Entire home

Crosswind Cottage managed by Beach Retreats FL Anna Maria Island

Outdoor dining table under covered patio with fan

Overview
Amenities
Policies
Location
Host

Exceptional

3 bedrooms2+ bathroomsSleeps 6

Popular amenities

Parking available
Dryer
Washer
Pet-friendly
Air conditioning
Pool

Explore the area

Holmes Beach, FL

Manatee Public Beach
‪3 min drive‬
Bean Point Beach
‪7 min drive‬
Anna Maria Beach
‪8 min drive‬
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
‪34 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

$500 deposit due at time of booking; balance due 30 days prior to arrival

Cancel 30+ days before arrival → Full refund

Cancel within 30 days → No refund

Extended stays (2+ weeks) or $20,000+ bookings → Full payment due 45 days prior

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

Add dates for prices

Amenities

Pool

Kitchen

Washing machine

Dryer

Pet-friendly

Air conditioning

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Similar properties

Enjoy the simple pleasures of your private backyard oasis

Pool
Hot tub
Kitchen
Washer

House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed

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 and H2O Watersportz. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

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 - 3 min drive - 1.8 km
Bean Point Beach - 7 min drive - 4.1 km
Anna Maria Beach - 8 min drive - 4.8 km

Getting around

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

Restaurants

‪Anna Maria Island Beach Cafe - ‬3 min drive
‪The Sandbar Restaurant - ‬5 min drive
‪Skinny's Place - ‬3 min drive
‪Hurricane Hanks - ‬9 min walk
‪Ginny's & Jane E's - ‬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.

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).

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

9.8/10

Cleanliness

9.8/10

Check-in

9.4/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

10/10 Excellent

Judith V.

19 Aug, 2024

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

Krystal C.

11 Feb, 2018

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

10/10 Excellent

Pamela T.

18 Oct, 2022

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

Great house. Great location. Has everything you need.

Stayed 7 nights in Oct 2022

10/10 Excellent

Jeff W.

7 Jul, 2023

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

Susan D.

11 Mar, 2023

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

10/10 Excellent

Vern K.

31 May, 2019

Amazing

Very clean and the pool was awesome!

Stayed 8 nights in May 2019

10/10 Excellent

Michelle R.

30 Mar, 2024

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

ASHLEY T.

29 Apr, 2024

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

Katrina C.

8 Nov, 2022

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

10/10 Excellent

Con L.

23 Oct, 2019

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

8/10 Good

Mary R., Chicago

6 Jan, 2022

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

Kristen S.

19 Jul, 2022

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

Sydnie K.

7 Jun, 2022

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

Red ( Mary) M., Ottawa, Ohio

14 Mar, 2022

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

10/10 Excellent

laura K.

28 Mar, 2021

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

10/10 Excellent

Joanne W.

13 Aug, 2022

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

Tracy L.

3 Jul, 2022

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

Verified traveller

5 Aug, 2021

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

8/10 Good

erika s.

11 Jun, 2023

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

Phillip S., Chicago

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

Stayed 14 nights in Feb 2018

10/10 Excellent

Christii H.

21 Jun, 2025

Stayed 7 nights in May 2025

10/10 Excellent

Carrie R.

20 Aug, 2024

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

Stayed 7 nights in Jun 2024

10/10 Excellent

Julianne R.

10 Aug, 2024

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

Stayed 7 nights in Apr 2024

10/10 Excellent

Tori R.

10 Aug, 2024

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

Stayed 7 nights in Mar 2024

10/10 Excellent

Verified traveller

11 Oct, 2023

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

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!