Compare Anna Maria Island Cottage Rentals

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Featured Cottages in Anna Maria Island

Cottage in the Shade, 3 min walk to beach, restaurants, and pickleball crt.

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.

Washer

Dryer

Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach

At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.

Pool

Kitchen

At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills.

Pool

Kitchen

Charming cottage , close to beach & bay.

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.

Kitchen

Washer

Pelican Perch: Tropical Paradise On The Beach Permit VRC17-000168

At this cottage, guests have access to features like laundry facilities. This beach cottage also has barbecue grills.

Kitchen

Washer

Bridge Street Pier Beach House + Dog-friendly

$478 nightly

$478 total

Nov 23 - Nov 24

Total with taxes and fees

Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills.

Pool

Hot Tub

The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!

At this cottage, guests have access to a gym, laundry facilities, and barbecue grills.

Kitchen

Washer

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.

Pool

Kitchen

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.

Pool

Kitchen

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Anna Maria Island

The Retreat at Anna Maria Island Inn

2305 Gulf Dr N Bradenton Beach FL

$146 nightly

$165 total

Oct 28 - Oct 29

Total with taxes and fees

Tropic Isle at Anna Maria Island Inn

101 22nd St Bradenton Beach FL

$183 nightly

$207 total

Oct 29 - Oct 30

Total with taxes and fees

9/10 Wonderful! (740 reviews)

Bali Hai Beachfront Resort and Spa

6900 Gulf Dr Holmes Beach FL

$228 nightly

$258 total

Nov 18 - Nov 19

Total with taxes and fees

Cottages

Book a cottage in Anna Maria Island
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Anna Maria Island. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Anna Maria Island better.

Cottage apartments in Anna Maria Island range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Anna Maria Island
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Anna Maria Island and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Anna Maria Island cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Anna Maria Island. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Anna Maria Island Cottages essential information

Accommodation	53 Cottages
Lowest Price	$165
Highest Price	$478
Popular accommodation	Cottage in the Shade, 3 min walk to beach, restaurants, and pickleball crt., Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach, Cozy cottage#2 at Tradewinds- 1BR, POOL and steps to beach.Unit#1 available too, Charming cottage , close to beach & bay. , Pelican Perch: Tropical Paradise On The Beach Permit VRC17-000168, Bridge Street Pier Beach House + Dog-friendly, The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!, Shell Cottage -With shared pool, 200 feet from the beach, Starfish Cottage - sleeps 4, with shared pool