Compare Vacation Rentals & Airbnb in Anna Maria Island, FL

9208 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Anna Maria Island, FL vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

9208 Rentals and Airbnb 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

Cozy, Relaxing Studio 17 Minutes From The Beach. - Anna Maria Island, FL
9.9 185 reviews

Cozy, Relaxing Studio 17 Minutes From The Beach.

cabin, Bradenton
This self-contained studio apartment is situated in a peaceful Bradenton neighbourhood, conveniently located within a 27km radius of Anna Maria Island's beaches and attractions, including IMG Academy (11 minutes' drive) and LECOM Park (5 minutes' drive).
The 1-bedroom, 1-bathroom unit sleeps 2 guests and features a fully equipped kitchenette with microwave, toaster, coffee maker and refrigerator, plus complimentary refreshments; ample parking with 24-hour security is provided.
Runaway Bay 184 - 1652814 - Anna Maria Island, FL
9.4 192 reviews

Runaway Bay 184 - 1652814

apartment, Bradenton Beach
Runaway Bay 185 - 1357300 is located in Bradenton Beach, just a short walk from the main beach area and less than a mile from Cortez Beach. This property has received excellent ratings for location, cleanliness and overall user experience.
The apartment has a floor area of 100 square metres and includes a well-equipped kitchen, a private patio, and access to a range of amenities, such as a swimming pool, tennis court, fitness centre, sauna, spa, and restaurant.
Waterfront View 10 Mins To Beach, Anna Maria Island & St Armands Circle/lido Key - Anna Maria Island, FL
9.4 16 reviews

Waterfront View 10 Mins To Beach, Anna Maria Island & St Armands Circle/lido Key

apartment, Bradenton
This Bradenton apartment is situated near the coast, less than 3.2 kilometres from Smugglers Cove Adventure Golf and within 4.8 kilometres of IMG Academy, IMG Bollettieri Tennis Academy, and IMG Soccer Academy.
This two-bedroom, two-bathroom condo offers 121 square metres of space, sleeping up to six guests and boasting a fully equipped kitchen, private balcony, free Wi-Fi, plus access to an on-site swimming pool, fitness centre, hot tub, and tennis court.
Palms Villa: Cozy & Minutes From Anna Maria Island - Anna Maria Island, FL
9.5 143 reviews

Palms Villa: Cozy & Minutes From Anna Maria Island

apartment, Bradenton
This two-bedroom apartment is situated in Shorewalk Vacation Villas, just a few kilometres from the beautiful beaches of Anna Maria Island and close to Bradenton's vibrant downtown. It has received excellent ratings for location, cleanliness, and user experience.
The apartment covers 85 square metres and comfortably sleeps four guests. It includes a fully equipped kitchen, two bathrooms, and a range of amenities such as a swimming pool, jacuzzi, and tennis courts.

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

1br Beach Getaway  Silver Sands #254 By Rva - Anna Maria Island, FL
9.2 98 reviews

1br Beach Getaway Silver Sands #254 By Rva

apartment, Longboat Key
Silver Sands #254 Resort By Rva is located on the beach, just 3 kilometres from Longboat Key Beaches and Cannons Marina, with Jewfish Key and Coquina Beach also within a 5 kilometre radius. The resort has received excellent ratings for location, cleanliness and user experience.
The self-catering apartment sleeps up to 4 guests and is equipped with a kitchen, a washing machine, a TV with a DVD player, and a comfortable sofa bed. Guests can enjoy a range of amenities, including a swimming pool, a jacuzzi, a garden, a tennis court, and barbecue facilities.
Beachside Oasis At Runaway Bay 229 - Anna Maria Island, FL
10 25 reviews

Beachside Oasis At Runaway Bay 229

apartment, Bradenton Beach
This beachfront flat in Bradenton Beach, Florida, is a short walk from Anna Maria Sound and less than 1.6km from the Bradenton Beach Marina and Bridge Street.
The two-bedroom, two-bathroom property sleeps six, boasts a fully equipped kitchen, in-unit laundry, private balcony, and access to a swimming pool, spa, fitness centre, and tennis court; nearby activities include watersports and visits to the Aluna Wellness Centre & Spa.
3br/bungalow W/ Heated Saltwater Pool Near Img/ami - Anna Maria Island, FL
9.9 78 reviews

3br/bungalow W/ Heated Saltwater Pool Near Img/ami

apartment, Bradenton
This Bradenton holiday home is conveniently located approximately 13 kilometres from Anna Maria Island and 8-10 minutes (approximately 8-10 kilometres) from IMG Academy.
The three-bedroom, two-bathroom property sleeps six guests and boasts a heated saltwater pool, Jacuzzi, private fenced backyard with barbecue, and coded lockbox access, plus fully equipped kitchen and spacious living area.
Gulf Watch 111 - Anna Maria Island - Condo 2 Bedro - Anna Maria Island, FL
9.2 42 reviews

Gulf Watch 111 - Anna Maria Island - Condo 2 Bedro

apartment, Bradenton Beach
This beachfront apartment is located just a kilometre from Bradenton Beach and the Historic Bridge Street Pier, with Anna Maria Sound and the Bradenton Beach Marina within 1.5 kilometres. The apartment has received excellent ratings for user experience, location, and cleanliness.
The two-bedroom, two-bathroom property offers a fully equipped kitchen, free Wi-Fi, and a DVD player, and guests can enjoy access to a swimming pool, a terrace, and barbecue grills.

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

Pn-near Beaches And Img, Pool, Tennis, Pickleball - Anna Maria Island, FL
9.7 175 reviews

Pn-near Beaches And Img, Pool, Tennis, Pickleball

apartment, Bradenton
This apartment is located in Bradenton, just 1.4 kilometres from Arcadeland and 2.6 kilometres from IMG Academy, offering easy access to popular attractions. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment spans 116 square metres, comfortably accommodating up to four guests in its two bedrooms and two bathrooms. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, tennis court, and a fully equipped kitchen, perfect for a relaxing and enjoyable stay.
Resort Gem - Anna Maria Island, FL
9.8 97 reviews

Resort Gem

apartment, Bradenton
This apartment is located in Bradenton's city centre, just a short walk from the waterfront and a variety of shops and restaurants. It has received excellent reviews from previous guests.
The property has two bedrooms and two bathrooms, comfortably accommodating up to six guests. It offers a range of amenities, including a swimming pool, jacuzzi, tennis court, and a garden, as well as a fully equipped kitchen and air conditioning.
Relax, Recharge & Repeat  Silver Sands #241 By - Anna Maria Island, FL
8.8 249 reviews

Relax, Recharge & Repeat Silver Sands #241 By

apartment, Longboat Key
Silver Sands #243s 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 very good ratings for cleanliness and user experience and an excellent rating for its location.
The smoke-free apartment building has two bedrooms and a sofa bed, suitable for a small family or group of friends. Guests can enjoy a peaceful garden setting, a swimming pool, tennis courts, barbeque facilities, free Wi-Fi and parking.
Beach Castle Resort, Pool, Private Beach! - Anna Maria Island, FL
9.8 56 reviews

Beach Castle Resort, Pool, Private Beach!

apartment, Longboat Key
Beach Castle Resort, offering a pool, tennis court, and private beach access, is situated on Longboat Key, less than 1.6km from Longboat Key Beaches and Cannons Marina, with Jewfish Key approximately 5km away.
This 66 square metre, one-bedroom waterfront apartment sleeps four, boasting a fully equipped kitchen, Smart TV, and access to on-site spa facilities, barbecue grills, and a garden.

Best Anna Maria Island, FL vacation rentals with parking

Sugary Sands 1 Bed Condo And One Block To Beach! - Anna Maria Island, FL
9.7 85 reviews

Sugary Sands 1 Bed Condo And One Block To Beach!

apartment, Bradenton Beach
This Bradenton Beach apartment boasts a prime waterfront location, steps from Bradenton Beach Marina, Bridge Street, and Fish Hole Adventure Golf, with Bradenton Beach and the Historic Bridge Street Pier within 800 metres.
The 55 square metre flat features one bedroom, one bathroom, sleeps four, and includes a fully equipped kitchen, laundry facilities, a balcony, free Wi-Fi, and access to a swimming pool and garden.
Steps From Beach! Heated Pool & Spacious Lanai! - Anna Maria Island, FL
10 172 reviews

Steps From Beach! Heated Pool & Spacious Lanai!

house, Holmes Beach
This Holmes Beach property is situated less than 0.32 kilometres from the beach and 0.16 kilometres from the free island trolley, offering easy access to Holmes Beach's restaurants and shops.
The three-bedroom, two-bathroom house sleeps six guests and boasts a fully equipped kitchen, shared heated pool, large screened lanai, free bikes, and beach equipment; enjoying modern decor throughout.
3br/3ba + Waterfront! Hot Tub + Pool + Beaches! - Anna Maria Island, FL
10 67 reviews

3br/3ba + Waterfront! Hot Tub + Pool + Beaches!

house, Cortez
Kingston's Hideaway is a waterfront property in a picturesque Cortez neighbourhood, located 3.2km from Anna Maria Island beaches and a short drive from Cortez Village's restaurants.
This three-bedroom, three-bathroom house sleeps eight guests, boasting a private pool, hot tub, 27-foot private dock, and patio with barbecue and fire pit; beach essentials including chairs, a wagon, cooler, umbrella and towels are provided.
Steps 2 Beach/walk 2 Bridge St/old Florida Charm - Anna Maria Island, 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.
©2026 cozycozy.com