Waterfront holiday rentals in Anastasia Island

Waterfront suite, Dogs are cool no pet fee

Newly remodeled, waterfront suite. See dolphins, Osprey, and more frolicking in our amazing backyard overlooking the Matanzas river, & did I mention the breathtaking sunsets. 6 minute drive to Crescent Beach, one of the most beautiful beaches in Florida. Close to downtown historic St Augustine 20 min, Amphitheater concert venue is 15 min. Private entrance, full on suite bath, fishing dock, kitchenette, pool, ample free parking & internet included. Professional pool cleaning is on Mondays.

Fan Fave Waterfront: Lion’s Bridge & Old Town View

Our reviews set us apart. WE'D LOVE TO HOST YOU! Walk across the Bridge of Lions to downtown St. Augustine with amazing restaurants and attractions. A short walk to historic downtown, less than 1 mile to Castillo de San Marcos fort. Anastasia State Park Beach, the Alligator Farm and lighthouse are less than two miles away. Several restaurants and bars only a few blocks away. Whether going to the old fort or Flagler College, our home provides a great base for exploring an amazing part of Florida!

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, just steps to the beach. 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, 10 minutes from historic downtown. Family friendly resort community w/ pools, tennis, pickleball and bocce’ ball courts. Beach chairs & towels provided.

Surfside Six, Direct Ocean Front, Ampitheatre

BEST spot to watch the sunrise, (and moonrise) on St Augustine Beach from every room in the condo and from the two direct beach front balconies! CORNER UNIT! TOP FLOOR! One balcony off the upstairs corner primary bedroom suite, walk in closet and ocean view King size beds in each bedroom. Anytime is a good time to be on the beach in St. Augustine! Winter Spring, Summer, or Fall! Besides being steps from the beach there are plenty of local eateries,great food, live music within walking distance.

DesignerHGTV•Pool•Walk/Bike to Attractions•Island

Off Street Parking 3 Min Drive/ 15 Min Walk to Historic Downtown 2 Min Drive to the St Augustine Amphitheater 2 Min Drive to Anastasia State Park Beach 1 Min Drive to Anastasia Fitness Club/Suana-Steam Rm/Pool Looking to get away from the hustle & bustle of the city? This designer home with an amazing pool is the perfect place to recharge. Downtown & the scenic beaches in Anastasia State Park are just a minutes away. With spacious living & modern amenities, the Home offers maximum comfort

Oceanfront Bliss: Beach Views

Welcome to your oceanfront oasis in St. Augustine Beach! Featuring a spacious king suite, a comfy queen bedroom with twin trundle, and a sleeper sofa, it offers stunning sunrise views, a modern boho surfer’s vibe, and an updated chef’s kitchen. Steps to one of the best beaches in the east coast and walk to lively local restaurants and bars, it’s minutes to St. Augustine’s Nights of Lights, Amphitheater, and more! This isn’t just a vacation rental—it’s your personal seaside escape. Book now!

Funshine - Vacation on a 43' Gulfstar Yacht

A unique, memorable place, anything but ordinary. Try living the boating lifestyle on a classic and quaint vintage 43 foot Gulf Star yacht. Only 1.2 miles to the historical St. Augustine Bayfront and less than 10 miles to many of our gorgeous beaches. This 2-bedroom 1.5 bath beauty allows you to experience a life on a live-a-board. You will vacation within a reasonable walking distance to many of the attractions in St Augustine, a winery, distillery, several museums, many restaurants.

Perfect location 2 Bedroom Private Hot Tub

Couples Retreat Near Downtown St. Augustine. 0.5 miles from the Bridge of Lions. Enjoy a secluded courtyard, relaxing water fountain, and new 4-person hot tub. Wine down and watch the sunset in a peaceful setting after a exploring. Off-street parking is included. Restaurants, bars, coffee shops, and local favorites are only steps away. Perfect for a romantic getaway, weekend escape, or special occasion. Special requests and accommodations are available to help make your stay unforgettable.

Windjammer 208, Oceanfront and Riverview

Beautiful newly renovated condo in Crescent Beach, with spectacular views of the beach as well as the Matanzas river. Coffee while watching sunrise on your east balcony and wine while watching the sunset on the Windjammer fishing pier, while dolphins are entertaining you. 10 miles from historic St Augustine, a couple of miles from Marine land and a variety of restaurants close by. Flatscreen TV'S in all the rooms for your convenience when the weather does not allow you on the beach.

On the Canal, by Beach, Kayaks, Dock, Fishing

> Canal front home > One small dog OK *with fee > Walkable to the beach and the intracoastal > Neighborhood beach walkover > Fully equipped and stocked kitchen > Extremely safe neighborhood > Private back porch w BBQ, overlooking the historic Treasure Beach canals > Fishing poles, 2 kayaks w/oars, 1 SUP, some beach gear > Fishing is welcome in the canal behind the house! > Books and games provided > Private parking > Washer Dryer > Keurig > 3 days of supplies (TP, trash bags, etc.)

St Augustine Beachside Home - Walk to Beach

Relax at our St Augustine Canal-front getaway! Great family destination just 15 min. to Historic Downtown St Augustine. Neighborhood features PRIVATE Beach Access with about a 10 minute walk to the Beach. Boating and Fishing at your Fingertips with private, over-the-water dock and ramp to floating dock where you can tie up your own boat/kayak/jet skis. The perfect end to your beachside dream day will be watching the sunset while on your private dock.

Boutique Beachside condo with easy access to beach

Skipper’s Hideaway is a charming beachside retreat that sleeps up to six, with a king bed, queen sofa pull-out, and twin daybed with trundle. Located on the ground floor for easy access, the condo offers a partial Atlantic Ocean view from the living room window. Just steps from Crescent Beach, this peaceful spot is perfect for relaxing. For more excitement, the shops, restaurants, and nightlife of downtown St. Augustine are only a 15-minute drive away.