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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Pineapple Cottage: 2BR Quaint Family- and Pet-Friendly Cottage

Bedrooms 2
Property type cottage
Minimum Stay 0 - 7 nights


About the property

Ready to Relax in 1492 Square Feet of Island Life?

Pineapple Cottage, centrally located on historic Pine Avenue in the city of Anna Maria, is the perfect place to slow down and catch your breath!

This Anna Maria Island cottage is tastefully decorated with wood floors, granite and stainless kitchen, tiled shower,professional linen service and comfortable furnishings. The master bedroom boasts a queen-sized bed with French doors leading to a private deck and backyard. The second bedroom holds two twin beds, and for added sleeping, a queen sofa bed is in the living room. Wireless internet, cable television and a washer and dryer are also included in this lovely vacation rental.

When not at the beach, a private, secluded pool is yours for the liking in the fenced backyard. An outdoor dining and grilling area are a nice addition to this charming cottage.

The Gulf of Mexico and Tampa Bay are equal distance and an easy stroll for your water and sand activities. On your way to or from the beach, you can enjoy some shopping or stop in at one of the restaurants on Pine Avenue. When you are ready to explore the island, you can hop on board the free AMI trolley that runs daily along the island and has a stop a few steps from your door.

So if you are ready to relax, Pineapple Cottage is just the place!

Contact us to reserve today and remember to ask us about our monthly discounted rates!

More Details

Property Manager
Coastal Cottages AMI
Speaks: english
Manager indicates their response time is:
Within an hour
Calendar last updated:
January 23, 2018

About Coastal Cottages AMI

I had been coming to Anna Maria Island for years, when my parents, who were from northern Michigan, first started spending their winters here. I have now called AMI home for over 20 years! I own An Island Place Realty and Coastal Cottages AMI, which handles vacation rentals.

Why Coastal Cottages AMI chose Anna Maria

On one of my visits to see my parents years ago, I ended up buying this house that was only steps away from the one they used to rent.

What makes this cottage unique

Pineapple Cottage has a smaller 1BR cottage in front of it. You can rent both rentals to accommodate larger parties! When booking ask about Island Place Cottage!

Guestbook comments from the manager

I had the best time ever! Florida is for sure the number one best vacation place! I saw a manatee and stayed in the best house EVER! The pool was also a favorite! We swam in it almost every day! Thank you soooo much for the best vacation ever!! We all enjoyed this very much!
Jul 2013
  • 1 of 23


Anna Maria Cottage Accommodation and Amenities

Property Type:
  • cottage
House Rules:
  • Max. occupancy: 6
  • children welcome
  • non smoking only
Location Type:
  • Downtown
  • Near The Ocean
  • Away From It All
  • Family
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning
  • Clothes Dryer
  • Hair Dryer
  • Internet
  • Linens Provided
  • Parking
  • Telephone
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Dining Area
  • 1 Bathroom
  • Bathroom 1 - toilet , shower , outdoor shower
  • Also includes an outdoor shower.
  • 2 Bedrooms, Sleeps 6
  • Bedroom 1 - includes one (1) queen bed
    Bedroom 2 - includes two (2) twin beds
  • Also available is one (1) queen sofa bed.
  • DVD Player
  • Satellite / Cable
  • Stereo
  • Television
  • Deck / Patio
  • Outdoor Grill
Pool / Spa:
  • Heated Pool
  • Private Pool
  • bay/sound
  • botanical garden
  • churches
  • cinemas
  • festivals
  • library
  • live theater
  • marina
  • museums
  • playground
  • recreation center
  • restaurants
  • winery tours
  • zoo
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • eco tourism
  • horseback riding
  • horseshoes
  • outlet shopping
  • photography
  • scenic drives
  • sight seeing
  • walking
  • whale watching
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • hiking
  • jet skiing
  • pier fishing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • sound/bay fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • wind-surfing
Distance from Nearest Trolley Stop: Few Steps • Nearest Trolley Stops: 73-N & 3-S (Pine Avenue at Crescent Drive)


Wonderful! 4.9/5 -
(9 traveler reviews)

88% Complete
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Pineapple Cottage: 2BR Quaint Family- and Pet-Friendly Cottage
average rating of 4.888889 based on 32 reviews

Charmant cottage

  • 4 of 5

Wir verbrachten eine Woche im August in diesem Haus und fühlten uns sehr wohl. Für eine vierköpfige Familie bietet dieses kleine Haus ausreichend Platz.

Die Abwicklung mit der Agentur war absolut unproblematisch , professionell, es gibt nichts zu beanstanden!

Die Betten empfanden wir leider als viel zu weich, deswegen nur 4 Sterne.

  • Submitted: Aug 20, 2017
  • Stayed: August 2017
  • Source: HomeAway
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0 0
United Kingdom


  • 5 of 5

This was our first visit to Anna Maria and it wont our the last,

Pineapple cottage is lovely it has everything you would need to make a fantastic holiday.

The pool was great for cooling off in the late afternoons before we went out for evening meals, It was lovely to just cross the road to get the free trolley bus that takes you all over the Island. I could go on and on but I will just say it was "perfect"

Doreen and Kenny. Liverpool , England

  • Submitted: Jun 13, 2013
  • Stayed: May 2013
  • Source: HomeAway
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3 0
Columbus, Ohio

Great for kids and dog!

  • 5 of 5

We had a great time at Pineapple Cottage. Really enjoyed the location and the kids especially loved walking to the pier. This was our first stay directly on Anna Maria and we would definitely visit again. We especially enjoyed the private backyard and the pool was well maintained. Thank you for such an enjoyable family vacation!

  • Submitted: Apr 23, 2012
  • Stayed: April 2012
  • Source: VRBO, from HomeAway
During this stay the property was under previous owner or management.
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7 0

Island Dreams

  • 5 of 5

This was our second year staying at the Pineapple Cottage...already booked for next year. Some of our family liked it so much while visiting, they will be renting An Island Place Cottage out front next year. What a wonderful vacation spot...great location, wonderful facilities, and a great place for our dogs! Just got back and can't wait for next year!

  • Submitted: Apr 10, 2012
  • Stayed: March 2012
  • Source: VRBO, from HomeAway
Owner's Response: Thank you! It was great having you come back this year, and we look forward to your visit next year, in both cottages!!! Sue, Gina, and Fritz!
During this stay the property was under previous owner or management.
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4 0

Cozy and Romantic

  • 5 of 5

This is the place to stay in Anna Maria. Great heated pool and outdoor area. Owner and Gina were the best. We stayed a week and will return in the future.

  • Submitted: Jan 17, 2012
  • Stayed: January 2012
  • Source: VRBO, from HomeAway
During this stay the property was under previous owner or management.
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3 1

Sue - thank you very much...

  • 5 of 5

Sue - thank you very much for letting us rent the Pineapple Cottage to allow our friends to spend the night here in Anna Maria Island. We absolutely love this area and the place is very nice. The pool with the jacuzzi jets was super relaxing. Thanks for all of your hospitality!! We want to come back next year for more than a few days.

Thanks again,

The Beckwith's

  • Submitted: Jul 19, 2009
  • Stayed: July 2009
  • Source: VRBO, from HomeAway
During this stay the property was under previous owner or management.
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5 0


Nearest Airport
20 Miles
Sarasota-Bradenton International Airport
Nearest Golf
3.6 Miles
Key Royale Golf Club
Nearest Motorway
18 Miles
Nearest Beach
0.25 Miles
2.5 Blocks
Other Activities:

Beach, fun and sun are waiting for you!

This family, elderly and pet friendly vacation rental is located on Florida's Anna Maria Island, a quaint barrier island nestled in the Gulf of Mexico south of Tampa Bay. Comprised of three cities—Anna Maria on the north end, Holmes Beach in the middle and Bradenton Beach to the south—AMI is one of the only places where the 'old Florida' charm still exists. The Island has every convenience needed, including multiple award winning restaurants, including Beach Bistro, Sandbar Restaurant, Sign of the Mermaid, and Waterfront Restaurant. There is also plenty of shopping available along historic Pine Avenue in Anna Maria and Bradenton Beach's historic Bridge Street. With the beach and the Bay just minutes away from your front door, there is plenty to do in the water. Kayaking, snorkeling, fishing, jet skiing, and parasailing are the more popular activities. With the Island only seven miles long, there is no need to drive when almost everything is within walking or biking distance. Plus, there is a free trolley service that runs the length of the Island every day. AMI truly has something for everyone, and everyone who visits falls in love with it. We are sure you will too! So, reserve your vacation home today . . . seven miles of pristine white beaches and beautiful sunsets await you!





    • Down Payment: 25% of base rental fee or $250, whichever is greater. Due at time of booking.
    • Property Damage Protection: $55
    • Administrative Fee: $75
    • Taxes (Florida State: 7%; Local Resort: 5%)
    • Cleaning Fee
    • Pet Fee (if applicable): $150

    • Balance due 30 days PRIOR TO arrival. Forms of payment accepted are cash, check, e-check, money order, and debit/credit card. Checks and money orders should be made payable to Coastal Cottages AMI. CCAMI accepts VISA, MasterCard, and Discover.
    • In lieu of aforementioned damage protection, a refundable $1000 security deposit is required. See Coastal Cottages AMI Terms and Conditions for details.
    • Rates are estimates, vary based on dates, and reflect rental fee only; taxes and additional fees will apply.
    • Monthly rates based on 28 days; monthly discount may be available.