Book a Anastasia Island Cottage

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Featured Cottages in Anastasia Island

Sun & Fun @ Can't Be Beat Beachfront Location!
Exterior

Sun & Fun @ Can't Be Beat Beachfront Location!

9.4 out of 10, Exceptional, (50)
"Property was as described and owner was very helpful. "
Sun & Fun @ Can't Be Beat Beachfront Location!
Waterfront Retreat, Heated Pool & Rooftop Deck - 2 Bed, Kitchen, Great Location
Terrace/patio

Waterfront Retreat, Heated Pool & Rooftop Deck - 2 Bed, Kitchen, Great Location

9.8 out of 10, Exceptional, (44)
"We had a fantastic trip. The house was conveniently located near the amphitheater, delicious restaurants and the beach. We couldn’t have asked for a better place to stay! "
Waterfront Retreat, Heated Pool & Rooftop Deck - 2 Bed, Kitchen, Great Location
Bryn Mawr Ocean Resort -A gated community loaded with amenities!
Exterior

Bryn Mawr Ocean Resort -A gated community loaded with amenities!

9.8 out of 10, Exceptional, (139)
"Best little beach house at Bryn Mahr!!!!"
Bryn Mawr Ocean Resort -A gated community loaded with amenities!
CHARMING 2/2 COTTAGE JUST A SHORT WALK TO THE BEACH/PET FRIENDLY/ WIFI
Exterior

CHARMING 2/2 COTTAGE JUST A SHORT WALK TO THE BEACH/PET FRIENDLY/ WIFI

9.6 out of 10, Exceptional, (198)
"We spent 6 days"
CHARMING 2/2 COTTAGE JUST A SHORT WALK TO THE BEACH/PET FRIENDLY/ WIFI
Ooo Laa Laaah. Fenced yard. Pets ok.
Exterior

Ooo Laa Laaah. Fenced yard. Pets ok.

9.8 out of 10, Exceptional, (147)
"This was our second stay at Ooo Laa Laaah. Great cottage with all you need on a quiet street and a short walk to the beach. We will most definitely return."
Ooo Laa Laaah. Fenced yard. Pets ok.
Anastasia Lodge-Family & Dog Friendly Beach Cottage
Property grounds

Anastasia Lodge-Family & Dog Friendly Beach Cottage

9.6 out of 10, Exceptional, (63)
"We had a wonderful stay. Nice location and plenty of room for our group of 4."
Anastasia Lodge-Family & Dog Friendly Beach Cottage
Private Beach Oasis, sleeps 4- Hot Tub! Heated Pool Available
Property grounds

Private Beach Oasis, sleeps 4- Hot Tub! Heated Pool Available

10.0 out of 10, Exceptional, (31)
"Perfect house for the two of us. Excellent location, within walking distance of restaurants and the beach."
Private Beach Oasis, sleeps 4- Hot Tub! Heated Pool Available
5 F Street - Sand Dollar East
Terrace/patio

5 F Street - Sand Dollar East

10.0 out of 10, Exceptional, (32)
"We had a great stay and love St, Augustine Beach. We have a dog and the beach and community is so dog friendly. "
5 F Street - Sand Dollar East
Coastal Cottage with community pool, free parking and boardwalk to beach- SCV 12
Property grounds

Coastal Cottage with community pool, free parking and boardwalk to beach- SCV 12

8.0 out of 10, Very good, (5)
"The only thing great about this property was the location, a 1 minute walk to the beach. The cottage was outdated but functional, when we arrived the it appeared that nothing had been cleaned, the showers had red and black mildew and the grease on the stove and backsplash appeared to not have been wiped in sometime, and the bed sheets had bugs in them. I purchased bleach and paper/plastic plates and utensils because I didn’t trust that anything had been cleaned. The linens provided had...
Coastal Cottage with community pool, free parking and boardwalk to beach- SCV 12
SCV 45: 2 BR 1 Bath Cottage, Updated With a True Open, Bright and Airy Feel
Property grounds

SCV 45: 2 BR 1 Bath Cottage, Updated With a True Open, Bright and Airy Feel

9.6 out of 10, Exceptional, (17)
"This house was perfect for our quick trip to the beach over spring break. We rented bikes from Drifters too and cruised all over Saint Augustine Beach. Lovely few days in Florida!"
SCV 45: 2 BR 1 Bath Cottage, Updated With a True Open, Bright and Airy Feel
Surf Crest Village #25 (Pelican Beach View) Ocean front 4 bedroom One pet only
Exterior

Surf Crest Village #25 (Pelican Beach View) Ocean front 4 bedroom One pet only

9.6 out of 10, Exceptional, (70)
"Perfect location! "
Surf Crest Village #25 (Pelican Beach View) Ocean front 4 bedroom One pet only
St Augustine 'island Cottage' - Walk to Beach
House (3 Bedrooms) | Interior

St Augustine 'island Cottage' - Walk to Beach

3.0 star property
10.0 out of 10, Exceptional, (4)
"Everything about this property is excellent!! We’ll book it again"
St Augustine 'island Cottage' - Walk to Beach
Charming Oceanfront Key West Style Cottage at Surf Crest Village #9
Property grounds

Charming Oceanfront Key West Style Cottage at Surf Crest Village #9

10.0 out of 10, Exceptional, (21)
"Clean and spacious and close to the beach. Really enjoyed our stay."
Charming Oceanfront Key West Style Cottage at Surf Crest Village #9
5 F Street - Sand Dollar West
Outdoor dining

5 F Street - Sand Dollar West

9.8 out of 10, Exceptional, (37)
"We had a wonderful experience at 5F Street, and would happily stay there again! It was perfect for my husband and I and our pup!"
5 F Street - Sand Dollar West
Surf Crest 23 Ocean front property 2 bedroom cottage steps to ocean
Property grounds

Surf Crest 23 Ocean front property 2 bedroom cottage steps to ocean

9.4 out of 10, Exceptional, (102)
"It was good"
Surf Crest 23 Ocean front property 2 bedroom cottage steps to ocean
DISCOUNT RATE Nov & Dec... St Augustine Beachside Cottage near Butler Beach
Exterior

DISCOUNT RATE Nov & Dec... St Augustine Beachside Cottage near Butler Beach

10.0 out of 10, Exceptional, (137)
"This was a great stay and so close to the beach! "
DISCOUNT RATE Nov & Dec... St Augustine Beachside Cottage near Butler Beach
The Crescent Moon : Pets welcome, beach 1 block
Property grounds

The Crescent Moon : Pets welcome, beach 1 block

10.0 out of 10, Exceptional, (202)
"Nice cottage by the beach! Great location!"
The Crescent Moon : Pets welcome, beach 1 block
St Augustine waterfront home on canal w/ private dock, walk to beach!
Terrace/patio

St Augustine waterfront home on canal w/ private dock, walk to beach!

10.0 out of 10, Exceptional, (7)
"Very clean, well stocked with creature comforts to make the stay easier! "
St Augustine waterfront home on canal w/ private dock, walk to beach!
Island Cottage at St. Augustine
Property grounds

Island Cottage at St. Augustine

Island Cottage at St. Augustine
The Anchor House- Anastasia Island- Walk to Downtown-Bike Ride to Beach
Terrace/patio

The Anchor House- Anastasia Island- Walk to Downtown-Bike Ride to Beach

10.0 out of 10, Exceptional, (1)
"Great house and location."
The Anchor House- Anastasia Island- Walk to Downtown-Bike Ride to 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Anastasia Island Hotel Reviews

Bliss By The Sea

Bliss By The Sea

10/10 Excellent
"It wss 11 miles from St Augustine and 1 mile to the beach. Otherwise, it was excellent. "
oscar 2-night trip
Posted 2 days ago
Bliss By The Sea

Find out more about Anastasia Island

Find out more about Anastasia Island

Anastasia Island Cottages information

Number of reviews
1,166
Accommodation
42 Cottages
Lowest Price
Highest Price

Explore a world of travel with Expedia

Explore a world of travel with Expedia