Holiday Homes in Anastasia Island

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Our top choices for Anastasia Island holiday homes

1. 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 €243
includes taxes & fees
15 Nov - 16 Nov
Tropical Pearl~Outdoor Oasis~Pets OK

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

Madeira Suite: Steps to Music, Markets & Florida Sun
St. Augustine
The price is €282
includes taxes & fees
10 Nov - 11 Nov
Madeira Suite: Steps to Music, Markets & Florida Sun

3. 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 €360
includes taxes & fees
13 Nov - 14 Nov
Fall & Holiday Deals! NEWLY Remodeled Oceanside Townhouse!!! Pets Pools Bikes!

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 €280
includes taxes & fees
12 Nov - 13 Nov
617 Sands Dr · 3 Bedroom Brand New House Near Beach | King Bed

5. Madeira Cottage - Amphitheater

Madeira Cottage - Amphitheater
St. Augustine
The price is €309
includes taxes & fees
16 Nov - 17 Nov
Madeira Cottage - Amphitheater

6. Starfish - Heated Pool & King Beds! Near Amphitheatre, Historic Downtown, Beach

Starfish - Heated Pool & King Beds! Near Amphitheatre, Historic Downtown, Beach
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 €469
includes taxes & fees
10 Nov - 11 Nov
Starfish - Heated Pool & King Beds! Near Amphitheatre, Historic Downtown, Beach

7. 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 €236
includes taxes & fees
15 Nov - 16 Nov
Beautiful home by the Bridge of Lions

8. 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 €319
includes taxes & fees
12 Nov - 13 Nov
Heated Cocktail Pool, Putt Putt, Bowling, BBQ, Nintendo, Ping Pong, Pet Friendly

9. Southwind - Screened Heated Pool! Near Amphitheatre, Historic Downtown, & Beach

Southwind - Screened Heated Pool! Near Amphitheatre, Historic Downtown, & Beach
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 €469
includes taxes & fees
10 Nov - 11 Nov
Southwind - Screened Heated Pool! Near Amphitheatre, Historic Downtown, & Beach

10. Lighthouse - Heated Pool & Firepit! Near Amphitheatre, Historic Downtown, Beach

Lighthouse - Heated Pool & Firepit! Near Amphitheatre, Historic Downtown, Beach
St Augustine
9.4 out of 10, Exceptional, (174 reviews)
"Great place ."
United States
Cathy
The price is €432
includes taxes & fees
10 Nov - 11 Nov
Lighthouse - Heated Pool & Firepit! Near Amphitheatre, Historic Downtown, Beach

11. Sail Away- Lovely Home, Heated Pool, Near Beach, Foosball Table, Pet Friendly

Sail Away- Lovely Home, Heated Pool, Near Beach, Foosball Table, Pet Friendly
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 €481
includes taxes & fees
15 Nov - 16 Nov
Sail Away- Lovely Home, Heated Pool, Near Beach, Foosball Table, Pet Friendly

12. 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 €408
includes taxes & fees
16 Nov - 17 Nov
Walk Downtown • Hot Tub • EV Charger • Fenced Yard

13. Grandview-Heated Pool & Game Room Near Amphitheatre, Historic Downtown, Beach

Grandview-Heated Pool & Game Room Near Amphitheatre, Historic Downtown, Beach
Saint Augustine
9.6 out of 10, Exceptional, (213 reviews)
"Great property and wonderful experience."
United States
Nicole A.
The price is €475
includes taxes & fees
10 Nov - 11 Nov
Grandview-Heated Pool & Game Room Near Amphitheatre, Historic Downtown, Beach

14. 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 €202
includes taxes & fees
16 Nov - 17 Nov
Spacious cozy home between downtown & the beach!

15. 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 €327
includes taxes & fees
10 Nov - 11 Nov
Anastasia Island Villa Duplex Single Level EV

16. Summer Breeze - Pool and Heated Spa Near Amphitheatre, Historic Downtown, Beach

Summer Breeze - Pool and Heated Spa Near Amphitheatre, Historic Downtown, Beach
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 €469
includes taxes & fees
10 Nov - 11 Nov
Summer Breeze - Pool and Heated Spa Near Amphitheatre, Historic Downtown, Beach

17. Sea Turtle- Heated Pool & King Beds, Near Amphitheatre, Historic Downtown, Beach

Sea Turtle- Heated Pool & King Beds, Near Amphitheatre, Historic Downtown, Beach
St. Augustine
9.8 out of 10, Exceptional, (84 reviews)
"The hosts were very friendly and replied quickly."
United States
Danielle J.
The price is €469
includes taxes & fees
10 Nov - 11 Nov
Sea Turtle- Heated Pool & King Beds, Near Amphitheatre, Historic Downtown, Beach

18. Beach house|Hot Tub, DT 7min, Games & Fenced Patio

Beach house|Hot Tub, DT 7min, Games & Fenced Patio
Davis Shores
9.6 out of 10, Exceptional, (28 reviews)
"Great stay in a great location"
United States
Luke T.
The price is €324
includes taxes & fees
10 Nov - 11 Nov
Beach house|Hot Tub, DT 7min, Games & Fenced Patio

19. The Southwind|Pool|3-Min Drive to Beach|Sleeps 10

The Southwind|Pool|3-Min Drive to Beach|Sleeps 10
St. Augustine
10.0 out of 10, Exceptional, (1 review)
"Perfect location! Property was clean and perfect for our getaway trip!"
United States
Rhonda K.
The price is €439
includes taxes & fees
10 Nov - 11 Nov
The Southwind|Pool|3-Min Drive to Beach|Sleeps 10

20. Davis Shores Luxury 3BR + Private Hot Tub | 25-Min Walk to Nights of Lights

Davis Shores Luxury 3BR + Private Hot Tub | 25-Min Walk to Nights of Lights
Davis Shores
8.0 out of 10, Very good, (1 review)
"We enjoyed our stay in this charming 3 bed / 3 bath home. We booked it just one day before arrival after changing our minimoon plans due to inclement weather in California, and we were grateful this place was available. Its proximity to Old Town and the hot tub were the main reasons we chose it.Check in was slightly delayed, as the cleaners were still there, so we couldn’t enter until around 5 PM. After being awake since 3 AM for our flight, we were tired, but it wasn’t a major issue. The bigger...
United States
Ariel B.
Davis Shores Luxury 3BR + Private Hot Tub | 25-Min Walk to Nights of Lights
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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