Vacation rentals with a pool in Anastasia Island

The Beach Retreat!

Beautiful St. Augustine Beach is the most amazing hidden gem in northern Florida. Family and pet-friendly condo within walking distance to pristine white sand beaches, fishing pier, local shops and restaurants. The Beach Retreat is a 2 bedroom / 2 bathroom air-conditioned unit sleeps four guests comfortably. If you Walk into the inviting living room where you’ll find a classic surf board on the wall, tasteful ocean home decor, comfortable leather sofas and a 42-inch LCD Smart TV and Free WiFi

Shell Shack Resort - Beachside Condo

Beautifully decorated & upgraded beachside 2 bed/2bath ground floor unit with an assigned parking spot right next to your patio entrance. Natural light fills the condo. The patio gets plenty of sunshine from its southern exposure positioning so it offers a great place to enjoy your coffee in the morning, wine at night, or to catch up on your tan. The sunshade allows for a private outdoor experience when you just want to sit quietly alone listening to the ocean waves crashing along the beach.

Historic Designer Home • Luxury Baths • Steps2DWTN

Off Street Parking for 2 vehicles 2 Min. walk to St George St 5 Min drive to Anastasia State Park Beach 6 Min drive to Fitness Club/Pool High Speed Starlink Internet Luxury Retreat in Historic Downtown. Indulge in a charming vacation rental featuring a spacious living room, gourmet kitchen, and luxury baths. Immerse yourself in the rich history and vibrant culture, with its charming streets and local attractions. Whether seeking adventure or relaxation, this retreat offers the perfect base.

Oceanside complex M33 1 Bed 1 Bath w/Heated Pool

1 bedroom condo with King Size Bed, Sleeper Sofa, 55" TV's in Living Room and Bedroom. Stairs to 3rd Floor unit with private patio. Fully Equipped Kitchen, Dishwasher, Washer/Dryer, WiFi, Cable TV, Clubhouse, Fitness Room, Tennis Courts, 2 Swimming Pools (1 heated), Shuffleboard Courts, Picnic Area with Grills & Private Beach Walkway about 5-10 minute walk to the beach and pools . Dog Friendly (1 DOG ONLY) with a $100 pet fee due on Check In. Must be able to climb stairs 3rd floor condo

Sun & Sea - Beach & Heated Pool, Pet Friendly!

Indulge in the comfort and style of this spacious one-bedroom king bedroom couple's retreat. Situated on the ground floor, this end unit is conveniently located within walking distance of restaurants and shops. This oceanfront complex offers top notch amenities, including a beach walkover, two pools (one heated), tennis courts, shuffleboard, a well-equipped gym, and a grill area, all within a secure gated community. Enjoy coastal proximity, with downtown St. Augustine only 10 minutes away.

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. Aug Oceanfront Home w/ Heated Pool & Firepit

Just steps from the ocean and a 10-minute drive to historic downtown St. Augustine, this one-of-a-kind 1970s pink three-story A-frame is the perfect backdrop for your next vacation, bachelorette party, or relaxing getaway. Inside, you’ll find a bright, cheerful space—ideal for popping mimosas in the morning or unwinding after a sun-soaked day with private beach access. Whether you're staying for the weekend or the season, you're sure to make lasting memories. I can’t wait to host you!

Sheepdog Hideway - on Anastasia Island near Amp!

Awesome, private guest suite located on Anastasia Island near the St Augustine Amphitheater! Walking distance to Anastasia State Park! Enjoy staying on the island without all the hustle of a hotel. We have beach cruiser bikes available for use! We are 1.5 miles from the closest public beach access and a 3 mile bike ride to downtown St Augustine! Update for COVID-19 pandemic: We will be spraying all hard surfaces with EPA-approved sanitizer to do our best to make sure surfaces are safe.

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**

Sunrise Special | Steps to Beach | Ocean Front

Our OCEAN FRONT condo is just a short boardwalk to miles of beautiful beaches. Updated, modern, comfy living in this 2 bedroom condo w a balcony that allows generous views of the ocean! Features 2 pools (1 heated), 5 hot tubs, tennis courts, a pickle ball court, and bocci. Just 10 mins from the fabulous Old Town Historic District. Enjoy a spectacular sunrise with your morning coffee. Relax with the whole family at this peaceful place to stay. Must be 23 to rent.

34|Ocean at St Augustine Beach

34|Ocean offers a luxurious seaside escape in St. Augustine Beach. Only 1 1/2 blocks from the public beach access and within a few minutes walk to the best restaurants and bars in St. Augustine Beach, the free splash park, and St. Augustine Pier, you’ll love the location of this condo and the laid-back, beachy environment. Completely gutted and renovated, we hope you will fall in love with the amenities of this spotless, clean condo!

Beautiful Ocean Side2/2.5 Condo with Pool

Sparkling New Beach Side Condo In the Heart Of St. Augustine Beach, Completely Updated 70" TV's In Living Room and Master Bedroom, 2nd Bedroom has 65" TV Fully Stocked Kitchen, 2 Parking Spaces, Walk to all the beach side restaurants with out having to drive. The Ocean is just a few steps away, there is a small ocean view from the patio. Historic Downtown is just a few miles away to explore all the rich history this town has to offer