Holiday 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.

St.Augustine Beach,Seaside at Anastasia,Condo

Seaside at Anastasia is directly across the street from the ocean, St. Johns pier, weekly farmers market, walk to great restaurants. Just minutes away from historical downtown Saint Augustine. Enjoy our heated pool and exercise room. This condo is a 3 bedroom, 2 bath, laundry room, full upgraded kitchen and patio with access to pool. No stairs to worry about. 1st floor Condo with parking directly in front of the unit. Handicapped parking and access to the unit is also in front of this condo.

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

2 Bedroom, Private Hot Tub, walk to Loins Bridge

Couples Retreat Near Downtown St. Augustine. 0.5 miles from the Bridge of Lions. Enjoy a secluded courtyard, relaxing water fountain, and new 4-person hot tub. Wine down and watch the sunset in a peaceful setting after a exploring. Off-street parking is included. Restaurants, bars, coffee shops, and local favorites are only steps away. Perfect for a romantic getaway, weekend escape, or special occasion. Special requests and accommodations are available to help make your stay unforgettable.

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.

Downtown • Parking for 2 + Wraparound Porch

Historic Whitney House • Newly renovated 1,700 sq ft designer home Private driveway parking for 2 • Steps to trolley & St. George Street Gourmet kitchen, 2 en-suite bedrooms, 3 luxury baths, Starlink WiFi, wrap-around porch + sunny deck. Fitness club & pool passes included. Modern luxury in the heart of historic downtown St. Augustine. Perfect for couples or small groups seeking modern luxury, easy parking, and a walkable base right in the heart of historic downtown St. Augustine.

Great 1 bedroom 1 bath condo with heated pool

Great condo in an Oceanside community You cannot see the ocean from this condo 5-10 minute walk to the beach Private boardwalk to the beach Condo is in 3rd floor must climb stairs no elevator **** Tennis courts 2 pools 1 heated Shuffle Board Gym Restaurants and bars you can walk to Pet Friendly with a $100 pet fee Only 1 dog is allowed and we must register the dog before you check in The security will not let you on the premises if the dog has not been registered Pull out couch

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**

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.

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.