Welcome to Crosswinds Cottage, a luxury Key West style home by the sea. Take a short five-minute walk to Anna Maria Island's world-renowned white sandy beaches or enjoy the private heated pool in your backyard oasis with palm trees swaying in the breeze. With two adult bikes available, explore Holmes Beach without a car and indulge in local food at nearby restaurants like Beach Bistro and Chateau Anna Maria.
Reviews
9.69.6 out of 10
Exceptional
Entire home
3 bedrooms3 bathroomsSleeps 6
Popular amenities
Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Air-conditioning
Add dates for prices
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Crosswind Cottage managed by Beach Retreats FL Anna Maria Island
π΄ Crosswind Cottage π 312 A 61st Street, Holmes Beach, FL 34217 π VRC19-000277 π‘ 3 Bedrooms | 2.5 Bathrooms | Sleeps 10 | Heated Pool | Game Room | Elevator π This home can park up to 3 vehicles π§ 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.
πβββββββWhile 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!
π 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) β 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
π² 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.
π Booking & Cancellation
No cancellation fees! Cancel 60+ days before arrival β Full refund Cancel within 60 days β No refund Extended stays & bookings $20,000+ β Full payment 90 days prior, non-refundable $500 deposit due at booking; balance due 60 days prior For reservations 21+ nights or $20,000+ β 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
βββββββπ This home can accommodate up to 3 vehicles
β οΈ Important Notes
Residential neighborhood β Quiet hours 10 PM β 7 AM
No changes permitted during the stay
β¨ With its resort-style amenities, spacious layout, and unbeatable location, Crosswind Cottage is the perfect Anna Maria Island escape for families and groups alike.
π 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.
Property amenities
Beach
Beach nearby
Pool/Spa
Heated pool
Private pool
Internet
Available in the house: Internet access
Parking and transport
Onsite parking options include a garage
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Hob
Microwave
Oven
Refrigerator
Toaster
Bedrooms
3 bedrooms
Bedsheets provided
Sofa bed
Bathroom
2.5 bathrooms
Hair dryer
Shower
Towels provided
Living spaces
Living room
Separate dining area
Entertainment
Books
DVD player
Games
Music library
TV with cable/satellite channels
Video games
Video library
Outdoor areas
Balcony
Barbecue grill
Garden
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Heating
Pets
Pet friendly
Suitability/Accessibility
If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
In-room accessibility
Lift
Smoke-free property
Services and conveniences
Iron/ironing board
Phone
Location highlights
In a village
In the city centre
Near a health/beauty spa
Near a hospital
Near an outlet shopping centre
Near the bay
Near the marina
Near the sea
Things to do
Arcade/game room
Bicycles
Golf
Heated pool
Optional golf privileges
Table tennis
Tennis
Water park
Water sports equipment
Basketball nearby
Birdwatching nearby
Ecotours nearby
Fishing nearby
Golfing nearby
Hiking/biking trails nearby
Horseback riding nearby
Jet skiing nearby
Kayaking nearby
Motor boating nearby
Mountain biking nearby
Parasailing nearby
Rafting nearby
Sailing nearby
Scuba diving nearby
Surfing/bodyboarding nearby
Swimming nearby
Theme park nearby
Water skiing nearby
Water tubing nearby
Wildlife walks nearby
Windsurfing nearby
Safety features
Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
Pets are allowed
Service animals are welcome, and are exempt from fees
Children and extra beds
Children are welcome
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
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
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 ecotours and hiking/biking trails nearby. Visit our Holmes Beach travel guide
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.
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).
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Crosswind Cottage managed by Beach Retreats FL Anna Maria Island Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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!
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.
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.
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.
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
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!
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)
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.
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!
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.
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!!
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!
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 wasnβt fixed. They sent someone but no fix. Thatβs the only negative i have. Otherwise it was a great house!
erika s.
Stayed 4 nights in Jun 2023
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
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