Family-friendly vacation rentals in Anastasia Island

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Top-rated family-friendly rentals in Anastasia Island

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Guest favorite

Guesthouse in St. Augustine

4.91 out of 5 average rating, 547 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

Home in Saint Augustine

4.99 out of 5 average rating, 388 reviews

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!

Guest favorite

Townhouse in St. Augustine

4.96 out of 5 average rating, 102 reviews

***Direct Beachfront Oceanfront~Incredible Views!

Located on Vilano Beach, St. Augustine, FL, this three-story townhome is waiting to make memories for you and your family. Located directly on the beach-designed to envelope the soul in tranquility, this three-story townhome includes three lovely bedrooms. The main floor boasts a gourmet kitchen, half bath, laundry room, family room, dining area, and ocean viewing area. A laundry room houses a full size washer and dryer. Ultra high speed Internet is provided and reaches to the beach!

Guest favorite

Rental unit in St. Augustine

4.93 out of 5 average rating, 624 reviews

2 Blocks to the Beach! Open, Airy, Beach Apt

Location, location, location! Bright 2nd floor beach apt, 2 blocks to the white sands of beautiful St. Augustine Beach! Spend your days at the beach and evenings exploring the historic downtown. The apartment has 2 bedrooms- 1 king and 2 twins, 1 bath, kitchen, dinning and living room with an open floor plan, balcony deck, outdoor shower, parking, Netflix, Roku TV, & wi-fi. Listen to the waves from the deck at night! Hosted by a local family who puts lots of love into their first home.

Guest favorite

Rental unit in Saint Augustine Beach

4.94 out of 5 average rating, 175 reviews

Modern & Comfy Beach Gem: Pool ~ Ocean Views ~ Pkg

Welcome to Turtle Trace St. Augustine, Anastasia Island - Oceanfront Steps to the Beach!! Right out the patio door is the spectacular pool and the amazing ocean! Updated unit is in beautifully maintained gated community. Come stay here and get that feeling of being at home, people come back year after year because they love it! You can see why so many people make this their home away from home. If you have any questions please email us and we will try our best to accommodate you!!

Guest favorite

Bungalow in Butler Beach

4.94 out of 5 average rating, 150 reviews

Crescent Moon: One block pet friendly beach!

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

Guest suite in Saint Augustine

4.88 out of 5 average rating, 694 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

Cottage in Saint Augustine

4.83 out of 5 average rating, 328 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.

Guest favorite

Condo in St. Augustine

4.93 out of 5 average rating, 142 reviews

"Captain Jacks" First Floor 2BR/2Bath Condo

First Floor 2BR-2BA, Beach/Pool. Remodeled in 2015 with all new appliances, YouTube TV, Xbox, walk-in shower. Complex is gated with private access to beach and pool. Entertainment: YouTube TV for Television in LR. Xbox in BR 2 Beach umbrella and chairs Boogie boards Beach toys Located on Anastasia Island, you are 15 minutes from downtown St. Augustine, St George St, and surrounded by a variety of attractions such as the Lighthouse and Alligator Farm.

Guest favorite

Rental unit in St. Augustine

4.94 out of 5 average rating, 329 reviews

Comfort of Home in Historic St Augustine

Charming apartment in the historic district with a completely updated bathroom with a large blue tooth enabled shower, double vanity, Carrera marble tile floor. The kitchen is new as well with all new appliances, cupboards and quartz countertop. My favorite part of this apartment is the large front porch and back porches where you can relax, enjoy your morning and evening beverages, people watch and in the front porch mingle with the neighbors...

Superhost

Guest suite in St. Augustine

4.84 out of 5 average rating, 345 reviews

Anastasia Island Tropical Treehouse

I am a beautiful beach house located 2 blocks from the back gate of Anastasia State Park, walking distance to the Beach, St. Augustine amphitheater, located in a quiet neighborhood on Anastasia Island. Two bedroom 1 bath private upstairs with a big covered porch where ocean waves can be heard often and full moons are seen rising. It's called the treehouse because the house is surrounded by a canopy of native Florida foliage.

Guest favorite

Rental unit in St. Augustine

4.94 out of 5 average rating, 225 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!