
Anastasia Island Holiday Rentals
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
Our top choices for Anastasia Island holiday rentals


3. Walk to St Aug Beach or Explore the Oldest City- 2 Bedroom villa with hot tub
Walk to St Aug Beach or Explore the Oldest City- 2 Bedroom villa with hot tub
4. Ocean Front 2 Bed 2 Bath With Ocean Front Pool, walk to restaurants
Ocean Front 2 Bed 2 Bath With Ocean Front Pool, walk to restaurants
5. Amazing Ocean Views, Steps to Beach, Walk to Restaurants, Shops, and Pier! $300 in Free Tickets!
Amazing Ocean Views, Steps to Beach, Walk to Restaurants, Shops, and Pier! $300 in Free Tickets!
6. St. Augustine Beach Community
St. Augustine Beach Community
7. Steps to Beach! Suite Bedrooms, Walk to Shops and Pier, Minutes to Downtown, $300 in Free Tickets!
Steps to Beach! Suite Bedrooms, Walk to Shops and Pier, Minutes to Downtown, $300 in Free Tickets!
8. Island Suite l Walk to Downtown!
Island Suite l Walk to Downtown!Find holiday rentals that suit your style
Top Anastasia Island Hotel Reviews

Guy Harvey Resort on St Augustine Beach
Find out more about Anastasia Island
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Anastasia Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Anastasia Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Anastasia Island. Seeing all the best attractions is bound to make you fall in love with Anastasia Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Anastasia Island short-term rentals, that won’t be hard to do.
Explore a world of travel with Expedia
- Winery Hotels in St. Augustine
- Luxury Hotels in St. Augustine
- Romantic Hotels in St. Augustine
- Pet Friendly Hotels in St. Augustine
- Hotels with Pool in Crescent Beach
- Lgbt Welcoming Hotels in Downtown Historic District
- Luxury Hotels in Vilano Beach
- Pet Friendly Hotels in St. Augustine Historic District
- Luxury Hotels in Anastasia Island
- Pet Friendly Hotels in Palm Coast
- Beach Hotels in Palm Coast
- Historic Hotels in Ponte Vedra Beach
- Cheap Hotels in Butler Beach
- Marineland Hotels
- Sawgrass Hotels
- Downtown Historic District Hotels
- Hotels near TPC Sawgrass
- Hastings Hotels
- Crescent Beach Hotels
- St. Augustine Hotels
- St. Augustine Historic District Hotels
- St. Augustine South Hotels
- St. Augustine Beach Hotels
- Hotels near Santa Maria Del Mar Catholic Church
- Hotels near Oak Bridge Club at Sawgrass
- Hotels near Spring Park
- St. Johns Hotels
- Saint Augustine Shores Hotels
- Green Cove Springs Hotels
- Vilano Beach Hotels
- Hotels near St. Augustine Beach
- San Mateo Hotels
- Hotels near St. George Street
- Palm Coast Hotels
- Hotels near Beverly Beach
- Butler Beach Hotels
- Ponte Vedra Hotels
- Whites Ford Hotels
- Condo Rentals in Palm Coast
- Villas in Palm Coast
- Apartments in Palm Coast
- Houseboats in Clay County
- Holiday Homes in Ponte Vedra Beach
- Resort in Anastasia Island
- B&B in Anastasia Island
- Holiday Homes in Anastasia Island
- B&B in St. Augustine
- Motels in St. Augustine
- Apartments in St. Augustine
- Motels in St. Johns
- B&B in Green Cove Springs
- Marriott Hotels & Resorts in Vilano Beach
- Flights from Ocala (OCF) to St. Augustine (UST)
- Flights from Copenhagen (CPH) to St. Augustine (UST)
- Flights from Boca Raton (BCT) to St. Augustine (UST)
- Flights from Morgantown (MGW) to St. Augustine (UST)
- Flights from Greensboro (GSO) to St. Augustine (UST)
- Flights from Galveston (GLS) to St. Augustine (UST)
- Flights from Grand Forks (GFK) to St. Augustine (UST)
- Flights from Los Angeles (LAX) to St. Augustine (UST)
- Flights from Youngstown (YNG) to St. Augustine (UST)
- Flights from Miami (MIA) to St. Augustine (UST)
- Flights from Liberia (LIR) to St. Augustine (UST)
- Flights from Louisville (SDF) to St. Augustine (UST)
- Flights to St. Augustine
- Flights to Flagler Beach
- Flights from Flagler Beach
- Flights from St. Augustine
- Romantic Holiday Packages Anastasia Island
- Visit Latrium
- Visit Butler Beach
- Visit St. Augustine
- Visit Ponte Vedra
- Bronson-Mulholland House
- Castillo de San Marcos National Monument
- Fort Mose Historic State Park
- St. George Street
- Palm Coast Holidays
- Gonzalez-Alvarez House
- Ponce de Leon's Fountain of Youth Archaeological Park
- World Golf Village - King & Bear Golf Course
- The Champions Club at Julington Creek
- Flagler College
- Anastasia Island Mini-Golf
- St. Augustine Alligator Farm Zoological Park
- Whites Ford Holidays
- Jungle Hut Road Park
- St. Augustine Holidays
- St. John's Golf and Country Club
- Bimini Road

















































































