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Anna Maria Island vacation rentals

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Top-rated vacation rentals in Anna Maria Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Condo in Holmes Beach
Beach, Pool, Tennis, Bikes, Close to Everything
This bright, newly renovated condo is conveniently located one block from award-winning beaches, a grocery store, pharmacy and many restaurants. If you want a peaceful getaway with a beautiful/quiet pool at the condo, outdoor bay water view seating area, quick access to the beach, this is for you. 2 bikes are included to explore beautiful Anna Maria Island. Price includes county vacation rent taxes, utilities/cable/Wifi. This condo's location has easy on-off island travel to Sarasota/Bradenton.
G$25,169 GYD per night
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Condo in Bradenton Beach
Beach Escape & Pool, steps to Gulf & restaurants
Located steps from the beach, Villa #1 (in this 5 unit quaint condo building) is close to everything Anna Maria Island has to offer. Perfect for a small family or a romantic getaway. 2 minute walk to beautiful Bradenton Beach as well as Bridge Street shops and waterfront restaurants. The heated pool is directly out your back door. New queen pull-out couch in the living room and a comfortable king bed in the master. Updated, well-appointed kitchen has everything you need to enjoy meals at home.
G$43,297 GYD per night
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Rental unit in Bradenton Beach
Playa Esmeralda INN suite #1A
* The Best on Bradenton Beach!! unit # 1A. with the 3C "Clean, Comfy, close to the beach! PLAYA ESMERALDA is a charming cottage studio ONLY 20 steps to the beach. This is a unique, nicely decorated with a island vibe, The Studio fits only two people, offers a queen bed, small bathroom and a Kitchenette. there is a futon that fits a child. parking space for one car included. Check-in is 3 Pm and check-out is 10 Am. Location is fabulous, you can walk to any place you need.!!!! PLAYA
G$44,415 GYD per night

Anna Maria Island house rentals

Home in Holmes Beach
The Peachy Beach House, steps to the gulf
G$59,009 GYD per night
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Home in Anna Maria
White Pearl-New Premier AMI Home with Sunset Views
G$168,990 GYD per night
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Home in Holmes Beach
Turtle Tyme: Beach 2 Blocks, Pool, Dog Friendly
G$64,508 GYD per night
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Home in Anna Maria
New Prof Decorated-Pool/Spa 5 minute walk 2 Ocean
G$147,840 GYD per night
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Home in Anna Maria
Bean Pt. Bungalow - Half duplex w/private pool
G$93,666 GYD per night
Home in Anna Maria
Anna Banana: 3 Houses to Beach North End AMI, Pool
G$105,117 GYD per night
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Home in Anna Maria
CHARMING HOUSE W/HEATED POOL,STEPS TO BEACH UNIT B
G$79,252 GYD per night
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Home in Holmes Beach
Cozy beach house with pool - 1 block from beach!
G$97,758 GYD per night
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Home in Bradenton Beach
5 STARS! Tropical Salt H2O Pool, Steps to BEACH!!
G$84,389 GYD per night
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Home in Holmes Beach
Backyard Bliss Anna Maria Island
G$72,272 GYD per night
Private room in Bradenton
LAKE HOUSE - MANATEE ROOM
G$8,128 GYD per night
Home in Holmes Beach
Sandy Toes: 1 Block to the Beach, Dog Friendly
G$42,150 GYD per night
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Anna Maria Island villa rentals

Villa in Holmes Beach
Calico - Family Oasis - Steps from the Sand
G$140,588 GYD per night
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Villa in Holmes Beach
Studio unit, Islands West Resort - Villa #2 Shrimp
G$16,286 GYD per night
Villa in Holmes Beach
1 Bedroom, Islands West Resort - Villa #5 Seashell
G$20,939 GYD per night
Villa in Holmes Beach
Modern 3BR 2nd-Floor | Balcony | Pool
G$58,798 GYD per night
Villa in HOLMES BEACH
Great location near Manatee Beach 1BR at Casa Coco
G$42,089 GYD per night
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Villa in Holmes Beach
Quiet 2BR | Patio | Pool | W/D
G$41,666 GYD per night
Villa in Holmes Beach
Comfortable 2BR | Patio | Pool |
G$42,723 GYD per night
Villa in Anna Maria
Close to beach - Bayside Cutie at Bayside Bungalow
G$33,629 GYD per night
Villa in Anna Maria
Barefoot by the Bay at Bayside Bungalow
G$35,955 GYD per night
Villa in Anna Maria
Bean Point Residence
G$140,649 GYD per night
Villa in Holmes Beach
Darling 4BR Gulffront | Patio | W/D
G$89,677 GYD per night
Villa in Holmes Beach
2 Bedroom, Islands West Resort - Villa #1 Sailfish
G$34,898 GYD per night

Anna Maria Island condo rentals

Condo in Holmes Beach
Beachfront Bungalow! Newly updated 1 bedroom!
G$60,278 GYD per night
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Condo in Holmes Beach
Beach Escape - Make Memories on Anna Maria Island!
G$47,467 GYD per night
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Condo in Holmes Beach
Beach Haven #204
G$47,588 GYD per night
Condo in Holmes Beach
1/1 STEPS to Beach w/ Heated POOL - Sleeps 4
G$30,638 GYD per night
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Condo in Holmes Beach
LOCATION! Cabana just steps from the beach!
G$40,185 GYD per night
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Condo in Holmes Beach
Anna Maria Beach Place...footsteps to the sands
G$27,284 GYD per night
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Condo in Holmes Beach
The Villas 2A by Duncan Real Estate
G$30,266 GYD per night
Condo in Holmes Beach
Spacious Condo On the Beach
G$61,124 GYD per night
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Condo in Holmes Beach
Island Beach Paradise, Close to Everything, Bikes
G$39,219 GYD per night
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Condo in Bradenton Beach
Best Beach getaway steps from the Gulf of Mexico
G$33,840 GYD per night
Condo in Holmes Beach
Lovely Beach View Condo on Anna Maria Island
G$46,107 GYD per night
Condo in Holmes Beach
Steps to the beach! Updated Condo at The Terrace
G$43,358 GYD per night
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Your guide to Anna Maria Island

Introduction

With its beautiful beaches and brilliant blue waters, this seven-mile barrier island offers a nostalgic idyll on the Gulf of Mexico. Over the years, residents have proudly resisted development, so Anna Maria’s vibe is decidedly low-key, with thatched-roof open-air bars and fresh fish restaurants dotting the waterfront. Here, where the island-wide speed limit is 35 miles per hour, the pace of life is literally slower. There are three small towns on the island — Bradenton Beach in the south, Holmes Beach in the middle, and the largest, Anna Maria, in the north — each with its own charms.


When is the best time to stay in a vacation rental in Anna Maria Island?

January through April and October through December are popular months to visit as they offer temperatures between 70 and 80 degrees Fahrenheit. April and May bring temperatures in the high 80s, and June through September can be quite hot, with temperatures in the 90s. If you opt to book one of the area’s vacation rentals for a winter holiday, make sure to pack a layer for cooler evenings.


What are the top things to do in Anna Maria Island?

Coquina Beach

You won’t have trouble finding a spot for your towel on this serene beach with sand dunes and waving beach grass. Although more sedate than nearby Manatee Public Beach, which draws more crowds, Coquina Beach doesn’t scrimp on amenities. There are picnic tables, bathrooms, and a lifeguard, making it an ideal spot for families. Bring a picnic, or fuel up at the Coquina Beach Cafe, which serves breakfast, fish tacos, and — for the grown-ups — frozen drinks at its tiki bar.

Coquina Baywalk

Get acquainted with the island’s unique ecosystem on this short walk through Leffis Key Preserve on an elevated wooden walkway. You’ll see mangrove trees alongside thousands of native plant species. You’re also likely to spot local wildlife such as geckos, crabs, stingrays, and birds — including the remarkable frigatebird, famous for showboating males who inflate an enormous red pouch under their beaks when courting.

Bean Point Beach

If you’re yearning for that Robinson Crusoe feel, Bean Point Beach is your best bet. Located on the northern tip of the island, this gorgeous stretch of sand is where the island’s founding family, chose to build their estate in 1892. Their homestead is long gone, but the beauty that drew them to the land is very much present. Off the beaten path, this public beach has no parking lots or lifeguard. What it does have is scenic splendor, a calming sense of privacy, and unobstructed sunset views.

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