Family-friendly holiday 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 St. Augustine

5 out of 5 average rating, 136 reviews

Southern Charmer w/Pool - Walk to Everything!

Stellar location...easily park and walk to historic sites! Spacious and modern inside but a classic Southern home on the outside. Lots of room to grill out or lounge around the heated saline pool. Beautiful views of the famed Mission from the upper/lower porches. And you'll appreciate how well stocked this home is too...if we don't provide it you probably don't need it! If you need another rental we have a 4 bedroom w/pool right next door. It's called Walk to Everything plus pool and Cottage.

Guest favourite

Home in St. Augustine

4.98 out of 5 average rating, 168 reviews

Serenity Now - On The Beach

Welcome to Serenity Now! This immaculate beachfront home was completely renovated with beautiful, new furniture and comfortable beds. Sleeps 10 easily in 5 bedrooms, 2.5 baths & hot, outdoor shower. Fully equipped kitchen & BBQ for easy family meals. Enjoy covered, wrap around decks & ocean views from nearly every room! Keyless entry & self check-in. *Service/emotional support animals not allowed b/c our family is severely allergic. 5/27-8/17 weekly rentals; but inquire for shorter stay.

Superhost

Home in Saint Augustine

4.78 out of 5 average rating, 125 reviews

Oceanside/pool view-Surf Crest Village-Pets welcom

This Beach Cottage has all the charms and amenities that you want for your vacation. HDTV with DVD's for those rainy afternoons, sit in the cabana on the beach, read a book, or go for a swim in the seasonally heated pool . We even have a high chair for small family members. You are 200 yards from the beach, and walking distance to putt putt, and 20 different restaurants. 2 bedrooms with bath/kitchen/living area on top floor, and a private living area w/2 bedrooms & bath downstairs as well.

Guest favourite

Townhouse in St. Augustine

4.91 out of 5 average rating, 125 reviews

Paradise Retreat*Vilano Beach*Sand & Ocean Breeze

Come and escape to the Florida sun and beaches at Paradise Retreat! This completely renovated home is only a few minute's walk to the beach with access to miles of tranquil, quiet stretches of beautiful sand, abundant sea seashells and a fantastic blue ocean. It is located in a quiet residential neighborhood, perfect for bike riding and evening walks under the stars. Paradise Retreat is your peaceful getaway only minutes to everything Vilano Beach and historic Saint Augustine has to offer.

Superhost

Flat in St. Augustine

4.81 out of 5 average rating, 185 reviews

Comfy and Quiet 5 min Walk to Historic Downtown

This conveniently located apartment is perfect for solo travelers, couples & friends! - Private outdoor patio with a charcoal BBQ, hammock & a table with chairs for dining - Bike or walk to the waterfront, shops, great local eats & attractions/activities - A short drive to groceries, multiple golf courses & awesome fishing spots - A well-equipped kitchen with all the basics, a coffee maker, a washer & dryer - Stay connected with complimentary WiFi, laptop-friendly workspace, parking.

Guest favourite

Townhouse in St. Augustine

4.96 out of 5 average rating, 104 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 favourite

Home in Saint Augustine

4.85 out of 5 average rating, 275 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

Apartment in St. Augustine

4.91 out of 5 average rating, 162 reviews

Unwind, relax and enjoy! King bed - beach items

St. Augustine Beach is the hidden gem of northeast Florida! Family and pet-friendly condo within walking distance to the pristine white sand beaches, fishing pier, local shops and restaurants. Sandy Feet Retreat is a 2 bedroom / 2 bath air-conditioned unit that sleeps up to four guests. Walk into the inviting living room where you’ll find tasteful beach decor, a classic surf board on the wall, a unique mermaid light, as well as comfortable sofas and a 50-inch LCD Smart TV and WiFi.

Guest favourite

Flat in St. Augustine

4.93 out of 5 average rating, 166 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 favourite

Flat in St. Augustine

4.97 out of 5 average rating, 134 reviews

C8 Perfect location in city, balcony, free parking

Relax in this cozy and comfortable upstairs apartment with balcony. Don't worry about the struggle of downtown parking, PARKING IS FREE on site (2 designated spots for your apartment). So many nearby attractions just steps (or a trolley ride) from the door including shopping on St. George St, restaurants and sandy beaches where you can rent paddle boards, kayaks, small sailboats and more. Netflix, Hulu, Roku, CNN, FOX, E, Bravo, HGTV, TLC, History, A&E, USA, Travel, and much more.

Guest favourite

Apartment in St. Augustine

4.93 out of 5 average rating, 258 reviews

~2 King Beds~Hot Tub~Walk to Beach~3 Bedroom

~2 KING Beds & 4 Twin Beds ~Hot Tub ~GROUND Floor ~Huge Soaking Tub in Master bath ~Free Covered Parking ~Great for Families ~ Patio ~ Pool not heated ~8 Minute Walk to Beach through complex (no street to cross) ~Private Beach Access ~Easy Self Check-In ~Gas BBQ Grill ~CORNER Unit Tons of Light ~Beach Items Provided ~15 Minute Drive to Downtown ~Smart TV (no cable) ~WIFI ~Washer Dryer ~Drip Coffee Pot Add my listing to your wishlist by clicking the ❤ in the upper right corner!

Guest favourite

Holiday home in St. Augustine

4.98 out of 5 average rating, 118 reviews

1st Street Retreat, Dog Friendly Updated Apartment

Welcome to 1st Street Retreat a newly updated open concept dog friendly studio apartment, 1 block to beach, withing walking/bike riding distance to local restaurants. Keurig coffee machine. Free WIFI & TV, linens, towels, kitchen & bathroom amenities. Outside retreat has a private entrance, fenced in yard with dog run, outside shower, BBQ, table & chairs, propane fire pit. We also provide beach chairs, beach cart and beach towels. There is a pet fee of $100.00 we allow 2 dogs