Crosswind Cottage managed by Beach Retreats FL Anna Maria Island

Photo gallery for Crosswind Cottage managed by Beach Retreats FL Anna Maria Island

A two-story house with a blue exterior, a front garage, and a balcony.
A swimming pool with blue chairs, surrounded by lush tropical vegetation.
A round glass table with wicker chairs on a wooden deck, surrounded by a white railing, overlooking a lush tropical garden.
A covered patio with a table set for dining, surrounded by wicker chairs, and a ceiling fan above.
A hallway with a wooden bench, a staircase, and a door.

Reviews

9.6 out of 10
Exceptional

Highlights

  • Family fun awaits
    Top-rated for families.
  • Arcade/game room
    A rare find - fun for all ages with on-site arcade/game room.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Bradenton Beach

Popular amenities

  • Balcony
  • Private pool
  • Waterpark access
  • Outdoor barbecue
  • Air-conditioning
  • Pet-friendly

Explore the area

View map
Holmes Beach, FL
  • Place, Bradenton Beach
    ‪8 min walk‬
  • Place, Holmes Beach Beaches
    ‪19 min walk‬
  • Place, Manatee Public Beach
    ‪2 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪37 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

King bed

1 King Bed

King Bed + Bunk bed with trundle!

1 King Bed and 3 Single Bunk Beds

King Bed with en-suite bathroom

1 King Bed

2 bathrooms, 1 half bathroom

Full bath

Toilet · Shower only

Full bath with tub

Toilet · Shower only

Half bath

Toilet

Spaces

Deck or patio
Kitchen
Balcony
Separate dining area
Garden
Dining area

Add dates for prices

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  • Pool
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  • Kitchen
  • Washing machine
9.8 out of 10, Exceptional, (62 reviews)
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About the area

Holmes Beach

Located in Holmes Beach, this holiday home is in the city centre and near the beach. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Travelling with kids? Consider Fish Hole Adventure Golf and Florida Maritime Museum at Cortez. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and mountain biking nearby.
View more Holiday homes in Holmes BeachOpens in a new window
Map
Holmes Beach, FL

What's nearby

  • Bradenton Beach - 8 min walk - 0.7 km
  • Holmes Beach Beaches - 19 min walk - 1.6 km
  • Manatee Public Beach - 2 min drive - 1.8 km
  • Anna Maria Sound - 3 min drive - 2.1 km
  • West Coast Surf Shop - 3 min drive - 2.5 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 39 min drive

Restaurants

  • ‪The Sandbar Restaurant - ‬5 min drive
  • ‪Anna Maria Island Beach Cafe - ‬3 min drive
  • ‪The Ugly Grouper - ‬4 min walk
  • ‪Ginny's & Jane E's - ‬4 min drive
  • ‪The Waterfront Restaurant - ‬6 min drive

Frequently asked questions

Does Crosswind Cottage managed by Beach Retreats FL Anna Maria Island have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at Crosswind Cottage managed by Beach Retreats FL Anna Maria Island?

As of 3 November 2026, prices found for a 1-night stay for 2 adults at Crosswind Cottage managed by Beach Retreats FL Anna Maria Island on 29 November 2026 start from NZ$5,637, 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.

Is Crosswind Cottage managed by Beach Retreats FL Anna Maria Island pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Crosswind Cottage managed by Beach Retreats FL Anna Maria Island?

On-site parking is available at the property.

What time is check-in at Crosswind Cottage managed by Beach Retreats FL Anna Maria Island?

Check-in begins at 4:00 PM.

What time is check-out at Crosswind Cottage managed by Beach Retreats FL Anna Maria Island?

Checkout is at 10:00 AM.

Where is Crosswind Cottage managed by Beach Retreats FL Anna Maria Island located?

This family-friendly Holmes Beach holiday home is located by the sea, within 1 mi (2 km) of Bradenton Beach, Holmes Beach Beaches and Manatee Public Beach. Palmetto Avenue Beach and West Coast Surf Shop are also within 2 miles (3 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 47 out of 56 reviews
Rating 8 - Good. 6 out of 56 reviews
Rating 6 - Okay. 3 out of 56 reviews
Rating 4 - Poor. 0 out of 56 reviews
Rating 2 - Terrible. 0 out of 56 reviews

9.8/10

Cleanliness

9.8/10

Check-in

9.4/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home was just as described and we could not have been happier! The home was clean and had everything you needed and then some. The beach equipment, bikes, and toys were great. We would easily stay here again.
Stayed 7 nights in Aug 2026
Response from Crosswind Cottage managed by Beach Retreats FL Anna Maria Island on 2 November 2026
We’re shell-ebrating this review, Stephanie! 🐚 Thank you, and come back soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, location, listing accuracy
THE HOUSE WAS SUPER CLEAN
Stayed 10 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location
It was very easy to get into and very well equipped. The management yeah is very proactive. - Great location for groceries, restaurants, getting on and off the island. But a bit away from the beach - not really walkable with chairs etc. The property it well equipped, but a little tired - bikes rusted, etc but it was very comfortable and easy to access.
Stayed 7 nights in Aug 2026
Response from Crosswind Cottage managed by Beach Retreats FL Anna Maria Island on 2 November 2026
Thank you for your review, Gretchen! 🌴 We’re so glad you found Crosswind Cottage, easy to access and well equipped. We appreciate your kind words about our team. Thank you also for the honest feedback on the bikes and general wear. We’ll be passing it along so we can keep the home in top shape. We hope to host you again! 🐚
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great House for Laid-back family vacation

We absolutely loved this house. It’s perfect with the pool in close proximity to the beach. It was very nice. We would definitely stay again!
Stayed 7 nights in Aug 2021
Response from VrboOwner on 8 August 2023
Hi Leah! Thank you for reviewing us. We are so happy to hear you enjoyed your stay! Looking forward to hosting you again in the future.
Verified review

10/10 Excellent

We absolutely loved this beach house!

House was beautiful and well taken care of. We loved the location and have no complaints.
Stayed 5 nights in Jan 2018
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house. Great location. Has everything you need.

Great house. Great location. Has everything you need.
Stayed 7 nights in Oct 2022
Response from VrboOwner on 8 August 2023
Hi Pamela, Thank you for taking the time to review our Beach Retreat, Crosswind Cottage. I am so glad to hear you enjoyed your stay. We agree, this is a great house! We look forward to hosting you the next time your travels bring you to Anna Maria Island!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome beach house

Great outdoor pool and hangout area, clean house and very close to the beach!
Stayed 7 nights in Jun 2023
Response from VrboOwner on 8 August 2023
Hi Jeff, Thank you for taking the time to review our Beach Retreat, Crosswind Cottage. We are thrilled to hear you enjoyed your stay. We love the backyard area and all the fun to be had at this property. We look forward to hosting you the next time your travels bring you to Anna Maria Island!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

anna marie island

It was lovely; everything you need including beach chairs, coolers, towels and umbrella
Stayed 14 nights in Feb 2023
Response from VrboOwner on 8 August 2023
Hi Susan, Thank you for taking the time to review our Beach Retreat, Crosswind Cottage. We are thrilled to hear you enjoyed your stay! We try to supply everything you could need during your stay so no extra packing is necessary. We look forward to hosting you the next time your travels bring you to Anna Maria island.
Verified review

10/10 Excellent

Amazing

Very clean and the pool was awesome!
Stayed 8 nights in May 2019
Response from VrboOwner on 8 August 2023
Thanks so much for the great review. We are always thrilled to hear that our guests enjoyed their stay at one of our BEACH RETREATS. We would welcome you back any time!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful home!!

This property was perfect. The location was close to the beach. It was VERY clean and the elevator was convenient for bringing up luggage and groceries. I would definitely stay again!
Stayed 7 nights in Aug 2024
Response from VrboOwner on 20 January 2025
Hi Judith, Thank you for taking the time to review our Beach Retreat, Crosswind Cottage. The elevator is definitely a major plus for this property! We hope to host you again the next time your travels bring you to Anna Maria Island!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best Florida vacation ever!

This was the best Florida beach vacation we have ever been on. The house was beautiful, spacious and well equipped. Management was great to deal with and helped by providing a digital info board to help find restaurants, rentals and tours. We just wish we could stay longer.
Stayed 5 nights in Jun 2023
Response from VrboOwner on 8 August 2023
Hi Patricia, Thank you for taking the time to review our Beach Retreat, Crosswind Cottage. We are thrilled to hear you enjoyed your stay! We think the digital boards are a great touch too! We look forward to hosting you the next time your travels bring you to Anna Maria island.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

We love AMI and this property was perfect for our family of 5. We could easily have fit another family comfortably. Loved the pool and game room. Walking distance to plenty of shops, restaurants, and the beautiful beach. We were here for Spring Break and it was definitely busy, but not much that it detracted from the fun.
Stayed 7 nights in Mar 2024
Response from VrboOwner on 25 April 2024
Hi Michelle, Thank you for taking the time to review our Beach Retreat, Crosswind Cottage. Spring break is one of the busiest times of the year for our little island, but we are thrilled to hear that did not distract from the fun. I am sure the pool and game room only added to the fun. This home is in a great location with close proximity to the beach, shops and dining. We do hope you decide to stay with us again the next time your travels bring you to the area.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely house!

We had a great stay. The house was lovely and very clean. We really enjoyed sitting on the balcony drinking our coffee in the morning! We were a group of adults, but the house would work well for families as well. The game room was great. Highly recommend!
Stayed 4 nights in Oct 2022
Response from VrboOwner on 8 August 2023
Hi Katrina, Thank you for taking the time to review our Beach Retreat, Crosswind Cottage. I am so glad to hear you enjoyed your stay. The game room is a great addition to the house! We look forward to hosting you the next time your travels bring you to Anna Maria Island.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Vacation!

The house was perfect! Our family had an amazing week. We arrived to some hiccups and the management took care of it immediately and could not have been easier to work with which spoke volumes about their company. I would absolutely recommend this home
Stayed 7 nights in Apr 2024
Response from VrboOwner on 9 May 2024
HI Ashley, Thank you for taking the time to review our Beach Retreat, Crosswind Cottage. We are thrilled to hear you enjoyed your stay! As a company, we strive to go above and beyond for each of our guests and are thrilled to hear we achieved that with the hiccups you experienced at the beginning of your trip. We do hope to host you again the next time your travels bring you to Anna Maria Island!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Exactly as advertised

Great property and was exactly as advertised. House was spotless. Very close to all amenities. Our first visit to AMI. We will be back.
Stayed 9 nights in Oct 2019
Verified review

8/10 Good

Liked: Cleanliness, check-in, location, listing accuracy

easy stay

property was great - clean, nicely decorated, close to beach, & beds were so comfortable! Only minor complaint is that someone came in unannounced - to leave a gift of chocolates fir the holiday - very sweet - but had us feeling a little uncomfortable that someone would come in without telling us. (One of us sleeping upstairs)
Stayed 7 nights in Dec 2021
Response from VrboOwner on 8 August 2023
Hi Mary, Thank you so much for taking the time to review our Beach Retreat. I am so happy to hear you enjoyed your holiday stay with us. I'm so sorry someone came in unannounced. We did want to try and get those all out prior to our guests checking in. We do look forward to hosting you again in the future.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect rental

This is house is perfect in every way. Has every amenity a family would need, the home is meticulously decorated, pool area is fantastic with lots of seating available. Located close to the beach, surrounded by other beautiful homes as well. We highly recommend this home. The elevator is quite useful for moving in and out. Lots of extra blankets available as well.
Stayed 6 nights in Jul 2022
Response from VrboOwner on 8 August 2023
Hi Kristen, Thank you for taking the time to review our Beach Retreat, Crosswind Cottage. I am so glad to hear you enjoyed your stay! This home is in a great location, and has a great outdoor area. We look forward to hosting you the next time your travels bring you to Anna Maria Island!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

2022 AMI Vacay

This house was perfect for what we needed. A 10 minute walk to the beach, and it was so convenient because the house had beach chairs, a wagon, and umbrella. After a long day at the beach we would relax by the pool. Communication with management was excellent and we absolutely loved the concierge board they had that updated us on trash pickup, pool cleaning and recommendations for the area. We would definitely stay here again!
Stayed 5 nights in May 2022
Response from VrboOwner on 8 August 2023
Hi Sydnie, Thank you for taking the time to review our Beach Retreat, Crosswind Cottage. I am so happy to hear you enjoyed your stay. We strive to go above and beyond for our guetss, and supply all the items you would need for the beach, except for your swim suit. We look foward to hosting you again the next time your travels bring you to AMI!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Girls get away

House was perfect for our girls get away. House was super clean and well stocked. The neighborhood is really quiet. Really nice neighbor lady next door we visited with a lot. Low traffic area. We stayed here a month and enjoyed every day. I would rent from here again. Mary B.
Stayed 28 nights in Feb 2022
Response from VrboOwner on 8 August 2023
Hi Mary, Thank you for taking the time to review our "Beach Retreat!" I'm so happy to hear you enjoyed your stay. We look forward to hosting you again in the future.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

We loved every minute!

My whole family enjoyed the beautiful house and location. The kids liked the beach and bike rides, and they loved swimming in the warm pool every day and night! The kitchen was well equipped. The elevator was awesome when the grandparents visited. And the bedrooms were cozy. I would stay here again:) The only suggestion I have is to have better window shades that provided more privacy and less light in from street lights and sunrise.
Stayed 7 nights in Mar 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great family vacation

We had a great time at the property. Everything we needed was there. Very clean and spacious. Great location! My only complaint is the living room furniture was very uncomfortable. I know that is silly for fun beaches and adventures near, but it rained a lot in the evenings and we were inside at times. Other than that, I would definitely recommend this rental. Thank you!!
Stayed 7 nights in Aug 2022
Response from VrboOwner on 8 August 2023
Hi Joanne, Thank you for taking the time to review our Beach Retreat, Crosswind Cottage. I am so happy to hear you enjoyed your stay! This home is a great space. I'm sorry to hear the living room furniture wasn't comfortable. We take all remarks seriously and will pass it along to the owners. We look forward to hosting you again the next time your travels bring you to Anna Maria Island.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxation

The house was just as posting described. Several pool & beach toys in the garage, as well as at home games. 2nd floor master bed is very firm, too firm for us. Elevator was great!
Stayed 7 nights in Jun 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Tranquil Stay

This property is just how it looks in the photos. The bedrooms are huge and the master bathroom is fantastic! We did not use the living room much as we were too busy playing ping pong or swimming in the pool. The beach is a short golf cart ride away and there is a public boat ramp 2 blocks over for vacationers bringing their boat. We loved the tranquil colors throughout the home and the elevator came in handy with unloading and loading back up. Emma and Claire were very responsive to our needs and seemed just as excited to have us there and we were to be there! We will certainly be back!
Stayed 7 nights in Jul 2021
Response from VrboOwner on 8 August 2023
Hi! Thank you for reviewing us. We are so happy to hear you enjoyed your stay! Looking forward to hosting you again in the future.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fall break

Great location for access to beaches, restaurants, grocery stores, and even the dog park. We love walking to the Ugly Grouper and feasting on the best coconut shrimp ever. House has a very nice lay out, especially traveling with teens. The master is on the second floor next to the kitchen and the kids bedrooms are on the third floor. Everyone gets a little privacy. My only complaint is that the internet keep failing and because of local construction the power keep flickering and at one point went out for an hour. The power company was fast to reply and repairs were made very quickly.
Stayed 7 nights in Oct 2023
Response from VrboOwner on 27 October 2023
Hi, Thank you for taking the time to review our Beach Retreat, Crosswind Cottage. We are thrilled to hear you enjoyed your stay! I am so sorry to hear about the intermittent internet issues. I am thrilled to hear everything was corrected quickly. We do hope to host you again the next time your travels bring you to Anna Maria Island.
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house!

We had a wonderful time renting this house. It was equipped with everything we needed. Super clean and lots of space. The kids loved the game room and the pool. The kitchen had everything we needed. Only major problem was the faucet in the kitchen had barely any pressure which made it very difficult to even do dishes. We called and it wasn’t fixed. They sent someone but no fix. That’s the only negative i have. Otherwise it was a great house!
Stayed 4 nights in Jun 2023
Response from VrboOwner on 8 August 2023
Hi Erika, Thank you for taking the time to review our Beach Retreat, Crosswind Cottage. We are thrilled to hear you enjoyed your stay. I am so sorry to hear about the faucet having no pressure during your stay. We have since gotten this fixed. We do hope you will give us another chance to exceed your expectations and visit with us the next time your travels bring you to Anna Maria Island.
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