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Crosswinds Cottage
- 3 bedrooms and 2.5 bathrooms in Holmes Beach, FL

  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage
  • Crosswinds Cottage

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At A Glance

  • Luxury Key West Style Home, Elevated private home-2,212 sq. ft.
  • Professionally decorated, Coastal themed furnishings
  • Elevator to all three floors
  • 3 bedrooms and 2.5 bathrooms, two king beds, four twins and a sleeper sofa, sleeps 2-6 in comfort
  • Master suite with spa tub and private balcony
  • Large private heated pool with tropical landscaping
  • Covered pool side lanai with BBQ grill and dining furniture-Two decorated private balconies
  • Flat Screen TV and cable in every bedroom. Smart TV in living room and bedroom, Wi-Fi,
  • Short 5 minute stroll to the Gulf-Close to local restaurants and shops
  • Close to city park with playground, skate park and tennis


View Floor Plan Tour Crosswinds Cottage

312 A 61st Street

Holmes Beach, FL 34217


Welcome to this luxury Key West style home by the sea! It is your place in the sun to make memories and unwind!

Crosswinds Cottage is just a short five minute walk to Anna Maria Island's world renowned white sandy beaches where you will enjoy time with family and friends while relaxing in the sun! Crosswinds Cottage is a gorgeous Key West style home offering a private heated pool, and plenty of room for family and friends to enjoy luxury accommodations. You are sure to fall in love with everything Crosswinds Cottage has to offer!

Perfectly located to provide privacy and relaxation, Crosswinds Cottage is just a short walk to one of the nicest beaches on Anna Maria Island and just a few minutes' walk to a beautiful city park with a children's playground, a skate park, and tennis courts. Locally operated restaurants and boutiques with delicious local food and quaint island themed gifts are just around the corner. The location of Crosswinds Cottage, in the heart of Holmes Beach, has something for everyone. With two adult bikes available for your convenience, you can easily explore the rest of the island without a car. The free Island Trolley Service is also available to inspire your adventure!

Enjoy the luxurious back yard with a private heated pool and palm trees swaying in the breeze. Here you will find the perfect blend of sun and cool shade with evening starlight twinkling overhead. The covered patio offers plenty of seating to enjoy cocktails or a delicious freshly grilled meal with family and friends. You can also enjoy a private cocktail or a cup of morning coffee on one of the other two private decks located off the living room and the master bedroom.

Make memories in the game area playing Ping Pong just next to the pool area. For quiet moments, enjoy four flat screen TVs, all with cable throughout the house. All bedrooms have flat screen TVs and two Smart TVs are located in the living room and large upstairs bedroom. High-speed wireless internet will let you keep in touch with the rest of the world - just remember, you are on vacation and it is time to relax!

Professional decorating, a romantic master suite, spa tub, solid wood cabinets, wood floors, volume ceilings and granite surfaces are just some of the fantastic amenities that you can expect from Crosswinds Cottage. There is also an elevator to all floors to accommodate guests or help with luggage. A laundry room is located on the main floor for your convenience.

Get ready to make memories at Crosswinds Cottage!

**Please keep in mind if the elevator becomes inoperable due to any reason, the stairs will be the only form of transportation to and from your unit**

Bedrooms & Bathrooms

There are 3 bedrooms and 2.5 bathrooms. This property conveniently sleeps up to 6. The Master bedroom has a King sized bed and so does the second bedroom. The third offers 2 twin beds and a twin with a pull out trundle for 4 twin beds total. There is also a queen sleeper sofa in the living room.


Crosswinds Cottage offers a fantastic location that is ideal for your Anna Maria Island getaway. Close to local shops and restaurants and only a short 5-7 minute stroll to the pristine Gulf beaches of the Gulf of Mexico. Offering a private heated pool with a covered lanai and mature tropical landscaping for your convenience. Enjoy quality time outdoors around the pool, grill up a delicious home cooked meal or simply try out some of the delicious local seafood--this versatile offers it all!

** If you would like to have your pool heated, we kindly ask that you please contact AMV at least 10 days prior to your arrival so that it ensures us ample time to fulfill your request. We do offer pool heat as needed as a courtesy to our guests at no additional charge. All of our pools and pool equipment are closely monitored by the pool company for your safety, we kindly ask that the controls not be tampered with- most of the systems are locked for this reason. Due to the island's strict 10pm noise ordinance, the pool heaters will not run overnight. Please remember, outdoor spas are not hot tubs (some properties have a spa, some have a hot tub). Generally speaking, our winter months are considered from November through April. During these months we do our best to ensure that the pools are heated to a temperature of 82 degrees. However, please be aware that even in Central Florida we do occasionally get cold spells that can send the temperatures down into the 30's for a few nights in a row. This will cause the pool water temperature to draw down to in the 70's and a pool pump will automatically shut down if the outside temperature gets too cold. The pump will then kick back on in the morning and begin re-heating of the pool back to 82, which may take several days depending on the severity of the cold spell. Ultimately, these situations are beyond our control. Other issues such as severe weather conditions, equipment malfunction, temporary loss of use of equipment or amenities due to maintenance purposes or other items do happen for time to time. Please be aware that AMV cannot issue refunds during your stay based on acts of God. However, please know that in the rare event of pool equipment malfunction during your stay, AMV will do everything in our power to expedite repairs as quickly as possible as we certainly want you to enjoy your heated pool and Florida sunshine to the fullest extent possible! Anna Maria Vacations thanks you in advance for your understanding on this issue.


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By: Trip Date: 07/29/2017

The Crosswinds Cottage was absolutely perfect. We enjoyed every minute of our vacation and this home. We had a large group and the house was big enough for everyone to have their own space and truly relax. It was our first time visiting AMI and we would come back to this home and the Island every year. emories were made at the Crosswind Cottage and on AMI. Thank you so much for wonderful accommodations and a great vacation.

Crosswinds Cottage

By: Trip Date: 06/25/2017

We just finished up our week at crosswinds cottage and i wanted to let you know what a wonderful time we had. It was our first visit to the island we fell in love with its beauty and relaxed atmosphere. The house was beautifully decorated. Even with a large group everyone was able to find their own space to relax. Thank you so much for a most memorable experience.

AMAZING doesn’t give this place justice

By: Trip Date: 06/12/2017

This place is beyond AMAZING. Big, clean, updated and perfect. Short walk to beach access or a less than 5 min drive to the “park beach entrance” once we got her we walked everywhere. Between 2 and 5 blocks in any direction will lead you to shops, restaurants, bars, convince stores or the beach. Great size pool and pool area. It doesn’t happen often but for the first time in a long time I got more than I paid for. Thank you

Hello Eric,
We are thrilled to hear that you enjoyed your stay at Crosswinds Cottage. This is truly a wonderful property! We would love to have you stay with us again for your next AMI stay-please don’t hesitate to contact us if you have any questions.

Great family stay !!!

By: Trip Date: 04/08/2017

We arrived at Crosswinds Cottage and we were so impressed that this property was exactly as the pictures as well as with an amazing location. Everything was in perfect condition and really clean. We enjoyed the short walk to the beach. Kitchen was fully stocked and all the bathrooms were spotless!! The ping-pong table was a lot of fun!!! We have to say that the elevator was a great use for my elder mother. Overall, we would love to stay here again in the future and definitely recommend this house to others.

Awesome location and house!

By: Trip Date: 12/16/2016

This beautifully decorated house provided the perfect location for our Florida vacation! We loved the short 6-7 minute walk to the beach and the high sided wagon provided to carry the furnished chairs, towels, and beach umbrella. The pool is perfect for relaxing during the day or lounging in and beside in the evening. The kitchen has every utensil and pot or pan that you could need, and there’s even an elevator if your day at the beach leaves you too tired to climb the few steps to the living room and/or bedrooms. We walked to nearby restaurants, bars, and shopping areas. We even enjoyed supper with our feet in the sand at a nearby restaurant while watching a spectacular sunset. You will not be disappointed, and you’ll leave refreshed and planning your return visit.-

Thank you for taking your time to let us know about your stay at Crosswinds Cottage.  We are happy to hear that you enjoyed your vacation and that the wonderful amenities the home provides added to your enjoyment.
This truly is a perfect home in a great location for a relaxing family vacation.  Please give us a call when you are ready to plan your next getaway !

Perfect Amenities, Great Family Fun

By: Trip Date: 12/16/2016

Crosswinds Cottage is filled with everything needed to relax and enjoy time with loved ones. The house is beautiful and we found everything we needed to enjoy our time there. The beach is a quick 6-7 minute walk around the corner and down a couple of blocks from the house. The bicycles, pool, game table, etc. were perfect for all ages to enjoy.

Thank you for letting us know about your stay at Crosswinds Cottage. We greatly appreciate your feedback!
We are happy to hear that you and your loved ones enjoyed your stay and the great amenities the home provides.
We would love to have you stay with us again for your future Anna Maria Island vacation needs!

Beautiful rental home

By: Trip Date: 06/09/2016

This vacation home was beautiful inside and out. Perfect location for shopping, the beach, nightlife, and relaxation. We loved the atmosphere so much that the majority of our vacation was spent lounging by the pool and cooking at “home” just enjoying each others company! Will definitely come back and recommend to my friends/family!