Entire home

Crosswind Cottage managed by Beach Retreats FL Anna Maria Island

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

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

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

9.6 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 6

Popular amenities

  • Parking available
  • Dryer
  • Pet friendly
  • Washer
  • Pool
  • Barbecue grill

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

🌴 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.

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: Internet access

Parking and transportation

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • 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.
  • Elevator
  • Wheelchair accessibility
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • In a village
  • In the city center
  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping mall
  • 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

Similar properties

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 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

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

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

About the neighborhood

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-Bradenton Intl. Airport (SRQ) - 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?

Check-out is at 10:00 AM.

Where is Crosswind Cottage managed by Beach Retreats FL Anna Maria Island located?

This family-friendly Holmes Beach vacation 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 mi (2 km).

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