Anastasia Island vacation rentals

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Top-rated vacation rentals in Anastasia Island

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Guest favorite

Apartment in St. Augustine

4.92 out of 5 average rating, 263 reviews

Toast Sunsets from the Wraparound Deck at a Coastal Oasis

A wonderful getaway, this property includes two airbnbs. A two story home with a detached guesthouse. These listings can be rented separately or together, if available. This listing is space is about 1,000 sq ft. You will have exclusive access to the second story apartment and wrap around porch. You will have one dedicated parking spot. There is a small backyard area with an outdoor shower that is shared with the other Airbnb. Access to the apartment is via keypad code. Were available if you need anything, but many times we only communicate with our guests through Airbnb! This Crescent Beach retreat is set back a bit from the road just 3 blocks from the ocean and 8 miles from downtown. Uber is the best way to get around without a vehicle. The Crescent Beach house is on A1A, set back a bit from the road. A1A is a moderatly busy two lane highway. However, you access the home from the backyard, which is also where you park, via a short grass road. Uber is the best way to get around if you do not have your own vehicle. This property includes two airbnbs. Each listing has one dedicated parking space in the rear of the property via a short grass backroad. The parking spaces are right next to each other.

Sep 23 – 30

G$21,834 GYD per night

Guest favorite

Cottage in St. Augustine

4.98 out of 5 average rating, 178 reviews

Bamboo Lane Hideaway near AMP, Downtown & Beaches

Sophisticated, tropical hideaway. Your retreat… quiet, respectful & peaceful. All are welcome here with love and respect. Perfect for singles, couples, looking to rest and relax or to explore this historic Florida shore, the ‘Bamboo lane hideaway’ offers unique accommodations complete with a custom-designed interior, laid-back beach vibe, and complimentary parking pass for downtown. Explore the nearby Lighthouse, Zoo, white-sand Beaches, Amphitheater & Downtown all less than 1.6 miles away.

Oct 31 – Nov 7

G$24,450 GYD per night

Guest favorite

Guest suite in St. Augustine

4.94 out of 5 average rating, 126 reviews

Saint Augustine Beach House

Conveniently located between both St. Augustine pier and Crescent beach. Walk or bike ride up the road 1/4 mile to the beach. Great area and neighborhood. Keypad private entrance for self check-in. First floor is all yours and sealed off from the upstairs in this 2 story home. One very large bedroom, living room, kitchen and full bath. It features a new king sized bed along with a 3 inch memory foam topper. This can be broken down into 2 separate xl twins if needed. Front and back decks.

May 3 – 10

G$23,881 GYD per night

Guest favorite

Apartment in St. Augustine

4.94 out of 5 average rating, 239 reviews

Private and lovely 1 bdrm Apt, 100ft to the Beach!

Over 100 years old, this property was originally a mechanics garage used to repair cars racing the beach. It has been remodeled for your beachside getaway! Just steps from the beach, in the middle of St Augustine Beach! Located on A St. it's a short walk to coffeeshops, restaurants and the beach, this location is unbelievable! Our apartment is one bedroom, one bath with a full kitchen and laundry. The living room has a pull out queen bed. It has all you need to relax after a day at the beach.

Jan 9 – 16

G$29,332 GYD per night

Guest favorite

Guest suite in St. Augustine

5.0 out of 5 average rating, 186 reviews

Entire guest suite short walk to beach.

Enjoy exploring beautiful, historical St. Augustine then kick back and take it easy at this private, quiet beach retreat within a short walk to the beach. Separate keyless entry allows for self check-in. Queen size bed, fully furnished, with amenities including a Keurig coffee maker, iron, hair dryer, beach cruiser bicycles, beach chairs, towels, umbrella and gas grill for cooking out. Flat screen TVs in both the living room and bedroom with Netflix and Amazon Prime included and Free WiFi

Nov 28 – Dec 5

G$24,048 GYD per night

Guest favorite

Condo in St. Augustine

4.88 out of 5 average rating, 181 reviews

The Salty Suite Resort style condo

This modern 1 bed/1 bath rental unit has access to a private walk way to 2 pools, beach (5 min walk from door to sand) & tennis courts all in a gated community right on famous A1A in the Oldest City in the Nation. Perfectly situated by the beach or a quick Uber ride to Downtown to check out the history of the Oldest City in the Nation & try some other great local restaurants. We provide an in room guidebook telling you all the must do's in the town & helpful hints too! See you soon!

Jan 6 – 13

G$28,610 GYD per night

Guest favorite

Guest suite in St. Augustine

4.99 out of 5 average rating, 345 reviews

Art Studio Space – Quiet – Walk to Beach

This very private studio apartment is on Anastasia Island, with its own entrance across the street to Anastasia State Park, which includes the St. Augustine Amphitheater in a quiet, friendly beach neighborhood. This ideal location is quite literally "a walk in the park" to a beautiful undeveloped Florida beach; or a 10 minute drive across the famous Bridge of Lions to historic downtown St. Augustine – with quick access to the many local attractions and great restaurants in the area.

Jul 27 – Aug 3

G$28,865 GYD per night

Guest favorite

Guest suite in Saint Augustine

4.88 out of 5 average rating, 649 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

Jul 29 – Aug 5

G$24,856 GYD per night

Guest favorite

Apartment in Saint Augustine

4.92 out of 5 average rating, 352 reviews

Charming "Treehouse" apartment

Let this unique 1 bdrm/1 bath (w/ claw-footed tub) apartment provide the relaxation and comfort you should expect when on vacation. The bedroom has a comfy queen-sized mattress and the red recliner in the living room has the potential to lull you into a dreamy state when you're not out exploring! The treehouse is close enough to attractions/beach/restaurants to walk or ride bikes (We have an assortment of bikes and beach paraphernalia for your use). Three day minimum.

Jan 23 – 30

G$19,587 GYD 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.

Aug 5 – 12

G$20,468 GYD per night

Guest favorite

Apartment in St. Augustine

4.97 out of 5 average rating, 266 reviews

Home away from Home close to everything!

An ideal place to stay while visiting our lovely historic St. Augustine. It's in a quiet neighborhood close to beaches, historic district, restaurants and stores. The unit is above the two-car garage where you enter to go up stairs to the 500 square foot apartment. It has a living room, full kitchen, bedroom and bathroom. It's a few short blocks to Intracoastal Waterway (ICW) where you can enjoy breath-taking walks. Short drive to everything!

Aug 2 – 9

G$14,062 GYD per night

Guest favorite

Townhouse in St. Augustine

4.92 out of 5 average rating, 100 reviews

Dunewalk 2 Spacious Crescent Beach Condo

3 Story condo with ocean views and a short walk on private road to Crescent Beach through the dunes. Very peaceful, all the amenities for the beach and fully stocked condo. Entire 2 bedroom unit to yourself. 8 miles from historic St. Augustine. Close to great restaurants, boat ramps, kayaking, boat rentals. Please do not rent this property if you intend to bring a pet/service animal it is strictly animal-free due to allergies.

Oct 24 – 31

G$26,081 GYD per night