⭐ 5
Dockside Dreams
Private Pool & Spa · Waterfront Dock
Fenced pool area with safety features — great for young families
From $450/night View Details
Book direct and save 10-15% compared to Airbnb & VRBO
Thanksgiving & Christmas Rentals AMI
Create magical holiday memories in paradise. Our homes are perfect for family gatherings.
Holiday Vacation Rentals Near Anna Maria Island
Holidays on the Gulf Coast hit differently: Thanksgiving dinner with the pool heated to 84°F, Christmas morning with dolphins visible from the dock, and New Year's Eve fireworks over the marina. Our homes accommodate the whole family with space to celebrate together.
Holiday weeks are our most popular booking period, with Thanksgiving and Christmas filling months in advance. AMI hosts community events including the Christmas parade down Pine Avenue, the Bridge Street holiday festival, and a spectacular New Year's Eve fireworks display visible from our properties.
Featured Rentals
Available Vacation Homes
Book direct and save 10-15% compared to Airbnb & VRBO
⭐ 5
The Oasis
Large Pool + 2 Hot Tubs · Mini Golf Course
Mini golf, 2 hot tubs, game area — kids never get bored
From $550/night View Details
⭐ 5
Sarasota Luxe
Downtown Location · Near St. Armands
Near Mote Marine aquarium and Sarasota children's attractions
From $425/night View Details
⭐ 5
River House
Pool & Spa · Sunset Views
Quiet neighborhood with pool safety gate — toddler-friendly
From $400/night View Details
Common Questions
Frequently Asked Questions
Should I book holidays early?
Yes! Holiday weeks sell out 6-12 months in advance.
Are there holiday rates?
Holiday weeks typically run 20-30% above standard rates. Thanksgiving week and Christmas-New Year's are our most popular periods and often book 3-6 months in advance. Spring break (March-April) also commands premium pricing. Summer rates are surprisingly affordable — 20-30% below peak season.
Can we have a holiday dinner?
Absolutely! All homes have fully-equipped kitchens for holiday feasts.
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