Anna Maria Island Vacation Rentals & Beach Rentals - 198 Rentals Available
198 Vacation rentals

" Fish Tales"- A two bedroom adorable cottage minutes walking to beach
Bradenton Beach Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Child friendly
$189.00
from $189.00 / night

Beach Dreams "DreamBoat Villa"
Bradenton Beach Apartment
- 1 bedroom 1
- 1 bathroom
- sleeps 5 5
- 2 nights min
- Air conditioning
$287.00
from $287.00 / night

Anna Maria Island Beach Palms 5B
Anna Maria Island Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$344.00
from $344.00 / night

Anna Maria Island Beach Paradise
Anna Maria Island Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Car not necessary
$458.00
from $458.00 / night

Anna Maria Island Beach Palace
Anna Maria Island House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$516.00
from $516.00 / night
Songbird Cottage
Anna Maria Island Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- min stay varies
- Child friendly
- Air conditioning
- Private garden
Responds fast! Avg. 1 hour 23 minutes
$104.00
from $104.00 / night
Absolute Anna Maria
Bradenton Beach Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$344.00
from $344.00 / night
Beach Dreams "Tangerine Dreams Villa "
Bradenton Beach Cottage
- 1 bedroom 1
- 1 bathroom
- sleeps 3 3
- 2 nights min
- Car not necessary
- Air conditioning
$155.00
from $155.00 / night
Certificate of Excellence
Oct To Dec 2020 SPECIAL -$1,899 Per Week - WRITE OR CALL
Anna Maria Island House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 59 minutes
Certificate of Excellence
$205.00
from $205.00 / night
Beach Dreams -"Dream Away Villa"
Anna Maria Island Cottage
- 1 bedroom 1
- 1 bathroom
- sleeps 3 3
- 2 nights min
- Beach/lakeside relaxation
- Car not necessary
$189.00
from $189.00 / night
Anna Maria Island Beach Breeze
Anna Maria Island Condo
- 2 bedrooms 2
- 1 bathroom
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Child friendly
- Car not necessary
$344.00
from $344.00 / night
Anna Maria Island Beach View 209
Bradenton Beach Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Child friendly
$396.00
from $396.00 / night
"Island Oasis" A single family North end canal home with pool
Anna Maria House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Air conditioning
- Private garden
$383.00
from $383.00 / night
Beach House on Anna Maria Island-Rental Openings
Holmes Beach Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$229.00
from $229.00 / night
Anna Maria Island Beach Castle
Anna Maria Island Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$396.00
from $396.00 / night
Amazing Beach Front Condo-Ocean views throughout!
Bradenton Beach Condo
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$655.00
from $655.00 / night
Beach Dreams " Sweet Dreams Villa"
Anna Maria Island Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Child friendly
$304.00
from $304.00 / night
Anna Maria Island Beach Palms 6B
Anna Maria Island House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$344.00
from $344.00 / night
Beach Paradise 5
Anna Maria Island Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$344.00
from $344.00 / night
The Anna Maria Island Beach Paradise 10
Anna Maria Island Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 3 3
- 6 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$164.00
from $164.00 / night
Anna Maria Island Beach Palms 2A
Anna Maria Island Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$344.00
from $344.00 / night
Gulf View Townhouse (Unit 2) remodeled, granite counters, new tile and carpet
Holmes Beach Townhouse
- 2 bedrooms 2
- 3 bathrooms
- sleeps 6 6
- 7 nights min
- Nearest beach 0.05 mi
- Swimming pool
- Child friendly
$172.00
from $172.00 / night
"Sea Story" A two bedroom cottage minutes walking to beach.
Bradenton Beach Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$189.00
from $189.00 / night
Anna Maria Island Beach Palms 7A
Bradenton Beach Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Child friendly
$344.00
from $344.00 / night
The Beach Palms 7A
Bradenton Beach Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Child friendly
$344.00
from $344.00 / night
Family Reunion Villa on Anna Maria Island, Florida
Bradenton Beach Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$262.00
from $262.00 / night
Anna Maria Island Beach Sands
Anna Maria Island Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$401.00
from $401.00 / night
Sandy Pointe #205
Holmes Beach Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Child friendly
- Air conditioning
$126.00
from $126.00 / night
The Beach Sands 203
Bradenton Beach Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$344.00
from $344.00 / night
Fun In The Sun- 304 Gulf Blvd, Anna Maria
Anna Maria House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Ask about pets
$243.00
from $243.00 / night
Islands End- 792 North Shore Dr, Anna Maria
Anna Maria House
- 2 bedrooms 2
- 1 bathroom
- sleeps 6 6
- 7 nights min
- Ask about children
- Ask about pets
$93.00
from $93.00 / night
A Puff Away East- 114 Magnolia Ave East, Anna Maria
Anna Maria House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Ask about children
- Air conditioning
$104.00
from $104.00 / night
Sandy Toes- 116 Palmetto Ave, Anna Maria
Anna Maria House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Ask about children
- Air conditioning
- Ask about pets
$108.00
from $108.00 / night
Palm Court Villas- 210 B Magnolia Ave, Anna Maria
Anna Maria House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Ask about children
- Air conditioning
- Pet friendly
$150.00
from $150.00 / night
Chateau Relaxo- 106 75th St, Holmes Beach
Holmes Beach House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
- Ask about pets
$136.00
from $136.00 / night
Seabatical- 225 Willow Ave, Anna Maria
Anna Maria House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$286.00
from $286.00 / night
4102GD-6. Modern 2 Bedroom Condo with Pool and Patio
Anna Maria Island House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$223.00
from $223.00 / night
The Cats Paw- 206 Palmetto Ave, Anna Maria
Anna Maria House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
- Ask about pets
$158.00
from $158.00 / night
Cedar Getaway Apartment- 102 Cedar Ave Apt., Anna Maria
Anna Maria House
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Ask about children
- Ask about pets
$100.00
from $100.00 / night
My Beach House- 101 Spring Ave, Anna Maria
Anna Maria House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Ask about pets
$260.00
from $260.00 / night
About Anna Maria Island
Only seven miles long, the island is divided into three cities: Holmes Beach, Bradenton Beach, and Anna Maria. This gives vacationers plenty of choices when it comes to choosing what to do and where to stay while visiting. An Anna Maria Island vacation rental right on the beach is the perfect option as home base since chain restaurants are pleasantly absent and the area remains untainted by numerous high rise buildings.
Climate
The average year-round temperature in Anna Maria Island is a comfortable 75 degrees making it an ideal destination to visit during any month. In the winter, the skies are cloudless and temperatures range from 75 degrees during the daytime to 50 degrees overnight. Trade winds influence the spring months with sunny, dry days that reach up to 90 degrees. Hot summer temperatures mixed with gentle breezes and cooling rains give way to glorious weather throughout late fall.Transit
The best way to tour this intimate seven-mile island is by hopping aboard the Anna Maria Island Trolley. It runs north to south from the Anna Maria City Pier to Coquina Beach stopping every few blocks for riders to hop on and off. The best part about it is that it is completely free to riders and offers the perfect opportunity for a burst of refreshing air conditioning on the way to the next activity. Parking can be scarce throughout the island, so the trolley is both a scenic ride and a necessity.Attractions
Part of Anna Maria Island’s charm is its well-preserved natural beauty. The Anna Maria Island Butterfly Park is a perfect place to see butterflies and plants local to the area. Similarly, the island’s scenic shoreline is an attraction in itself. For people who love to visit the beach and soak up sun, Anna Maria Island has several gorgeous beaches to enjoy.· Bean Point is at the very northern tip of the island and is a local secret offering stunning views of the sunset from its pristine and tranquil beach.
· Manatee Beach is a large public beach with lifeguards on duty and ample beach space for undisturbed bliss.
· Cortez Beach has calm waters and light surf and is a family-oriented destination. Although no lifeguards are on duty here, it’s one of the best beaches on Anna Maria Island.
The local museums and art galleries are popular attractions as well and great alternatives to outdoor activities. After a morning spent relaxing in an Anna Maria Island vacation rental, people can spend a fun afternoon at the Anna Maria Island Historical Museum and Park. Visitors to the museum and park can learn about the island’s history, take part in a scavenger hunt, and tour the cottage that fell into the bay. Other indoor attractions include The Studio, where exhibits, workshops and lectures are held, as well as Bradenton’s Village of the Arts where artists live and work.
Shopping & Dining
Anna Maria Island offers a variety of shopping options ranging from eclectic seaside shops to popular outlets. Pine Avenue, “the greenest little main street in America,” is lined with boutiques leading up to the City Pier, and Holmes Beach has blocks of shops filled with adorable keepsakes. Mixed in amongst the folksy storefronts is an array of award-winning dining options as well. Whether you’re looking for a grouper sandwich at a casual beachside joint, or a romantic waterfront experience, Anna Maria Island has many options to choose from. With tables in the sand, the Sandbar is always a good choice for a quintessential island meal.Events
When planning a trip to Anna Maria Island, make arrangements to stay in a vacation rental during one of the city’s awesome annual events. Anna Maria Island Heritage Day in February features the wares and skills of local artists and crafters, and attendees can take part in activities, enjoy lively music and participate in old-fashioned games for kids. In March, Island CityFest features a kids’ zone, arts, crafts and more. Later in Spring, the Bridge Street Merchants host the Blues, Brews & BBQ event for locals and visitors to enjoy. Outdoor Market Sundays take place November through April, and Winterfest in December wraps up the year’s festivities. On Anna Maria Island, fun events happen year-round, so there will always be something to do.Free from commercialism and where shoes are optional, Anna Maria Island is a premier beach destination that visitors flock to year-round. Book a vacation rental to live the laidback lifestyle of a true Anna Maria Islander and fully experience the island’s Floridian charm. The beaches are beckoning!
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.