Family-friendly vacation rentals in Anastasia Island

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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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Guest favorite

An outdoor seating area features multiple blue Adirondack chairs arranged around a circular stone patio, complemented by a small green table. A lamp post stands nearby, and a flag flutters gently in the breeze, surrounded by lush greenery and tall palm trees.

Guesthouse in St. Augustine

4.91 out of 5 average rating, 577 reviews

Captain's Quarters Tiny House

Welcome to our newly spacious and private renovated bathroom with our outdoor shower. See photos! This Tiny House has all you need for a cozy, private stay while visiting St. Augustine. The Tiny House sits on 3/4 acres. You will feel the tranquility of this magical property and only 10 minutes to Vilano Beach or the Historic Downtown. The studio is equipped with a sink, toilet, kitchenette, coffee/tea. Commune with nature in your Private Exotic Outdoor Shower, hottub (closed July & August).

Guest favorite

A spacious bedroom features a light-colored wooden floor and a ceiling fan overhead. A decorative desk and chair are positioned against the wall, accompanied by a wall-mounted mirror and potted plants. Colorful artwork, including a cow painting, enhances the inviting atmosphere.

Home in St. Augustine

4.92 out of 5 average rating, 306 reviews

NEW Island bungalow - Cozy & Classy

Perfect cozy bungalow for a stay in the nations oldest city. Huge bedroom with a new king bed. Living room with a sleeper sofa and TV. Coffee station, french press, microwave, and mini fridge. Full of artwork. Paintings and a sculpture. Huge stone tiled shower. Located off Anastasia Blvd with great restaurants, coffee shop, pubs and fun for the kids! Located 1 mile the the Anastasia beach state park and then a little over a mile to the beach!! Does not have a kitchen. Walk to Alligator Farm!

Top guest favorite

A grand oceanfront pool is surrounded by palm trees and lounge chairs. The clear blue water reflects the sky, while a spacious area for sunbathing is visible nearby. The beach can be seen in the distance, creating a relaxing atmosphere.

Condo in Palm Coast

4.96 out of 5 average rating, 264 reviews

Luxury Condo on Cinnamon beach

Our beautiful cinnamon beach condo is one of the most peaceful small beach town destinations! Only steps away from the Atlantic Ocean golden sand beaches. Top of line amenities including grand oceanfront pool, separate kids pool across the street, splash pad, kids activity room, adults clubhouse, fitness center, hot tub, & Cafe. Located in a gated safe community with St Augustine, Flagler beach near by. The condo is spacious. Private patio with table for 6 to enjoy Florida sunsets

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, 274 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 scenic view from the balcony shows a large pool surrounded by lounge chairs, with the ocean and sandy beach visible in the background. Lush green landscaping enhances the outdoor area, offering a serene atmosphere for relaxation under a clear blue sky.

Apartment in St. Augustine

4.93 out of 5 average rating, 170 reviews

Ocean View 3br Condo! Indoor pool, steps to beach

Tastefully updated 3 bedroom 2 bath beach condo offers panoramic ocean and pool views from the living room, dining room, master bedroom, and balcony. This unit is located on the 4th floor (top floor of the building) with elevator access, and has recently been entirely renovated. This complex has an Oceanside pool/ hot tub/kiddie pool as well an indoor heated pool, sauna, tennis courts, racquetball court, and fitness center in the clubhouse. Only 15 minute drive to historic downtown!

Guest favorite

A glass of wine rests on a decorative table, with a backdrop of city roofs and greenery. The view captures distant church spires under a bright blue sky dotted with clouds, creating a serene atmosphere for relaxation.

Condo in St. Augustine

4.87 out of 5 average rating, 216 reviews

Rooftop View | Near Eats, Waterfront & Attractions

Located in one of the best spots in the heart of town and ready to welcome you! - An awesome rooftop terrace with outdoor seating to enjoy city & bay views - Walking distance to the waterfront, shops, great local eats & attractions/activities - A short drive to groceries, several golf courses & awesome fishing spots - A fully-equipped kitchen with a dishwasher, washer/dryer & detergent provided - Good WiFi, laptop-friendly workspaces, Smart TV (connect to your own accounts)

Guest favorite

The cottage features a welcoming exterior with a covered porch and two bright blue adirondack chairs. Soft blue walls are complemented by decorative trim, while lush greenery and pebbled landscaping enhance the inviting atmosphere. A privacy fence and palm trees are visible in the background.

Bungalow in Butler Beach

4.94 out of 5 average rating, 187 reviews

Crescent Moon: soft sand beach, pets welcome

The Crescent Moon, east of A-1A, is a charming 1/1 cottage, for small family, 2 friends or one couple. ONE CAR ONLY. Pet friendly cottage and beach. Soothing mornings, evenings to relax in the breeze! Simple 1 block stroll to the soft sand beach. No busy roads to cross. Pet fee $10 a night (for one or two pets, max) to be paid upon departure in cash left in an envelope for housekeeper. Honor system. No pet over 75 pounds. The local taxes of 5% are listed under community fee.

Guest favorite

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 St. Augustine

4.88 out of 5 average rating, 724 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

Guest favorite

The living area features a comfortable gray sofa and armchairs, arranged around a coffee table on a patterned rug. A television is placed on a wooden media console, while natural light enters through a window, complemented by blinds and soft drapes.

Apartment in St. Augustine

4.91 out of 5 average rating, 541 reviews

2 Blocks to the Beach! Modern Beach Escape

Location, location, location! Come spend days at the beach and evenings exploring the historic downtown! This apt is a 2 block walk to the beach with 2 bedrooms- 1 king and 2 twins, 1 bath, open kitchen, dining & living room, spacious deck, beachy backyard, private outdoor shower, 2 parking spaces, wi-fi, and easy access to all St. Augustine has to offer. Beach chairs, towels and an umbrella are also included. Hosted by a local family who puts lots of love into their first home.

Guest favorite

A wooden boardwalk leads from a grassy area to a sandy beach, with gentle waves lapping at the shore. The expansive ocean stretches in the distance under a clear blue sky, creating a serene coastal scene.

Cottage in St. Augustine

4.83 out of 5 average rating, 349 reviews

Sea La Vie Beach Studio.

Our renovated studio is on a quiet cul-de-sac, one block from the beach! It is one side of a duplex and is perfectly located within walking distance to restaurants, family-friendly activities, nightlife, and public transport. It is across the street from the pier and the piers weekly farmers market. It is a short drive to historic downtown St Augustine. The neighborhood is quiet and safe. Our place is good for couples, solo adventurers and business travelers.

Superhost

A bright and airy living space is presented, featuring a comfortable gray sofa and a patterned armchair. Natural light floods in through sliding glass doors, revealing views of lush greenery and the ocean. Neutral-toned decor enhances the relaxed, beach-inspired ambiance.

Condo in St. Augustine

4.8 out of 5 average rating, 205 reviews

1st Floor Oceanfront 1 BR Condo w/Private Balcony

Relax in this clean and cozy one bedroom/one bathroom condo directly overlooking Crescent Beach's beautiful dunes and sandy beaches. This first floor condo features a private oceanfront balcony with a breathtaking view of the ocean only a short walk away from the beach and pool. Condo includes high speed wi-fi, full kitchen stocked with dishes and cookware, comfy king bed, and much more. This condo is ideal for couples looking for a relaxing getaway.

Guest favorite

A charming two-story apartment building is surrounded by lush greenery, featuring palm trees and colorful plants. The front entrance is accessible via a paver pathway bordered by mulch and rocks, with a balcony visible on the second floor where guests can enjoy the outdoor view.

Apartment in St. Augustine

4.94 out of 5 average rating, 248 reviews

See the ocean & walk to the beach in 3 minutes!

See & hear the Atlantic Ocean from Seas the Day on Pelican Way, a 2 bedroom/1 bathroom apartment that has everything you will need to vacation in St. Augustine! Seas the Day is located in a quiet, beach-front residential neighborhood where you can walk to the beach in just 3 minutes. Seas the Day's beach aka Butler Beach is one of the most beautiful and the least crowded beach in St. Augustine!