Crosswind Cottage managed by Beach Retreats FL Anna Maria Island
🌴 Crosswind Cottage 📍 312 A 61st Street, Holmes Beach, FL 34217 📌 VRC19-000277 🏡 3 Bedrooms | 2.5 Bathrooms | Sleeps 10 | Heated Pool | Game Room | Elevator 🚗 This home can park up to 3 vehicles 🎧 Quiet hours at 10p-7a: please respect neighbors
Welcome to Crosswind Cottage, a spacious island retreat designed for comfort, fun, and relaxation. With three king bedrooms, a private pool, game room, and multiple balconies, this home offers the perfect blend of luxury and coastal charm. Centrally located in Holmes Beach, you'll be just moments from the Gulf's sparkling waters, shops, and restaurants.
📝While most of our properties rent only from Saturday to Saturday, exceptions can be made. Please reach out to us prior to booking if you would like to arrive or depart on alternate dates, or stay for fewer than 7 nights. We would love to host you!
🛏 Sleeping Arrangements
Primary Suite: King bed + ensuite bath with walk-in shower, jetted tub, double vanity, & private toilet room
Bedroom 2: King bed
Bedroom 3: King bed + twin bunk + twin trundle (3 twins total) → plenty of options for kids or groups
Game Room with foosball, basketball, giant Connect-Four, seating area & TV
Elevator access to all levels for easy convenience
Balconies:
Private balcony off primary suite (seating area)
Balcony off living space (dining table + wicker chairs)
Covered Patio: Grill + outdoor dining table for 6
Fenced Yard with tropical landscaping, palm trees & pool loungers
Smart TVs: Living room, game room, and large upstairs bedroom + flat screens in all rooms (5 total)
Fully Equipped Kitchen with stainless steel appliances, coffee maker, Keurig, blender, & air fryer
Laundry: Extra-large washer & dryer
Beach Supplies: 2 adult bikes, wagon, and beach towels
Comfort: Central A/C + ceiling fans in every room
Professional linens for a hotel-level experience
🚲 Island Living
Located in the heart of Holmes Beach, you're close to Anna Maria Island's best dining, shopping, and activities. Hop on a bike, load up the beach wagon, or catch the free island trolley to explore everything from Bean Point to Bridge Street.
📅 Booking & Cancellation
No cancellation fees! Cancel 60+ days before arrival → Full refund Cancel within 60 days → No refund Extended stays & bookings $20,000+ → Full payment 90 days prior, non-refundable $500 deposit due at booking; balance due 60 days prior For reservations 21+ nights or $20,000+ → 10% deposit due at time of booking. Third party travel insurance cost is due at time of purchase Third-party travel insurance through Beach Retreats is non-refundable No changes permitted within 60 days of arrival or during stay We highly recommend cancelation insurance
All changes/cancellations must be in writing
🚗 This home can accommodate up to 3 vehicles
⚠️ Important Notes
Residential neighborhood → Quiet hours 10 PM – 7 AM
No changes permitted during the stay
✨ With its resort-style amenities, spacious layout, and unbeatable location, Crosswind Cottage is the perfect Anna Maria Island escape for families and groups alike.
📩 Book your stay now at Beach Retreats
🛜 This home features Silicon Travel. With Silicon Travel's firewall place in place, you can prevent internet access to any malicious activity in a Vacation rental home. Any guest device (WebCam, Baby Monitor, etc) can be added for a set time and will be removed automatically upon departure.
Our prices include all fees. No hidden fees.
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning
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This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
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 H2O Watersportz. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and hiking nearby.
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 39 min drive
Restaurants
Anna Maria Island Beach Cafe - 3 min drive
The Ugly Grouper - 4 min walk
The Sandbar Restaurant - 5 min drive
Ginny's & Jane E's - 4 min drive
Slim's Place - 4 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 18 Apr 2026, prices found for a 1-night stay for 2 adults at Crosswind Cottage managed by Beach Retreats FL Anna Maria Island on 26 Apr 2026 start from £295, 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 a 10-minute walk of Bradenton Beach and Island Gallery West. Holmes Beach Beaches and Manatee Public Beach are also within 1 mile (2 km).
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Great house. Great location. Has everything you need.
Great house. Great location. Has everything you need.
Pamela T.
Stayed 7 nights in Oct 2022
Response from VrboOwner on 8 Aug 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!
Great outdoor pool and hangout area, clean house and very close to the beach!
Jeff W.
Stayed 7 nights in Jun 2023
Response from VrboOwner on 8 Aug 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!
It was lovely; everything you need including beach chairs, coolers, towels and umbrella
Susan D.
Stayed 14 nights in Feb 2023
Response from VrboOwner on 8 Aug 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.
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!
Judith V.
Stayed 7 nights in Aug 2024
Response from VrboOwner on 20 Jan 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
10/10 Excellent
Vern K.
31 May 2019
Amazing
Very clean and the pool was awesome!
Vern K.
Stayed 8 nights in May 2019
Response from VrboOwner on 8 Aug 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!!
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.
Patricia W.
Stayed 5 nights in Jun 2023
Response from VrboOwner on 8 Aug 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.
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.
Michelle R.
Stayed 7 nights in Mar 2024
Response from VrboOwner on 25 Apr 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.
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
ASHLEY T.
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!
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!
Katrina C.
Stayed 4 nights in Oct 2022
Response from VrboOwner on 8 Aug 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.
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)
Mary R.
Stayed 7 nights in Dec 2021
Response from VrboOwner on 8 Aug 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.
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.
Kristen S.
Stayed 6 nights in Jul 2022
Response from VrboOwner on 8 Aug 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!
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!
Sydnie K.
Stayed 5 nights in May 2022
Response from VrboOwner on 8 Aug 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!
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.
Red ( Mary) M.
Stayed 28 nights in Feb 2022
Response from VrboOwner on 8 Aug 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.
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.
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!!
Joanne W.
Stayed 7 nights in Aug 2022
Response from VrboOwner on 8 Aug 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.
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!
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!
Verified traveller
Stayed 7 nights in Jul 2021
Response from VrboOwner on 8 Aug 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.
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.
Verified traveller
Stayed 7 nights in Oct 2023
Response from VrboOwner on 27 Oct 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.
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!
erika s.
Stayed 4 nights in Jun 2023
Response from VrboOwner on 8 Aug 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.
Verified
10/10 Excellent
Phillip S.
6 Mar 2018
As good as the pictures
This place is great...well decorated, maintained and furnished. Pool was refreshing and the setting was nicely laid out. You get morning and afternoon sun on both the front and rear sides of the house.
Elevator was helpful for "move in and move out" purposes, but did not use for anything other than that.
They have a great supply of pool and beach toys and essentials in the garage...wagon, umbrella, beach blanket, towels etc. Ten minute walk to beach.
Kitchen appliances and utensils were new and most adequate for the tasks necessary when cooking.
Rear balcony is great for breakfast, lunch or dinner sitting outside and overlooking the pool.
Management staff...Emma and Claire were responsive and helpful when needed.
Absolutely no complaints.
Phil and Gail
Chicago
Très bien, très propre et service impeccable.Frédérick
Frédérick L.
Stayed 7 nights in Aug 2025
Response from VrboOwner on 9 Sept 2025
Hi Frederick,
Thank you for taking the time to review our Beach Retreat, Crosswind Cottage. We are thrilled to hear you enjoyed your stay!
Verified
6/10 Okay
Robert S.
28 Nov 2022
Liked: Cleanliness, check-in, communication
House was nice but for what we paid…..
When you pay almost $2/K per night, you except some level of little extras to just be there. Like toilet paper. Like garbage bags ( there was 1). Decent soap. The place was nice but the minor, neglected items really made us think we could babe done better
Robert S.
Stayed 4 nights in Nov 2022
About the host
Hosted by Beach Retreats
Beach Retreats Vacation Rentals
As a small boutique rental agency, we pride ourselves on selecting only a handful of the newest, most pristine vacation rentals. We have chosen homes to suit all group sizes and specifications without compromising the highest standards we hold ourselves to. Being this discerning has earned us the trust of many vacationers who have come back year after year.
We are also one of the few agencies with a focus on homes from Anna Maria Island to Siesta Key. We know that while many people are happy to return to the same vacation spot year after year, others like to try out new places. We hope our personalized service and spectacular homes will allow you to truly experience the islands as they were meant to be!
Languages:
English
Premier Host
They consistently provide great experiences for their guests