Holiday Rentals in Anna Maria, FL

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Anna Maria, FL holiday rentals
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2991 Holiday rentals and Airbnb in Anna Maria, FL

Best family friendly Anna Maria, FL holiday rentals

Among the 2991 accommodations in Anna Maria, FL, here are the 4 best family friendly rentals

Bright Condo In The Palms, Close To Everything! - Anna Maria, FL
9.9 108 reviews

Bright Condo In The Palms, Close To Everything!

apartment, Holmes Beach
This Holmes Beach condo, a short walk or cycle from the beach and local restaurants, offers convenient access to Anna Maria Island's attractions.
Sleeping five guests, this two-bedroom, one-bathroom apartment features a fully equipped kitchen with dishwasher, private deck, three bikes, a beach wagon, and modern amenities including new high-impact windows and mattresses.
Runaway Bay 151- Beach, Bay, Pool And Gym - Anna Maria, FL
9.8 12 reviews

Runaway Bay 151- Beach, Bay, Pool And Gym

apartment, Bradenton Beach
This beachfront Bradenton Beach apartment, situated directly across the street from the beach and close to Cortez Beach and Coquina Beach, offers unparalleled access to the Gulf Coast's stunning sands.
The two-bedroom, two-bathroom condo sleeps six, boasts a fully equipped kitchen with dishwasher, includes a washer/dryer, and offers complimentary use of bikes, beach chairs, and other equipment alongside access to a heated pool, tennis court, and other on-site amenities.
204 M² House ∙ 4 Bedrooms ∙ 8 Guests - Anna Maria, FL
9.9 59 reviews

204 M² House ∙ 4 Bedrooms ∙ 8 Guests

house, Anna Maria
This family-friendly four-bedroom house is situated in Anna Maria, a short 1.6km walk from Anna Maria Beach and 1.6km from Bean Point Beach.
The property features a private pool, spa tub, barbecue grill, and a fully equipped kitchen, making it perfect for families or groups of up to eight guests.
Spectacular Northshore Anna Maria Home W/ Private Pool  1 Block To Beach - Anna Maria, FL
9.2 108 reviews

Spectacular Northshore Anna Maria Home W/ Private Pool 1 Block To Beach

apartment, Anna Maria
Villa Di Palma is situated in the desirable North end of Anna Maria Island, within walking distance of fine dining and entertainment options.
The five-bedroom, four-bathroom property, which spans 316 square meters, features a private swimming pool, a spa, a garden, and a terrace, ideal for families and groups of up to 12 guests.

Best Anna Maria, FL holiday rentals with a pool

Among the 2991 accommodations in Anna Maria, FL, here are the 4 best rentals with a pool

The Palm Leaf Home - Anna Maria, FL
9.5 43 reviews

The Palm Leaf Home

house, Anna Maria
The Palm Leaf home is situated in Anna Maria, Florida, a short 1.8km walk from Anna Maria Island and a 1km walk from Anna Maria City Pier, with Sarasota Bradenton International Airport approximately 29km away.
This 163 square metre property offers three bedrooms, two bathrooms, a fully equipped kitchen with dishwasher, private patio, swimming pool, free Wi-Fi, and parking, comfortably accommodating families or groups.
Sea Whisper: North End Gem W/ Pool & Dock - Anna Maria, FL
9.6 154 reviews

Sea Whisper: North End Gem W/ Pool & Dock

apartment, Anna Maria
This three-bedroom waterfront home is situated just outside the historic Green Village district, a short walk (less than 1.6 km) from Anna Maria Beach.
The 139 square metre property boasts a private pool, spa tub, and fenced garden, comfortably accommodating up to seven guests, with amenities including a fully equipped kitchen, free Wi-Fi, and barbecue grills.
Beach Escape | Pool | Walk Everywhere - Anna Maria, FL
9.8 41 reviews

Beach Escape | Pool | Walk Everywhere

apartment, Bradenton Beach
This Bradenton Beach flat is situated directly across the street from Anna Maria Island's beaches, less than 0.2 km from Holmes Beach and Anna Maria, and a short distance from Longboat Key and Sarasota.
The self-catering apartment sleeps four guests, offering a queen bed, sleeper sofa, fully equipped kitchen including a dishwasher, free Wi-Fi, a community swimming pool, and an outdoor grill, all within easy reach of the free island trolley.
Felicity: Luxury Bayfront Home, Heated Pool, Hot Tub And More! - Anna Maria, FL
10 50 reviews

Felicity: Luxury Bayfront Home, Heated Pool, Hot Tub And More!

apartment, Anna Maria
This luxurious beachfront property is located on Anna Maria Island's North Shore Drive, offering direct beach access and stunning views of the Sunshine Skyway Bridge.
This four-bedroom, eight-guest holiday home boasts approximately 271 square metres of living space, including expansive terraces, a private pool, hot tub, full kitchen with three ovens, and kayaks for guest use.

Frequently asked questions about holiday rentals in Anna Maria, FL

  • What are some interesting places to visit in or near Anna Maria, FL?

    Anna Maria Island is packed with things to see and do. The historic Anna Maria City Pier is a must-visit, offering stunning views of the Gulf of Mexico. For a bit of nature, check out the Bean Point Preserve, a haven for birdwatching and enjoying the beach. If you're looking for a bit of history, the Anna Maria Island Museum is a great place to learn about the island's past.
  • What are the best Airbnb and holiday rentals in Anna Maria, FL?

  • Which walking or cycling routes are the best in Anna Maria, FL?

    For a scenic stroll, try the Pine Avenue Walkway, which runs along the waterfront. If you're feeling adventurous, you can cycle the entire length of Anna Maria Island on the dedicated bike path, taking in the beautiful beaches and charming neighbourhoods. Don't forget to stop at the Anna Maria City Pier for a break and to enjoy the views.
  • What are the most popular Airbnbs in Anna Maria, FL?

  • What sports or outdoor activites can visitors enjoy in and around Anna Maria, FL?

    Anna Maria Island is a paradise for watersports enthusiasts. You can try your hand at kayaking, paddleboarding, or even kitesurfing in the calm waters of the Gulf of Mexico. Fishing is also very popular, with plenty of charter boats available for deep-sea adventures. For a more relaxed experience, why not rent a beach cruiser and explore the island at your own pace?
  • What are the best holiday rentals with a pool in Anna Maria, FL?

  • What other towns or cities can be easily accessed from Anna Maria, FL?

    Anna Maria Island is perfectly located for exploring the surrounding area. You can easily drive to Bradenton, which is home to the South Florida Museum and the Bishop Museum of Science and Nature. Sarasota, known for its vibrant arts scene and beautiful beaches, is also within easy reach. For a day trip, consider visiting the St. Armand's Circle in Sarasota, a popular shopping and dining destination.
  • What are the best rentals for families and kids in Anna Maria, FL?

  • What amenities are commonly available in vacation rentals in Anna Maria, FL?

    Vacation rentals in Anna Maria Island are typically well-equipped with modern amenities to make your stay comfortable. Most rentals offer private pools, hot tubs, fully equipped kitchens, laundry facilities, and high-speed internet. Many also have balconies or patios with stunning views of the Gulf of Mexico.
  • What are the best rentals or Airbnbs with a jacuzzi in Anna Maria, FL?

  • What time of year is best to rent a vacation rental Anna Maria, FL?

    The best time to visit Anna Maria Island is during the shoulder seasons, from April to May and September to October. The weather is still warm and sunny, but the crowds are smaller and prices are more affordable. If you're looking for a more lively experience, you can visit during the peak season, from December to April, but be prepared for higher prices and larger crowds.

Popular destinations

Best Anna Maria, FL holiday rentals with a balcony

Charming Beach Condo Steps To Beach | Heated Pool | Sleeps 4 - Anna Maria, FL
9.0 9 reviews

Charming Beach Condo Steps To Beach | Heated Pool | Sleeps 4

apartment, Bradenton Beach
This Bradenton Beach apartment, a short 0.003 km stroll from the beach and 0.002 km from Anna Maria Island's shores, offers convenient access to the free island trolley.
The 45 square metre self-catering flat features one bedroom, one bathroom, sleeps four, and includes a fully equipped kitchen, swimming pool, terrace, and free Wi-Fi.
Emerald Shores West - Anna Maria, FL
No reviews

Emerald Shores West

house, Anna Maria
This Anna Maria Island bungalow offers direct access to the island, situated 26 kilometres from Sarasota Bradenton International Airport and 29 kilometres from the Sarasota International Convention Centre and John And Mable Ringling Museum Of Art.
This 132 square metre property features one bedroom, one bathroom, and accommodates up to 11 guests with air conditioning, a private entrance, a balcony with outdoor furniture, a barbecue, and an outdoor swimming pool.
Island Breeze: Steps To Beach, Heated Pool & Spa, Huge Verandah By Anna Maria Life Vacation Rentals - Anna Maria, FL
9.8 29 reviews

Island Breeze: Steps To Beach, Heated Pool & Spa, Huge Verandah By Anna Maria Life Vacation Rentals

apartment, Anna Maria
This two-bedroom apartment is located on Beach Avenue in Anna Maria, just a short walk from the beautiful beaches of Anna Maria Island.
The 110 square metre property features a private pool and spa, a spacious verandah with rocking chairs, a patio dining table for four, a fenced yard, a charcoal grill, a covered poolside lounge, and parking for four vehicles.
Buttonwood Cottage - Anna Maria, FL
8.5 2 reviews

Buttonwood Cottage

house, Anna Maria
Buttonwood Cottage, a beachfront property in Anna Maria, Florida, is a 6-minute walk from Anna Maria Island and a 5-minute walk from Anna Maria City Pier, offering easy access to the beach and local attractions.
This three-bedroom, two-bathroom house boasts 179 square metres of floor space, accommodating up to 15 guests and featuring a private pool, free Wi-Fi, and private parking; nearby activities include visiting The John and Mable Ringling Museum of Art (within 32 kilometres).

Best Anna Maria, FL holiday rentals with parking

Pet-friendly Bradenton Home 1.5 Mi To Cortez Beach - Anna Maria, FL
10 61 reviews

Pet-friendly Bradenton Home 1.5 Mi To Cortez Beach

house, Cortez
This property is situated in Bradenton, Florida, approximately 5 kilometres from the beach and 10 kilometres from the Greens of Manatee Golf Club. It enjoys excellent ratings for location, cleanliness, and overall user experience.
This two-bedroom home spans 93 square metres and comfortably accommodates up to four guests. It features a fully equipped kitchen, air conditioning, a private terrace, a garden, a spa, and parking.
Charming, Newly Renovated 2br/2bath Condo On Beach - Anna Maria, FL
9.8 107 reviews

Charming, Newly Renovated 2br/2bath Condo On Beach

apartment, Bradenton Beach
This Bradenton Beach condo offers direct beach access via a deeded crosswalk, situated conveniently near a free trolley stop and across the street from the beach.
The two-bedroom, two-bathroom apartment sleeps six, boasting a fully remodelled interior with stainless steel appliances, granite countertops, and a heated pool, plus on-site amenities including a fitness centre, tennis courts, and kayak/bike hire.
One Block To Beach -Ohana Hale Beachside Studio C - Anna Maria, FL
9.6 446 reviews

One Block To Beach -Ohana Hale Beachside Studio C

apartment, Bradenton Beach
This Bradenton Beach studio apartment is situated just 46 metres from the Gulf of Mexico and a short stroll from Bridge Street's shops and restaurants, with IMG Academy approximately 12 kilometres away.
The self-catering unit sleeps two guests and features a queen-size bed, a small kitchen with microwave and mini-fridge, a private deck, and access to a shared rooftop deck offering Gulf views; beach chairs, umbrella, and towels are provided.
Batemans  Ami Canal-front Luxury Home W/ Pool & Private Dock - Anna Maria, FL
10 73 reviews

Batemans Ami Canal-front Luxury Home W/ Pool & Private Dock

apartment, Anna Maria
This canal-front house is located in Anna Maria, a 0.9km walk from Anna Maria Island and 0.8km from the Anna Maria City Pier.
The 236 square metre property boasts four bedrooms, a private pool and spa, a fully equipped kitchen and a terrace with garden views, making it ideal for families or groups of friends.
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