See all properties
Entire home

Crosswind Cottage managed by Beach Retreats FL Anna Maria Island

Family-friendly holiday home in Holmes Beach with a water park

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

View of home from road
Large heated pool
Outdoor balcony off of dining room
Outdoor dining table under covered patio with fan
Foyer upon entry

Reviews

9.6 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 6

Popular amenities

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

Explore the area

View 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

Rooms & beds

3 bedrooms (sleeps 6)

Common Space

1 Queen Bed, 1 Double Sofa Bed and 1 Single Bunk Bed

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

About this property

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.

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Spacious secluded backyard oasis
Caribbean Surf managed by Beach Retreats FL Anna Maria Island
  • Pool
  • Kitchen
  • Washer
  • Dryer
9.4 out of 10, (55 reviews)
Caribbean Surf managed by Beach Retreats FL Anna Maria Island

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

Pets allowed
default

Smoking

Smoking is not permitted

Important information

You need to know

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

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 Bean Point Beach and Anna Maria Beach. Travelling with kids? Consider Fish Hole Adventure Golf, or check out an event or a game at LECOM Park. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
View more Holiday homes in Holmes BeachOpens in a new window
Map
Holmes Beach, FL

What's nearby

  • Bradenton Beach - 6 min walk - 0.6 km
  • Holmes Beach Beaches - 14 min walk - 1.2 km
  • Manatee Public Beach - 2 min drive - 1.8 km
  • Bean Point Beach - 6 min drive - 4.1 km
  • Anna Maria Beach - 7 min drive - 4.8 km

Getting around

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

Restaurants

  • ‪The Ugly Grouper - ‬4 min walk
  • ‪Anna Maria Island Beach Cafe - ‬3 min drive
  • ‪Dunkin' - ‬5 min drive
  • ‪Skinny's Place - ‬3 min drive
  • ‪Hurricane Hanks - ‬9 min walk

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.

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

Yes, pets are allowed at this 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.
Learn moreOpens in a new window
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

9.8/10

Cleanliness

9.8/10

Check-in

9.4/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Pamela T.

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

10/10 Excellent

Judith V.

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

10/10 Excellent

Con L.

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

10/10 Excellent

Kristen S.

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

10/10 Excellent

Joanne W.

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

10/10 Excellent

Frédérick L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Très bien, très propre et service impeccable.Frédérick
Stayed 7 nights in Aug 2025

10/10 Excellent

ASHLEY T.

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

10/10 Excellent

Michelle R.

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

10/10 Excellent

Verified traveller

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

10/10 Excellent

Jeff W.

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

10/10 Excellent

Patricia W.

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

8/10 Good

erika s.

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

10/10 Excellent

Susan D.

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

6/10 Okay

Robert S., Alexandria, VA

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
Stayed 4 nights in Nov 2022

10/10 Excellent

Katrina C.

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

6/10 Okay

Nicole S.

Liked: Check-in, communication, location, listing accuracy

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, 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

10/10 Excellent

Sydnie K.

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

10/10 Excellent

Clare P.

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

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, 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

8/10 Good

Mary R., Chicago

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

10/10 Excellent

Yosvany R.

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

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

10/10 Excellent

Leah S.

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

10/10 Excellent

Verified traveller

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

10/10 Excellent

Patti K.

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

Relaxing

Beautiful Home, everything we expected and more
Stayed 7 nights in Jun 2021

About the host

Hosted by Beach Retreats

Host profile image
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
Tell us how we can improve our siteShare feedback

Hotels

Holiday Rentals