, Ocean Views

Affordable and Ocean View Condo! Steps from Pool!

Coastal Chic Condo!
Destinations to explore
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- Daytona International Speedway
- EverBank Stadium
- Daytona Boardwalk Amusements
- Summer Haven st. Augustine FL
- Lightner Museum
- St Augustine Amphitheatre
- Daytona Lagoon
- Fountain of Youth Archaeological Park
- Kathryn Abbey Hanna Park
- VyStar Veterans Memorial Arena
- Adventure Landing Jacksonville Beach
- Ocean Center
- Ravine Gardens State Park
- Saint Augustine Town Plan Historic District
- St Johns Town Center
- TPC Sawgrass
- Daytona Beach Bandshell
- University of North Florida
- St. Augustine Alligator Farm Zoological Park
- Embry Riddle Aeronautical University
- Anastasia State Park
- Ocean Walk Shops
- Memorial Park
- Vilano Beach Fishing Pier




