Crosswind Cottages - Sprawling 3 bed 2.5 bath heated pool elevator FREE WIFI Sleeps 9

neighborhood of Holmes Beach Vacation Rentals
  • Sleeps 9
  • 3 Bedrooms
  • 2.5 Bathrooms
  • 1800 sqft.
  • Pets Allowed
  • Accessible


For the most updated rates please click the link to our direct site Sprawling 3 bed 2.5 bath LUXURY Single Family Home with HEATED pool and ELEVATOR Welcome to this luxury Key West style home by the sea! It is your place in the sun to make memories and unwind! Crosswinds Cottage is just a short five minute walk to Anna Maria Island's world renowned white sandy beaches where you will enjoy time with family and friends while relaxing in the sun! Crosswinds Cottage is a gorgeous Key West style home offering a private heated pool, and plenty of room for family and friends to enjoy luxury accommodations. You are sure to fall in love with everything Crosswinds Cottage has to offer! Perfe...

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  • Balcony
  • Beach Chairs
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Furniture
  • Tennis
  • Books
  • Game Room
  • Games
  • Ping Pong Table
  • Satellite / Cable
  • TV
  • Air Conditioning
  • Bed Linens Provided
  • Dryer
  • Hair Dryer
  • Heating
  • Iron & Board
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Garage
  • Living Room
  • Parking
  • Telephone
  • Blender
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Grill
  • Ice Maker
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Heated Pool
  • Indoor Pool
  • Pool
  • Private Pool
  • Children welcome
  • Elevator
  • Snowbird & Monthly Stay Rental
  • Wheelchair Accessible
  • Activities / Restaurants Guide
  • Alarm Clock
  • Beach Umbrellas
  • Child Highchair
  • Cooking Utensils
  • Dining Area
  • Freezer
  • Jetted Bath Tub
  • Outdoor Gas Grill
  • Terrace / Balcony

Location Info


Nightly rates range from $399.00 to $999.00



Check-In Time : 04:00 PM
Check-Out Time : 10:00 AM
  • Pet(s) Allowed
  • Suitable for Children

General Policies

House Rules

Terms & Conditions

Cancellation Policy

Cancellations made 30 days prior to arrival result in a refund of 70% of the grand total. Reservations over $20,000 must be cancelled 45 days prior to arrival to receive a refund of 70% of the grand total. Cancellations made within 30 days are non refundable. If over $20,000, cancellations made within 45 days are non refundable.


(Based on 10 reviews)

New favorite place

"Loved the house and location!! Will def recommend and hopefully return soon!!"

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. "

Best beach house ever!

"We have stayed in several other properties in Anna Maria but this one was the best ever! The pictures are accurate. Emma and Claire are friendly and available. The beds are super comfortable. We were able to have a family get together during one of the days and everyone had an area to hang out without being on top of each other. Renting this property again for sure!"

Family vacation

"I absolutely loved this property, it was super well equipped and very clean. We were 6 with 3 of them in their 80s and one with 4 months after knee surgery. Thanks God the elevator was working and worked the whole time otherwise it would have been a challenging week. The beach access is more than a 5 min walk !"

Great house!

"This house is great - from the decor to the layout and furnishings - it is just like the photos, if not better. We were very comfortable and enjoyed our stay very much, despite the absolutely foul weather! The only reason for 4 stars instead of 5 is that my requests (by email and by text, in the time frame the property manager required) to check in an hour or two before 4pm were never answered by the property manager. The other standard communications from the property manager were clear and helpful."

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