Anna Maria Island, FL Short term rentals

3934 available short term rental offers

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Anna Maria Island, FL short term rentals
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Best Short term and Weekly rentals in Anna Maria Island, FL

Best family friendly Anna Maria Island, FL Short term rentals

Among the 3934 accommodations in Anna Maria Island, FL, here are the 4 best family friendly rentals

4br Coastal Haven | Private Pool Near Ami Beaches! - Anna Maria Island, FL
9.9 84 reviews
Anna Maria Island, FL
07/11 – 07/25
$423/nighttotal: $5922 (14 )

4br Coastal Haven | Private Pool Near Ami Beaches!

4 7
apartment , Bradenton
This spacious Bradenton vacation home, located in a quiet neighborhood, offers easy access to Anna Maria Island beaches (within 5-15 minutes' drive), Palma Sola Bay fishing pier (walking distance), and Robinson Preserve (3 miles away) for kayaking and biking.
The 1,924-square-foot house features four bedrooms, two bathrooms, sleeps up to ten guests, includes a private pool (heating optional), a fully equipped gourmet kitchen, and provides beach gear, fast Wi-Fi, and all linens and toiletries.
May, June Specials ,Beachfront, Private Beach On The Waterfront, Bring Your Dog - Anna Maria Island, FL
9.6 199 reviews
Anna Maria Island, FL
06/28 – 06/29
$1135/nightfor 1 night

May, June Specials ,Beachfront, Private Beach On The Waterfront, Bring Your Dog

3 2
apartment , Anna Maria
This beachfront home is located in Anna Maria, a short 5-minute walk from the Anna Maria City Pier and the free trolley.
The 2,200 square foot apartment boasts three bedrooms, two bathrooms, and can accommodate up to eight guests, with amenities including a private beach, a Jacuzzi, a spacious deck with waterfront views, and a fully equipped kitchen.
Beautiful 2 Bedroom 2 Bath Fully Furnished Condo Close To Beaches - Anna Maria Island, FL
9.6 51 reviews
Anna Maria Island, FL
07/17 – 07/24
$198/nighttotal: $1386 (7 )

Beautiful 2 Bedroom 2 Bath Fully Furnished Condo Close To Beaches

2 2
apartment , Bradenton
This Bradenton rental is conveniently located just a mile from Arcadeland and a mile and a half from IMG Academy, making it an ideal spot for families and groups visiting the area. The apartment has received excellent ratings from previous guests, highlighting its comfortable accommodations and convenient amenities.
The 2-bedroom, 2-bathroom apartment offers 1170 square feet of space, accommodating up to 6 guests. The rental features a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a tennis court, and a spa, providing plenty of opportunities for relaxation and recreation.
Mycataleya Beautiful Florida Condo (Bradenton) - Anna Maria Island, FL
9.2 41 reviews
Anna Maria Island, FL
07/17 – 07/24
$193/nighttotal: $1351 (7 )

Mycataleya Beautiful Florida Condo (Bradenton)

2 2
apartment , Bradenton
This Bradenton condo, near the Greens of Manatee Golf Club (3.3 miles) and Sarasota Bradenton International Airport (6.2 miles), offers convenient access to area attractions including The John and Mable Ringling Museum of Art and The Dali Museum.
This recently renovated 1,080-square-foot unit features two bedrooms, two bathrooms with a hot tub, a private terrace, and accommodates up to seven guests, boasting a fully equipped kitchen, swimming pool, and tennis court.

Best Anna Maria Island, FL lodging with a balcony

Pineapple Cottage, Walk To The Beach &Pine Ave, Tropical Oasis Pool And Spa. - Anna Maria Island, FL
9.8 72 reviews
Anna Maria Island, FL
08/03 – 08/07
$733/nighttotal: $2932 (4 )

Pineapple Cottage, Walk To The Beach &Pine Ave, Tropical Oasis Pool And Spa.

4 3
apartment , Anna Maria
This Anna Maria Island vacation home is situated near Anna Maria Beach, less than a mile from the Anna Maria Island Museum and Historical Park and Bean Point Beach, and within a 10-minute drive of Historic Green Village and Bay Boulevard Beach.
This smoke-free rental boasts four bedrooms, three bathrooms, and accommodates eight guests, featuring a private pool, jacuzzi, full kitchen with dishwasher, free WiFi, and a terrace; grills are available for outdoor entertaining.
Island Tiki Vibes 2 - Steps To Beach - Outdoor Bar - Anna Maria Island, FL
Anna Maria Island, FL
08/03 – 08/07
$353/nighttotal: $1412 (4 )

Island Tiki Vibes 2 - Steps To Beach - Outdoor Bar

2 3
apartment , Bradenton Beach
This 2-bedroom, 2-bathroom condo in Bradenton Beach offers unparalleled proximity to the beach, just a 2-minute walk away, and is 4.6 miles from Anna Maria City Pier.
This air-conditioned unit features a fully equipped kitchen, complimentary WiFi and private parking, a private balcony, and an outdoor bar, accommodating up to 13 guests.
Views! Beachfront! New!-gulf Front!~heated Pool! - Anna Maria Island, FL
Anna Maria Island, FL
07/10 – 07/12
$1683/nighttotal: $3366 (2 )

Views! Beachfront! New!-gulf Front!~heated Pool!

4 7
apartment , Bradenton Beach
This waterfront vacation home in Bradenton Beach is located in a district just a short walk from Bradenton Beach and Bridge Street, offering convenient access to local attractions.
This 2300 square foot residence accommodates up to 9 guests with 4 bedrooms and 4 bathrooms, featuring a private hot tub, garden, balcony, on-site fitness center, and a fully equipped kitchen with an oven, stovetop, refrigerator, coffee maker, and microwave.
Beachfront Studio  Cabana #5b By Rva - Anna Maria Island, FL
9.1 317 reviews
Anna Maria Island, FL
01/05 – 01/12
$309/nighttotal: $2163 (7 )

Beachfront Studio Cabana #5b By Rva

1 2
studio , Longboat Key
Cabana Beach Club #5b Resort By Rva is a beachfront condo building conveniently located on Longboat Key, within a 10-minute walk of Longboat Key Beaches and Cannons Marina. The resort has excellent user, location, and cleanliness ratings.
The condo offers direct access to Longboat Key's pristine beaches and features fully equipped kitchens, laundry facilities, barbecue grills, balconies, and a sofa bed in the living room for additional sleeping space. Guests can also enjoy a swimming pool, tennis court, parking, and a garden.

Frequently Asked Questions about short term rentals in Anna Maria Island, FL

  • What attractions should you visit during a week-long stay on Anna Maria Island, Florida?

    A week on Anna Maria Island offers plenty to explore! Spend a day at the beautiful Anna Maria Island Beach, known for its calm, shallow waters. Visit the historic Anna Maria City Pier, a great spot for fishing and people-watching. Explore the natural beauty of the Anna Maria Island Nature Preserve. For a taste of local history, check out the Island History Museum. Don't miss a sunset stroll along Bean Point, offering breathtaking views. You could also easily dedicate a day to exploring nearby Bradenton Beach and Holmes Beach, enjoying their unique shops and restaurants.
  • What are the best short term rentals in Anna Maria Island, FL?

  • What attractions should you visit when you spend a month on Anna Maria Island, Florida?

    A month gives you time for a deeper dive! In addition to the attractions listed above, consider renting bikes and exploring the entire island's extensive paved pathways. Take a dolphin watching tour. Visit the nearby Robinson Preserve for more extensive nature trails and wildlife viewing. Spend an afternoon exploring Cortez Village, a historic fishing village with a vibrant arts scene and fresh seafood. Consider day trips to nearby destinations like St. Petersburg or Sarasota for a change of pace. You might even want to take a boat trip to Egmont Key State Park for a unique island experience.
  • What are the best short term rentals with a pool in Anna Maria Island, FL?

    Anna Maria Island Beach Palms 2b, Steps To The Beach Island Paradise and South Bay Inn are the best short term rentals with a pool in Anna Maria Island, FL.

  • Can visitors to Anna Maria Island, Florida witness any unique natural cycles, like cherry blossom season or autumn colors?

    Anna Maria Island doesn't experience the dramatic autumn colors of the northern states or the cherry blossoms of Japan. However, you can witness the nesting season for various shorebirds and sea turtles, primarily during the warmer months. The best time to see sea turtle nests is generally between May and October.
  • What are the best short term rentals with a jacuzzi in Anna Maria Island, FL?

  • What are the most meaningful ways to engage with locals and discover the culture on Anna Maria Island, Florida?

    The best way to connect with locals is to frequent the smaller, locally-owned restaurants and shops. Chat with the staff – many are long-time residents who can share insights. Attend local events – check community calendars for farmers' markets, art walks, or concerts. Consider visiting the Anna Maria Island Historical Society for a deeper understanding of the island's past. Simply striking up conversations with people while enjoying the beaches or exploring the town can lead to interesting interactions.
  • What are the best short term rentals for families and kids in Anna Maria Island, FL?

  • Are there any distinctive cultural activities or hands-on workshops on Anna Maria Island, Florida?

    Anna Maria Island has a thriving arts scene. You can find various art galleries showcasing local artists' work. While scheduled workshops may vary, checking local listings may reveal pottery classes, painting classes, or other creative pursuits. The island's relaxed atmosphere lends itself to a more informal style of cultural engagement; more often, opportunities arise organically through interactions with locals.
  • What are some secret spots or hidden treasures to visit on Anna Maria Island, Florida?

    While many spots are well-known, exploring the quieter stretches of beach away from the main areas offers a sense of seclusion. The northern end of the island, near Bean Point, often has fewer crowds. Exploring the back streets of Anna Maria City can reveal charming little shops and cafes tucked away from the main thoroughfares. The mangroves offer beautiful, quiet spots for kayaking or paddleboarding.
  • What should not be left out of your suitcase if you are going to Anna Maria Island, Florida?

    Pack light clothing, swimwear, sunscreen (essential!), sunglasses, a hat, and comfortable walking shoes. Don't forget insect repellent, especially if you plan on exploring the natural areas. A reusable water bottle is a must, and if you're planning on watersports, bring appropriate gear.
  • What are the most popular festivals on Anna Maria Island, Florida?

    Anna Maria Island hosts various smaller, local events throughout the year. Information on specific dates and events is best found by checking local event listings closer to your travel dates. There isn't one single large, nationally-known festival specifically tied to the island.
  • Where should you try the best local food on Anna Maria Island, Florida?

    The Beach Bistro is a popular upscale choice, known for its elegant ambiance and creative dishes. Rod & Reel Pier offers casual dining with waterfront views and fresh seafood. The Sandbar Restaurant is another popular spot for its beachfront location and relaxed atmosphere. Exploring the smaller, locally-owned cafes and restaurants will also reveal many hidden culinary gems.

Nearby regions

Best Anna Maria Island, FL lodging with a kitchen

Cozy Home With Modern Kitchen, Lanai, & Washer/dryer- Perfect For Group Stays - Anna Maria Island, FL
9.6 5 reviews
Anna Maria Island, FL
07/11 – 07/25
$234/nighttotal: $3276 (14 )

Cozy Home With Modern Kitchen, Lanai, & Washer/dryer- Perfect For Group Stays

3 7
apartment , West Bradenton
This West Bradenton vacation rental, near Bradenton Beach and attractions like Mote Marine Laboratory & Aquarium and The Bishop Museum of Science and Nature, offers convenient access to the Gulf Coast. This single-story, 1,580-square-foot home sleeps eight guests and features a fully equipped kitchen, screened patio, in-unit laundry, and free parking for two vehicles.
Charming 3-bedroom House On The Water In Delightful Cortez Minutes To The Beach - Anna Maria Island, FL
Anna Maria Island, FL
06/27 – 06/28
$818/nightfor 1 night

Charming 3-bedroom House On The Water In Delightful Cortez Minutes To The Beach

3 6
apartment , Cortez
This Cortez waterfront home offers easy access to Anna Maria Island beaches and is minutes from Cortez Beach and Coquina Beach.
The three-bedroom, three-bathroom house sleeps six guests and includes a king, queen, and twin bed, modern amenities such as WiFi and an EV charger, and an elevator.
New Listing On Ami! Walk To Fabulous Beach Front! - Anna Maria Island, FL
9.9 134 reviews
Anna Maria Island, FL
06/27 – 07/04
$233/nighttotal: $1631 (7 )

New Listing On Ami! Walk To Fabulous Beach Front!

1 2
apartment , Holmes Beach
This secluded apartment in Sandy Pointe II, Holmes Beach, is just a few minutes' walk from a quiet section of AMI beach. It has excellent user, location, and cleanliness ratings.
The apartment has 2 bedrooms, 2 bathrooms, and can accommodate 4 guests. It features a well-appointed and stylish interior with King and twin beds, a fully-equipped kitchen, a washer/dryer, and a heated pool with restrooms on the property. Beach chairs, umbrellas, water floats, and toys are provided for guests' convenience.
King Bed + Anna Maria Island Beaches + Beach Gear! - Anna Maria Island, FL
9.9 149 reviews
Anna Maria Island, FL
06/28 – 06/29
$291/nightfor 1 night

King Bed + Anna Maria Island Beaches + Beach Gear!

1 2
apartment , Bradenton
This Bradenton condo, near Palma Sola Causeway Beach and a five-minute drive from Anna Maria Island's Gulf beaches, offers convenient access to local attractions like the South Florida Museum and Ringling Museum of Art.
The one-bedroom, one-bathroom unit sleeps four guests and features a fully equipped kitchen with spices, beach supplies (towels, chairs, umbrella, cooler), free on-site parking, a canal-side setting with a boat ramp, and a picnic table with grill.

Best Anna Maria Island, FL lodging with laundry available

Island Time: Gulf Front Condo 20 Ft To The Beach With Shared Pool - Anna Maria Island, FL
9.6 61 reviews
Anna Maria Island, FL
01/05 – 01/12
$264/nighttotal: $1848 (7 )

Island Time: Gulf Front Condo 20 Ft To The Beach With Shared Pool

1 2
apartment , Holmes Beach
This beachfront condo in Holmes Beach offers easy access to Bradenton Beach and Island Gallery West (both within 1 mile), and Palmetto Avenue Beach and Holmes Beach Beaches (within 2 miles).
The 990-square-foot unit features one bedroom, sleeps four, and includes a fully equipped kitchen, 1.5 bathrooms, a private terrace, and access to a swimming pool, fitness center, tennis court, and on-site parking.
Stylish And Modern Shorewalk Condo Close To Top Beaches, Heated Pools, Hot Tub, Img Academy, Dining - Anna Maria Island, FL
9.0 20 reviews
Anna Maria Island, FL
07/17 – 07/20
$227/nighttotal: $681 (3 )

Stylish And Modern Shorewalk Condo Close To Top Beaches, Heated Pools, Hot Tub, Img Academy, Dining

2 2
apartment , Bradenton
This Shorewalk condo rental in Bradenton is conveniently located near top beaches, IMG Academy, and 6.2 miles from Sarasota Bradenton International Airport.
This spacious 1170-square-foot, two-bedroom, two-bathroom unit sleeps up to 11 guests and boasts a private tennis court, multiple pools (including a heated one and a hot tub), a fully equipped kitchen, and a balcony with lake views.
Bradenton Breeze - Anna Maria Island, FL
9.9 72 reviews
Anna Maria Island, FL
07/02 – 07/06
$268/nighttotal: $1072 (4 )

Bradenton Breeze

1 5
apartment , Bradenton
This two-bedroom apartment is located in a quiet neighborhood, just six miles from the beach and minutes from Anna Maria Island. It has received excellent ratings for user experience, location, and cleanliness.
The apartment has two bedrooms, two bathrooms, and can comfortably accommodate up to five guests. Amenities include a swimming pool, a garden, a fully equipped kitchen, and parking.
Bradenton Beach/anna Maria Island, Img Academy, Longboat Key, Sarasota - Anna Maria Island, FL
9.8 110 reviews
Anna Maria Island, FL
08/02 – 08/09
$195/nighttotal: $1365 (7 )

Bradenton Beach/anna Maria Island, Img Academy, Longboat Key, Sarasota

2 2
apartment , Bradenton
This family-friendly condo is located near the beach in Bradenton, within easy reach of both Arcadeland and IMG Academy. Guests consistently rate this apartment excellent for its location, cleanliness, and overall experience.
The two-bedroom, two-bathroom condo spans 1170 square feet and comfortably accommodates up to four guests. Amenities include a private patio, a fully equipped kitchen, a swimming pool, a jacuzzi, a tennis court, and free WiFi, making this a great choice for families or groups looking for a relaxing and enjoyable vacation.
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