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 direct beach access, thoughtful design, and unforgettable views, this home delivers 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.
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
About the area
Anna Maria
Located in Anna Maria, this holiday home is on the waterfront. The area's natural beauty can be seen at Bean Point Beach and Bradenton 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. Kayaking, scuba diving and water tubing offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours nearby.
Anna Maria Island Museum and Historical Park - 14 min walk - 1.2 km
Bean Point Beach - 2 min drive - 1.7 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 48 min drive
Restaurants
Anna Maria Island Beach Cafe - 7 min drive
The Ugly Grouper - 4 min drive
The Sandbar Restaurant - 11 min walk
The Waterfront Restaurant - 19 min walk
Ginny's & Jane E's - 8 min walk
Frequently asked questions
Is The Gulf Lookout: A beachfront escape pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at The Gulf Lookout: A beachfront escape?
As of 5 July 2026, prices found for a 1-night stay for 2 adults at The Gulf Lookout: A beachfront escape on 3 September 2026 start from NZ$1,487, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
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. Anna Maria Beach is 1.5 mi (2.4 km) away.