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Anna Maria Island, FL vacation rentals
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Best Vacation rentals and Airbnb offers in Anna Maria Island, FL

Best family friendly Anna Maria Island, FL vacation rentals

Among the 9208 accommodations in Anna Maria Island, FL, here are the 4 best family friendly rentals

Closest To Beach  New Remodel  Pickleball Tennis - Anna Maria Island, FL
10 6 reviews

Closest To Beach New Remodel Pickleball Tennis

apartment, Bradenton Beach
This 2-bedroom, 2-bathroom condo in Bradenton Beach offers direct access to a private beach and is located within the Runaway Bay complex on Anna Maria Island, steps from the island's largest heated saltwater pool.
This pet-friendly vacation rental accommodates up to 6 guests and features a screened terrace with lagoon views, on-site fitness center, fishing pier, and access to tennis, pickleball, bocce, and shuffleboard courts.
House W/ Heated Pool & Arcade Games - Anna Maria Island, FL
9.6 76 reviews

House W/ Heated Pool & Arcade Games

house, Bradenton
This Bradenton house is conveniently located just a short drive from Palma Sola Causeway Park, approximately 11 miles from the Ringling Museum of Art, and 30 miles from Tropicana Field. The property has consistently received excellent ratings for user experience, location, and cleanliness.
The vacation rental comfortably sleeps 10 guests and features 3 bedrooms within its 1650 square feet of space. Enjoy amenities such as a private pool, free Wi-Fi, air conditioning, a fully equipped kitchen, and free parking.
Tranquil Luxury Condo Near Anna Maria Island Beach, 2 Heated Pools, Hot Tubs,img - Anna Maria Island, FL
9.8 74 reviews

Tranquil Luxury Condo Near Anna Maria Island Beach, 2 Heated Pools, Hot Tubs,img

apartment, South Bradenton
This Bradenton condo rental is conveniently located within three miles of IMG Academy, Smugglers Cove Adventure Golf, and the IMG Bollettieri Tennis Academy.
This two-bedroom, two-bathroom unit sleeps six, boasting a fully equipped kitchen, free Wi-Fi, a private terrace, and access to a swimming pool, jacuzzi, and tennis court; housekeeping is available upon request.
Best Location! Heated Pool~steps To Beach/shops! - Anna Maria Island, FL
10 36 reviews

Best Location! Heated Pool~steps To Beach/shops!

apartment, Holmes Beach
This 1-bedroom, 1-bathroom villa at Islands West Resort is located in Holmes Beach, a 2-minute walk from Holmes Beach and close to shops and dining.
This dog-friendly accommodation sleeps up to 4 guests with a king bed and a queen sleeper sofa, and features a shared heated pool, onsite BBQ grills, laundry facilities, and provided beach essentials.

Best Anna Maria Island, FL vacation rentals with a pool

Among the 9208 accommodations in Anna Maria Island, FL, here are the 4 best rentals with a pool

"Paradise" By The Private (Heated) Pool Light! - Anna Maria Island, FL
9.5 164 reviews

"Paradise" By The Private (Heated) Pool Light!

apartment, Cortez
This Cortez vacation rental, located one mile from the Gulf Coast beaches, offers a secluded tropical escape.
The property features a private heated pool, large screened lanai, BBQ grill, outdoor shower, complete kitchenette, queen-sized bed, updated bathroom, Wi-Fi, Smart TV, washer, dryer, and accommodates two guests.
2br Gulfside Paradise  Longboat Key By Rva - Anna Maria Island, FL
9.1 330 reviews

2br Gulfside Paradise Longboat Key By Rva

apartment, 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.
2nd Floor Retreat  Silver Sands #251 By Rva - Anna Maria Island, FL
8.7 129 reviews

2nd Floor Retreat Silver Sands #251 By Rva

apartment, Longboat Key
Silver Sands #251 Resort By Rva is located on Longboat Key, just a short walk from Longboat Key Beaches and Cannons Marina, and within a 3-mile radius of Coquina Beach and Bradenton Beach. Guests consistently rate the accommodation very good for its location, cleanliness, and overall experience. This smoke-free condo features a fully equipped kitchen, a TV with a DVD player, a washing machine, and a sofa bed for additional sleeping arrangements. Amenities include a garden, barbecue grills, a swimming pool, a tennis court, and a terrace or balcony for outdoor relaxation and dining.
The Boathouse - Anna Maria Island, FL
10 59 reviews

The Boathouse

house, Anna Maria
This unique house offers a private tropical setting on the edge of Lake LaVista in Anna Maria, with opportunities to observe manatees.
This luxurious treehouse-style retreat for two features a king-sized bed, an en-suite bathroom with a rain shower, a well-equipped kitchenette, and exclusive access to a heated swimming pool and private garden, all complemented by an expansive outdoor living space with a Weber gas grill.

Frequently Asked Questions about vacation rentals in Anna Maria Island, FL

  • What are the must-see sights on Anna Maria Island, Florida?

    Anna Maria Island boasts beautiful beaches, of course! The Bean Point is a must-see for its stunning sunsets and views. The Anna Maria City Pier is a great place to fish or just relax and watch the Gulf. Historic Bridge Street in Bradenton Beach offers unique shops and restaurants. And don't forget to explore the nature preserves like the Anna Maria Island Nature Preserve and the Leffis Key Preserve.
  • What are the best Airbnb and vacation rentals in Anna Maria Island, FL?

    Standard 2 Bedroom B, Spectacular Beach & Dolphin Views Huge Private Balcony 2br/2ba Upstairs Villa and Anna Maria Island Beach Palms 2b are the most popular Airbnb and vacation rentals in Anna Maria Island, FL among travelers.

  • Are there unique natural phenomena on Anna Maria Island, Florida?

    The island's location on the Gulf Coast means you'll see amazing sunsets. The beaches are known for shelling, with a variety of shells washing ashore. You might even spot dolphins playing in the waters near the shore. Birdwatching is also popular, with various species frequenting the island's natural areas.
  • What are the most popular Airbnbs in Anna Maria Island, FL?

  • What essentials should you bring along for a trip to Anna Maria Island, Florida?

    Pack light clothing, swimwear, sunscreen, sunglasses, a hat, and comfortable walking shoes. Don't forget insect repellent, especially for evenings. A beach umbrella and beach chairs will make your beach days more enjoyable. And of course, a camera to capture those amazing sunsets!
  • What are the best vacation rentals with a pool in Anna Maria Island, FL?

    Standard 2 Bedroom B, Anna Maria Island Beach Palms 2b and Do You Love The Beach? are the best vacation rentals with a pool in Anna Maria Island, FL.

  • What famous events or festivals are happening on Anna Maria Island, Florida?

    Anna Maria Island doesn't have large-scale, internationally known festivals. However, throughout the year, smaller local events take place, including the annual Christmas boat parade and various art walks. Check local event listings closer to your travel dates for the most up-to-date information.
  • What are the best rentals for families and kids in Anna Maria Island, FL?

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) on Anna Maria Island, Florida?

    A daily budget can vary greatly depending on your travel style. For a comfortable trip, expect to spend around $150-$300 per person per day. This includes mid-range accommodation, meals, some activities, and local transportation. Budget-conscious travelers could likely manage on less, while luxury travelers will spend significantly more.
  • What are the best rentals or Airbnbs with a jacuzzi in Anna Maria Island, FL?

  • Where can you find the best restaurants serving local dishes on Anna Maria Island, Florida, and what are the must-try specialties?

    The Beach Bistro is a fine-dining establishment known for its fresh seafood. Rod & Reel Pier offers casual dining with waterfront views. Many restaurants feature fresh seafood, which is a local specialty. Key lime pie is a must-try dessert, reflecting Florida's citrus heritage.
  • What are some less-famous attractions on Anna Maria Island, Florida that are worth the visit?

    The Anna Maria Island Historical Society Museum offers a glimpse into the island's past. Exploring the quieter beaches away from the main tourist areas provides a more peaceful experience. Take a leisurely bike ride along the island's scenic paths. Consider kayaking or paddleboarding through the mangroves.
  • What are the best activities for engaging with locals and understanding their culture on Anna Maria Island, Florida?

    Visiting local shops and art galleries allows you to interact with business owners. Attending smaller community events offers opportunities to meet residents. Simply striking up conversations with people you meet on the beach or in restaurants can provide insights into island life. The laid-back atmosphere makes it easy to connect with people.
  • What unique natural landscapes and terrain features can travelers explore on Anna Maria Island, Florida?

    Anna Maria Island features beautiful beaches with soft, white sand. The mangrove forests provide unique ecosystems to explore via kayak or paddleboard. The island's relatively flat terrain makes it easy to explore on foot or by bike.
  • How many days are ideal for visiting Anna Maria Island, Florida, and what are some itinerary suggestions?

    Three to five days is a good amount of time to explore Anna Maria Island at a relaxed pace. Spend a day relaxing on the beach, another exploring Bridge Street, and perhaps a day kayaking or visiting the nature preserves. Consider a sunset cruise for a memorable experience.

Nearby regions

Best Anna Maria Island, FL vacation rentals with a balcony

94 M² Bungalow ∙ 2 Bedrooms ∙ 5 Guests - Anna Maria Island, FL
10 1 review

94 M² Bungalow ∙ 2 Bedrooms ∙ 5 Guests

bungalow, Holmes Beach
This bungalow in Holmes Beach offers direct bay access and waterfront views on Anna Maria Island, located within 1 mile of beaches, marinas, restaurants, and museums.
This 1000 sq ft single-level home accommodates up to 5 guests with 2 bedrooms, a full kitchen, air conditioning, a garden, fitness center, and complimentary kayaks, beach chairs, and bicycles.
Happy Turtle A: 60 Steps To Beach + Sun Room - Anna Maria Island, FL
9.7 114 reviews

Happy Turtle A: 60 Steps To Beach + Sun Room

apartment, Bradenton Beach
This family-friendly vacation home is located in Bradenton Beach, just steps from the beach and a short walk to popular attractions like Aluna Wellness Center & Spa, Fish Hole Adventure Golf, and Bradenton Beach Marina. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This 2-bedroom rental comfortably accommodates up to 5 guests and offers 1100 square feet of living space. It features a fully equipped kitchen, a private yard, a terrace or balcony, a spa, and parking, making it perfect for families and groups seeking a relaxing and enjoyable beach getaway.
Family Friendly Coastal Escape With Pool And Game Room - Anna Maria Island, FL
10 3 reviews

Family Friendly Coastal Escape With Pool And Game Room

house, West Bradenton
This recently renovated vacation home is located in West Bradenton, 1.8 miles from Palma Sola Causeway Park and 11 miles from Sarasota Bradenton International Airport.
This 400 sq ft house accommodates up to 12 guests with 3 bedrooms and 2 bathrooms, featuring a swimming pool, garden, game room with table tennis, and a fully equipped kitchen.
Beautiful 2 Bedroom 2 Bath Fully Furnished Condo Close To Beaches - Anna Maria Island, FL
9.6 53 reviews

Beautiful 2 Bedroom 2 Bath Fully Furnished Condo Close To Beaches

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.

Best Anna Maria Island, FL vacation rentals with parking

Riverfront 2br  Near Anna Maria Island - Anna Maria Island, FL
9.7 117 reviews

Riverfront 2br Near Anna Maria Island

apartment, West Bradenton
This West Bradenton rental is a private apartment within a mansion, five miles from Anna Maria Island and a block from a county boat ramp.
The two-bedroom, one-bathroom unit sleeps four, boasts Manatee River views, includes a full kitchen with fridge, freezer, and microwave, and offers access to kayaking and jet skiing.
Beachfront · Heated Pool & Spa · Balcony Views - Anna Maria Island, FL
10 1 review

Beachfront · Heated Pool & Spa · Balcony Views

apartment, Bradenton Beach
Seagrape Cottage, an apartment on Anna Maria Island, is located a short walk from Cortez Beach and within walking distance of Bridge Street's shops and restaurants.
This accommodation features four bedrooms, four bathrooms, and a capacity for nine guests, along with a private heated pool, spa, fenced backyard, wrap-around porch, and a patio for dining.
Resort-style Condo 6 Mi To Bradenton Beach! - Anna Maria Island, FL
10 2 reviews

Resort-style Condo 6 Mi To Bradenton Beach!

house, Bradenton
This resort-style condo in Bradenton is located 7.7 miles from the John and Mable Ringling Museum of Art and 5.6 miles from Sarasota Bradenton International Airport.
This 1170 square foot apartment accommodates up to 11 guests with 2 bathrooms, featuring a full kitchen, air conditioning, a swimming pool, hot tub, terrace, tennis court, and on-site parking.
Playa Esmeralda  Inn Suite  2 - Anna Maria Island, FL
9.6 40 reviews

Playa Esmeralda Inn Suite 2

apartment, Bradenton Beach
This Bradenton Beach apartment rental, a second-floor cottage on South Anna Maria Island, is one block from the Gulf of Mexico and a short walk from Bridge Street's restaurants and shops.
The one-bedroom, one-bathroom unit sleeps four with a king bed, queen pull-out sofa, full kitchen, and includes beach chairs, umbrellas, and towels; free parking is available.