Vacation rentals with a pool in Anastasia Island

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.

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!

Downtown • Historic Whitney House • Luxury Baths!

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.

Sunset Cove 2 - Pool - Sea Views - Walkable

Stunning new luxury 2br/2.5ba pool home with peeks of Salt Run and Anastasia State Park: * Pool Heat Available for $30 per day - Contact us after booking for details * Private pool + backyard * Parking for 3 cars * 2 king bedrooms w/ en-suite bathrooms & smart TVs w/ Netflix * 2 min drive (or 20 minute walk) to historic downtown St. Augustine * 2 min drive to the beach (Anastasia State Park) * 5 min walk to lighthouse, Alligator farm, restaurants & bars * Fully stocked and equipped kitchen

Incredible Waterfront Townhome

As close to the water as you can get! Our building is considered the best in the complex which is waterfront, very private and peaceful. Perched on the Point we have fantastic views overlooking the intracoastal's oyster beds, mangroves, exotic birds, fish and bald eagles!. The sunsets are incredible. A fisherman's paradise. There is a private boat dock and a small boat ramp to launch your kayak. Watch dolphins put on a show almost daily from your lanai. The beach is right across the street!

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.

Windjammer 208, Oceanfront and Riverview

Beautiful newly renovated condo in Crescent Beach, with spectacular views of the beach as well as the Matanzas river. Coffee while watching sunrise on your east balcony and wine while watching the sunset on the Windjammer fishing pier, while dolphins are entertaining you. 10 miles from historic St Augustine, a couple of miles from Marine land and a variety of restaurants close by. Flatscreen TV'S in all the rooms for your convenience when the weather does not allow you on the beach.

Music on Marilyn- Steps from the Amp! •Jacuzzi•

Nights of Lights & mere seconds from the St. Augustine Amphitheater— a short bike ride to the beach and downtown, this modern escape is 3 beds and 2 baths. Welcome to Music on Marilyn! This is the quintessential St. Augustine experience. Nestled on a quiet street that dead ends to the intracoastal, walking distance to the St. Augustine Amphitheater, Lighthouse, Anastasia Park, Alligator Farm and much more! St. Augustine Beach and historic downtown are just a short bike ride away.

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**

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.

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.