Vacation rentals in Anastasia Island

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Top-rated vacation rentals in Anastasia Island

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Top guest favorite
A well-maintained landscape showcases vibrant green grass and neatly trimmed shrubs, with palm trees lining the pathway. An expansive view of the ocean is visible in the background, framed by a boardwalk leading to the beach. Two residential buildings are seen in the scene.
Condo in St. Augustine
4.99 out of 5 average rating, 190 reviews

SeaPlace, Ocean View, Poolside 2/3 Walk to Beach

Beautiful St. Augustine Beach ocean and pool views from this 2/2.5 townhouse style condo, just steps to the beach. Come enjoy everything this vibrant city has to offer. 2 quiet bedrooms and bathrooms upstairs. 2 private balconies. Downstairs is a full kitchen, dining area for 6 (or well lit workspace), half bathroom, living area w/ new 65" TV, 10 minutes from historic downtown. Family friendly resort community w/ pools, tennis, pickleball and bocce’ ball courts. Beach chairs & towels provided.

Top guest favorite
A private balcony offers unobstructed views of the ocean and nearby sandy beach. Two white bar-style chairs are positioned at a small table, inviting relaxation while enjoying the scenery. Lush greenery can be seen in the foreground, complementing the coastal setting.
Condo in St. Augustine Beach
5 out of 5 average rating, 150 reviews

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.

Top guest favorite
A compact kitchen area features wooden shelving displaying various ceramic bowls, pots, and decorative items. The full-size stove is positioned under a light fixture, with a dark sink and wooden countertop enhancing functionality. Artwork and plants add touches of decor above the counter.
Guesthouse in St. Augustine
4.89 out of 5 average rating, 314 reviews

Tiny House three blocks from beach!

The tiny house at the Crescent Beach house is a one bedroom one bath detached guesthouse ! The bedroom includes a queen bed and closet. There is a great kitchen with a full size stove/oven, keurig, and microwave. Wifi and large smart tv for own subscriptions, no cable. Beach chairs, towels, and umbrella included! Soak in the great Florida beach lifestyle. There’s a board walk beach access at the end of the street ! This tiny house is adjacent to a two story home which is a separate Airbnb!

Top guest favorite
A living room area is presented with a comfortable gray sofa, accent pillows, and a wooden coffee table. Light-colored side tables with lamps complement the arrangement. A decorative rug adds warmth to the space, while a serene wall art piece depicts a coastal scene.
Condo in St. Augustine
4.99 out of 5 average rating, 108 reviews

Beach Therapy - 2 Bdrm Condo, 3 Min Walk to Beach!

Our freshly renovated two-bedroom, two-bath Oceanside condominium is perfect for your next getaway. Only 50 yards away from direct access to beautiful and peaceful Crescent Beach--go from door to shore in just three minutes! Enjoy your morning coffee (or happy hour cocktail) in the screened patio overlooking the swimming pool. A short 15-minute drive to downtown St. Augustine and all it has to offer. Don’t miss the holiday season “Nights of Lights” which runs from November 18-January 31.

Top guest favorite
A cozy living room is shown, featuring a spacious light-colored sofa and a patterned accent chair. A television is placed on a white media console. Large sliding glass doors open to a view of the exterior landscape, allowing natural light to brighten the space.
Townhouse in St. Augustine
4.97 out of 5 average rating, 122 reviews

Affordable and Ocean View Condo! Steps from Pool!

Creston House 8B is a perfect getaway location, quaint, and well maintained. It is a private apartment, including roomy living room with queen sleeper sofa, and dining room. Fully equipped kitchen is adjacent, and desk area for your computer. The bedroom includes a comfy king size bed, and 32' TV. All linens are provided. The resort is an oceanfront complex with a large pool and private beach access. Enjoy time relaxing on porch area, just steps from the large pool. Just unpack and enjoy!

Top guest favorite
A spacious bedroom is furnished with a king bed, complemented by decorative pillows and a throw blanket. A large area rug with colorful patterns covers the tiled floor. Natural light enters through two windows, framed by light curtains, while a bedside lamp adds soft illumination.
Guest suite in St. Augustine
4.95 out of 5 average rating, 755 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.

Top guest favorite
A wooden walkway leads from a grassy area to the sandy beach, flanked by two benches on either side. The beach is visible in the distance, with gentle waves and a clear blue sky above.
Home in St. Augustine
4.97 out of 5 average rating, 290 reviews

St Augustine Beachside Home - Walk to Beach

Time to Relax at our St Augustine canal front getaway! Great family destination just 15 min. to Historic Downtown St Augustine. Neighborhood features PRIVATE Beach Access with a less than 10 minute . walk, depending on pace, to the Beach. Boating and Fishing at your Fingertips with private, over-the-water dock and ramp to floating dock where you can tie up your own boat/kayak/jet skis. The perfect end to your beachside dream day will be watching the sunset while on your private dock.

Top guest favorite
A shaded outdoor area features a hammock with striped fabric, inviting relaxation. Stone pavers lead to a landscaped garden area with green foliage and seating. A patio setting is visible in the background, complete with table and chairs for outdoor dining.
Apartment in St. Augustine Beach
4.88 out of 5 average rating, 283 reviews

Low Tide - Beach Bungalow

LowTide part of Sage Tides Triplex - East of A1A beach Blvd , ground floor, old-Florida (build in 1923!) pet-friendly 2 bedroom, cozy unit (900 sf) with a private yard & patio/garden living space & two hammocks. Located on a dead-end street easy walk (2 houses away) to the beach. Yes, old Tile floors, some with cracks but cool for your feet or pets & easy to sweep. Sleeps 2 comfortably, 3-4 tight . There is one full bath (shower only) new in 2022 and the kitchen is fully equipped.

Guest favorite
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.
Condo in St. Augustine
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!

Top guest favorite
A light-filled living area is depicted, featuring a spacious couch positioned against a vibrant artwork of a clownfish. Sliding glass doors lead to a serene outdoor space, while colorful paintings adorn the walls, adding artistic charm to the room.
Guest suite in St. Augustine
4.99 out of 5 average rating, 488 reviews

Art Studio Space – Quiet – Walk to Beach

This very private studio apartment is on Anastasia Island, with its own entrance across the street to Anastasia State Park, which includes the St. Augustine Amphitheater in a quiet, friendly beach neighborhood. This ideal location is quite literally "a walk in the park" to a beautiful undeveloped Florida beach; or a 10 minute drive across the famous Bridge of Lions to historic downtown St. Augustine – with quick access to the many local attractions and great restaurants in the area.

Top guest favorite
The exterior of Casa Coquina is presented, featuring a charming façade with rounded archways. A light blue garage door complements the neutral-colored walls. Lush greenery, including palm trees and decorative plants, enhances the inviting entryway, while a driveway leads to the garage.
Home in St. Augustine
4.99 out of 5 average rating, 122 reviews

Casa Coquina Walk to Downtown Clean Quiet Spacious

Casa Coquina offers a uniquely central location for your visit to the nation's oldest city. Located across from Salt Run Waterway & walking distance to many restaurants & entertainment, this newly renovated home offers 2 bedrooms & 2 full bathrooms, large living room, Florida room & outdoor patio. It is a 2-minute drive to Historic Downtown & 5-minute drive to our beautiful beaches. The huge tree-shaded yard is completely fenced in for child/pet safety & total privacy. Enjoy!

Top guest favorite
The open living area features wooden floors and natural light from multiple windows. A compact dining table with folding chairs is set next to a breakfast bar. The kitchen is partially visible in the background, showcasing cabinetry and accessories.
Apartment in St. Augustine
4.93 out of 5 average rating, 407 reviews

Charming "Treehouse" apartment

Let this unique 1 bdrm/1 bath (w/ claw-footed tub) apartment provide the relaxation and comfort you should expect when on vacation. The bedroom has a comfy queen-sized mattress and the black recliner in the living room has the potential to lull you into a dreamy state when you're not out exploring! The treehouse is close enough to attractions/beach/restaurants to walk or ride bikes (We have an assortment of bikes and beach paraphernalia for your use). Three day minimum.

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