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Family-friendly holiday rentals in Anastasia Island

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Anastasia Island

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite
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.
Home in Butler Beach
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.

Guest favourite
Apartment in St. Augustine Beach
4.92 out of 5 average rating, 212 reviews

Beachfront St. Augustine Escape* Pool & Ocean View

Welcome to Turtle Trace, your beachfront getaway on Anastasia Island in beautiful St. Augustine! This condo offers direct pool & beach access, sweeping ocean views, and just minutes from Historic Downtown. Perfect for families, couples, or anyone wanting the ultimate coastal escape. Why You’ll Love It 🏖 Steps to the beach & pool right outside your patio door 🌅 Enjoy amazing sunrise views over the Atlantic 🏡 Gated, beautifully maintained community 🍴 Walk to restaurants, cafes & grocery stores

Guest favourite
A scenic view reveals a sandy beach framed by rolling dunes and lush greenery. A wooden boardwalk leads to a shaded gazebo overlooking the ocean. The sky is clear with scattered clouds, creating a peaceful atmosphere by the water.
Condo in Butler Beach
4.84 out of 5 average rating, 347 reviews

Shell Shack - Resort Beachside Condo

Beautifully decorated & upgraded beachside 2 bed/2bath ground floor unit with an assigned parking spot right next to your patio entrance. Natural light fills the condo. The patio gets plenty of sunshine from its southern exposure positioning so it offers a great place to enjoy your coffee in the morning, wine at night, or to catch up on your tan. The sunshade allows for a private outdoor experience when you just want to sit quietly alone listening to the ocean waves crashing along the beach.

Top Guest favourite
A spacious living area features a light gray sectional sofa with a chaise, positioned on a natural fiber rug. A round mirror enhances the sense of space, while a dining area is visible in the background, complete with wooden chairs and a table.
Villa in St. Augustine Beach
5.0 out of 5 average rating, 129 reviews

VILLA One

The Villas are designed for short stays, long weekends or for a unique styled location for brands to shoot their products. The space features warm tones, natural finishes and local art for an effortless vibe that allows visitors to relax the second they walk in the door. Complete with two bedrooms, two bathrooms and a backyard complete with tropical landscaping, lounge area, dining and outdoor shower. One of 4 Villas located in St. Augustine Beach. Not pet friendly. @staugustinebeachvillas

Top Guest favourite
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 Butler Beach
4.99 out of 5 average rating, 210 reviews

SeaPlace Ocean & Pool Views, 2/3 Steps to Beach

Beautiful St. Augustine Beach ocean & pool views from this 2/2.5 townhouse style condo steps to the beach. Come enjoy everything this vibrant city has to offer. Two quiet bedrooms and bathrooms upstairs. 2 private balconies. Downstairs is a full kitchen, dining area for 6, half bathroom, living area w/ newer 65" TV. 10 minutes from historic downtown. Family friendly resort community w/ pools, tennis, pickleball, basketball and bocce’ ball courts. Book now and let the island magic begin.

Top Guest favourite
A screened lanai offers a comfortable wooden bench, with a vibrant mural piece on the wall. The space provides sweeping views of the lush greenery and palm trees beyond, as the sun rises over the horizon, creating a serene outdoor retreat.
Apartment in St. Augustine Beach
4.96 out of 5 average rating, 115 reviews

Oceanfront Bliss: Beach Views

Welcome to your oceanfront oasis in St. Augustine Beach! Featuring a spacious king suite, a comfy queen bedroom with twin trundle, and a sleeper sofa, it offers stunning sunrise views, a modern boho surfer’s vibe, and an updated chef’s kitchen. Steps to one of the best beaches in the east coast and walk to lively local restaurants and bars, it’s minutes to St. Augustine’s Nights of Lights, Amphitheater, and more! This isn’t just a vacation rental—it’s your personal seaside escape. Book now!

Top Guest favourite
Home in St. Augustine Beach
4.87 out of 5 average rating, 310 reviews

Sunny, family friendly Sol Mate Beach Cottage

Our renovated beach cottage is one block to the beach, walking distance to restaurants and ice cream, nightlife, public transport, family-friendly activities. Across the street is the pier, volleyball courts, splash pad and weekly Wednesday farmers market. A short drive to the oldest city in the US and a grocery store! You’ll love our adorable beach cottage because of the location, the neighborhood and the beach is gorgeous. Our place is good for couples, solo adventurers, and families.

Guest favourite
A view overlooking the ocean reveals gentle waves and a clear blue sky. Green palm fronds are positioned in the foreground, while a red-roofed gazebo is visible on the beach, blending with the natural coastal landscape.
Condo in Butler Beach
4.91 out of 5 average rating, 253 reviews

What a View! Sand & Sea!

Welcome to the most beautiful white sand beach via a short wood walkway from condo over a small dune! Or drive out 4x4 only. Later take a tour of the oldest city in the US Historic St Augustine! We are a tropical small resort with a private balcony and ocean views. Two pools / hot tub / grills/tables/loungers right below condo. We are on the 3rd floor. Of course it’s for THE VIEW (August through November free cancelling/refund if a hurricane is predicted/island issues evacuation.

Guest favourite
The image captures a serene beach at sunset, where the sun is partially obscured by clouds, creating soft orange and blue hues in the sky. Tall grasses sway gently in the foreground, framing the scene of the calm ocean waves reflecting the fading light.
Guest suite in Butler Beach
4.89 out of 5 average rating, 796 reviews

Beach and Serenity

6 BLOCKS to BEACH, off of the intercostal! Studio apartment, sleeps up to 4. Quiet neighborhood, close to all. Several restaurants/shops within walking distance. Beach bikes included, perfect for bike rides along the beach. Private entrance off of porch, which includes chairs to relax in, beach toys, towels, chairs. *yes, we are pet friendly, however, ONE PET PER STAY WITH APPROVAL *also, we cannot split weekends, so please book accordingly, fridays and Saturdays booked together

Top Guest favourite
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.
Condo in St. Augustine Beach
4.96 out of 5 average rating, 200 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!

Top Guest favourite
The exterior of a one-story unit is displayed with a red metal roof and a welcoming porch. A colorful umbrella provides shade over outdoor seating. A grill is positioned nearby, and landscaped areas with flowers enhance the entrance.
Cottage in Butler Beach
4.92 out of 5 average rating, 300 reviews

Livin’ the Dream at St. Augustine Beach

Bright beachy unit with all amenities including community pool, close public beach access and essentials including bedding, towels, beach cruiser bikes and grill. Enclosed porch and outside deck are ideal for grilling out or hanging out. My home is located in Peppertree RV Resort . The public beach access is a short 10 minute walk away. The unit has parking for two vehicles with extra parking available in an overflow lot. A washer and dryer are located inside the unit.

Top Guest favourite
A balcony table is set for two, featuring white plates and cups, with expansive ocean views. Lush greenery and sandy beach can be seen in the distance under a clear blue sky, creating a serene and inviting outdoor space.
Condo in St. Augustine Beach
4.98 out of 5 average rating, 262 reviews

Ocean Front Gem: Top Floor Corner Unit

Top floor, direct oceanfront, 2 bedroom, 2 bathroom corner end unit condo with elevator and unobstructed beach views from both bedrooms, living room, dining room, kitchen and private balcony in beautiful St Augustine Ocean and Racquet Resort. We also offer for rent the condo immediately next door, Ocean Front Escape: https://www.airbnb.com/h/saint-augustine-oceanfrontescape. Our checkin process is contact free. We use a smart lock on the front door.

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