Anastasia Island holiday rentals

We found 4,899 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Anastasia Island

Showing deals for:25 Dec - 1 Jan

Living area
Pool
Terrace/patio
Living area
Exceptional
(10 reviews)

Backyard Paradise / Pool, Fire Pit, Games, & Kayaks on Canal Front near Beach

St. Augustine

8% off
AU$8,872
for 7 nights, 1 home
AU$1,267 per night
includes taxes & fees
Backyard Paradise / Pool, Fire Pit, Games, & Kayaks on Canal Front near Beach
Living area
Interior
Interior
Pool
Exceptional
(65 reviews)

Beach Condo Newly Renovated

St. Augustine

8% off
AU$3,562
for 7 nights, 1 apartment
AU$509 per night
includes taxes & fees
Beach Condo Newly Renovated
Private kitchen
Property grounds
Living area
Dining
Exceptional
(9 reviews)

Fall & Holiday Deals! NEWLY Remodeled Oceanside Townhouse!!! Pets Pools Bikes!

St. Augustine

6% off
AU$3,729
for 7 nights, 1 home
AU$533 per night
includes taxes & fees
Fall & Holiday Deals! NEWLY Remodeled Oceanside Townhouse!!! Pets Pools Bikes!
Living area
Living area
Dining
Property grounds
Exceptional
(30 reviews)

St Augustine Beach Condo steps from the beach!

St. Augustine

8% off
AU$3,821
for 7 nights, 1 apartment
AU$546 per night
includes taxes & fees
St Augustine Beach Condo steps from the beach!
Fireplace
Night time View of deck
Living Room
Exterior
Exceptional
(144 reviews)

Sunburst Cottage Beachside

St. Augustine

8% off
AU$2,620
for 7 nights, 1 home
AU$374 per night
includes taxes & fees
Sunburst Cottage Beachside
Room
Beach
Heated pool
Enjoy the amazing 180-degree ocean view that stretches on for miles and miles.
Exceptional
(116 reviews)

Private Ocean Front Balcony with Unbeatable Top Floor View & Heated Pool

St. Augustine

8% off
AU$2,861
for 7 nights, 1 apartment
AU$409 per night
includes taxes & fees
Private Ocean Front Balcony with Unbeatable Top Floor View & Heated Pool
Interior
Beach
Dining
Living area
Wonderful
(19 reviews)

PET-FRIENDLY BEACH HOUSE WITH HOT TUB JUST FIVE MIN WALK FROM BEACH ACCESS !

St. Augustine

8% off
AU$4,104
for 7 nights, 1 home
AU$586 per night
includes taxes & fees
PET-FRIENDLY BEACH HOUSE WITH HOT TUB JUST FIVE MIN WALK FROM BEACH ACCESS !
Property grounds
Property grounds
Private kitchen
Interior
Excellent
(17 reviews)

Coquina A202: Seaside Oasis Beach front Condo

St. Augustine

8% off
AU$2,436
for 7 nights, 1 apartment
AU$348 per night
includes taxes & fees
Coquina A202: Seaside Oasis Beach front Condo
Proximity to the Atlantic Ocean and beach entry pool
We love Ocean Villas!
Welcome in!
Pool #2 -heated in winter
Exceptional
(82 reviews)

Florida Daydreamin!—close to downtown & oceanviews

St. Augustine

8% off
AU$3,958
for 7 nights, 1 apartment
AU$565 per night
includes taxes & fees
Florida Daydreamin!—close to downtown & oceanviews
Lounge in the sun or cool off in the pool.
Relax in our screened in lanai and enjoy the in ground pool.
Cook dinner in your fully stocked kitchen.
Get comfy in our living room with seats for everyone.
Exceptional
(56 reviews)

Relax in this pool home close to multiple beaches and tourist attractions!

Palm Coast

7% off
AU$2,554
for 7 nights, 1 home
AU$365 per night
includes taxes & fees
Relax in this pool home close to multiple beaches and tourist attractions!
Dining
Private kitchen
Exterior
Living area
Exceptional
(7 reviews)

Private Pool Steps to Beach Walk to Restaurants

St. Augustine

8% off
AU$7,147
for 7 nights, 1 home
AU$1,021 per night
includes taxes & fees
Private Pool Steps to Beach Walk to Restaurants
Living area
Property grounds
Interior
Private kitchen
Exceptional
(17 reviews)

Renovated 2-bedroom condo in charming Crescent Beach, St. Augustine, FL

St. Augustine

8% off
AU$4,048
for 7 nights, 1 apartment
AU$578 per night
includes taxes & fees
Renovated 2-bedroom condo in charming Crescent Beach, St. Augustine, FL
Bright, fully updated eat-in kitchen featuring a spacious breakfast bar with barstools, modern lighting, stainless steel appliances, and an open layout perfect for cooking and gathering.
Beautiful zero-entry oceanfront pool surrounded by palm trees, lounge chairs, and sweeping shoreline views, offering a true resort-style experience.
Enjoy an airy, modern living area with updated furnishings, coastal accents, and an inviting layout perfect for lounging with family and friends.
Chef-Friendly Kitchen & Cozy Living Room View: flat-top range, updated appliances, and stylish lighting create the perfect space to cook, dine, and gather.
Exceptional
(21 reviews)

Resort Condo w/Beach Access, Balcony, Lagoon Pool

St. Augustine

6% off
AU$6,096
for 7 nights, 1 apartment
AU$871 per night
includes taxes & fees
Resort Condo w/Beach Access, Balcony, Lagoon Pool
Location, location, location! Steps to beach & pool. Amazing views!
beach goes on for miles!
Off your private balcony, you can see the quiet pool & awe inspiring ocean view.
The intracoastal waterway right off of downtown St. Augustine.
Exceptional
(64 reviews)

Oceanfront St Augustine Beach Condo/ Steps to Pool + Beach

St. Augustine

8% off
AU$3,298
for 7 nights, 1 apartment
AU$471 per night
includes taxes & fees
Oceanfront St Augustine Beach Condo/ Steps to Pool + Beach
Private kitchen
Terrace/patio
Property grounds
Property grounds
Exceptional
(95 reviews)

Oceanview Condo: Beach Access, Pool, Pet-Friendly - 15min to Downtown!

St. Augustine

8% off
AU$3,705
for 7 nights, 1 apartment
AU$529 per night
includes taxes & fees
Oceanview Condo: Beach Access, Pool, Pet-Friendly - 15min to Downtown!
Dining
Private kitchen
Living area
Interior
Exceptional
(95 reviews)

Newly Remodeled Oceanfront Condo: 2 Bed, 2 Bath, w/a Beautiful View of the Ocean

St. Augustine

8% off
AU$2,210
for 7 nights, 1 apartment
AU$316 per night
includes taxes & fees
Newly Remodeled Oceanfront Condo: 2 Bed, 2 Bath, w/a Beautiful View of the Ocean
Interior
Private kitchen
Room
Pool
Exceptional
(7 reviews)

Tradewinds Condominium Top Floor - Ocean View Condo #113

St. Augustine

8% off
AU$2,572
for 7 nights, 1 apartment
AU$367 per night
includes taxes & fees
Tradewinds Condominium Top Floor - Ocean View Condo #113
There is a second bathroom sink and vanity area.
The pool door closes in cold or windy weather, so there's always a place to swim
The beautiful boardwalk to the beach.
Cozy up with a glass of wine or cup of coffee after a day on the beach.
Exceptional
(21 reviews)

Ocean Gallery “Butler Beach Bungalow”, a 1 bdrm coastal oasis

St. Augustine

6% off
AU$3,193
for 7 nights, 1 apartment
AU$456 per night
includes taxes & fees
Ocean Gallery “Butler Beach Bungalow”, a 1 bdrm coastal oasis
Coastal Dreams St. Augustine Beach Condo - 3rd Floor Garden, Pool & Ocean View
Aerial of Coastal Dreams St. Augustine Beach Condo just steps from the beach.
Bright Living Room with Ocean View Balcony
Comfortable coastal living decor.
Coastal Dreams St. Augustine Beach Condo - Well Manicured Grounds View
Exceptional
(10 reviews)

Ocean View Condo Steps to St. Augustine Beach - 2 Pools

St. Augustine

8% off
AU$4,243
for 7 nights, 1 apartment
AU$606 per night
includes taxes & fees
Ocean View Condo Steps to St. Augustine Beach - 2 Pools
Breakfast nook goals.
Flow through kitchen, dining area, living room.
Sunshine by day, chill vibes by night.
Kitchen essentials.
Exceptional
(26 reviews)

Spacious Remodel|Bikes|Steps to Beach

St. Augustine

8% off
AU$6,255
for 7 nights, 1 apartment
AU$894 per night
includes taxes & fees
Spacious Remodel|Bikes|Steps to Beach
Dining area with a wooden table set for four, perfect for meals and gatherings.
Entertainment center with a flat-screen TV and decorative shelving.
A beach access path surrounded by greenery, perfect for a quiet stroll with open views.
Clean and functional sink area, perfect for meal prep and easy cleanup.
Exceptional
(8 reviews)

Balcony Beach View | Steps to Beach | Pools | Hot Tubs | Pickleball | Short Walk to Local Restaurants

St. Augustine

9% off
AU$5,467
for 7 nights, 1 apartment
AU$781 per night
includes taxes & fees
Balcony Beach View | Steps to Beach | Pools | Hot Tubs | Pickleball | Short Walk to Local Restaurants
Private kitchen
Living area
Beach
Private kitchen
Exceptional
(43 reviews)

Fall & Holiday DEALS! Oceanfront Luxury Townhouse with Kayak 2 Pools & 2 Bikes!

St. Augustine

5% off
AU$4,805
for 7 nights, 1 home
AU$686 per night
includes taxes & fees
Fall & Holiday DEALS! Oceanfront Luxury Townhouse with Kayak 2 Pools & 2 Bikes!
Living room
Property grounds
Property grounds
Master bedroom has lots of closet space
Exceptional
(136 reviews)

Oceanview, Pool Side, Townhome

St. Augustine

8% off
AU$2,446
for 7 nights, 1 home
AU$349 per night
includes taxes & fees
Oceanview, Pool Side, Townhome
Exterior
Pool
Property grounds
Living area
Exceptional
(7 reviews)

Sandy Sea Turtle Pet-Friendly Condo w/ Ocean Views

St. Augustine

13% off
AU$3,923
for 7 nights, 1 apartment
AU$560 per night
includes taxes & fees
Sandy Sea Turtle Pet-Friendly Condo w/ Ocean Views
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

The friendly city of Anastasia Island awaits you

The beaches and wildlife provide a pleasant backdrop to your holiday home in Anastasia Island. This welcoming city attracts visitors thanks to its bird watching and camping. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Anastasia Island

Do you want to discover attractions to visit during your stay? Venture out of your cosy holiday rental and check out everything that makes Anastasia Island a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • St. Augustine Alligator Farm Zoological Park (2.1 mi / 3.3 km)
  • San Sebastian Winery (3.6 mi / 5.8 km)
  • World Golf Village (14.9 mi / 24 km)
  • World Golf Village - King & Bear Golf Course (16 mi / 25.8 km)
  • Ocean Course at Hammock Beach Golf Resort (18 mi / 29 km)
  • Hammock Beach Ocean Course (18.1 mi / 29.1 km)

Exploring the beaches and other natural features in Anastasia Island

Travellers enjoy Anastasia Island for its seaside and island views. Whether you're an adventurous traveller or just want to take in the scenery, Anastasia Island is a great place to get outside. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • St. Augustine Beach (2.1 mi / 3.3 km)
  • Butler Beach (3.1 mi / 4.9 km)
  • Ponce de Leon's Fountain of Youth Archaeological Park (4.3 mi / 6.9 km)
  • Butler Beach State Park (4.6 mi / 7.4 km)
  • Vilano Beach (4.9 mi / 7.9 km)
  • Matanzas Inlet (10.7 mi / 17.2 km)

Frequently asked questions

What is the most popular type of holiday home accommodation in Anastasia Island?
The most popular types of holiday homes in Anastasia Island are condos. Hoping for something different? Stayz has plenty of options to match the needs of our guests, so you'll see holiday properties in loads of shapes and sizes. The perfect fit is ready and waiting for you — find yours today.
How much does it cost to rent a holiday home in Anastasia Island?
Length of stay, property type and season are some factors that can influence the price of a holiday home. Simply add your dates of travel to find your dream escape. From comfy cottages to expansive luxury villas, all Stayz holiday homes offer unbeatable value.
How much does it cost to rent a beach house in Anastasia Island?
Prices for beach houses in Anastasia Island can differ depending on the style and size of the property and when you're travelling. All you have to do is enter your travel dates into Stayz and how many guests to view your options and prices. From there you can use the filters to tailor your search by ratings, nearby activities, amenities and more.
What are popular home amenities in Anastasia Island?
When it comes to home amenities that people look for in Anastasia Island, tennis, a nearby waterfront and a water view are the most popular. With Stayz holiday homes, you'll have options to match your taste and style, whether you're travelling with relatives, friends or even pets.
Can I find two-bedroom holiday homes in Anastasia Island?
Anastasia Island has 1 ,352 two-bedroom holiday properties to pick from. Book a holiday home with all the comfort and privacy you need at a price you'll love on Stayz.
Are there holiday homes with WiFi in Anastasia Island?
Anastasia Island has 627 holiday homes with WiFi, so you can stay connected during your trip. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming TV shows with the family to catching up on social media, these Stayz homes make it a cinch to go online.
How old do you have to be to rent a holiday home in Anastasia Island?
The minimum required age is typically 16, 18 or 21. It can differ from property to property on Stayz, so check the rules of your preferred Anastasia Island holiday home before booking your escape.
How long can I rent a holiday home in Anastasia Island for?
The amount of time you can rent an Anastasia Island holiday home for varies depending on the property. Simply enter your travel dates to see available options that offer long-term stays. They include all you require to make your extended getaway more comfortable and enjoyable, such as laundries and air conditioning. Some properties might also offer weekly or monthly discounted prices, so you can stick around for longer for less.

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