Anna Maria holiday rentals

We found 4,937 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Anna Maria by choosing from 602 houses, 33 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:27 Nov - 4 Dec

Swimming Pool
Sitting Area
Bedroom3
Boat Dock
Exceptional
(16 reviews)

Waterfront, Boat Dock, Kayaks, Fishing, Pool, Spa. 4BR / 9Beds / Sleeps14

Palmetto

7% off
S$5,973
for 7 nights, 1 home
S$853 per night
includes taxes & fees
Waterfront, Boat Dock, Kayaks, Fishing, Pool, Spa. 4BR / 9Beds / Sleeps14
Pool
Anna Maria, Florida's ocean is your ultimate fun zone!
Shopping on Anna Maria Island is like discovering hidden gems!
Your ideal mix of style, convenience, and comfort is ready and waiting for you.
Exceptional
(56 reviews)

Luxury Family Escape: Spacious 4BR, Pool, Close to AMI, Dining & Attractions!

Bradenton

7% off
S$4,893
for 7 nights, 1 home
S$699 per night
includes taxes & fees
Luxury Family Escape: Spacious 4BR, Pool, Close to AMI, Dining & Attractions!
Living area
Pool
Outdoor dining
Property grounds
Exceptional
(137 reviews)

6 Bedrooms - Waterfront,pool, dock, great for families. Big yard, lots of room.

Bradenton

8% off
S$10,277
for 7 nights, 1 home
S$1,468 per night
includes taxes & fees
6 Bedrooms - Waterfront,pool, dock, great for families. Big yard, lots of room.
Aerial view with Gulf of Mexico in the backround.
Quiet Beaches.
Pool
Living room
Exceptional
(280 reviews)

Beach Access, heated pool, and new spa. Pickleball and playground along the bay!

Bradenton Beach

7% off
S$4,775
for 7 nights, 1 home
S$682 per night
includes taxes & fees
Beach Access, heated pool, and new spa. Pickleball and playground along the bay!
Living area
Interior
Private kitchen
Dining
Exceptional
(18 reviews)

5BR with New Heated Pool ! 6mi from AMI Beach & IMG Academy! Spring Break Sales

Bradenton

11% off
S$4,716
for 7 nights, 1 home
S$674 per night
includes taxes & fees
5BR with New Heated Pool ! 6mi from AMI Beach & IMG Academy! Spring Break Sales
Marina
Private kitchen
Terrace/patio
Living area
Exceptional
(110 reviews)

75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated

Anna Maria

8% off
S$4,293
for 7 nights, 1 home
S$613 per night
includes taxes & fees
75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated
Dining
Private kitchen
Pool
Interior
Exceptional
(61 reviews)

Newly Renovated Family Vacation Rental with Pool & Spa

Bradenton

8% off
S$2,475
for 7 nights, 1 home
S$354 per night
includes taxes & fees
Newly Renovated Family Vacation Rental with Pool & Spa
Inside photo of the Shorewalk clubhouse.
Come play golf on several luxurious courses in the Sarasota/Bradenton area.
Completely renovated kitchen with all new appliances.
Living area
Exceptional
(124 reviews)

Spacious Lakeview Retreat By IMG & Anna Maria Island w/ Resort Pools & Hot Tubs

Bradenton

7% off
S$1,689
for 7 nights, 1 apartment
S$241 per night
includes taxes & fees
Spacious Lakeview Retreat By IMG & Anna Maria Island w/ Resort Pools & Hot Tubs
Pool
Private kitchen
Living area
Dining
Exceptional
(62 reviews)

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

Bradenton

7% off
S$2,941
for 7 nights, 1 home
S$420 per night
includes taxes & fees
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
Private kitchen
Island Time! Bridge St.
Perfect private outdoor space rain or shine.
Deck off MBR
Exceptional
(197 reviews)

2 BR 2 Full BA on Anna Maria Island just steps to Beach!

Bradenton Beach

8% off
S$3,436
for 7 nights, 1 home
S$491 per night
includes taxes & fees
2 BR 2 Full BA on Anna Maria Island just steps to Beach!
Master bedroom
Overhead view of the heated pool and Gulf beach across the street.
Kitchen view
Sitting area with pullout
Exceptional
(42 reviews)

Bradenton Beach Resort Condo - Anna Maria Island

Bradenton Beach

8% off
S$4,199
for 7 nights, 1 room
S$600 per night
includes taxes & fees
Bradenton Beach Resort Condo - Anna Maria Island
Terrace/patio
Sports court
Private kitchen
Interior
Exceptional
(45 reviews)

Beautiful Blue Beach House Kids & Pets OK Aug, Sept, Oct, Nov, Dec DISCOUNTS! Beautiful Blue Beach House/AMIsland White Sand Beaches

Bradenton

6% off
S$2,163
for 7 nights, 1 home
S$309 per night
includes taxes & fees
Beautiful Blue Beach House Kids & Pets OK Aug, Sept, Oct, Nov, Dec DISCOUNTS! Beautiful Blue Beach House/AMIsland White Sand Beaches
Interior
Living area / king size bed with balcony, overlooking the beach.
spare bedding & pillows for the futon is in the closet.
Condo pool with tables and chairs and large shaded seating area!
Exceptional
(5 reviews)

The Pelican's Perch, a Beachfront studio condo w/ balcony

Bradenton Beach

16% off
S$2,374
for 7 nights, 1 apartment
S$339 per night
includes taxes & fees
The Pelican's Perch, a Beachfront studio condo w/ balcony
Room
Outdoor dining
Wood floors and decorated in a combination of beach and shabby chic
Seating for 4 or 6 with a little squeeze.
Exceptional
(24 reviews)

Charming and Updated 1 Bedroom in Runaway Bay on Bradenton Beach

Bradenton Beach

7% off
S$2,822
for 7 nights, 1 apartment
S$403 per night
includes taxes & fees
Charming and Updated 1 Bedroom in Runaway Bay on Bradenton Beach
Room
Beach
Exterior
Outdoor dining
Exceptional
(102 reviews)

Low Rider - Bottom Unit -

Bradenton Beach

8% off
S$4,581
for 7 nights, 1 home
S$654 per night
includes taxes & fees
Low Rider - Bottom Unit -
Room
Terrace/patio
Dining
Interior
Exceptional
(13 reviews)

Gracie's Cottage 15 min to Beach

Bradenton

8% off
S$3,161
for 7 nights, 1 home
S$452 per night
includes taxes & fees
Gracie's Cottage 15 min to Beach
Amped Fitness is within walking distance from the condo.
Watch the sunrise at the Bradenton Beach. Great place for a morning run or walk.
Come play golf on several luxurious courses in the Sarasota/Bradenton area.
Inside photo of the Shorewalk clubhouse.
Exceptional
(161 reviews)

Beautiful Resort Retreat By IMG & Anna Maria Island w/ Resort Pools & Hot Tubs

Bradenton

7% off
S$1,723
for 7 nights, 1 apartment
S$246 per night
includes taxes & fees
Beautiful Resort Retreat By IMG & Anna Maria Island w/ Resort Pools & Hot Tubs

  • 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)
  • Splash Island Water Park (13.7 mi / 22.1 km)
  • Harborside Golf Course at Longboat Key Club (16.3 mi / 26.2 km)
  • Links on Longboat (16.3 mi / 26.2 km)
  • Aluna Wellness Center & Spa (4 mi / 6.5 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 rental accommodation in Anna Maria?
Houses are the most popular kind of holiday rental in Anna Maria, according to our data. Even if you have a different idea about what you'd like, Vrbo 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 rental in Anna Maria?
The average price for a holiday rental 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 rental 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 Vrbo 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 rentals in Anna Maria?
Yes. You can choose from 729 holiday rentals that allow pets in Anna Maria. Several of our pet-friendly holiday rentals 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 Vrbo.
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 rentals and enjoy a pool day every day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the perfect place to make a splash!
What are popular rental amenities in Anna Maria?
The most popular rental 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, Vrbo holiday properties come with the best amenities for fun and relaxation with your loved ones.
Are there large group holiday rentals 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, Vrbo will help you find a large group rental to suit the occasion.
Are there holiday rentals 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 rentals. 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 rentals in Anna Maria?
Yes, you can take your pick from 41 one-bedroom rentals in Anna Maria. Whether you want a cosy cottage or a cabin, Vrbo'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 rentals 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 Vrbo.
Are there holiday rentals with WiFi in Anna Maria?
Pick from 191 holiday rentals 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 Vrbo.
How can I find holiday rentals with air conditioning in Anna Maria?
Choose from 723 holiday rentals 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 rental in Anna Maria?
The minimum required age is typically 16, 18 or 21. It can differ from property to property on Vrbo, so look at the rules of your preferred Anna Maria holiday home before booking your trip.
How long can I rent a holiday rental 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 Vrbo'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.

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