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Crosswind Cottage managed by Beach Retreats FL Anna Maria Island

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Outdoor dining
A heated pool
Interior
Exterior
Fridge, microwave, oven, stovetop

Reviews

9.6 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 6

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Pet-friendly
  • Pool
  • Air conditioning

Explore the area

View in a map
Holmes Beach, FL
  • Place, Manatee Public Beach
    ‪2 min drive‬
  • Place, Bean Point Beach
    ‪6 min drive‬
  • Place, Anna Maria Beach
    ‪7 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪30 min drive‬

Room options

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4.9 out of 5, Exceptional, 57 reviews
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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

🌴 Crosswind Cottage

📍 312 A 61st Street, Holmes Beach, FL 34217
📌 VRC19-000277 | 3 Bedrooms | 2.5 Bathrooms | Sleeps 10 | Heated Pool | Game Room | Elevator

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.

🛏 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

Total: 3 bedrooms, 2.5 bathrooms

🛁 Bathrooms

Primary Suite Bath: Walk-in shower, jetted tub, double vanity, hair dryer

Guest Bath: Shower/tub combo + generous vanity, hair dryer

Powder Room: On main level

🌟 Features & Amenities

Private Heated Pool with in-pool bench seating

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
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

⚠️ 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.
During your stay at this vacation home, you're just a quick walk from Bradenton Beach. You'll find features like a water park, laundry facilities, and an arcade/game room. Enjoy your stay with amenities like a private pool and a kitchen in the vacation home.
  • Air-conditioned home with private pool, kitchen, and washing machine
  • Splash around at the water park
  • Amenities include laundry facilities and an elevator
  • Onsite recreation includes tennis courts
  • 7 minutes by car from Bean Point Beach and 7 minutes from Anna Maria Beach
This vacation home offers its guests a water park. Barbecue grills, an arcade/game room, and a garden are also featured at the family-friendly vacation home.

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)

General

  • Bicycles
  • Garden

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • Pets are welcome
  • Service animals 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
Onsite 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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

Property is also known as

Vrbo Property
3 bed 2 Bath Heated Pool Elevator Ping Pong Free Wifi
279271
3 bed 2.5 bath Heated Pool Elevator Ping Pong FREE WIFI

Reviews

Crosswind Cottage managed by Beach Retreats FL Anna Maria Island Reviews

9.6

Exceptional

9.8/10

Cleanliness
Rating 10 - Excellent. 44 out of 52 reviews
Rating 8 - Good. 5 out of 52 reviews
Rating 6 - Okay. 3 out of 52 reviews
Rating 4 - Poor. 0 out of 52 reviews
Rating 2 - Terrible. 0 out of 52 reviews

Reviews

10/10 Excellent

Frédérick L.

Liked: Cleanliness
Très bien, très propre et service impeccable.Frédérick
Stayed 7 nights in Aug 2025

10/10 Excellent

Christii H.

Stayed 7 nights in May 2025

10/10 Excellent

Carrie R.

Liked: Cleanliness
Stayed 7 nights in Jun 2024

10/10 Excellent

Judith V.

Liked: Cleanliness

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

10/10 Excellent

Julianne R.

Liked: Cleanliness
Stayed 7 nights in Apr 2024

10/10 Excellent

Tori R.

Liked: Cleanliness
Stayed 7 nights in Mar 2024

10/10 Excellent

ASHLEY T.

Liked: Cleanliness

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

10/10 Excellent

Michelle R.

Liked: Cleanliness

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

10/10 Excellent

Verified traveller

Liked: Cleanliness

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

10/10 Excellent

Jeff W.

Liked: Cleanliness

Awesome beach house

Great outdoor pool and hangout area, clean house and very close to the beach!
Stayed 7 nights in Jun 2023

10/10 Excellent

Patricia W.

Liked: Cleanliness

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

8/10 Good

erika s.

Liked: Cleanliness

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

10/10 Excellent

Susan D.

Liked: Cleanliness

anna marie island

It was lovely; everything you need including beach chairs, coolers, towels and umbrella
Stayed 14 nights in Feb 2023

6/10 Okay

Robert S., Alexandria, VA

Liked: Cleanliness

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
Stayed 4 nights in Nov 2022

10/10 Excellent

Katrina C.

Liked: Cleanliness

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

10/10 Excellent

Pamela T.

Liked: Cleanliness

Great house. Great location. Has everything you need.

Great house. Great location. Has everything you need.
Stayed 7 nights in Oct 2022

10/10 Excellent

Joanne W.

Liked: Cleanliness

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

10/10 Excellent

Kristen S.

Liked: Cleanliness

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

6/10 Okay

Nicole S.

4th of July trip

Property was close to everything. Walking distance to beach and dining. Was difficult to walk to the beach with everything (beach umbrellas, cooler, etc) nothing to bring everything in so we had to drive over and drop off everything and half of family then go back and park and walk. Tried to use the jets in the master tub but it seems they haven’t been used… lots of black flakes came out into the water. I drained, cleaned and reran as this isn’t uncommon when unused (did this at least 5 times) and gave up and was unable to use as there were still black floating all in the tub. Neighborhood has lots of rentals. People next door were renting and really nice. We enjoyed the parade on the 4th of July. We were able to walk to the end of the road and watch. Cute little quaint town. We painted sand dollars at a shop nearby and enjoyed coffee and donuts at the donut experience. Overall the trip was a lot of fun!
Stayed 3 nights in Jul 2022

10/10 Excellent

Tracy L.

Liked: Cleanliness

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

10/10 Excellent

Sydnie K.

Liked: Cleanliness

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

10/10 Excellent

Clare P.

Liked: Cleanliness

The house was clean, well stocked, close to everything

We had a great time. Loved the property!!
Stayed 4 nights in May 2022

10/10 Excellent

Red ( Mary) M., Ottawa, Ohio

Liked: Cleanliness

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

8/10 Good

Mary R., Chicago

Liked: Cleanliness

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

10/10 Excellent

Yosvany R.

Liked: Cleanliness

Great Amenities

We had an excellent time on this property. The house is stocked with everything and I reiterate everything you may need. From board games to bicycles, pool and beach items. The kitchen even has seasons powders in good condition left behind. You don't need to bring anything just the food to cook. Very nice and quite neighborhood. House is updated, new kitchen appliances, clean. Pool is well maintained. The closest beach access is 7 blocks away so not really close if your are hauling a bunch of stuff, but if not you can use the bike or in my case I would drop everyone and all items in the car and come back and take the bike. Text management on the day of arrival as they may let you check in early as long as the house is ready. I was lucky and got in at noon. Overall was a pleasant stay and I recommend this property and Beach Retreats management.
Stayed 4 nights in Sep 2021