Skip to content
Some info has been automatically translated. Show original language

Anna Maria Island vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Anna Maria Island

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

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 ESMERALDA COTTAGE has the best location in Anna Maria island/ Bradenton Beach, for such a good price you can rest and party. just 20 steps from the white sandy beach and a block away from Bridge street with shopping center, tiki bars, high end restaurants and beach restaurants, Mini golf for kids, everything is with walking distance!!.. it is definitely a place for your next vacation!!!! and if you want to go further.. just wait for the free yellow trolley to take you around! no need for a car! this property has a parking spot and a nice deck where they will be able to rest. PLAYA ESMERALDA has the BEST location in Bradenton beach; there is not need for a car since everything you need is within walking distance! come and enjoy your vacation!!
$210 per night
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.
$208 per night
SUPERHOST
Rental unit in Holmes Beach
AMI Ohana Beach Resort A with fabulous salt pool!
The location is perfectly situated in the middle of the island with quick access to the beach (3 minute walk from door to shore without crossing Gulf Drive), Publix grocery store, Walgreens, Manatee Public Beach, shopping, restaurants and more. The free trolley stop is steps away offering an affordable way to explore the whole island. Ohana Beach Retreat is a newly renovated triplex in Holmes Beach on Anna Maria Island. Come enjoy our heated salt water pool in an oasis of palm trees.
$259 per night

Anna Maria Island house rentals

Private room in Pinellas Park
Free coffee, breakfast, beach essentials.
$22 per night
SUPERHOST
Home in Anna Maria
New Prof Decorated-Pool/Spa 5 minute walk 2 Ocean
$728 per night
SUPERHOST
Private room in Largo
Splash room with bathroom, 5 miles to the beach
$40 per night
SUPERHOST
Home in Holmes Beach
Cozy beach house with pool - 1 block from beach!
$440 per night
SUPERHOST
Home in Holmes Beach
The Peachy Beach House, steps to the gulf
$282 per night
SUPERHOST
Home in Bradenton Beach
50 Steps to Beach. Hot Tub! 1bd modern cottage
$374 per night
Home in Anna Maria
CHARMING HOUSE W/HEATED POOL,STEPS TO BEACH UNIT B
$343 per night
SUPERHOST
Home in Bradenton Beach
5 STARS! Tropical Salt H2O Pool, Steps to BEACH!!
$410 per night
SUPERHOST
Home in Holmes Beach
Waterfront home with private dock
$214 per night
SUPERHOST
Home in Anna Maria
Anna Banana: 3 Houses to Beach North End AMI, Pool
$531 per night
SUPERHOST
Home in Anna Maria
3BR Dog Friendly | Pool | Deck | W/D
$517 per night
Home in Anna Maria
Charming island home with gas grill & heated
$543 per night

Anna Maria Island villa rentals

Villa in Holmes Beach
Calico - Family Oasis - Steps from the Sand
$596 per night
SUPERHOST
Villa in Holmes Beach
Vacay in luxury! So close to the beach!
$77 per night
Villa in Holmes Beach
Stunning villa close to the beach!
$99 per night
Villa in HOLMES BEACH
Great location near Manatee Beach 1BR at Casa Coco
$190 per night
SUPERHOST
Villa in Anna Maria
Barefoot by the Bay at Bayside Bungalow
$170 per night
Villa in Holmes Beach
Quiet 2BR | Patio | Pool | W/D
$197 per night
Villa in Holmes Beach
Modern 3BR 2nd-Floor | Balcony | Pool
$276 per night
Villa in Holmes Beach
Comfortable 2BR | Patio | Pool |
$199 per night
Villa in Anna Maria
Bean Point Residence
$754 per night
Villa in Anna Maria
Adorable Condo. Perfect for Romantic Vacay!
$159 per night
Villa in Holmes Beach
Darling 4BR Gulffront | Patio | W/D
$425 per night
Villa in Longboat Key
WATERFRONT CONDO, PRIVATE BOAT DOCK, BEACH ACCESS!
$86 per night

Anna Maria Island condo rentals

Condo in Bradenton Beach
★Right on the beach ★ Relax and Enjoy ♥ Sunsets!
$277 per night
SUPERHOST
Condo in Holmes Beach
Beach, Pool, Tennis, Bikes, Close to Everything
$119 per night
SUPERHOST
Condo in Holmes Beach
1/1 STEPS to Beach w/ Heated POOL - Sleeps 4
$144 per night
SUPERHOST
Condo in Holmes Beach
Anna Maria Beach Place...footsteps to the sands
$129 per night
SUPERHOST
Condo in Holmes Beach
Sea Breeze ~ The Perfect Getaway
$182 per night
SUPERHOST
Condo in Bradenton Beach
Best Beach getaway steps from the Gulf of Mexico
$160 per night
Condo in Holmes Beach
The Villas 2A by Duncan Real Estate
$143 per night
Condo in Holmes Beach
Beachfront Bungalow! Newly updated 1 bedroom!
$285 per night
SUPERHOST
Condo in Holmes Beach
Anna Maria Island-just a few steps to the beach
$108 per night
SUPERHOST
Condo in Holmes Beach
Spacious Condo On the Beach
$289 per night
SUPERHOST
Condo in Bradenton Beach
Beachfront condo in paradise
$256 per night
SUPERHOST
Condo in Holmes Beach
Beach Haven #204
$225 per night

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.