A wooden pier extending into calm water at sunset.

Anastasia Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Anastasia Island vacation rentals

The Beach Club by Coolvacay

The Beach Club by Coolvacay
3.5 star property
St. Augustine
9.8 out of 10, Exceptional, (13 reviews)
"Awesome spot"
United States
Sherman
The price is CA $275
CA $401 total
includes taxes & fees
Jul 8 - Jul 9
The Beach Club by Coolvacay

215 Beachers Lodge Direct Ocean Front Crescent Beach One Bedroom Condo

215 Beachers Lodge Direct Ocean Front Crescent Beach One Bedroom Condo
Crescent Beach
9.0 out of 10, Wonderful, (63 reviews)
"Great place to stay on the beach"
United States
Jim S.
The price is CA $195
CA $411 total
includes taxes & fees
Jul 9 - Jul 10
215 Beachers Lodge Direct Ocean Front Crescent Beach One Bedroom Condo

Coastal Charm Getaway

Coastal Charm Getaway
Butler Beach
9.2 out of 10, Wonderful, (21 reviews)
"Very pet friendly and a comfortable environment. We enjoyed the stay at this safe property immensely! Eould book again!"
United States
Deb W.
The price is CA $216
CA $522 total
includes taxes & fees
Jul 12 - Jul 13
Coastal Charm Getaway

Beacher's Lodge Studio Suite with onsite front desk and staff

Beacher's Lodge Studio Suite with onsite front desk and staff
Crescent Beach
9.0 out of 10, Wonderful, (90 reviews)
"Great location, just steps from the beach and a short drive to downtown St Augustine. Very clean and the front desk people were super sweet and helpful. "
United States
Terri W.
The price is CA $241
CA $302 total
includes taxes & fees
Jul 12 - Jul 13
Beacher's Lodge Studio Suite with onsite front desk and staff

Oceanfront 3BR,Game Room, Crescent Beach Retreat!

Oceanfront 3BR,Game Room, Crescent Beach Retreat!
Crescent Beach
9.6 out of 10, Exceptional, (39 reviews)
"Great house and location! Kids loved the retro video games and my husband and I loved the view. "
United States
Stefanie S.
The price is CA $255
CA $762 total
includes taxes & fees
Jul 2 - Jul 3
Oceanfront 3BR,Game Room, Crescent Beach Retreat!

Direct Ocean Front Condo With Heated Pool Located Directly on the Ocean

Direct Ocean Front Condo With Heated Pool Located Directly on the Ocean
Crescent Beach
9.4 out of 10, Exceptional, (187 reviews)
"Great location, easy checkin, had everything we needed"
United States
William M.
The price is CA $183
CA $389 total
includes taxes & fees
Jul 17 - Jul 18
Direct Ocean Front Condo With Heated Pool Located Directly on the Ocean

Waterfront suite, Dogs are cool! no pet fee!

Waterfront suite, Dogs are cool! no pet fee!
Butler Beach
10.0 out of 10, Exceptional, (24 reviews)
"Nice place and easy communication with the host"
United States
Emily H.
The price is CA $160
CA $206 total
includes taxes & fees
Jul 12 - Jul 13
Waterfront suite, Dogs are cool! no pet fee!

3 minute walk to the beach, outdoor shower, pet friendly, close to downtown

3 minute walk to the beach, outdoor shower, pet friendly, close to downtown
Butler Beach
9.8 out of 10, Exceptional, (27 reviews)
"Clean, well appointed space for family and pets. Consistent and helpful communication from owner. Close to Beach and shopping. "
United States
Amy
3 minute walk to the beach, outdoor shower, pet friendly, close to downtown

This vacation home is the embodiment of Comfort, Conveniences and Location.

This vacation home is the embodiment of Comfort, Conveniences and Location.
Butler Beach
9.6 out of 10, Exceptional, (113 reviews)
"Great place to stay. Great location to go anywhere and nice being so close to the beach!"
United States
Laura M.
The price is CA $214
CA $533 total
includes taxes & fees
Jul 6 - Jul 7
This vacation home is the embodiment of Comfort, Conveniences and Location.

Oceans 13 Unit A

Oceans 13 Unit A
3.0 star property
St. Augustine
10.0 out of 10, Exceptional, (4 reviews)
"Love that you are walking distance to restaurants and beach will be back soon"
United States
Belinda
The price is CA $241
CA $594 total
includes taxes & fees
Jul 16 - Jul 17
Oceans 13 Unit A

Ocean Front 1 Bed room Condo With Heated Pool just outside the balcony Unit 101

Ocean Front 1 Bed room Condo With Heated Pool just outside the balcony Unit 101
Crescent Beach
9.4 out of 10, Exceptional, (130 reviews)
"Great location and the accommodations were good!"
United States
Julie L.
The price is CA $156
CA $355 total
includes taxes & fees
Jul 16 - Jul 17
Ocean Front 1 Bed room Condo With Heated Pool just outside the balcony Unit 101

Oceanfront Patio Suite with daily housekeeping and welcoming front desk staff

Oceanfront Patio Suite with daily housekeeping and welcoming front desk staff
Crescent Beach
8.8 out of 10, Excellent, (9 reviews)
"Nice location (right on the ocean). Employees were all very friendly, and helpful. The dog walk area was a little out of the way. The coffee in the condo was very weak. The television in the living room was very nice. We asked for maintenance to lubricate the sliding door to the patio, and they responded very quickly."
United States
Scott B.
The price is CA $298
CA $372 total
includes taxes & fees
Jul 6 - Jul 7
Oceanfront Patio Suite with daily housekeeping and welcoming front desk staff

Home away from home! Short walk to the beach and more! Prime Location!

Home away from home! Short walk to the beach and more! Prime Location!
St. Augustine
10.0 out of 10, Exceptional, (49 reviews)
"Lovely place, contrained everything needed for your stay. Excellent location in proximity to the beach and conveniences. Very good value."
United States
Diana
The price is CA $223
CA $495 total
includes taxes & fees
Jul 6 - Jul 7
Home away from home! Short walk to the beach and more! Prime Location!

Island Suite l Walk to Downtown!

Island Suite l Walk to Downtown!
Davis Shores
10.0 out of 10, Exceptional, (38 reviews)
"Great place, close to attractions and owners are very nice! Definitely would stay again! "
United States
Regina S.
The price is CA $156
CA $544 total
includes taxes & fees
Jul 2 - Jul 3
Island Suite l Walk to Downtown!

Center of Saint Augustine Beach

Center of Saint Augustine Beach
St. Augustine
9.6 out of 10, Exceptional, (34 reviews)
"Great location, beautiful apartment, so much more homey than staying in a hotel. We hope to stay again in the future!"
United States
Thomas C.
The price is CA $270
CA $652 total
includes taxes & fees
Jul 14 - Jul 15
Center of Saint Augustine Beach

1 Bedroom Ocean Side Condo w/ Heated Pool and Private Walkway to the beach b24

1 Bedroom Ocean Side Condo w/ Heated Pool and Private Walkway to the beach b24
St. Augustine
9.6 out of 10, Exceptional, (202 reviews)
"Very clean, great hosts"
United States
Angela
The price is CA $151
CA $367 total
includes taxes & fees
Jul 19 - Jul 20
1 Bedroom Ocean Side Condo w/ Heated Pool and Private Walkway to the beach b24

St. Augustine Beach, Florida: 2 bed/2 bath (Beachfront PetFriendly Free Parking)

St. Augustine Beach, Florida: 2 bed/2 bath (Beachfront PetFriendly Free Parking)
Butler Beach
10.0 out of 10, Exceptional, (23 reviews)
"This location was awesome! It was a very short walk to the private access beach which was great! We definitely enjoyed our stay."
United States
Juli M.
The price is CA $204
CA $614 total
includes taxes & fees
Jul 9 - Jul 10
St. Augustine Beach, Florida: 2 bed/2 bath (Beachfront PetFriendly Free Parking)

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!
Saint Augustine
9.8 out of 10, Exceptional, (134 reviews)
"Great location! "
United States
Chris H.
The price is CA $211
CA $674 total
includes taxes & fees
Jul 16 - Jul 17
Steps to Beach! Suite Bedrooms, Walk to Shops and Pier, Minutes to Downtown, $300 in Free Tickets!

Beacher's Oceanfront Balcony Suite with onsite Front Desk and Staff

Beacher's Oceanfront Balcony Suite with onsite Front Desk and Staff
Crescent Beach
9.4 out of 10, Exceptional, (18 reviews)
"Beautiful view of the Atlantic!! Great location!"
United States
Beverly P.
The price is CA $319
CA $402 total
includes taxes & fees
Jul 22 - Jul 23
Beacher's Oceanfront Balcony Suite with onsite Front Desk and Staff

Beach Villa ~ Pet Friendly ~ Fenced Yard ~ Steps to the Beach!!!

Beach Villa ~ Pet Friendly ~ Fenced Yard ~ Steps to the Beach!!!
Saint Augustine
9.8 out of 10, Exceptional, (79 reviews)
"Nice property, great location "
United States
Jason G.
The price is CA $222
CA $833 total
includes taxes & fees
Jul 13 - Jul 14
Beach Villa ~ Pet Friendly ~ Fenced Yard ~ Steps to the Beach!!!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Anastasia Island Hotel Reviews

Find out more about Anastasia Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia