Anna Maria holiday rentals

We found 4,617 holiday rentals — enter your dates for availability

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July 2025

August 2025

Find the perfect place for you stay in Anna Maria by choosing from 784 houses, 52 flats and other holiday rentals. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the amenities that you need and want, which might include parking and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Anna Maria

Showing deals for:3 Oct - 10 Oct

Exceptional

(31 reviews)

Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home

Bradenton, FL

7% off

AU$430 per night

includes taxes & fees

Exceptional

(5 reviews)

Welcome to our beautiful home, located near Anna Maria Island & IMG Academy.

Bradenton, FL

7% off

AU$492 per night

includes taxes & fees

Exceptional

(8 reviews)

Blue Palm: Pool - Hot Tub - Beach - Games - Outdoor Shower - Grill - IMG - King

Bradenton, FL

11% off

AU$537 per night

includes taxes & fees

Very good

(5 reviews)

Welcome to our gorgeous remodelled home! Near Anna Maria and Bradenton beach.

Bradenton, FL

6% off

AU$512 per night

includes taxes & fees

Exceptional

(7 reviews)

1lvl, htd pool, 4 bd, 2.5bth, 2 king, sunroom, private, close2beach! NO DMG

Bradenton, FL

7% off

AU$597 per night

includes taxes & fees

Exceptional

(7 reviews)

Near AMI/Sarasota-Heated Pool-Hot Tub-Putting Green-Backyard Games-Game Room

Bradenton, FL

7% off

AU$643 per night

includes taxes & fees

Exceptional

(30 reviews)

Waterfront Views 1 mile to Fort DeSoto & St Pete Beach! Fabulous Area, Low Rates

Tierra Verde, FL

15% off

AU$542 per night

includes taxes & fees

Don't compare prices because nothing compares to Jubilee. Come see to believe!

Exceptional

(12 reviews)

Private Luxury Waterfront Estate 🌿 Step into the Jubilee Sanctuary.

Bradenton, FL

9% off

AU$6,414 per night

includes taxes & fees

Plenty of seating options for beautiful dining at home

Exceptional

(6 reviews)

LUXE beach getaway 5mins from water. 3xKING BR, large heated pool + new playland

Bradenton, FL

11% off

AU$964 per night

includes taxes & fees

Beautiful Longboat Key Beach at Sunset. x street

Exceptional

(87 reviews)

Country Club Long Boat Key Beach Villa 2B 3BA Pool No Hurricane Damage

Longboat Key, FL

7% off

AU$352 per night

includes taxes & fees

Exceptional

(5 reviews)

Spacious 4Bed-4Ba Retreat! Heated Pool, Trendy Rooms,Games, Min to beaches & IMG

Bradenton, FL

7% off

AU$593 per night

includes taxes & fees

Exceptional

(84 reviews)

Anna Maria Island Townhouse - Simply Beautiful! The Perfect Vacation Location!

Holmes Beach, FL

8% off

AU$734 per night

includes taxes & fees

Exceptional

(23 reviews)

House plus Guest House...5BD/4BA! Heated Pool and Hot Tub..minutes to beaches

Bradenton, FL

7% off

AU$893 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Anna Maria

Palmetto Avenue Beach

Find the best place to stay - Anna Maria

Adorable Beach cottage just steps Bean Point beach!

Sleeps 8 · 3 bedrooms · 2 bathrooms

Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!

Sleeps 10 · 4 bedrooms · 2 bathrooms

Anna Maria Island Rentals - Beach Front - "Angels Envy" -Rod & Reel Pier Retreat

Sleeps 4 · 2 bedrooms · 2 bathrooms

Sandy Cheeks: Ground-level home with plunge pool. Close to pier, park, & Bay!

Sleeps 6 · 3 bedrooms · 2 bathrooms

Beachy Boathouse Cottage, 2 BR,1BA, Private Pool, Steps to Beach and Bay-

Sleeps 5 · 2 bedrooms · 1 bathroom

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, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

The waterfront setting of Anna Maria is ready to explore

The island views and surrounding scenery provide a peaceful ambience to your holiday home in Anna Maria. Renowned for its bird watching, fishing and surfing, this city welcomes all visitors. Lido Beach and Tampa Bay are just a couple of the must-see attractions in the area. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Anna Maria

Do you want to discover attractions to visit in the city? Venture out of your holiday home and experience everything that makes Anna Maria a fun place to get away to. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Sarasota Jungle Gardens (15.8 mi / 25.4 km)
Mote Marine Laboratory & Aquarium (16.7 mi / 26.9 km)
Aluna Wellness Center & Spa (4 mi / 6.5 km)
Splash Island Water Park (13.7 mi / 22.1 km)
Harborside Golf Course at Longboat Key Club (16.3 mi / 26.2 km)
Islandside Golf Course at Longboat Key Club (16.3 mi / 26.2 km)

Exploring the natural features in Anna Maria

Travellers enjoy Anna Maria for its island views, beaches and sunrises. Whether you're looking for adventure or just want to appreciate the scenery, Anna Maria is a great place to get outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

Lido Beach (18.2 mi / 29.3 km)
Tampa Bay (19.8 mi / 31.9 km)
Anna Maria Beach (0.7 mi / 1.1 km)
Bean Point Beach (0.8 mi / 1.2 km)
Bradenton Beach (2 mi / 3.2 km)
Holmes Beach Beaches (2.4 mi / 3.8 km)

Seasonal weather in Anna Maria

If you're planning a holiday around the weather, August, July, September and June are the hottest months to visit, when temperatures average 28°C.

Transport to and around Anna Maria

The nearest airport is in Sarasota, FL (SRQ-Sarasota-Bradenton Intl.), located 14.8 mi (23.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to St. Petersburg, FL (SPG-Albert Whitted), which is 17.3 mi (27.8 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Anna Maria?

Houses are the most popular kind of holiday home in Anna Maria, according to our data. Even if you have a different idea about what you'd like, Stayz has properties in many shapes and sizes. Filter our options to find your perfect Anna Maria pad.

How much does it cost to rent a holiday home in Anna Maria?

The average price for a holiday home in Anna Maria is based on a number of factors, such as length of stay, property type and season. Whether you're dreaming about a villa with space for extended family or an apartment for just you and the kids, just enter your dates of travel to view stays with great value.

How much does it cost to rent a beach house in Anna Maria?

The average price for a holiday home by the beach in Anna Maria depends on when you're going and the type and size of property you're looking for. Find prices easily and quickly on Stayz by entering your travel dates. Then use the handy filter tool to pick the number of bedrooms and amenities that you prefer, such as air conditioning, a pool and WiFi.

Are there pet-friendly holiday homes in Anna Maria?

Yes. You can choose from 729 holiday homes that allow pets in Anna Maria. Several of our pet-friendly holiday homes come with a garden for your fur child to play around in, special dog beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect digs on Stayz.

Can I rent a house with a pool in Anna Maria?

Pack your swimsuit and pool noodle, because there are 607 houses with a private pool in Anna Maria. Base yourself at one of these sought-after holiday homes and enjoy a pool day every day. Simply enter your travel dates into Stayz, then use the "pool" filter to find the perfect place to make a splash!

What are popular home amenities in Anna Maria?

The most popular home amenities people are searching for in Anna Maria include a fireplace, a beach view and an ocean view. Whether you're taking a trip with your besties, family or even pets, Stayz holiday properties come with the best amenities for fun and relaxation with your loved ones.

Are there large group holiday homes in Anna Maria?

With 73 properties that can host 10 or more people in Anna Maria, there's no need to limit the invite list. From fun family get-togethers to special events like birthday and Christmas parties, Stayz will help you find a large group home to suit the occasion.

Are there holiday homes in Anna Maria that welcome kids?

Bring the whole group together for fun-filled adventures in Anna Maria at one of our 729 family-friendly holiday homes. Many of these stays offer conveniences that are great for getaways with the little ones, including dining rooms, bunk beds and entertainment areas. Just check the "Properties good for families" filter box and book your favourite.

What are the top attractions for families in Anna Maria?

There are plenty of awesome things to see and do with the family in Anna Maria, including:

Coquina Beach
Anna Maria Beach
Bradenton Beach

Are there one-bedroom holiday homes in Anna Maria?

Yes, you can take your pick from 41 one-bedroom homes in Anna Maria. Whether you want a cosy cottage or a cabin, Stayz's one-bedroom properties are just right if you don't require huge amounts of space. One of the best parts about having your own place? You'll never need to share your getaway with strangers.

Can I find two-bedroom holiday homes in Anna Maria?

Anna Maria has 159 two-bedroom properties that you can choose from. Enjoy a holiday home with all the comfort and privacy you want at a price that's hard to resist on Stayz.

Are there holiday homes with WiFi in Anna Maria?

Pick from 191 holiday homes with WiFi in Anna Maria. If you'd like to disconnect from the world during your break, but still want to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Stayz.

How can I find holiday homes with air conditioning in Anna Maria?

Choose from 723 holiday homes with air conditioning in Anna Maria offering that cooling breeze and extra comfort level. Simply enter your preferred travel dates and then make use of our filter tool to help you locate properties with air conditioning.

How old do you have to be to rent a holiday home in Anna Maria?

The minimum required age is typically 16, 18 or 21. It can differ from property to property on Stayz, so look at the rules of your preferred Anna Maria holiday home before booking your trip.

How long can I rent a holiday home in Anna Maria for?

It's down to the Anna Maria property. To browse available options offering extended stays, just enter your travel dates and number of people into Stayz's search page. You can enjoy having the property to yourself, along with the comforts of home like a fully-equipped kitchen, air conditioning and a backyard where the little ones can play. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.