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 favourite

Home in Saint Augustine

4.99 out of 5 average rating, 364 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 (5 miles) and St. Augustine Beach (3 miles). The home is 100% HANDICAPPED ACCESSIBLE! Convenient shopping and close by restaurants. Full kitchen, spacious living area, large bedrooms, ceiling fans. Pet friendly! (Some restrictions apply, advance notice required!) Base rate covers up to 4 guests and there's a small extra charge for 5 or more. Motorcycle friendly! We also do live on the property!

Sep. 20 – 27

$222 CAD per night

Guest favourite

Home in Saint Augustine

4.91 out of 5 average rating, 222 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!

Aug. 3 – 10

$232 CAD per night

Guest favourite

Townhouse in Saint Augustine

4.99 out of 5 average rating, 103 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!

Oct. 28 – Nov. 4

$250 CAD per night

Guest favourite

Apartment in St. Augustine

4.92 out of 5 average rating, 590 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.

Oct. 30 – Nov. 6

$225 CAD per night

Guest favourite

Apartment in Saint Augustine

4.93 out of 5 average rating, 118 reviews

5 walking minutes to the beach

Walk 5 minutes on a quiet street to the beach access. Your apartment covers the first floor of this home, located in a quiet, residential neighborhood. This sunny apartment has been totally renovated, with two large bedrooms, a fully equipped new kitchen with granite counter tops, Mexican tile floors, WiFi, cable TV, Netflix, two flat screen TVs, washer/dryer, and dishwasher. It has a completely fenced-in yard with a large covered patio. One dog is welcome. There is no pet fee.

Nov. 24 – Dec. 1

$250 CAD per night

Guest favourite

Bungalow in Butler Beach

4.93 out of 5 average rating, 122 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.

Aug. 29 – Sep. 5

$225 CAD per night

Guest favourite

Guest suite in Saint Augustine

4.88 out of 5 average rating, 653 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

Aug. 11 – 18

$185 CAD per night

Superhost

Cottage in Saint Augustine

4.81 out of 5 average rating, 302 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.

Oct. 10 – 17

$165 CAD per night

Superhost

Condo in St. Augustine

4.95 out of 5 average rating, 128 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.

Oct. 14 – 21

$230 CAD per night

Guest favourite

Guest suite in St. Augustine

4.84 out of 5 average rating, 324 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.

Dec. 13 – 20

$229 CAD per night

Guest favourite

Apartment in St. Augustine

4.95 out of 5 average rating, 310 reviews

Comfort of Home in St Augustine

Charming apartment in the historic district with a completely updated bathroom with a deep soaking tub and a separate shower, double vanity, Carrera marble tile. 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 where you can relax, enjoy your morning and evening beverages, people watch and mingle with the neighbors...

Aug. 2 – 9

$229 CAD per night

Guest favourite

Guesthouse in St. Augustine

4.91 out of 5 average rating, 531 reviews

Captain's Quarters Tiny House

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).

Dec. 20 – 27

$137 CAD per night