Entire home

The Gulf Lookout: A beachfront escape

Photo gallery for The Gulf Lookout: A beachfront escape

A wooden boardwalk leading to a building with a white fence and palm trees. - The Gulf Lookout: A beachfront escape (Anna Maria)
An aerial view of a coastal residential area with houses, a beach, and a clear sky. - The Gulf Lookout: A beachfront escape (Anna Maria)
A living room with a sofa, armchairs, and a coffee table. There are framed pictures on the wall and a kitchen in the background. - The Gulf Lookout: A beachfront escape (Anna Maria)
A wooden deck with white railings, wicker chairs, and a small gazebo. - The Gulf Lookout: A beachfront escape (Anna Maria)
A dining area with a wooden table and wicker chairs, a chandelier, and a view of the outdoors through large windows. - The Gulf Lookout: A beachfront escape (Anna Maria)
The Gulf Lookout: A beachfront escape provides a hot tub and more. Stay connected with free in-room WiFi.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Add dates for prices

About this property

The Gulf Lookout: A beachfront escape

  • Welcome to The Gulf Lookout, a beautifully appointed 4-bedroom, 3.5-bath coastal retreat located off Oak Avenue in the charming City of Anna Maria. This exceptional Gulf-front home offers stunning panoramic views with a peaceful park situated between the property and the beach, providing both privacy and easy access to the sugar-sand shoreline.

    Featuring spacious living areas, multiple balconies, and an ideal layout for families and groups, The Gulf Lookout blends comfort, style, and an unbeatable location—just steps from local shops, dining, and everything that defines the Anna Maria lifestyle.

    Enjoy breathtaking sunsets from the rooftop deck, accessed through the back unit guest bedroom via a steep stairway and compact entry. The home also offers a private game room with mini-split A/C, located above the main house and accessed from the back unit living room balcony — creating the perfect space for entertainment and relaxation. With two separate units, this house is perfect for a multi-family vacation. The direct beach access, thoughtful design, and unforgettable views, that this home delivers makes for the ultimate coastal getaway.

    NOTE: For security and insurance purposes, there are exterior-only video cameras on the premises.

    ***OVERCROWDING CONSEQUENCES***
    Maximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.

Similar properties

About the area

Located in Anna Maria, this holiday home is on the waterfront. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Looking to enjoy an event or a game while in town? See what's going on at LECOM Park, or consider a night out at Tarpon Bay Grill and Tiki Bar. Discover the area's water adventures with kayaking and scuba diving nearby, or enjoy the great outdoors with hiking/biking trails and ecotours. Visit our Anna Maria travel guide
View more Holiday homes in Anna Maria
Map
Anna Maria, FL

What's nearby

  • A coastal town with a long sandy beach, clear blue ocean, and residential buildings along the shore.
    Bradenton Beach
    1 min walk - 0.1 miles
  • A beach with white sand, sparse grass, and a cloudy sky.
    Palmetto Avenue Beach
    5 min walk - 0.3 miles
  • A small building with an American flag, surrounded by palm trees and a clear blue sky.
    Anna Maria Island Museum and Historical Park
    14 min walk - 0.8 miles
  • A sunset over a grassy field with a path leading to the water.
    Bean Point Beach
    2 min drive - 1.1 miles
  • Island Players
    11 min walk - 0.6 miles

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    48 min drive

Restaurants

  • The Sandbar Restaurant
    11 min walk
  • Anna Maria Island Beach Cafe
    7 min drive
  • The Ugly Grouper
    4 min drive
  • Ginny's & Jane E's
    8 min walk
  • The Waterfront Restaurant
    19 min walk

Frequently asked questions

Is The Gulf Lookout: A beachfront escape pet-friendly?

No, pets are not allowed at this property.

How much is parking at The Gulf Lookout: A beachfront escape?

On-site parking is available at the property.

What time is check-in at The Gulf Lookout: A beachfront escape?

Check-in begins at 3:00 PM.

What time is check-out at The Gulf Lookout: A beachfront escape?

Checkout is at 10:00 AM.

Where is The Gulf Lookout: A beachfront escape located?

Situated on the waterfront, this holiday home is within 1 mi (2 km) of Bradenton Beach and Bean Point Beach. Palmetto Avenue Beach and Island Players are also within 15 minutes.

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Reviews

The Gulf Lookout: A beachfront escape Reviews

10

Exceptional

10

Cleanliness

10

Location
Rating 10 - Excellent. 1 out of 1 reviews
Rating 8 - Good. 0 out of 1 reviews
Rating 6 - Okay. 0 out of 1 reviews
Rating 4 - Poor. 0 out of 1 reviews
Rating 2 - Terrible. 0 out of 1 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house is the perfect location and layout for a group of traveling friends or generational family. The main house is large and fully stocked. While the appearance in photos is slightly outdated, it’s spotless with no odd smells or strong cleaning fragrance. The back apartment is accessible up a tight, spiral staircase but is also pretty equipped. The only annoyance we had was that the rental company requires you to put the thermostat on 80 when you check out, so it took us almost a full 24 hours to cool the house to 72 (we were only there for 2 full days). The beach is literally steps from the door and the street is quiet even though it’s a public parking street. If you’re traveling with a group, the parking on the property might accommodate 2 cars. We had a bigger SUV and had to parallel park across the entire space to fit. Overall it was a wonderful place to stay. One of the girls in our group actually booked it while we were there to return with their family in 2 months.
Stayed 3 nights in Sep 2026