Waterfront vacation rentals in Anastasia Island

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Top-rated waterfront rentals in Anastasia Island

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Home in St. Augustine

4.88 out of 5 average rating, 359 reviews

Waterfront Fisherman’s Treasure at Crescent Beach

Enjoy waking up in a quiet Treasure Beach neighborhood having coffee on the screened-in back porch, or enjoy the dock, watching a variety of birds, wildlife and fish jumping in the canal. All you need is a pole. Take a 5 minute ride from the house to ocean access and walk our beautiful Crescent Beach. A short drive away, there's shopping, entertainment and great restaurants in St. Augustine (Oldest City in the USA). We look forward to your stay and know you will make memories to last a lifetime.

Sep 12 – 19

$142 per night

Guest favorite

Condo in St. Augustine

4.92 out of 5 average rating, 126 reviews

Anastasia Island 1 ~ Beach, Relax & Explore

Large one-bedroom condo with open space living, kitchen and dinning room full of natural light leading from the balcony. Bedroom has a large walk-in closet and a king bed with access to balcony. The condo comes complete with a full kitchen, washer and dryer, high-speed fibre internet, pots and pans and basic pantry items. This condo sleeps up to 4 people, best suited for 2 adults and 2 children. Queen air mattress with deep sheets and topper for optimum comfort, and a single mattress in closet.

Nov 29 – Dec 6

$131 per night

Guest favorite

Condo in St. Augustine Beach

4.85 out of 5 average rating, 197 reviews

Oceanside Condo - heated pool, hot tubs, beach

A newly renovated 4-bed beach condo decorated with a peaceful ocean theme will be the perfect beach house for your St. Augustine stay! With 2 swimming pools, 5 jacuzzis, tennis & pickleball courts, & private walkways to the beach, this centrally located spot will have you both entertained and relaxed while on vacation. The nautical tri-bunk room is fun for the family, the classic coastal master bedroom is serene, & the martini bar adds a festive element. You'll always remember this vacation!

Nov 9 – 16

$121 per night

Guest favorite

Condo in St. Augustine

4.98 out of 5 average rating, 113 reviews

SeaPlace, Ocean View, Poolside 2/3 Walk to Beach

Beautiful St. Augustine Beach ocean and pool views from this 2/2.5 townhouse style condo, steps to world class beaches. Come enjoy everything this vibrant city has to offer. 2 quiet bedrooms and bathrooms upstairs. 2 private balconies. Downstairs is a full kitchen, dining area for 6 (or well lit workspace), half bathroom, living area w/ new 65" TV ( w/ cable & WiFi). 10 minutes from historic downtown. Family friendly resort community w/ pools, tennis courts. Beach chairs & towels provided.

Dec 1 – 8

$171 per night

Guest favorite

Condo in St. Augustine

4.94 out of 5 average rating, 132 reviews

1st Floor beach condo, Heated pool & tennis, clean

This beautifully decorated premium unit on the first floor is located in the Premier Ocean Village Club. Walk out your private screened patio to the heated pool or take a short walk to the unheated pool or the Atlantic Ocean. Ocean Village Club is a gated community with private beach access that offers 2 pools (1 heated), tennis, shuffleboard, fitness center, and grilling/picnic pavilion. Just minute away from the leading attractions, restaurants, and shopping in Historic St. Augustine!

Aug 22 – 29

$151 per night

Guest favorite

Condo in St. Augustine

4.97 out of 5 average rating, 148 reviews

Ocean Front Condo only Steps to the Beach.

Self-Check-In, Covid-19 Protocol Cleaning Utilized, Ground level, oceanfront unit w/ 2 bedrooms/2 baths at Sea Place, a quaint seaside community. Has updated kitchen & walk-in shower, washer/dryer, wifi, cable & covered patio. Amenities: 2 pools (not heated), tennis, racquetball, & beach access; 4 beach chairs & umbrella provided. Located near shops, restaurants & historic St. Augustine. 2 nights min stay. Max: 4 guests. No pets (per HOA), smoking or parties please. No BBQ grill per HOA.

Oct 29 – Nov 5

$178 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

$97 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

$120 per night

Guest favorite

Home in St. Augustine

4.98 out of 5 average rating, 125 reviews

Luxurious Oceanfront Home

Brand new, oceanfront home professionally designed with luxurious finishes and incredible ocean views. Relax on the sprawling back deck overlooking the water after a game of bocce ball. Stroll down the private sidewalk, just steps to the beautiful, white-sand beach. Cook a gourmet meal in the state-of-the-art kitchen, or grill out on the deck using the gas grill or Green Egg. Sit around the fire pit under the stars and roast marsh mellows while listening to the ocean waves.

Oct 30 – Nov 6

$289 per night

Guest favorite

Apartment in St. Augustine

4.92 out of 5 average rating, 342 reviews

Bougainvillea way, steps to town center, romantic.

Bougainvillea Way is cozy, romantic and part of a Key West, gingerbread style home situated on the San Sabastian Harbor in Saint Augustine, Lincolnville Historic district. The setting will take you back in time to a very relaxing place close enough to walk to the town center and attractions and far enough away to relax in your quiet space. Our place is close to everything. Easy walk to the town center and to the best local restaurants. Short walk to playground.

Dec 20 – 27

$115 per night

Guest favorite

Condo in St. Augustine

4.99 out of 5 average rating, 193 reviews

Ocean Gallery: 2 pools/resort amenities

Bright, airy and beachy, this condo at Ocean Gallery pairs resort-style amenities with an exceptionally clean, stylish and comfortable condo. Perfect for a couple or one family, it sleeps up to 4 in beds (primary bed sleeps 2; pullout sofa in living area sleeps 2 additional guests - perfect for kids). You’ll be a few steps from 1 of the 2 pools, and a 5 minute leisurely stroll through the complex will take you to the beach!

Dec 20 – 27

$254 per night

Guest favorite

Condo in St. Augustine

4.86 out of 5 average rating, 288 reviews

Beaches are Open!!! St Augustine Oceanfront Condo

Beachers Lodge is right on the ocean! All rooms are disinfected after each stay as a precautionary measure to ensure a safe stay. Bedroom with king bed. New flooring, furniture, new shower, fresh paint, towels, linens! Kitchenette with oven, living room with queen sleeper sofa and dining area. Living room opens to ocean-front patio on first floor with limited ocean views. The unit is < 400 sq Ft total. 15 min from downtown.

Jun 17 – 24

$139 per night