Entire home
Crosswind Cottage managed by Beach Retreats FL Anna Maria Island
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Reviews
9.6 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 6
Popular amenities
Explore the area

Holmes Beach, FL
- Place, Bradenton Beach6 min walk
- Place, Island Gallery West8 min walk
- Place, Holmes Beach Beaches14 min walk
- Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)29 min drive
Rooms & beds
3 bedrooms (sleeps 6)
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
🚗 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
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
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.
📍 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
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
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.
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning
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Beach Bliss managed by Beach Retreats FL Anna Maria Island
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9.8 out of 10, Exceptional, (58 reviews)
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
- Island Gallery West - 8 min walk - 0.7 km
- Holmes Beach Beaches - 14 min walk - 1.2 km
- Manatee Public Beach - 2 min drive - 1.8 km
- AMI Paddleboard Adventures - 3 min drive - 2.1 km
Getting around
Restaurants
- The Ugly Grouper - 4 min walk
- Anna Maria Island Beach Cafe - 3 min drive
- The Sandbar Restaurant - 5 min drive
- Anchor Inn - 4 min drive
- Ginny's & Jane E's - 4 min drive
Frequently asked questions
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 window9.8/10
Cleanliness
9.8/10
Check-in
9.4/10
Communication
9.6/10
Location
9.8/10
Listing accuracy
Reviews
Verified
2 September 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Aug 2021
Verified
10/10 Excellent
Krystal C.
11 February 2018
We absolutely loved this beach house!
Krystal C.
Stayed 5 nights in Jan 2018
Verified
10/10 Excellent
Pamela T.
18 October 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house. Great location. Has everything you need.
Pamela T.
Stayed 7 nights in Oct 2022
Verified
10/10 Excellent
Jeff W.
7 July 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome beach house
Jeff W.
Stayed 7 nights in Jun 2023
Verified
10/10 Excellent
Susan D.
11 March 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
anna marie island
Susan D.
Stayed 14 nights in Feb 2023
Verified
10/10 Excellent
Judith V.
19 August 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home!!
Judith V.
Stayed 7 nights in Aug 2024
Verified
10/10 Excellent
Vern K.
31 May 2019
Amazing
Vern K.
Stayed 8 nights in May 2019
Verified
10/10 Excellent
Patricia W.
1 July 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Best Florida vacation ever!
Patricia W.
Stayed 5 nights in Jun 2023
Verified
10/10 Excellent
Michelle R.
30 March 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay
Michelle R.
Stayed 7 nights in Mar 2024
Verified
10/10 Excellent
ASHLEY T.
29 April 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Vacation!
ASHLEY T.
Stayed 7 nights in Apr 2024
Verified
10/10 Excellent
Katrina C.
8 November 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely house!
Katrina C.
Stayed 4 nights in Oct 2022
Verified
10/10 Excellent
Con L.
23 October 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Exactly as advertised
Con L.
Stayed 9 nights in Oct 2019
Verified
8/10 Good
Mary R.
6 January 2022
Liked: Cleanliness, check-in, location, listing accuracy
easy stay
Mary R.
Stayed 7 nights in Dec 2021
Verified
10/10 Excellent
Kristen S.
19 July 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect rental
Kristen S.
Stayed 6 nights in Jul 2022
Verified
10/10 Excellent
Sydnie K.
7 June 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
2022 AMI Vacay
Sydnie K.
Stayed 5 nights in May 2022
Verified
10/10 Excellent
Red ( Mary) M.
14 March 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Girls get away
Red ( Mary) M.
Stayed 28 nights in Feb 2022
Verified
10/10 Excellent
laura K.
28 March 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved every minute!
laura K.
Stayed 7 nights in Mar 2021
Verified
10/10 Excellent
Joanne W.
13 August 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great family vacation
Joanne W.
Stayed 7 nights in Aug 2022
Verified
10/10 Excellent
Tracy L.
3 July 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Relaxation
Tracy L.
Stayed 7 nights in Jun 2022
Verified
10/10 Excellent
Verified traveller
5 August 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Tranquil Stay
Verified traveller
Stayed 7 nights in Jul 2021
Verified
10/10 Excellent
Verified traveller
11 October 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fall break
Verified traveller
Stayed 7 nights in Oct 2023
Verified
8/10 Good
erika s.
11 June 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house!
erika s.
Stayed 4 nights in Jun 2023
Verified
10/10 Excellent
Phillip S.
6 March 2018
As good as the pictures
Phillip S.
Stayed 14 nights in Feb 2018
Verified
10/10 Excellent
Frédérick L.
6 September 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Frédérick L.
Stayed 7 nights in Aug 2025
Verified
6/10 Okay
Robert S.
28 November 2022
Liked: Cleanliness, check-in, communication
House was nice but for what we paid…..
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!
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
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