Anna Maria Island, FL Short term rentals

5813 available short term rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Anna Maria Island, FL short term rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Short term and Weekly rentals in Anna Maria Island, FL

Best family friendly Anna Maria Island, FL Short term rentals

Among the 5813 accommodations in Anna Maria Island, FL, here are the 4 best family friendly rentals

2 Mi To Bradenton Beach: Water-view Home W/ Bbq - Anna Maria Island, FL
10 70 reviews

2 Mi To Bradenton Beach: Water-view Home W/ Bbq

apartment, Cortez
This Bradenton holiday home is ideally situated near Anna Maria Island, LECOM Park, and the Mote Marine Laboratory & Aquarium, offering easy access to local attractions.
Sleeping up to eight guests, this three-bedroom, two-bathroom property boasts a fully equipped kitchen, in-unit laundry, four smart TVs, a private patio with gas grill and cornhole, and the option of golf cart hire (waiver may apply).
Orange Oasis: Clean, Heated Pool, Near Beaches. - Anna Maria Island, FL
9.9 125 reviews

Orange Oasis: Clean, Heated Pool, Near Beaches.

apartment, Bradenton
This three-bedroom Bradenton holiday home is situated in a quiet neighbourhood, less than 13 kilometres from Anna Maria Island and close to GT Bray Park, IMG Academy, and Pinebrook Ironwood Golf Course.
The self-catering property sleeps eight guests across two king-size, one queen-size bedroom and a daybed, offering a private fenced backyard with a pool, a Weber grill, garage parking, high-speed Wi-Fi, and multiple TVs with streaming services.
Coastal Vibes | 10 Ppl | Pool | Games | Playground - Anna Maria Island, FL
10 28 reviews

Coastal Vibes | 10 Ppl | Pool | Games | Playground

apartment, Bradenton
This four-bedroom, two-bathroom Bradenton holiday home is located approximately 6km from Anna Maria Island, 5km from IMG Academy, and 3km from GT Bray Park, offering easy access to beaches and sporting facilities.
Sleeping up to ten guests, the property boasts a private pool and gazebo with BBQ, a games room with projector, a modern kitchen, and ample driveway parking for boats or jet skis; three bedrooms and two sofa beds provide comfortable accommodation.
Shorewalk Gem - 2br Condo, Community Pools, Near Great Beaches & Golf! - Anna Maria Island, FL
9.6 68 reviews

Shorewalk Gem - 2br Condo, Community Pools, Near Great Beaches & Golf!

apartment, Bradenton
This two-bedroom apartment is located in Bradenton, just 1.4 kilometres from Arcadeland and 2.6 kilometres from IMG Academy, making it a convenient base for exploring the area. It has consistently received excellent user ratings, indicating a high level of satisfaction from previous guests.
The apartment spans 109 square metres and can comfortably accommodate up to six guests. It comes equipped with a range of amenities, including a swimming pool, fitness centre, tennis court, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.

Best Anna Maria Island, FL short term rentals with a balcony

Just Beachy | Putting Green, Heated Pool + Lanai + Arcade - Anna Maria Island, FL
9.6 20 reviews

Just Beachy | Putting Green, Heated Pool + Lanai + Arcade

apartment, Bradenton
This four-bedroom apartment is situated in Bradenton, just a 24-kilometre drive from Bradenton Beach and within a 32-kilometre drive of Coquina Beach and Anna Maria Island. The 187 square metre property boasts a private heated pool, a spacious outdoor area with a lanai and fire pit, and a fully equipped kitchen, accommodating up to eight guests.
Anna Maria Beach Place #5. Directly Across Street From The Beach With Pool. - Anna Maria Island, FL
9.7 262 reviews

Anna Maria Beach Place #5. Directly Across Street From The Beach With Pool.

apartment, Holmes Beach
This apartment is located just a 10-minute walk from Bradenton Beach, Manatee Public Beach, and Anna Maria Sound, making it an ideal base for exploring the area. The property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The apartment features a well-equipped kitchen, a comfortable living area with a sofa bed, and a private balcony offering stunning ocean views. Guests can enjoy access to a swimming pool, spa, fitness centre, and restaurant on site, as well as free Wi-Fi and barbecue grills for outdoor dining.
Ami, 2 Heated Pools, Img, 2 Hot Tubs, Pickleball. - Anna Maria Island, FL
10 3 reviews

Ami, 2 Heated Pools, Img, 2 Hot Tubs, Pickleball.

apartment, Bradenton
This 2nd-floor flat in Bradenton is conveniently located just 1.6 kilometres from IMG Academy and 13.4 kilometres from Anna Maria Island.
This 109 square metre apartment offers accommodation for six guests with two bedrooms and two bathrooms, featuring a private balcony with pond views, a fully equipped kitchen, high-speed WiFi, and access to communal amenities including swimming pools and jacuzzis.
Large 3br Home, Heated Pool! Close To Beach, Img - Anna Maria Island, FL
10 9 reviews

Large 3br Home, Heated Pool! Close To Beach, Img

apartment, Bradenton
This Bradenton holiday home boasts a prime coastal location, less than 3.2km from De Soto National Memorial, Robinson Preserve, and Palma Sola Botanical Park, and under 9.6km from the Bishop Museum of Science and Nature.
The four-bedroom, four-bathroom property sleeps nine guests and offers a private pool, tennis court, free Wi-Fi, and a fully equipped kitchen; enjoy nearby attractions including AMI Paddleboard Adventures.

Frequently asked questions about short term rentals in Anna Maria Island, FL

  • What attractions should one visit during a week-long stay on Anna Maria Island, Florida?

    A week on Anna Maria Island offers plenty! Spend a day exploring the pristine beaches – Bean Point is a must-see for its stunning sunsets and views. Rent bikes and cycle the length of the island, stopping at the charming shops and cafes along Pine Avenue. Visit the Anna Maria Island Historical Society Museum to learn about the island's rich past. For nature lovers, a trip to the Anna Maria Island Nature Reserve is essential for birdwatching and exploring the mangroves. Consider a boat tour to see dolphins or go kayaking in the calm waters. Don't forget to enjoy some delicious seafood at the many restaurants along the coast.
  • What are the best short term rentals in Anna Maria Island, FL?

  • What attractions should one visit when spending a month on Anna Maria Island, Florida?

    A month gives you time to truly explore! Beyond the initial week's activities, consider taking a day trip to nearby Sarasota or St. Petersburg. Explore the many smaller beaches and coves along the island – perhaps try the quieter sections of Coquina Beach. Go fishing – charter a boat or try your luck from the pier. Take a sunset cruise for a different perspective of the coastline. Visit the galleries and art studios that dot the island. Explore the local farmers' markets for fresh produce and local crafts. For a different pace, spend some time simply relaxing on the beach, reading a book, and enjoying the Gulf's gentle waves.
  • What are the best short term rentals with a pool in Anna Maria Island, FL?

  • Can visitors to Anna Maria Island, Florida witness any unique natural cycles, like cherry blossom season or autumn colours?

    Anna Maria Island doesn't experience the vibrant autumn colours found further north, nor does it have cherry blossoms. However, you can witness the nesting of various seabirds, particularly during spring and summer. The changing tides and the diverse marine life provide their own natural spectacles throughout the year.
  • What are the best short term rentals with a jacuzzi in Anna Maria Island, FL?

  • What are the most meaningful ways to engage with locals and discover the culture on Anna Maria Island, Florida?

    The best way to connect with locals is to visit the smaller, family-run businesses. Chat with the staff at local shops, restaurants, or art galleries. Attend a local event – check for community gatherings or performances. Consider taking a guided nature walk or kayak tour; the guides are often long-time residents who can share their knowledge of the island's history and ecology. Simply striking up conversations with people you meet on the beach or in cafes can also lead to interesting interactions.
  • What are the best short term rentals for families and kids in Anna Maria Island, FL?

  • Are there any distinctive cultural activities or hands-on workshops on Anna Maria Island, Florida?

    Anna Maria Island has a vibrant arts scene. Several galleries offer workshops in painting, pottery, or other crafts. Check local listings for seasonal events, which may include live music performances, theatre productions, or craft fairs. The island's laid-back atmosphere lends itself to a more relaxed style of cultural engagement, often found in casual interactions with the community.
  • What are some secret spots or hidden treasures to visit on Anna Maria Island, Florida?

    While Anna Maria Island is relatively small, some lesser-known gems include exploring the quieter stretches of beach south of the Bridge Street area. Take a walk along the shoreline at low tide to discover hidden shells and marine life. Explore the mangrove tunnels by kayak for a unique perspective of the island's ecosystem. The small, local parks away from the main tourist areas offer peaceful escapes.
  • What should not be left out of your suitcase if you are going to Anna Maria Island, Florida?

    Pack light clothing suitable for warm weather, swimwear, sunscreen (essential!), sunglasses, a hat, and insect repellent. Comfortable walking shoes or sandals are a must, as is a reusable water bottle to stay hydrated. Don't forget your camera to capture the stunning sunsets and beach scenes!
  • What are the most popular festivals on Anna Maria Island, Florida?

    Anna Maria Island hosts several smaller, local events throughout the year. Information on specific dates and events is best found by checking local listings closer to your travel dates. While there aren't large, nationally recognised festivals specifically tied to the island itself, the surrounding areas often have events that are easily accessible.
  • Where should one try the best local food on Anna Maria Island, Florida?

    For fresh seafood, The Sandbar Restaurant is a popular choice. The Waterfront Restaurant offers stunning views alongside its menu. Beach Bistro is known for its upscale dining experience. Many smaller cafes and eateries along Pine Avenue and Bridge Street offer delicious, casual dining options, showcasing local ingredients and flavours.

Nearby regions

Best Anna Maria Island, FL short term rentals with a kitchen

Your Tropical Paradise With Heated Saltwater Pool - Anna Maria Island, FL
9.9 406 reviews

Your Tropical Paradise With Heated Saltwater Pool

apartment, Bradenton
This holiday home is located in Bradenton, just 2.6 kilometres from Smugglers Cove Adventure Golf and 4.7 kilometres from IMG Academy. The property has received excellent ratings for its cleanliness, location, and overall experience.
The 158 square metre property is ideal for families or groups of up to eight people, with four bedrooms and two bathrooms. Enjoy a refreshing dip in the private pool, relax in the fenced garden, or take advantage of the outdoor barbecue grills.
Coastal Dream: New Pool/hot Tub. Ami. Img. Lecom. - Anna Maria Island, FL
9.9 70 reviews

Coastal Dream: New Pool/hot Tub. Ami. Img. Lecom.

apartment, Bradenton
This Village Green apartment in Bradenton, Florida, is situated 9.6km from Anna Maria Island beaches, 3.2km from Palma Sola Bay, and a 10-minute drive from IMG Academy.
This spacious 174 square metre, three-bedroom, two-bathroom dwelling sleeps eight, boasting a renovated split-plan layout, a fully equipped kitchen, YouTube TV, high-speed internet, off-street parking, and a screened porch.
Main St Gem! Walk To Shops, Dining & Beach! - Anna Maria Island, FL
9.6 37 reviews

Main St Gem! Walk To Shops, Dining & Beach!

apartment, Holmes Beach
Life's a Beach bungalow in Holmes Beach, Florida, is situated steps from the beach and a short distance (approximately 0.16 km) from the free AMI trolley stop, offering easy access to local shops and restaurants.
This one-bedroom, one-bathroom duplex bungalow sleeps up to three guests and features a full kitchen, a trundle bed, shared access to a heated saltwater pool, spa, and gas grill, plus on-site parking and complimentary starter supplies.
Palma Sola Bay Gem  Heated Pool Near Img! - Anna Maria Island, FL
9.9 69 reviews

Palma Sola Bay Gem Heated Pool Near Img!

apartment, Bradenton
Driftwood Cottage, a four-bedroom Bradenton holiday home, is situated approximately 16-24km from Holmes Beach, Manatee Public Beach, Palma Sola Pier, Portosueno Park, and IMG Academy.
This pet-friendly property sleeps up to 10 guests across two bathrooms, boasting a private heated pool (October-May, extra charge), a fully equipped gourmet kitchen, and extensive beach gear provision.

Best Anna Maria Island, FL short term rentals with laundry available

The Lovely Family House - Anna Maria Island, FL
9.9 55 reviews

The Lovely Family House

apartment, Bayshore Gardens
This three-bedroom, two-bathroom Bayshore Gardens apartment is conveniently located within walking distance of IMG Academy and State College of Florida, and a short drive (approximately 16 km) from Anna Maria Island's beaches.
Sleeping up to 11 guests, the property boasts a private screened-in pool, ample parking for four cars plus RV/trailer space, and numerous amenities including bikes, beach gear, and a foosball table, perfect for families or groups.
One Block To Beach -Ohana Hale Beachside Studio C - Anna Maria Island, FL
9.6 445 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.
Seabreeze B · Pet-friendly · Heated Pool - Anna Maria Island, FL
9.4 33 reviews

Seabreeze B · Pet-friendly · Heated Pool

apartment, Holmes Beach
This Holmes Beach apartment, situated near AMI Paddleboard Adventures and West Coast Surf Shop, offers easy access to Bradenton Beach and Manatee Public Beach, both within a 5-minute drive (approximately 3.2km).
The 70 square metre property features two bedrooms, a sofa bed, a fully equipped kitchen, private balcony, and access to an on-site swimming pool, fitness centre, tennis court and barbecue grills.
Welcome To Your Salty Escape - 10 Minutes From The Beach! - Anna Maria Island, FL
9.8 52 reviews

Welcome To Your Salty Escape - 10 Minutes From The Beach!

apartment, Bradenton
This Bradenton vacation home is situated just 5 kilometres from Blake Medical Center, arcadeland, and Manatee Golf Course, offering easy access to local attractions and amenities. The property has received excellent ratings for location, cleanliness, and overall user experience.
This 4-bedroom, 2-bathroom property spans 151 square metres and comfortably accommodates up to 8 guests. Enjoy a range of amenities including a private pool, jacuzzi, fitness centre, and spa, perfect for a relaxing and enjoyable stay.
©2026 cozycozy.com