House holiday rentals in Anastasia Island

Home in St. Augustine Beach

4.99 out of 5 average rating, 177 reviews

Beachside, SUPER CLEAN, Oasis Yard, Summer Retreat

"We had an absolutely fantastic time staying at Dominick’s place. From start to finish, everything exceeded our expectations" * 100% 5-star rating ⭐ * Less than 500 steps to St Augustine Beach! ⛱️ * Super comfortable and meticulously clean. ✨️ * Huge Private Oasis Backyard, BBQ, Speakers, LOTS of seating 🌴 * towels + beach chairs + beach cart ⛱️ * 100% cotton sheets and towels ☁️ * comfy beds, pillows, extra pillows + blankets, living room * Fully stocked kitchen * On the Golden Mile

FamilyLocationBackyard

An expansive backyard features a refreshing saltwater pool and a hot tub, surrounded by lush turf landscaping. A two-story building with a wooden staircase overlooks the serene outdoor space, framed by palm trees and vibrant plants. Lounge chairs are positioned nearby for relaxation.

4.99 out of 5 average rating, 162 reviews

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.

ValueFamilyWalkability

4.98 out of 5 average rating, 158 reviews

A coastal cottage with a modern design features a light-colored exterior and a metal roof. The entryway is adorned with teal shutters and a bright front door. Two white adirondack chairs are positioned on the porch, surrounded by well-maintained landscaping and palm trees.

Home in Crescent Beach

Seaside at Crescent Beach, 150 steps to the ocean

150 steps to beach sand of the ocean. SEASIDE beach cottage, built in 2021, at A Avenue - At the ramp to Crescent Beach ( 32080) 5 miles south of St. Augustine Beach. 20 minutes to The Nation's Oldest City. Great restaurants in the area. Rent a kayak -Boat ramp, fishing outfitter 3 blocks away. Open floor plan 2 story 3 br. and loft and 2 1/2 baths and a laundry room. Master BR downstairs. Soaring ceilings , good variety of space. Great vacation/family get-together spot. 2 Porches .

FamilyLocationSleep quality

The exterior of the cottage is showcased, featuring a bright blue metal roof, white brick walls, and charming blue shutters. A patio with outdoor seating is visible, surrounded by lush greenery and palm trees under a colorful sunset sky.

4.98 out of 5 average rating, 317 reviews

Entire House w/ Backyard Hideaway - WALK TO BEACH

PARADISE ON PALMETTO: Unwind by the waves or at home in the backyard oasis. A true beach escape, we are nestled between the Atlantic Ocean & Intracoastal Waterway, walking distance to the beach and river. This bright, newly updated cottage is two blocks from the ocean and a 15 minute drive to the restaurants, bars, and attractions in Historic Downtown St. Augustine. Experience this ideal base to explore the Nation’s Oldest City! PARKING & WASHER/DRYER INCLUDED. SUPER CLEAN. NO CONTACT CHECK-IN.

LocationFamilyAmenities

The two-story beach house is framed by a lush green lawn and palm trees, featuring a spacious front porch with white chairs. Large windows and a gabled roof enhance the inviting appearance. A clear blue sky serves as the backdrop.

4.9 out of 5 average rating, 179 reviews

Beach & Serenity; The Perfect Location in St. Aug

Forget your worries in this spacious and serene space. Beautiful beach house 6 blocks to beach, 2 blocks to intercoastal Drive on to the beach at one end of the street, Easy walk to the best sunsets at the marsh Restaurants at each end of the street Upstairs and downstairs screened porches *PLEASE NOTE, AND THIS IS IMPORTNAT * We cannot split weekends. Friday and Saturday nights booked together *ONE PET PER STAY W/ APPROVAL *no washer/dryer available, hang dry only *STRICT CHECK IN/OUT TIMES

ValueLocationPets

A modern home is surrounded by a well-kept backyard featuring a private pool and spacious patio. Comfortably arranged lounge chairs provide a relaxing spot. The exterior showcases light-colored siding and elevated balconies, with palm trees dotting the landscape for a tropical feel.

4.89 out of 5 average rating, 114 reviews

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

FamilyLocationAmenities

A spacious balcony is seen, featuring two wicker chairs positioned at a small round table. The wood decking extends outward, providing an unobstructed view of the ocean and nearby palm trees against a backdrop of partly cloudy blue skies.

4.99 out of 5 average rating, 142 reviews

Memory Maker - Vacation with Friends and Family

Modern, beautiful beach house with views of the ocean and tons of space for family fun. Home is one block from the ocean and is stocked with beach chairs, boogie boards and sand toys. Enjoy two ocean view balconies, a large open concept kitchen, living room and dining room, and board games for evenings of laughs with friends. This ultimate beach house is close to local restaurants and is an eight mile drive to historic downtown St. Augustine with shopping, tours, museums and live music.

ValueLocationAccess

4.94 out of 5 average rating, 233 reviews

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.

ValueLocationAccuracy

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.

4.99 out of 5 average rating, 136 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!

FamilyValueLayout

A charming home is framed by lush greenery and distinctive palm trees. The gravel driveway leads to a welcoming porch with comfortable seating. The light blue exterior is complemented by large windows, allowing natural light to brighten the inviting entryway.

4.97 out of 5 average rating, 128 reviews

Family/Dog Friendly | Walk to Beach | Fenced Yard

⭐ 4.97 Stars · 120 Reviews · Airbnb Guest Favorite — One of St. Augustine's most-loved beach homes. Casa Desoto is a 4-bedroom, 8-guest beach retreat where Crescent Beach is a 10-min walk or a straight drive onto the sand. Come home to a fully fenced backyard with hammock, corn hole, fire pit & grill while the dog runs free. Every inch is stocked for your crew — beach wagon, chairs, boogie boards, and even a pack 'n play. You just bring the sunscreen.

LocationFamilyCondition

4.99 out of 5 average rating, 153 reviews

Aerial view of a home surrounded by lush greenery near a waterway, featuring a long dock extending into the water. The structure is illuminated, highlighting the inviting exterior against the twilight sky.

Home in Crescent Beach

Gorgeous Views, Golf cart w/beach access!

Beautiful home with outstanding view & access to the Intracoastal. Watch dolphins play, yachts cruise by or catch the sunset from the dock. If you're feeling adventurous, jump on a kayak or paddle board & explore the quaint islands nearby. If the ocean is calling, take a 2 min ride with the included 6 seater golf cart (must sign waiver) & drive right on to Crescent beach. Grab a surf or boogie board for some extra excitement!

FamilyLocationBarbecue

The kitchen area features wooden cabinetry, a stove, and a refrigerator. A ceiling fan is present above a bar counter with seating, while a dining table is positioned nearby. Natural light streams in through a window, creating a welcoming environment.