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

Ocean Minded By Beach Boutique Rentals - Anna Maria, FL
10 31 reviews

Ocean Minded By Beach Boutique Rentals

house, Anna Maria
This ground-floor holiday flat on Anna Maria Island is situated just a short walk from the beach and offers convenient access to the shops and restaurants along Pine Avenue, with the AMI trolley also readily available.
This family-friendly accommodation boasts a private tropical garden with a heated lagoon-style swimming pool and jacuzzi, accommodating up to eight guests with three bedrooms, each featuring an ensuite bathroom, air conditioning, internet, and a fully equipped kitchen.
Private Pool Home-boat Dock-arcade Games! - Anna Maria, FL
9.7 80 reviews

Private Pool Home-boat Dock-arcade Games!

apartment, West Bradenton
This West Bradenton holiday home enjoys a convenient location, approximately 16 kilometres from Sarasota Bradenton International Airport and 19 kilometres from The John and Mable Ringling Museum of Art, offering easy access to beaches and a boat ramp.
The four-bedroom property boasts a private pool, free Wi-Fi, a fully equipped kitchen, and free private parking, comfortably accommodating families or groups and providing all the amenities needed for a relaxing West Bradenton getaway.
Ocean Star! 7 Bdrms/ 7.5 Baths! Beaches 5min> Walk! - Anna Maria, FL
9.8 106 reviews

Ocean Star! 7 Bdrms/ 7.5 Baths! Beaches 5min> Walk!

apartment, Bradenton Beach
This seven-bedroom holiday home is situated in Holmes Beach, a short walk (under 2km) from Bradenton Beach and less than 1.6km from Holmes Beach's centre, offering easy access to Cortez Beach (1.9km) and the John and Mable Ringling Museum of Art (24km).
The property boasts a private pool and spa, a fully equipped kitchen including a dishwasher, free Wi-Fi, and parking; perfect for large families or groups seeking a self-catering stay near Bradenton Beach.
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.

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

Sea Spray 4: *Heated Pool *Pet-friendly *Steps To Beach *Shops, Dining Close - Anna Maria, FL
9.8 42 reviews

Sea Spray 4: *Heated Pool *Pet-friendly *Steps To Beach *Shops, Dining Close

apartment, Anna Maria
This Anna Maria house is situated just a short walk from the beach, the Island Players, and historic landmarks, making it ideal for exploring the area's attractions. The property benefits from excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The 3-bedroom, 2-bathroom property provides ample space for up to 6 guests, with a total floor area of 133 square metres. Guests can enjoy a private pool, barbecue grills, and access to a water park, as well as modern amenities like a fully equipped kitchen, a DVD player and a balcony.
Coconut Cottage~private Heated Pool~block To Shops - Anna Maria, FL
9.9 69 reviews

Coconut Cottage~private Heated Pool~block To Shops

apartment, Anna Maria
Coconut Cottage, a three-bedroom holiday home on Anna Maria Island's north end, is located a short 0.8 km walk from Pine Avenue's shops and restaurants and the beach.
This pet-friendly property sleeps eight, boasting a private heated pool, fully equipped kitchen with granite worktops, and is close to Palmetto Avenue Beach; an adjacent cottage, Kiwi Cottage, can also be rented for larger groups.
Sea La Vie Beach House - Luxury Home W/ Pool, Spa, Dock & Canal Access On Anna Maria - Anna Maria, FL
10 86 reviews

Sea La Vie Beach House - Luxury Home W/ Pool, Spa, Dock & Canal Access On Anna Maria

apartment, Anna Maria
This waterfront property is situated in Anna Maria, just 1.8 kilometres from Anna Maria Island and a 7-minute walk from Anna Maria City Pier.
The four-bedroom house, spanning 262 square metres, features a private pool, a Jacuzzi, and a fully equipped kitchen, ideal for families or groups seeking a relaxing and comfortable stay.
Beach Bliss | Waterfront Pool & Spa | Dock, Golf C - Anna Maria, FL
9.9 67 reviews

Beach Bliss | Waterfront Pool & Spa | Dock, Golf C

apartment, Anna Maria
This four-bedroom, three-bathroom Anna Maria Island holiday home is located on the north end, within walking distance of Tampa Bay and Pine Avenue.
The spacious property sleeps eight guests, offering a king-size bed in the master suite, further king-size beds and bunk beds in additional bedrooms, a fully equipped kitchen including dishwasher, and amenities such as BBQ grill, bikes, paddleboards, kayaks, and a golf cart.

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

An Island Getaway At Palm Tree Villas - Anna Maria, FL
9.3 330 reviews

An Island Getaway At Palm Tree Villas

house, Holmes Beach
This property is located in Holmes Beach, Florida, just 3.2 kilometres from Captain Mike's Fishing Charters, 6.4 kilometres from Bradenton Beach Marina, and a 7-minute drive from Anna Maria City Pier. The villa boasts a very good user rating, an excellent location rating and an excellent cleanliness rating.
The accommodation offers a private patio, a barbecue, a fully equipped kitchen and free parking. Guests can enjoy a refreshing dip in the private pool and stay connected with free Wi-Fi access.
Cabana Breeze - Anna Maria, FL
10 2 reviews

Cabana Breeze

house, Anna Maria
Cabana Breeze is a beachfront property on Anna Maria Island, a two-minute walk from Anna Maria City Pier and 29 kilometres from Sarasota Bradenton International Airport.
This four-bedroom, two-bathroom holiday home sleeps fifteen guests and boasts a private pool, terrace, free Wi-Fi, and parking; enjoy the fully equipped kitchen and fitness centre.
Luxe Ami Stay! Saltwater Pool And Rooftop Views - Anna Maria, FL
9.4 63 reviews

Luxe Ami Stay! Saltwater Pool And Rooftop Views

apartment, Anna Maria
This Anna Maria Island holiday home is ideally situated just steps from Bayfront Park, Bay Boulevard Beach, and Anna Maria City Pier, with Historic Green Village and the Anna Maria Island Museum within 1.6km.
This eight-guest property boasts a private pool, fully equipped kitchen, in-unit laundry, three-and-a-half bathrooms, a balcony, and is close to many attractions.
Runaway Bay 146 - Bay Views, Beach Access, Pool And Gym - Anna Maria, FL
9.7 115 reviews

Runaway Bay 146 - Bay Views, Beach Access, Pool And Gym

apartment, Bradenton Beach
This Bradenton Beach apartment is ideally situated just a short walk from the beach and a few blocks from the free trolley stop, making it easy to explore the island. It has received excellent user ratings, so you can be sure of a comfortable and enjoyable stay. The property offers a spacious layout with a king-size bed in the master bedroom, two twin beds in the guest room, and a queen-size sleeper sofa in the living room, accommodating up to six guests. Guests can enjoy a range of amenities and activities, including a heated pool, private beach access, tennis court, fitness centre, and a screened patio with pond views.

Best Anna Maria, FL holiday rentals with parking

Heated Pool, Pickleball & Mini Golf  18 Guests - Anna Maria, FL
9.9 87 reviews

Heated Pool, Pickleball & Mini Golf 18 Guests

apartment, Bradenton
This five-bedroom, three-bathroom house, sleeping up to 18 guests, enjoys a prime location near Bradenton, Florida, approximately 16km from Bradenton Beach and Manatee Public Beach, and within easy driving distance of the IMG Academy and Robinson Preserve.
The property boasts a resort-style backyard with a heated pool, pickleball court, mini-golf, basketball court, children's playground, and covered patio; inside, a fully equipped kitchen, game room, five Smart TVs, laundry facilities, and ample parking for five cars cater to large families or groups.
Low Fall Rates Now: Off Bridge St & By The Beach - Anna Maria, FL
9.5 52 reviews

Low Fall Rates Now: Off Bridge St & By The Beach

apartment, Bradenton Beach
This Bradenton Beach flat is ideally located less than 0.2 km from Bridge Street, the Anna Maria Island pier, and a 0.3 km stroll from the beach.
The self-catering property offers one bedroom, one bathroom, sleeping up to two guests, and includes a fully equipped kitchen, private parking, beach essentials (chairs, umbrella, cooler, wagon), and a patio; a welcome book provides local information.
Steps 2 Beach/walk 2 Bridge St/old Florida Charm - Anna Maria, FL
9.8 188 reviews

Steps 2 Beach/walk 2 Bridge St/old Florida Charm

apartment, Bradenton Beach
"Reel Paradise" is a one-bedroom apartment situated just a short walk from the white sands of Cortez Beach and a few minutes from the lively Bridge Street, offering easy access to restaurants, shops, and entertainment. The property has been consistently rated excellent for location, cleanliness, and overall experience by previous guests.
The apartment is comfortably sized at 37 square meters and can accommodate up to two guests. It features a well-equipped kitchen, a private garden, and access to shared amenities like outdoor seating areas, gas grills, a washer and dryer, and beach equipment.
Steps To The Beach! Condo With Pool At The Terrace - Anna Maria, FL
9.9 111 reviews

Steps To The Beach! Condo With Pool At The Terrace

apartment, Holmes Beach
This Holmes Beach holiday apartment is situated 200 steps (approximately 0.2km) from the beach, close to Walgreens, various restaurants, a Publix supermarket, and the free island trolley.
The two-bedroom, two-bathroom property sleeps six guests, offering a fully equipped kitchen with a Keurig and blender, private balconies, in-unit laundry, high-speed internet, and access to a shared heated pool and garage containing beach equipment (chairs, umbrellas, tent, cart, inflatable stand-up paddleboard, bicycles).
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