free call:877-326-5406

Penthouses at Gulf Stream

Anna Maria Island » Penthouses at Gulf Stream

The Penthouses at Gulf Stream are located on Anna Maria Island and is nestled between the Gulf of Mexico and Sarasota Bay. This resort is perfectly located to enjoy the white sandy beaches that Anna Maria Island is famous for and the area’s many cultural and amusement activities including 17 championship golf courses, museums, shopping, boating, kayaking and nature parks just to name a few. Sorry, no pets. Non-smoking units ONLY.

Resort Layout

Request Reservation

Unit Amenities

Each Penthouse Resort unit is comprised of two bedrooms and two bathrooms. The master bedroom has a king size bed and a private master bath. The second bedroom is outfitted with twin beds and a semi private bath. Each condo residence has a full size fully equipped kitchen which has a full size refrigerator freezer, stove, dishwasher, and microwave. Each kitchen has ample cookware and small appliances. If there is anything extra you need, just ask and we’ll get it to you. Every unit has its own washer and dryer. There are three televisions in each unit, one in each of the bedrooms and one in the living room that is accompanied by a DVD player and stereo CD player. A quick elevator ride to the first floor takes you out to the large heated pool and spa.  

Resort Activities and Amenities

During your stay with us you don't need to worry about beach chairs, beach Umbrellas,or beach towels. We provide them, along with wireless internet service, bicycles, games and a book exchange for you. All free of charge. Make sure to attend one or all of our weekly activities, whether it be one of our welcome breakfasts, Hot dog roast, chicken roast, shell hunting and crafting, learning about our island sea turtles, taking a tour of the island or sipping Florida Dreamsicles and playing trivia games by the pool with LouAnn, our activities director is always ready to help make your vacation truly memorable.

Resort Team Favorites

While you’re here, make sure to check out some of our staff’s favorite places. Anna Maria Island has a vast array of dining choices from barefoot beach places to five star haute cuisine and our staff all have their favorites. LouAnn and Mark both love the Rod and Reel Pier, located at the north end of the island. It is old Florida at its best. They have a great Grouper Rueben sandwich. The Rod and Reel is also a great fishing pier. Mark remembers fishing there with his dad when he was a little kid and now enjoys doing the same with his nephew. It is a great place to make memories.


Hands down, Lorilai’s favorite is the Sign of the Mermaid for incredibly interesting and sophisticated cuisine  and decadent desserts. You can’t beat the ambiance in this beautifully restored 1913 “island cracker” house.  

Gloria’s favorite is the Waterfront Restaurant which is a cozy place with an 1800’s fireplace and a great view of the skyway bridge. It offers a varied and delicious menu at a reasonable price point. Everyone agrees that if you’re looking to watch the sunset, go to the Sandbar Restaurant where they serve the best pina colada on the island and they have a sunset competition each night. If you guess the closet time of sunset, you win a bottle of champagne. After dinner, LouAnn says to make sure and take a quick trip to Tyler’s Ice cream shop in Cortez for the “yummiest” home made ice cream.



Tom aka TC enjoys a cool beverage at the Island Time Bar & Grill after work, and for breakfast Cortez Cafe is the best.



All of the shopping on the island is unique and interesting. You won’t find any chain shops on the island, just locally owned, wonderful and charming places. Lorilai loves the Sand Dollar for gifts, specialty clothing, candles and other fun stuff. Gloria is particularly fond of the shops on Bridge Street. She also loves the new Island Flea Market, an open air market under a canopy of chiki huts where, she says, your husband can enjoy a sandwich while you shop for local goods. Whether its art galleries, clothing shops or gift arcades, there’s a wonderful variety here on our Island.


Boating, jet skiing, kayaking, sailing and biking opportunities abound. Lorilai really enjoys kayaking on the north end of the island off bean point and at Robinson Preserve, where there is abundant wild life and flats fishing. Mark enjoys boating on the intracoastal and out to Egmont Key, where the box turtles and hundreds of bird species reside. Gloria really enjoys her bike rides on the island bike paths. There are several fishing captains and sunset sailing boats for your enjoyment as well. Stop by the office anytime to find out more about what the island has to offer.   




Resort News

If you are an owner at this resort, you can find updated information here.

 Owner Information


Calendar of Events


The Anna Maria Island Historical Society Museum is a must for visitor to the island. Tour the exhibits in the recently updated Museum building, learn about the old Belle Haven Cottage originally located on the pier, and see the old city jail house. The museum is fun for all ages, and gives visitors a taste of Anna Maria Island from days past. The Museum is located at 402 Pine Avenue.


The Island Players Theater offers several different shows each season running from October to May. Tickets are $20 each or purchase a season ticket for $92.50 at the box office or by phone. The Island Players Theater is located at the corner of Gulf Drive and Pine Avenue. A fun place to catch a play, the Players Theater is a gorgeous and historical landmark of Anna Maria.


Anna Maria Island may only be seven miles long and one mile wide, but it does offer fabulous nature viewing opportunities. One of the areas most unique nature features can be found on the south end of Anna Maria Island at gorgeous Leffis Key. Open from sunrise to sundown, Leffis Key offers amazing Mangrove tunnel lined  boardwalk trails, salt marsh lagoons and the Island’s best bird watching. Also, use this handy guide to spot both white and brown pelicans around Anna Maria Island’s Leffis Key! Leffis Key overlooking Sarasota Bay.



There are tons of great places to SHOP for unique items on Anna Maria Island. Whether you are looking for island themed gifts and souvenirs, local art or just gorgeous little things, you’ll be sure to find it in one of the great shops on the island.



Across Anna Maria Island there are several great parks with kid friendly activities. Find play ground equipment, a skatepark, concessions, and all the outdoor fun your kids could hope for. If you are looking to head off island for nature viewing check out our list of parks and preserves in Manatee county.



With so many equipment rental shops on Anna Maria Island there are lots of options for entertaining activities. Rent just about any type of equipment you need on the island including kayak/canoes, bikes, jet skis, beach accessories, golf carts, fly boarding, baby rentals and much more! Check out the ANNA MARIA ISLAND BICYCLE GUIDEfor route suggestions and more.



Anna Maria Island has a fabulous art scene with many local creatives offering their wares in galleries across the island. While visiting Anna Maria Island be sure to stop in one of the galleries listed, and take a piece of paradise home with you. If you visit the Island in November, be sure to visit annual event  Arts Hop



Sunset is one of the most magical times on Anna Maria Island. Always the best way to end the day or get the evening started, sunset is the time of day to reflect on the incredible beauty of the Anna Maria Island experience. You can’t leave the island without catching at least one sunset


BAY FEST is the largest running event on Anna Maria Island. This event takes place on Pine Avenue. At Bay Fest you’ll enjoy food, music, vendors and a car show.


The Anna Maria Fall Fest happens in the Holmes Beach city field at 5901 Marina Drive in Holmes Beach. Taking place just before Halloween, this event kicks off with a Halloween Parade starting at Anna Maria Island elementary and ending at the city field.


Trick or Treating house to house is not a popular tradition among island neighborhoods. Therefore, the Anna Maria Island Chamber of Commerce hosts a Three City Wide Trail of Treats sponsored by local businesses. The Trail of Treats starts with a kids costume contest at the Chamber of Commerce located at 5313 Gulf Drive. After the contest kids and parents are welcome to stroll around the Holmes Beach town center collecting candy from businesses from 4-6pm. After cruising through Holmes Beach, head up to Pine Avenue or down to Bridge Street for additional trick or treating from 5-8pm. Typically this event happens on or just before Halloween depending if the Holiday falls on a weekend.


Anna Maria Islanders greatly anticipate Stone Crab Season. Starting in mid October, Floridians and Island locals begin harvesting Stone Crabs by the bucket load. The Cortez Stone Crab Festival , happening in early November, is a fabulous way to enjoy this locally sourced seafood.


Wrapping up autumn events the annual Arts Hop is a great way to experience local arts, crafts, music and food. This island wide celebration of arts and culture is organized by the Cultural Connections of Anna Maria Island. This three day event includes art walks, theater performances and a beach front chorus and orchestra performance called “Symphony on the Sand”.

Enjoy Annual Events Anna Maria Island Style



From the Desk of TC, Sales

Call Tom in sales for prices and detail on Penthouse of Gulf Stream at 941-778-6667

Bradenton top retirement spot says magazine & Sarasota's Van Wezel ranked as No. 1 performance hall by Venues Today

BRADENTON — The Friendly City continues to gain national attention as a great place to live, largely thanks to the vibrant, downtown arts scene. Selected by Where to Retire Magazine as a top retirement destination

The Houston-based publication launched in 1992 with the goal of helping its readers find the ideal place to retire.

“Boomers love the relaxing charm of Bradenton, and the residents live up to its motto – The Friendly City,” said Mary Lu Abbott, editor of Where to Retire, in a statement.

“Bradenton possesses qualities important to today’s retirees. They find plenty of action in the nationally recognized arts community, including the Manatee Players theater and the Village of the Arts, where they meet and mingle with dozens of artists living and working together in restored cottages.”

She also notes that with the $6.2 million transformation of the Bradenton Riverwalk, scheduled for completion in October, the downtown entertainment scene “will get even livelier.”

Last month, AmericanStyle Magazine issued a statement that its survey participants voted Bradenton the second-best small city arts destination in the country, up from No. 10 last year and No. 22 in 2010.

“Bradenton, a sunny locale 45 miles south of Tampa, may not be on your radar for arts destinations yet, but it should be,” reads the opening sentence of the blurb on page 66 of the new summer edition of the Baltimore-based publication. “It’s home to Florida’s largest art colony, the Village of the Arts.”

Wade Tatangelo, features writer, can be reached at 745-7057. Follow


Sarasota's Van Wezel ranked as No. 1 performance hall by Venues Today

Read more here: