Compare Vacation Rentals & Airbnb in Anna Maria Island, FL

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Anna Maria Island, FL vacation rentals
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6231 Rentals and Airbnb in Anna Maria Island, FL

Best family friendly Anna Maria Island, FL vacation rentals

Among the 6231 accommodations in Anna Maria Island, FL, here are the 4 best family friendly rentals

5 Miles To Beaches, Private Pool, 4 Bedrooms! - Anna Maria Island, FL
10 7 reviews
Anna Maria Island, FL
10/07 – 12/07
$804/nighttotal: $1608 (2 )

5 Miles To Beaches, Private Pool, 4 Bedrooms!

1 7
apartment , Bradenton
This four-bedroom accommodation in Bradenton is located 5.8 kilometres from Manatee Public Beach and 7.9 kilometres from Coquina Beach, offering convenient access to the Gulf coast and a mere 5.8-kilometre distance to IMG.
This family-friendly apartment sleeps eight guests and features air conditioning, Wi-Fi, a swimming pool, garden, parking, and complimentary beach supplies, with a dedicated office space and baby equipment available.
Spacious Pet Friendly 3br Home W/ Private Pool & Spa In Palma Sola - Anna Maria Island, FL
8.0 1 review
Anna Maria Island, FL
20/06 – 27/06
$497/nighttotal: $3479 (7 )

Spacious Pet Friendly 3br Home W/ Private Pool & Spa In Palma Sola

3 8
apartment , Bradenton
This Palma Sola, Bradenton holiday home is minutes from Anna Maria Island's beaches and a short drive from Bradenton's city centre.
The 237-square-metre property boasts three bedrooms, two bathrooms, sleeps nine guests, and includes a private pool, jacuzzi, and fully equipped kitchen; optional pool heating is available September to April.
Hot Tub Retreat • Minutes To Ami Beach + Near Img - Anna Maria Island, FL
10 75 reviews
Anna Maria Island, FL
10/07 – 12/07
$614/nighttotal: $1228 (2 )

Hot Tub Retreat • Minutes To Ami Beach + Near Img

1 7
apartment , West Bradenton
This Palma Sola house, situated steps from Robinson Preserve and a short distance from Anna Maria Island, offers easy access to both nature and beaches.
Sleeping nine guests in three bedrooms, this West Bradenton holiday home boasts a fully equipped kitchen, two bathrooms, in-home entertainment, child-friendly amenities including a travel cot and high chair, plus beach essentials such as chairs, umbrellas, and towels for use during your stay.
4411 Shorewalk 15 Min To Beach And 5 Mins To Img - Anna Maria Island, FL
8.9 1670 reviews
Anna Maria Island, FL
03/08 – 07/08
$341/nighttotal: $1364 (4 )

4411 Shorewalk 15 Min To Beach And 5 Mins To Img

2 3
house , Bradenton
This two-bedroom house in Bradenton is ideally located just 15 minutes from the beach and 5 minutes from IMG Academy, making it perfect for families or groups looking for a relaxing and convenient stay. The house has consistently received excellent ratings for its location, cleanliness, and overall experience.
The house is spacious and comfortable, providing a relaxing retreat after a day of exploring the area. Guests can enjoy a range of amenities, including a private pool, a hot tub, and a fully equipped kitchen.

Best Anna Maria Island, FL vacation rentals with a pool

Among the 6231 accommodations in Anna Maria Island, FL, here are the 4 best rentals with a pool

My Seaside Escape - Anna Maria Island, FL
Anna Maria Island, FL
10/07 – 12/07
$642/nighttotal: $1284 (2 )

My Seaside Escape

4 7
house , Bradenton
This Bradenton holiday home is conveniently located 9 kilometres from Sarasota Bradenton International Airport and 12.5 kilometres from The John and Mable Ringling Museum of Art, offering easy access to local attractions.
The 159 square metre property boasts four bedrooms, two bathrooms, sleeps seventeen guests, and includes a private pool, fully equipped kitchen, free Wi-Fi, and on-site parking.
Barefoot Bungalow, Heated Pool & Spa, Game Room Foosball - Anna Maria Island, FL
9.6 142 reviews
Anna Maria Island, FL
20/06 – 27/06
$785/nighttotal: $5495 (7 )

Barefoot Bungalow, Heated Pool & Spa, Game Room Foosball

1 8
apartment , Bradenton
This family-friendly holiday home is located in a peaceful residential neighbourhood in Bradenton, just 13 kilometres from the white sand beaches of Anna Maria Island, 6 kilometres from the Bradenton Area Convention Center, and 4.5 kilometres from Blake Medical Center. The property has excellent user, location and cleanliness ratings, making it a popular choice for families and groups.
This spacious four-bedroom property spans 186 square metres and comfortably accommodates up to 12 guests. The home features a large recreation room, a private saltwater pool and spa, a fully equipped kitchen with a gas grill, and a range of family-friendly amenities including a playhouse, beach toys, and a stroller.
Gulf Coast Getaway Pool Mini Putt Fenced Yard - Anna Maria Island, FL
Anna Maria Island, FL
10/07 – 12/07
$661/nighttotal: $1322 (2 )

Gulf Coast Getaway Pool Mini Putt Fenced Yard

1 7
house , Palmetto
This detached house in Palmetto is situated 17.7 kilometres from Sarasota International Convention Centre and 16.1 kilometres from Sarasota Bradenton International Airport.
This property offers 167 square metres of living space, accommodating up to 14 guests across 3 bedrooms and 2 bathrooms, with amenities including a swimming pool, garden, and on-site parking.
Gulfside 2br Condosilver Sands #257s - Anna Maria Island, FL
9.1 161 reviews
Anna Maria Island, FL
16/08 – 17/08
$805/nightfor 1 night

Gulfside 2br Condosilver Sands #257s

2 5
apartment , Longboat Key
Silver Sands #257s Resort By Rva is located on Longboat Key, a short 10-minute walk from the beach and Cannons Marina, with Coquina Beach and Bradenton Beach within a 3-mile radius. The resort has received excellent user ratings for its location and cleanliness, and is highly recommended for travellers seeking a comfortable and convenient stay.
The apartment offers a spacious 2-bedroom layout with a sofa bed, accommodating multiple guests comfortably. The resort provides a range of amenities, including a swimming pool, tennis court, garden, and barbecue grills, perfect for enjoying the beautiful surroundings.

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! Bean Point is a must-see for its stunning sunsets and views. The historic Anna Maria City Pier offers great fishing and people-watching opportunities. The Island's nature preserves, like the Anna Maria Island Turtle Walk, are also popular spots for wildlife viewing.
  • What are the best Airbnb and vacation rentals in Anna Maria Island, FL?

    Standard 2 Bedroom A, 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?

    Yes, Anna Maria Island is known for its abundant wildlife. Sea turtle nesting season (May-October) is a special time to witness these amazing creatures. Dolphin sightings are common, and birdwatching is excellent, especially in the mangroves and coastal areas. The island's beaches are also home to various shells and sand dollars.
  • 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 (essential!), sunglasses, a hat, and insect repellent. Comfortable walking shoes are a must, as is a reusable water bottle to stay hydrated in the Florida sun. Don't forget your beach towel and a good book!
  • What are the best vacation rentals with a pool in Anna Maria Island, FL?

    Standard 2 Bedroom A, 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 is the average daily budget you should plan for (accommodation, food, transportation, activities) on Anna Maria Island, Florida?

    A daily budget will vary greatly depending on your travel style. For a mid-range trip, you could expect to spend approximately $200-$400 per day for a couple, including accommodation, meals, some activities, and local transportation like taxis or ride-sharing services. Budget-conscious travelers could likely manage on less, while those seeking luxury accommodations and experiences would spend significantly more.
  • What are the best rentals for families and kids 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 upscale seafood. Rod & Reel Pier offers casual waterfront dining with fresh seafood. The Sandbar Restaurant is another popular spot for seafood and waterfront views. Many restaurants feature fresh, local seafood, which is a must-try specialty.
  • What are the best rentals or Airbnbs with a jacuzzi in Anna Maria Island, FL?

  • What are some less-famous attractions on Anna Maria Island, Florida that are worth the visit?

    Exploring the smaller, quieter beaches away from the main tourist areas is a great way to experience the island's natural beauty. Rent bikes and cycle the length of the island, stopping at various beaches along the way. Consider visiting the Anna Maria Island Historical Society Museum for a glimpse into the island's past.
  • What are the best activities for engaging with locals and understanding their culture on Anna Maria Island, Florida?

    Visiting local shops and businesses allows you to interact with residents. Attend local events or farmers' markets, if any are scheduled during your visit. Simply chatting with people you meet at the beach or in restaurants can provide insights into local life. The island has a laid-back atmosphere, and many residents are happy to share information about their community.
  • What unique natural landscapes and terrain features can travelers explore on Anna Maria Island, Florida?

    Anna Maria Island is characterized by its beautiful beaches, mangrove forests, and coastal dunes. The island's relatively flat terrain makes it easy to explore on foot or by bike. Exploring the shoreline at low tide reveals various seashells and marine life.
  • How many days are ideal for visiting Anna Maria Island, Florida, and what are some itinerary suggestions?

    Three to four days is a good amount of time to explore Anna Maria Island at a relaxed pace. A possible itinerary could include: Day 1: Beach time and exploring Anna Maria City. Day 2: Visit Bean Point and explore the northern beaches. Day 3: Nature preserve visit and possibly a boat tour. Day 4: Relax on the beach, enjoy water activities, and savor a final sunset.
  • How is the weather on Anna Maria Island, Florida, in high season?

    High season (winter) on Anna Maria Island is generally sunny and warm, with average temperatures ranging from 15°C to 24°C. Expect some humidity, and occasional showers are possible.

Nearby regions

Best Anna Maria Island, FL vacation rentals with a balcony

New 3 Bedroom The Oasis At One Particular Harbour Condo - Anna Maria Island, FL
9.9 213 reviews
Anna Maria Island, FL
05/01 – 12/01
$408/nighttotal: $2856 (7 )

New 3 Bedroom The Oasis At One Particular Harbour Condo

2 2
apartment , Bradenton
This Bradenton apartment is conveniently located just 8 kilometres from Anna Maria City Pier and 24 kilometres from the John and Mable Ringling Museum of Art, offering easy access to both attractions. Guests have consistently praised the apartment's excellent location, cleanliness, and overall experience.
The apartment is equipped with a kitchen, laundry facilities, and a balcony, ideal for a comfortable stay. Enjoy the amenities, including a swimming pool, jacuzzi, spa, fitness centre, and free parking, as well as the benefits of air conditioning, free Wi-Fi, and a garden.
Villa With Heated Pool And Swim-up Tiki Bar! Close To Beach - La Mer - Anna Maria Island, FL
9.6 40 reviews
Anna Maria Island, FL
20/06 – 27/06
$974/nighttotal: $6818 (7 )

Villa With Heated Pool And Swim-up Tiki Bar! Close To Beach - La Mer

4 8
apartment , Holmes Beach
This Holmes Beach beachfront property, a 137 square metre holiday home, is situated a short 10-minute walk from Island Gallery West and Bradenton Beach, and within 2km of Holmes Beach and Manatee Public Beaches.
Offering four bedrooms, three bathrooms, and sleeping up to eight guests, this self-catering residence boasts a private pool, Jacuzzi, and convenient amenities including a washing machine, dishwasher, and free Wi-Fi.
Shorewalk Sunny Bella Rosa  2br Villa  2 Pools & Hot Tubs  Near Img / Beaches - Anna Maria Island, FL
9.8 224 reviews
Anna Maria Island, FL
02/10 – 08/10
$225/nighttotal: $1350 (6 )

Shorewalk Sunny Bella Rosa 2br Villa 2 Pools & Hot Tubs Near Img / Beaches

2 3
apartment , Bradenton
This two-bedroom apartment is located in South Bradenton, just 1.6 kilometres from the IMG Tennis Academy and a 15-20 minute drive from Anna Maria, Bradenton, and Longboat Key beaches. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The apartment offers 119 square metres of living space, comfortably accommodating up to four guests. Enjoy a range of amenities including a swimming pool, Jacuzzi, tennis court, and a fully equipped kitchen, ensuring a relaxing and enjoyable stay.
Beachfront Studio  Cabana #5b By Rva - Anna Maria Island, FL
9.1 317 reviews
Anna Maria Island, FL
02/10 – 08/10
$324/nighttotal: $1944 (6 )

Beachfront Studio Cabana #5b By Rva

1 3
studio , Longboat Key
Cabana Beach Club #5b Resort By Rva is situated on Longboat Key beach, just a 1.6km walk from Longboat Key Beaches and Cannons Marina, and within 5km of Jewfish Key and Coquina Beach. This resort has received excellent ratings for location, cleanliness and overall user experience.
The apartment offers a comfortable living space with a balcony and a sofa bed. Guests can enjoy a range of amenities including a swimming pool, tennis court, a garden and a terrace.

Best Anna Maria Island, FL vacation rentals with parking

Shorewalk 202/4625 - Bradenton-condo 2 Bedroom/ 2 Bath, 5 Miles From Anna Maria Island And Near Img, Maximum Occupancy Of 4 People. - Anna Maria Island, FL
10 26 reviews
Anna Maria Island, FL
16/07 – 23/07
$314/nighttotal: $2198 (7 )

Shorewalk 202/4625 - Bradenton-condo 2 Bedroom/ 2 Bath, 5 Miles From Anna Maria Island And Near Img, Maximum Occupancy Of 4 People.

1 4
apartment , Bradenton
This two-bedroom apartment is located in the Shorewalk community in Bradenton, just 8 kilometres from the IMG campus and a 24-kilometre drive from the beaches of Anna Maria Island and Longboat Key. The property has received excellent ratings for its location, cleanliness, and overall experience.
The apartment offers 125 square metres of living space and comfortably accommodates up to four guests. It comes equipped with a range of amenities including a fully fitted kitchen, a screened porch, two TVs, and a washer/dryer, as well as access to two heated outdoor pools, two Jacuzzis, two tennis courts, shuffleboard, six stocked fishing ponds, a clubhouse, and barbecue grills.
Shorewalk Rental By Owner/condo 2bed/2bath/img Academy /Anna Maria Island - Anna Maria Island, FL
9.6 141 reviews
Anna Maria Island, FL
07/08 – 09/08
$316/nighttotal: $632 (2 )

Shorewalk Rental By Owner/condo 2bed/2bath/img Academy /Anna Maria Island

2 2
apartment , Bradenton
This two-bedroom apartment is located on 43rd Street West in Bradenton, just a short distance from Cortez Road and within easy reach of Anna Maria Island, Longboat Key, and Siesta Key beaches. It has received excellent user ratings, making it a popular choice for travellers.
The 85 square metre apartment comfortably sleeps four guests and features a fully equipped kitchen, two bathrooms, and a terrace or balcony. Enjoy the on-site amenities including two swimming pools, two whirlpool spas, a playground, tennis courts, a basketball court, and a clubhouse with ping-pong and pool tables.
Guava Getaway - Anna Maria Island, FL
8.9 27 reviews
Anna Maria Island, FL
20/06 – 27/06
$364/nighttotal: $2548 (7 )

Guava Getaway

2 2
house , Holmes Beach
This holiday home is located just a two-minute walk from Anna Maria Island beach and 1.3 kilometres from the centre of Holmes Beach, offering easy access to the area's attractions. The property has received very good user ratings and excellent location and cleanliness ratings.
The two-bedroom house can accommodate up to six guests and has a floor area of 121 square metres. The property has a range of amenities, including a fully-equipped kitchen, air conditioning, a washing machine, a swimming pool, a garden, parking, free Wi-Fi, and cable TV.
Simply Adorable, Spacious And Cozy Beach Home - Anna Maria Island, FL
9.3 64 reviews
Anna Maria Island, FL
03/08 – 07/08
$253/nighttotal: $1012 (4 )

Simply Adorable, Spacious And Cozy Beach Home

2 3
apartment , Cortez
This charming house is located near the beach in Cortez, within easy reach of attractions like Arcadeland, Manatee Golf Course, and Blake Medical Center. It consistently receives excellent ratings for location, cleanliness, and user experience.
The property offers two bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, air conditioning, a garden, parking, free Wi-Fi, and outdoor grilling facilities.
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