Holiday Homes in Anastasia Island

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Our top choices for Anastasia Island holiday homes

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

Fall & Holiday Deals! NEWLY Remodeled Oceanside Townhouse!!! Pets Pools Bikes!
St. Augustine
10.0 out of 10, Exceptional, (11 reviews)
"Portside is the perfect location. Just steps from the pool and the beach! The host is incredibly responsive and provided us with all the info we needed for a wonderful week. The home is great, comfortable, and we had an amazing time. We definitely want to go back!"
United States
Anonymous traveller
The price is AU$577
includes taxes & fees
18 Nov - 19 Nov
Fall & Holiday Deals! NEWLY Remodeled Oceanside Townhouse!!! Pets Pools Bikes!

2. Tropical Pearl~Outdoor Oasis~Pets OK

Tropical Pearl~Outdoor Oasis~Pets OK
St. Augustine
8.0 out of 10, Very good, (4 reviews)
"Great getaway, close to the beach and restaurants. Pool is nice and you have great room to relax."
United States
LORIN A.
The price is AU$404
includes taxes & fees
15 Nov - 16 Nov
Tropical Pearl~Outdoor Oasis~Pets OK

3. Starfish - Screened Heated Pool, 6 Bedrooms, Near Downtown & Amphitheatre

Starfish - Screened Heated Pool, 6 Bedrooms, Near Downtown & Amphitheatre
St. Augustine
9.6 out of 10, Exceptional, (163 reviews)
"We really enjoyed our stay!! Nice open floor plan, plenty of space for our group, nice pool, quiet neighborhood, convenient to beach and downtown. Host prompt and very accommodating."
United States
Heather B.
The price is AU$734
includes taxes & fees
15 Nov - 16 Nov
Starfish - Screened Heated Pool, 6 Bedrooms, Near Downtown & Amphitheatre

4. 617 Sands Dr · 3 Bedroom Brand New House Near Beach | King Bed

617 Sands Dr · 3 Bedroom Brand New House Near Beach | King Bed
St. Augustine
10.0 out of 10, Exceptional, (12 reviews)
"Great stay in a great location for doing activities in St. Augustine! Easy checkin and checkout directions. Would definitely stay here again. "
United States
Pat B.
The price is AU$456
includes taxes & fees
15 Nov - 16 Nov
617 Sands Dr · 3 Bedroom Brand New House Near Beach | King Bed

5. Madeira Suite: Steps to Music, Markets & Florida Sun

Madeira Suite: Steps to Music, Markets & Florida Sun
St. Augustine
The price is AU$471
includes taxes & fees
16 Nov - 17 Nov
Madeira Suite: Steps to Music, Markets & Florida Sun

6. Madeira Cottage - Amphitheater

Madeira Cottage - Amphitheater
St. Augustine
The price is AU$513
includes taxes & fees
17 Nov - 18 Nov
Madeira Cottage - Amphitheater

7. Southwind - Screened Heated Pool, Near Beach, Downtown & Amphitheatre

Southwind - Screened Heated Pool, Near Beach, Downtown & Amphitheatre
St. Augustine
9.6 out of 10, Exceptional, (151 reviews)
"The home was beautiful. We enjoyed the pool and the proximity to everything."
United States
Kathy S.
The price is AU$734
includes taxes & fees
15 Nov - 16 Nov
Southwind - Screened Heated Pool, Near Beach, Downtown & Amphitheatre

8. Beautiful home by the Bridge of Lions

Beautiful home by the Bridge of Lions
Davis Shores
9.4 out of 10, Exceptional, (12 reviews)
"Very clean, nice area, convenient to tourist locations"
United States
Lori
The price is AU$367
includes taxes & fees
29 Nov - 30 Nov
Beautiful home by the Bridge of Lions

9. Lighthouse & Beach Retreat - Heated Pool, Near Beach, Downtown & Amphitheatre

Lighthouse & Beach Retreat - Heated Pool, Near Beach, Downtown & Amphitheatre
St Augustine
9.4 out of 10, Exceptional, (174 reviews)
"Great place ."
United States
Cathy
The price is AU$675
includes taxes & fees
17 Nov - 18 Nov
Lighthouse & Beach Retreat - Heated Pool, Near Beach, Downtown & Amphitheatre

10. Heated Cocktail Pool, Putt Putt, Bowling, BBQ, Nintendo, Ping Pong, Pet Friendly

Heated Cocktail Pool, Putt Putt, Bowling, BBQ, Nintendo, Ping Pong, Pet Friendly
St. Augustine
10.0 out of 10, Exceptional, (13 reviews)
"wonderful spot to stay, especially with kids! the property is fun, clean, and ready to host you! great supplies in the kitchen for cooking and comfy beds. our group of 4 moms and 4 children had a splendid 2 night stay!"
United States
Adrienne M.
The price is AU$692
includes taxes & fees
14 Dec - 15 Dec
Heated Cocktail Pool, Putt Putt, Bowling, BBQ, Nintendo, Ping Pong, Pet Friendly

11. St Augustine whole house w/ hot tub near downtown

St Augustine whole house w/ hot tub near downtown
St. Augustine
The price is AU$982
includes taxes & fees
14 Dec - 15 Dec
St Augustine whole house w/ hot tub near downtown

12. Seascape 2

Seascape 2
3.0 star property
St. Augustine
The price is AU$742
includes taxes & fees
8 Dec - 9 Dec
Seascape 2

13. Sail Away - Heated Pool, Walk to Amphitheatre, Pet Friendly, Near Beach

Sail Away - Heated Pool, Walk to Amphitheatre, Pet Friendly, Near Beach
St. Augustine
10.0 out of 10, Exceptional, (82 reviews)
"Perfect place for a girlfriend weekend! Host was accommodating, plenty of room for 8 women. Loved the pool and proximity to the beach and The Amp."
United States
Julie
The price is AU$711
includes taxes & fees
17 Nov - 18 Nov
Sail Away - Heated Pool, Walk to Amphitheatre, Pet Friendly, Near Beach

14. Summer Breeze - Private Pool, Heated Spa, Near Beach, Downtown & Amphitheatre

Summer Breeze - Private Pool, Heated Spa, Near Beach, Downtown & Amphitheatre
St. Augustine
9.8 out of 10, Exceptional, (53 reviews)
"The property was beautiful and super clean! We had a wonderful vacation!!"
United States
Catina S.
The price is AU$734
includes taxes & fees
15 Nov - 16 Nov
Summer Breeze - Private Pool, Heated Spa, Near Beach, Downtown & Amphitheatre

15. Grandview - Heated Pool, 6BR, Near Beach, Downtown & Amphitheatre

Grandview - Heated Pool, 6BR, Near Beach, Downtown & Amphitheatre
Saint Augustine
9.6 out of 10, Exceptional, (213 reviews)
"Great property and wonderful experience."
United States
Nicole A.
The price is AU$731
includes taxes & fees
17 Nov - 18 Nov
Grandview - Heated Pool, 6BR, Near Beach, Downtown & Amphitheatre

16. Walk Downtown • Hot Tub • EV Charger • Fenced Yard

Walk Downtown • Hot Tub • EV Charger • Fenced Yard
Davis Shores
10.0 out of 10, Exceptional, (6 reviews)
"The area was quiet and the house is well furnished with everything you would need to cook. The house very clean and smelled great. "
United States
Beck M.
The price is AU$611
includes taxes & fees
16 Nov - 17 Nov
Walk Downtown • Hot Tub • EV Charger • Fenced Yard

17. Spacious cozy home between downtown & the beach!

Spacious cozy home between downtown & the beach!
Davis Shores
10.0 out of 10, Exceptional, (21 reviews)
"This host was extremely helpful and offered to assist every step of the way. The condo was very nice and clean and in a perfect location to walk downtown or drive to the beac or other restaurants. Perfect stay! "
United States
Keith U.
The price is AU$339
includes taxes & fees
18 Nov - 19 Nov
Spacious cozy home between downtown & the beach!

18. Anastasia Island Villa Duplex Single Level EV

Anastasia Island Villa Duplex Single Level EV
Davis Shores
10.0 out of 10, Exceptional, (2 reviews)
"This house is amazing. Close to beaches and restaurants. Very nice quiet neighborhood."
United States
louise c.
The price is AU$533
includes taxes & fees
15 Nov - 16 Nov
Anastasia Island Villa Duplex Single Level EV

19. Sea Turtle - Heated Pool, 5 King Beds, Near Amphitheatre & Downtown

Sea Turtle - Heated Pool, 5 King Beds, Near Amphitheatre & Downtown
St. Augustine
9.6 out of 10, Exceptional, (85 reviews)
"The hosts were very friendly and replied quickly."
United States
Danielle J.
The price is AU$739
includes taxes & fees
17 Nov - 18 Nov
Sea Turtle - Heated Pool, 5 King Beds, Near Amphitheatre & Downtown

20. Charming 3-bedroom house in amazing St. Augustine; quiet, clean and comfortable

Charming 3-bedroom house in amazing St. Augustine; quiet, clean and comfortable
Davis Shores
10.0 out of 10, Exceptional, (46 reviews)
"Very cute and clean house in a very convenient area. Would stay there again"
United States
Chrissy H.
The price is AU$619
includes taxes & fees
16 Nov - 17 Nov
Charming 3-bedroom house in amazing St. Augustine; quiet, clean and comfortable
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.

Learn more about Anastasia Island

Discover the seaside area of Anastasia Island—beaches, natural beauty and top sights like St. Augustine Beach.

A wooden bridge over water with a lighthouse in the background.

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