Anna Maria holiday rentals

We found 4,924 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Anna Maria by choosing from 604 houses, 29 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:11 Dec - 18 Dec

dining room with seating for 8
Four barstools and large area for eating
Interior
Living area
Exceptional
(87 reviews)

Large pool/spa home minutes from beach with arcade games and canal for fishing.

Bradenton

7% off
S$3,612
for 7 nights, 1 home
S$516 per night
includes taxes & fees
Large pool/spa home minutes from beach with arcade games and canal for fishing.
Rainbow at The Cut House
Kitchen
Manatee River with 120 ft dock
Landscaping behind the Cut House
Exceptional
(64 reviews)

Snead Island Cut Home - Oceanfront near Anna Maria , Boat docking, pet friendly

Palmetto

8% off
S$3,441
for 7 nights, 1 home
S$492 per night
includes taxes & fees
Snead Island Cut Home - Oceanfront near Anna Maria , Boat docking, pet friendly
Your ideal mix of style, convenience, and comfort is ready and waiting for you.
Anna Maria, Florida's ocean is your ultimate fun zone!
Living, lounging, cooking—our space does it all.
Shopping on Anna Maria Island is like discovering hidden gems!
Exceptional
(56 reviews)

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

Bradenton

7% off
S$4,353
for 7 nights, 1 home
S$622 per night
includes taxes & fees
Luxury Family Escape: Spacious 4BR, Pool, Close to AMI, Dining & Attractions!
Bikes and helmets are included with your stay to explore the island.
Eat your grilled catch of the day poolside in our new outdoor dining set for 8.
It's cocktail hour!
Tropical Beach Access point only 2 blocks down 48th Street
Exceptional
(121 reviews)

Sunset Landing AMI Beach House. 6BR/4.5BA. Private pool. 2 blks to beach.

Holmes Beach

7% off
S$6,738
for 7 nights, 1 home
S$963 per night
includes taxes & fees
Sunset Landing AMI Beach House. 6BR/4.5BA. Private pool. 2 blks to beach.
Take An Incredible Stroll Through The Ringling Museum In Sarasota!
Longboat Pass
Front Wrought Iron Private Gates Entering- “Sea La Vie” Pond, Meditation Garden.
Beachfront Local Restaurant. Perfect For Sunset on The Beach.
Exceptional
(83 reviews)

Heated Pool~Massive Spanish Home~Water Views~Sunset Deck~Grill~WIFI~Near Beaches

Bradenton

8% off
S$6,256
for 7 nights, 1 home
S$894 per night
includes taxes & fees
Heated Pool~Massive Spanish Home~Water Views~Sunset Deck~Grill~WIFI~Near Beaches
Dining
Private kitchen
Exterior
Interior
Wonderful
(17 reviews)

Pool | Hot Tub | Waterfront Views | Sunsets

Bradenton

10% off
S$5,183
for 7 nights, 1 home
S$740 per night
includes taxes & fees
Pool | Hot Tub | Waterfront Views | Sunsets
Terrace/patio
Private kitchen
Room
Marina
Exceptional
(111 reviews)

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

Anna Maria

8% off
S$4,284
for 7 nights, 1 home
S$612 per night
includes taxes & fees
75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated
Dining
Outdoor dining
Private kitchen
Private kitchen
Exceptional
(157 reviews)

OCTOBER, Nov & Dec DISCOUNTS! Cortez Boat Resort/AMIsland White Sand Beaches BOAT DOCK & LAUNCH on site

Cortez

6% off
S$3,474
for 7 nights, 1 home
S$496 per night
includes taxes & fees
OCTOBER, Nov & Dec DISCOUNTS! Cortez Boat Resort/AMIsland White Sand Beaches BOAT DOCK & LAUNCH on site
Bonus sun room with cute fireplace (non-functional!)
Desk/office space
Living area
Pool
Exceptional
(63 reviews)

Amazing heated pool & spa just minutes from Anna Maria Island

Bradenton

7% off
S$3,326
for 7 nights, 1 home
S$475 per night
includes taxes & fees
Amazing heated pool & spa just minutes from Anna Maria Island
Living area
Private kitchen
Dining
Pool
Exceptional
(61 reviews)

Newly Renovated Family Vacation Rental with Pool & Spa

Bradenton

8% off
S$2,440
for 7 nights, 1 home
S$349 per night
includes taxes & fees
Newly Renovated Family Vacation Rental with Pool & Spa
Exterior
Beach
Property grounds
Property grounds
Exceptional
(97 reviews)

Resort Gem

Bradenton

7% off
S$1,622
for 7 nights, 1 apartment
S$232 per night
includes taxes & fees
Resort Gem
Terrace/patio
Private kitchen
Dining
Living area
Exceptional
(65 reviews)

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

Bradenton

7% off
S$2,712
for 7 nights, 1 home
S$387 per night
includes taxes & fees
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
Sitting area with pullout
Overhead view of the heated pool and Gulf beach across the street.
Entry and dining view
Master bedroom
Exceptional
(42 reviews)

Bradenton Beach Resort Condo - Anna Maria Island

Bradenton Beach

8% off
S$4,191
for 7 nights, 1 room
S$599 per night
includes taxes & fees
Bradenton Beach Resort Condo - Anna Maria Island
Dining
Interior
Private kitchen
Interior
Exceptional
(44 reviews)

3 Minute walk to beautiful AMI beach! Old Florida Charm with a Modern Flair!

Holmes Beach

7% off
S$1,910
for 7 nights, 1 apartment
S$273 per night
includes taxes & fees
3 Minute walk to beautiful AMI beach! Old Florida Charm with a Modern Flair!
Condo pool with tables and chairs and large shaded seating area!
Living area / king size bed with balcony, overlooking the beach.
Interior
Dining table looking into kitchenette, fridge, microwave, two burner stove.
Exceptional
(5 reviews)

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

Bradenton Beach

12% off
S$2,493
for 7 nights, 1 apartment
S$356 per night
includes taxes & fees
The Pelican's Perch, a Beachfront studio condo w/ balcony
Private kitchen
Beach
Outdoor dining
Room
Exceptional
(103 reviews)

Low Rider - Bottom Unit -

Bradenton Beach

8% off
S$4,519
for 7 nights, 1 home
S$646 per night
includes taxes & fees
Low Rider - Bottom Unit -
Living area
Bookcases open to let in more sunlight from the bedroom.
A great place to watch beach goers on their way to Bean Point.
Open kitchen with eat-at-island and drop-leaf table for additional dining.
Exceptional
(206 reviews)

Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!

Anna Maria

8% off
S$4,667
for 7 nights, 1 home
S$667 per night
includes taxes & fees
Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!
Terrace/patio
Living area
Pool
Private kitchen
Exceptional
(13 reviews)

Hometown Paradise- Canalfront home with dock and heated pool

Bradenton

8% off
S$4,065
for 7 nights, 1 home
S$581 per night
includes taxes & fees
Hometown Paradise- Canalfront home with dock and heated pool
Front: Kids park, pickleball, basketball, and access intercoastal 2 blocks.
Beach
Exterior
Interior
Exceptional
(309 reviews)

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

Bradenton Beach

8% off
S$5,992
for 7 nights, 1 home
S$856 per night
includes taxes & fees
Beach Access, heated pool, and new spa. Pickleball and playground along the bay!
Come play golf on several luxurious courses in the Sarasota/Bradenton area.
Watch the sunrise at the Bradenton Beach. Great place for a morning run or walk.
Inside photo of the Shorewalk clubhouse.
Amped Fitness is within walking distance from the condo.
Exceptional
(161 reviews)

Charming 2BR Condo By IMG Academy & Anna Maria Island w/ Heated Pools & Hot Tubs

Bradenton

7% off
S$1,831
for 7 nights, 1 apartment
S$262 per night
includes taxes & fees
Charming 2BR Condo By IMG Academy & Anna Maria Island w/ Heated 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)
  • 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)
  • Manatee Golf Course (8.8 mi / 14.1 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.

More holiday ideas