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Anna Maria Island cottages

We found 157 cottages — enter your dates for availability

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any cottage rentals in Anna Maria Island?
Pick from 157 cottage rentals around Anna Maria Island. Take your loved ones on a memorable trip to Holmes Beach or check out other well-known cities like Bradenton Beach and Anna Maria. Wherever you're headed, our cottages present the opportunity to disconnect from technology and enjoy a relaxing getaway without constant distractions.
How much does it cost to stay in a cottage rental in Anna Maria Island?
Scroll through our cottage rental listings in Anna Maria Island for a good idea of prices. If you want to save, use our "Discounts" filter. It'll show you any cottages offering special deals, whether that's a monthly, weekly or new listing discount.
When is the best time to rent a cottage in Anna Maria Island?
Consider visiting in January, when the mercury ranges from around 14ºC (57ºF) to 19ºC (66ºF). This is the most popular time of year to get a cottage rental in Anna Maria Island.
Where can I rent an Anna Maria Island holiday cottage with great views?
When looking for your cottage rental in Anna Maria Island, take advantage of our "Location" filter. This will help you narrow down the sorts of areas you'd like to stay in, whether that's around nature or somewhere more central.
Does Anna Maria Island have any lakeside cottages?
Glorious views of glistening water, the beauty of nature and outdoor recreation are just a few of the things to enjoy in one of Vrbo's lakeside cottage rentals. Try our "Location" filter and click on "Lake" to find out if there are any cosy stays in Anna Maria Island close to the water.
What are the top things to do in Anna Maria Island?
Head out and experience everything Anna Maria Island has to offer from the comfort and privacy of your cottage rental. We recommend doing a little research on the things you'd like to see and do, so you can plan the perfect escape.
Why should I book my holiday cottage with Vrbo?
Vrbo provides customer support from the moment you book until the end of your trip, so every aspect of your stay is stress-free. Plus we think our cottage rentals are pretty special — think amenity-packed pads ideal for families and rustic options perfect for an escape for two. You can also take advantage of flexible cancellation policies and other benefits like payment and deposit protection. And when you sign up to our One Key™ rewards programme, you can earn and spend OneKeyCash™* on eligible bookings on Vrbo. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo.

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