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Anastasia Island · St. Augustine, Florida

Your Anastasia Island Vacation Rental

Madison By The Sea is a pet friendly vacation rental on the south end of Anastasia Island, a 4 minute walk to Crescent Beach and a short drive to the rest of the island.

Aerial view of Anastasia Island toward the Matanzas River
The Matanzas River side of Anastasia Island

Where Madison By The Sea is

Madison By The Sea sits on the south end of Anastasia Island, St. Augustine. Fort Matanzas is about 7 minutes south. Anastasia State Park and the St. Augustine Lighthouse are about 15 minutes north.

7 minutessouth to Fort Matanzas National Monument
15 minutesnorth to Anastasia State Park
16 minutesnorth to the St. Augustine Lighthouse
4 milesof protected beach inside the state park
Hang out roomwith a smart TV, sleeper sofa and kitchenette
The Best of Both

The quiet south end of the island

A quiet street

Madison By The Sea is on the south end of Anastasia Island, on a residential street where the nights are calm and the porch is yours.

A short walk to the beach

Crescent Beach is about 4 minutes on foot, so the sand is part of every day of your stay.

A short drive to the rest of the island

Fort Matanzas is about 7 minutes south, Anastasia State Park about 15 minutes north and historic downtown about 18 minutes from the house.

Your Island Home

A whole house on the island, room by room

Come back from the lighthouse, the state park or Fort Matanzas to a house with space for everyone, a covered hot tub on the screened porch and a fenced yard.

Sleeps 8across 5 beds
3 bedroomsplus a bonus room
2 full bathsfor the whole group
Fenced backyardfor small dogs, with approval
Wi-Fi and a deskfor a work day if you need one
Garage and drivewayparking at the house
Living room with a smart TV
The living room, set up for movie nights
Kitchen island and dining bench
The kitchen island and dining bench
Primary bedroom with a queen bed
The primary bedroom, a queen bed
Bedroom with a desk for working
A bedroom with a desk for a work day
Bunk room for the kids
The bunk room the kids claim first
Second full bathroom
The second full bath
Seating on the screened porch
The screened porch, beside the hot tub
Gas grill in the fenced backyard
The gas grill in the fenced backyard

Check Your Dates See every amenity

Island day trips from the house

Fort Matanzas National Monument

4.4 miles south, about 7 minutes

A coquina watchtower completed in 1742 that guarded the southern approach to Spanish St. Augustine. The park also protects about 300 acres of dunes, marsh and maritime forest, with a boardwalk nature trail and both river and ocean beaches.

Anastasia State Park

8.2 miles north, about 15 minutes

Four miles of protected shoreline, the Ancient Dunes Nature Trail, wildlife viewing, and kayak and paddleboard rentals through Anastasia Watersports. There is an entrance fee per vehicle.

St. Augustine Lighthouse

8.6 miles north, about 16 minutes

The island's landmark lighthouse and maritime museum, right on the way into town.

St. Augustine Beach pier park

6.2 miles north, about 12 minutes

Splash pad, playground, pavilion and a farmers market every Wednesday. More on St. Augustine Beach.

Room for everyone after a day out

Come back to 3 bedrooms and a separate hang out room with a large smart TV, a full size sleeper sofa and a kitchenette. The bunk room has a twin XL over a queen, the kitchen has counter seating for 3, and the dining table seats 6, so the whole group can spread out or come together.

Hang out room with orange sofa and a painted sunburst on the wall
Hang out room
Bunk room with a twin XL over queen bunk bed
Bunk room
Living room with gray sectional and leather chairs
Living room sectional
Kitchen with navy island and counter stools
Kitchen island

What guests say about the house

"Madison by the Sea is the perfect place for a family getaway to reconnect and make memories. The house is sparkling clean with up to date appliances and furnishings. There are many extras in the kitchen and baths. The bonus room for the kids to play in gave everyone space."

Terry · iTrip · 5 stars

"Home had everything needed for a comfortable stay. Lots of room for the five of us. Had room for more."

Tracy I. · VRBO · 5 stars

"Everything was smooth, very clean and equipped home. Would stay again!"

Alicia A. · VRBO · 5 stars

Questions about Anastasia Island

Where on Anastasia Island is Madison By The Sea?

On the southern part of the island in Crescent Beach, about 4 minutes on foot from the beach.

How far is Anastasia State Park?

About 8 miles north, roughly a 15 minute drive. The park charges an entrance fee per vehicle.

How close is Fort Matanzas?

About 4.4 miles south, roughly a 7 minute drive.

Can I bring my dog?

Yes, small dogs are welcome at the house with approval before booking, and leashed dogs are allowed on St. Johns County beaches.

More of the island

St. Augustine Beach · Crescent Beach · Historic St. Augustine · Local guide

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