Entire home
The Gulf Lookout: A beachfront escape
Photo gallery for The Gulf Lookout: A beachfront escape





Popular amenities
- Spa pool on site
- Garage parking available
- Kitchen
- Washing machine
- Air-conditioning
- Barbecue
Rooms & beds
4 bedrooms (sleeps 8)
3 bathrooms
Bathroom 1
Bathroom 2
Bathroom 3
Spaces
Kitchen
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 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.
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.
Add dates for prices
Have a question?
Get instant answers with AI powered search of property information and reviews.
Similar properties

Waterfront house with pool - bring boat and rod - close to Gulf and Bay Beaches
Anna Maria
Waterfront house with pool - bring boat and rod - close to Gulf and Bay Beaches
Anna Maria
- Pool
- Kitchen
- Washing machine
- Dryer
9.6 out of 10, Exceptional, (81 reviews)
9.6/10
Exceptional
(81 reviews)

A Time Out: *Quaint Cottage *Heated Pool *Across the street from the Bay!
Anna Maria
A Time Out: *Quaint Cottage *Heated Pool *Across the street from the Bay!
Anna Maria
- Pool
- Kitchen
- Washing machine
- Dryer
9.2 out of 10, Wonderful, (37 reviews)
9.2/10
Wonderful
(37 reviews)

North end AMI, 5* luxury home in one of the prettiest towns on gulf coast!
Anna Maria
North end AMI, 5* luxury home in one of the prettiest towns on gulf coast!
Anna Maria
- Pool
- Kitchen
- Washing machine
- Dryer
9.8 out of 10, Exceptional, (217 reviews)
9.8/10
Exceptional
(217 reviews)

MAY, JUNE SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog
Anna Maria
MAY, JUNE SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog
Anna Maria
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
9.6 out of 10, Exceptional, (199 reviews)
9.6/10
Exceptional
(199 reviews)

Bayside Retreat with Pool and Bay Views! Near Beaches, Shops, and Dining
Anna Maria
Bayside Retreat with Pool and Bay Views! Near Beaches, Shops, and Dining
Anna Maria
- Pool
- Kitchen
- Washing machine
- Dryer
9.6 out of 10, Exceptional, (76 reviews)
9.6/10
Exceptional
(76 reviews)

Newly-Renovated, Dog-Friendly Home w/ Private Heated Pool & Streaming Services
Anna Maria
Newly-Renovated, Dog-Friendly Home w/ Private Heated Pool & Streaming Services
Anna Maria
- Pool
- Kitchen
- Washing machine
- Dryer
9.0 out of 10, Wonderful, (73 reviews)
9.0/10
Wonderful
(73 reviews)

Bayfront Escape with Stunning Water Views and Steps to Bean Point
Anna Maria
Bayfront Escape with Stunning Water Views and Steps to Bean Point
Anna Maria
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.2 out of 10, Wonderful, (17 reviews)
9.2/10
Wonderful
(17 reviews)

Custom Home Walking Distance from the Gulf ! NOT LISTED ON FACEBOOK <br>
Anna Maria
Custom Home Walking Distance from the Gulf ! NOT LISTED ON FACEBOOK <br>
Anna Maria
- Pool
- Kitchen
- Washing machine
- Dryer
9.6 out of 10, Exceptional, (144 reviews)
9.6/10
Exceptional
(144 reviews)

Tides Inn- Family home with tropical pool area.
Anna Maria
Tides Inn- Family home with tropical pool area.
Anna Maria
- Pool
- Spa pool
- Kitchen
- Washing machine
9.4 out of 10, Exceptional, (49 reviews)
9.4/10
Exceptional
(49 reviews)

Charming cottage located close to beach - Private heated pool!
Anna Maria
Charming cottage located close to beach - Private heated pool!
Anna Maria
- Pool
- Kitchen
- Washing machine
- Dryer
9.4 out of 10, Exceptional, (116 reviews)
9.4/10
Exceptional
(116 reviews)

Seaside Manor! Pool, Spa and Beach Walk!
Bradenton Beach
Seaside Manor! Pool, Spa and Beach Walk!
Bradenton Beach
- Pool
- Spa pool
- Kitchen
- Washing machine
9.4 out of 10, Exceptional, (48 reviews)
9.4/10
Exceptional
(48 reviews)

Mermaid Cove: Updated Forida Cottage w/pool, hot tub
Anna Maria
Mermaid Cove: Updated Forida Cottage w/pool, hot tub
Anna Maria
- Pool
- Spa pool
- Kitchen
- Washing machine
9.8 out of 10, Exceptional, (38 reviews)
9.8/10
Exceptional
(38 reviews)

Called in Sic! Luxury Home with Pool, Spa, Rooftop Deck and Walk to Beach
Anna Maria
Called in Sic! Luxury Home with Pool, Spa, Rooftop Deck and Walk to Beach
Anna Maria
- Pool
- Spa pool
- Kitchen
- Washing machine
9.6 out of 10, Exceptional, (60 reviews)
9.6/10
Exceptional
(60 reviews)

Villa Rozafa
Cozy,spacious,walking distance from downtown white sandy beach.
Anna Maria
Villa Rozafa Cozy,spacious,walking distance from downtown white sandy beach.
Anna Maria
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
9.2 out of 10, Wonderful, (9 reviews)
9.2/10
Wonderful
(9 reviews)

Bellablu: A Waterfront Haven, The Ideal Retreat for Your Next Getaway!
Anna Maria
Bellablu: A Waterfront Haven, The Ideal Retreat for Your Next Getaway!
Anna Maria
- Pool
- Kitchen
- Washing machine
- Dryer
9.0 out of 10, Wonderful, (16 reviews)
9.0/10
Wonderful
(16 reviews)

Pete's Blue Heaven: Steps to beach w/heated pool
Anna Maria
Pete's Blue Heaven: Steps to beach w/heated pool
Anna Maria
- Pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (34 reviews)
10/10
Exceptional
(34 reviews)

Ship Watch: Private Beach, North End, Dog Friendly by Anna Maria Life Vacation Rentals
Anna Maria
Ship Watch: Private Beach, North End, Dog Friendly by Anna Maria Life Vacation Rentals
Anna Maria
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
8.8 out of 10, Excellent, (51 reviews)
8.8/10
Excellent
(51 reviews)

Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w/pool!
Anna Maria
Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w/pool!
Anna Maria
- Pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (33 reviews)
10/10
Exceptional
(33 reviews)

Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach
Anna Maria
Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach
Anna Maria
- Pool
- Kitchen
- Washing machine
- Dryer
9.8 out of 10, Exceptional, (78 reviews)
9.8/10
Exceptional
(78 reviews)

Kingfish: *Canalfront *Paddleboards *Putt Putt *Heated Pool *Hot Tub
Anna Maria
Kingfish: *Canalfront *Paddleboards *Putt Putt *Heated Pool *Hot Tub
Anna Maria
- Pool
- Spa pool
- Kitchen
- Washing machine
9.6 out of 10, Exceptional, (62 reviews)
9.6/10
Exceptional
(62 reviews)

Anna Maria Beach Cottage 110 Traditional beach cottage, moments from the sand!
Anna Maria
Anna Maria Beach Cottage 110 Traditional beach cottage, moments from the sand!
Anna Maria
- Pool
- Kitchen
- Washing machine
- Dryer
9.8 out of 10, Exceptional, (43 reviews)
9.8/10
Exceptional
(43 reviews)

Beach Bliss: Perfect location, pool, views, steps to beach
Anna Maria
Beach Bliss: Perfect location, pool, views, steps to beach
Anna Maria
- Ocean view
- Pool
- Kitchen
- Washing machine
10.0 out of 10, Exceptional, (27 reviews)
10/10
Exceptional
(27 reviews)

Bella Vista: Bay front with gorgeous views and outdoor living space.
Anna Maria
Bella Vista: Bay front with gorgeous views and outdoor living space.
Anna Maria
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.4 out of 10, Exceptional, (23 reviews)
9.4/10
Exceptional
(23 reviews)

8 Palms: Gorgeous heated pool and lounge area, with putt-putt!
Anna Maria
8 Palms: Gorgeous heated pool and lounge area, with putt-putt!
Anna Maria
- Pool
- Spa pool
- Kitchen
- Washing machine
9.8 out of 10, Exceptional, (17 reviews)
9.8/10
Exceptional
(17 reviews)

Luxury 4 bedroom, 3 bath private home with a heated pool in the heart of Anna Maria.
Anna Maria
Luxury 4 bedroom, 3 bath private home with a heated pool in the heart of Anna Maria.
Anna Maria
- Pool
- Kitchen
- Washing machine
- Dryer
9.2 out of 10, Wonderful, (20 reviews)
9.2/10
Wonderful
(20 reviews)

Naut 2 Shabby Cottage-Awesome Pool Area, Pine Ave location close to everything
Anna Maria
Naut 2 Shabby Cottage-Awesome Pool Area, Pine Ave location close to everything
Anna Maria
- Pool
- Spa pool
- Kitchen
- Washing machine
9.6 out of 10, Exceptional, (80 reviews)
9.6/10
Exceptional
(80 reviews)

Saltwater Serenity | Canal Front w/ Heated Pool Near Anna Maria Island
Cortez
Saltwater Serenity | Canal Front w/ Heated Pool Near Anna Maria Island
Cortez
- Pool
- Kitchen
- Washing machine
- Dryer
9.8 out of 10, Exceptional, (16 reviews)
9.8/10
Exceptional
(16 reviews)

Elevated North-End Home Near the Beach!
Anna Maria
Elevated North-End Home Near the Beach!
Anna Maria
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.4 out of 10, Exceptional, (6 reviews)
9.4/10
Exceptional
(6 reviews)

The Sunset Place- Unbeatable location. Gorgeous Sunsets. Updated Coastal Gem
Anna Maria
The Sunset Place- Unbeatable location. Gorgeous Sunsets. Updated Coastal Gem
Anna Maria
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (44 reviews)
10/10
Exceptional
(44 reviews)

Beachview Retreat: Steps to the beach, Gulf views!
Anna Maria
Beachview Retreat: Steps to the beach, Gulf views!
Anna Maria
- Ocean view
- Kitchen
- Washing machine
- Dryer
9.8 out of 10, Exceptional, (41 reviews)
9.8/10
Exceptional
(41 reviews)
About the area
Anna Maria
Located in Anna Maria, this holiday home is by the ocean. The area's natural beauty can be seen at Bean Point Beach and Anna Maria Beach. Looking to enjoy an event or a game while in town? See what's happening at LECOM Park or IMG Bollettieri Tennis Academy. Scuba diving, water tubing and parasailing offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours nearby.

Anna Maria, FL
What's nearby
- Bradenton Beach - 1 min walk - 0.2 km
- Palmetto Avenue Beach - 1 min walk - 0.2 km
- Island Players - 11 min walk - 0.9 km
- 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
Tell us how we can improve our siteShare feedback
