Vacation rentals with outdoor seating in Anastasia Island

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Top-rated outdoor seating rentals in Anastasia Island

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Guest favorite

Cottage in St. Augustine

4.98 out of 5 average rating, 179 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 29 – Nov 5

G$24,528 GYD per night

Guest favorite

Guest suite in St. Augustine

4.94 out of 5 average rating, 127 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.

Sep 30 – Oct 7

G$23,929 GYD per night

Guest favorite

Guest suite in St. Augustine

5.0 out of 5 average rating, 190 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

Mar 8 – 15

G$24,096 GYD per night

Guest favorite

Townhouse in St. Augustine

4.93 out of 5 average rating, 101 reviews

Penthouse Artist Haven Ocean front Penthouse

Nestled along a pristine stretch of semi-private beach is this historic artists haven offering an absolute beachfront location like no other. This unique home is split into 3 separate floors, where you will be renting the entire top penthouse level. Inside you will find open studio living with a luxe king bed and a front and rear balcony. Enjoy uninterrupted ocean views from the panoramic windows while you relax & watch dolphins play in the surf and stunning sunsets spread across the sky.

Dec 30 – Jan 6

G$127,644 GYD per night

Guest favorite

Guesthouse in St. Augustine

4.88 out of 5 average rating, 102 reviews

Island’s Edge Guest Cottage on Anastasia Island.

Fresh and clean, marsh front private cottage with bright new path lights and amazing views. Walk or pedal from this adorable cottage to any of the local attractions. Nestled between the state park, our famous AMP, great beaches & downtown, everything is close by. Your deck is perfect for a bbq, bird watching & cocktail sunsets. Sorry no marsh access. Park trails are close as is the beach. You have to stroll over to the Saturday morning market at “the Amp”. You’re gonna love it here.

Jul 31 – Aug 7

G$23,479 GYD per night

Guest favorite

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.

Nov 19 – 26

G$30,506 GYD per night

Guest favorite

Condo in St. Augustine

4.88 out of 5 average rating, 182 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 27 – Feb 3

G$28,894 GYD per night

Guest favorite

Guest suite in St. Augustine

4.99 out of 5 average rating, 348 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.

Mar 6 – 13

G$27,902 GYD per night

Guest favorite

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

Sep 18 – 25

G$24,906 GYD per night

Guest favorite

Townhouse in St. Augustine

4.92 out of 5 average rating, 102 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.

Jan 13 – 20

G$26,011 GYD per night

Guest favorite

Home in St. Augustine

4.9 out of 5 average rating, 151 reviews

Charming home with great amenities

Are you looking for a great family friendly place to relax close to St. Augustine and the beaches? This charming home with a relaxed vibe in St Augustine Shores is the place for you. You are just 5 miles from downtown and the beaches in a quiet neighborhood. Relax on the lanai, listen to sound of the fountain in the koi pond in private fenced back yard. You can access the community pool on the intracoastal for a $5 fee.

Oct 2 – 9

G$23,366 GYD per night

Guest favorite

Guesthouse in St. Augustine

4.99 out of 5 average rating, 316 reviews

Pelican Guesthouse-Spacious/Quiet/Comfortable

Quiet, spacious guesthouse with light filled interiors. Very comfortable beds and immaculately kept. 10 min from gorgeous beaches and the old world charm of St Augustine historic downtown. Friendly neighborhood and accessible to beautiful walks along the Matanza River. Self check in, private entrance, two flat screened TV's, full kitchen (stove, large refrigerator and microwave) Full laundry room and off street parking.

Aug 19 – 26

G$23,018 GYD per night