Holiday rentals with a pool in Anastasia Island

Guest suite in St. Augustine

A serene waterfront view is captured at sunset, showcasing a pool surrounded by lush grass and palm trees. A shaded seating area is positioned next to the pool, overlooking the water where boats can be seen in the distance.

4.93 out of 5 average rating, 666 reviews

Waterfront suite, Dogs are cool no pet fee

Newly remodeled, waterfront suite. See dolphins, Osprey, and more frolicking in our amazing backyard overlooking the Matanzas river, & did I mention the breathtaking sunsets. 6 minute drive to Crescent Beach, one of the most beautiful beaches in Florida. Close to downtown historic St Augustine 20 min, Amphitheater concert venue is 15 min. Private entrance, full on suite bath, fishing dock, kitchenette, pool, ample free parking & internet included. Professional pool cleaning is on Mondays.

4.99 out of 5 average rating, 437 reviews

The exterior of a single-story house is displayed, featuring a sloped roof and an inviting entryway. Green grass surrounds the home, complemented by mature trees and landscaped bushes. A concrete driveway leads up to the entrance, providing accessible access.

Home in St. Augustine

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!

4.94 out of 5 average rating, 217 reviews

The living room is furnished with two light-colored sofas and a central coffee table, creating a spacious and inviting space. A decorative fireplace is framed by mirrors and artwork, while natural light filters in through shuttered windows and greenery adds a touch of nature.

Home in St. Augustine

Historic Whitney House •Designer•Steps2Attractions

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.

A view framed by lush tropical plants reveals the expansive waterway, with its calm, reflective surface. The image captures a serene outdoor space, featuring stone flooring leading towards the grassy area and water, emphasizing the natural surroundings.

4.97 out of 5 average rating, 101 reviews

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!

4.91 out of 5 average rating, 117 reviews

A private balcony overlooks the beach with ocean waves gently lapping at the shore. Two lounge chairs are positioned on the balcony, creating a serene spot to enjoy the view. The sky displays a mix of blue with scattered clouds, adding to the coastal atmosphere.

Flat in St. Augustine

oceanview summer beach

Relax with the whole family at this peaceful beach place to stay. Four open heated swimming pools, tennis courts, pickball, basketball courts, kids playground make for a comfortable vacation home for the whole family. 24-hour gate provides you with a safe and comfortable living environment facing the sea and an unparalleled sunrise every day. If you've had enough of the sea, across the neighborhood is a national park. 15 minutes from the Saint Augustine, convenient transportation.（No pet）

4.87 out of 5 average rating, 222 reviews

An aerial view captures the vibrant pink A-Frame home against a backdrop of serene ocean waves and a clear sky. The surrounding palm trees and nearby beach create an inviting coastal atmosphere. The beach is easily accessible, with well-defined paths leading to the sandy shoreline.

Home in St. Augustine

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!

Superhost

Guest suite in St. Augustine

4.95 out of 5 average rating, 766 reviews

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.

A bright, enclosed balcony is depicted with a comfortable chair, a small table, and a decorative area rug. Large glass windows showcase expansive ocean views, while light wood paneling complements the aqua-tiled feature wall. Ocean breezes are welcomed through the open layout.

4.93 out of 5 average rating, 105 reviews

Newly Remodeled Ocean View Condo-Upgrades Galore!!

Welcome to the Newly Renovated Ocean View Antastasia Condo, relax and enjoy this bright and airy 5th floor condo with a gorgeous coastal theme. Wood ceilings, brand new kitchen w/stainless steel appliances & aqua tiled feature wall & more! Ceiling fans & flat screen TV's in every room. Features stunning, breathtaking Ocean views with an enclosed glass balcony that opens to enjoy the ocean breezes and to hear the ocean waves. Wake up to a beautiful sunrise with your morning coffee!

A vibrant sunset casts warm hues across the sky, with wispy clouds highlighted by the fading light. A palm tree stands prominently in the foreground, while a wooden boardwalk leads toward the beach and the ocean, framed by patches of greenery.

5 out of 5 average rating, 144 reviews

BEAUTIFUL OCEAN VIEW 2 BEDROOM CONDO WITH POOL

BEAUTIFUL OCEAN VIEW 2 BEDROOM CONDO JUST STEPS TO THE BEACH. COME AND STAY IN THIS RECENTLY REMODELED CONDO WITH PRIVATE TROPICAL COURTYARD, AND 2 OCEAN VIEW COURTYARDS OFF THE MASTER BEDROOM AND LIVING ROOM. WITH SO MUCH TO DO IN ST. AUGUSTINE, YOU CAN CHOOSE AN ADVENTUROUS, HISTORICAL, OR RELAXING VACATION TO MAKE YOUR BEST MEMORIES. THERE IS PLENTY OF SPACE IN THIS LARGE 1300 SQFT CONDO. THE BEACH IS VERY LARGE WITH LOTS OF PLAY SPACE AND CAN EVEN FEEL LIKE A PRIVATE BEACH.

4.79 out of 5 average rating, 111 reviews

A heated pool is positioned at the foreground, surrounded by a spacious deck featuring lounge chairs and outdoor tables. A grassy area is situated near the pool, while the condo units with balconies are visible in the background. Bright umbrellas provide shade for guests.

Flat in St. Augustine

Oceanfront Condo with Balcony!

Enjoy coffee or cocktails on the third-floor balcony overlooking the ocean! 1 bedroom (queen bed)/1 bathroom condo with direct beach access and a heated pool downstairs. Be on the beach in 4 minutes with your private boardwalk! Heated pool, outdoor showers for pets & people, bbqs near the pool, communal laundry, elevators & ice centers. Pet-friendly condo and leashed pets permitted on the beach. The condo is a 15-20 minute drive south of the St. Augustine downtown area.

Apartment in St. Augustine Beach

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.

4.95 out of 5 average rating, 176 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!

A comfortable living area is showcased with a light-colored sofa and armchair. Natural light flows in through sliding glass doors. A flat-screen TV is mounted on the wall, and a coffee table rests on a wooden floor, surrounded by decorative items.