6231 Holiday rentals and Airbnb in Anna Maria Island, FL
9.7 88 reviews
Anna Maria Island, FL
24/09 – 27/09
A$619/nighttotal: A$1857 (3 )
Family Friendly-sunny Private Pool Oasis- Close To Beaches, Shopping, And Restaurants
3 8
apartment , Bradenton
This Bradenton holiday home is conveniently located just one mile from Blake Medical Center and within six miles of IMG Academy and De Soto National Memorial, making it ideal for families visiting these locations. The property has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience. The three-bedroom property spans 146 square metres and comfortably accommodates up to eight guests. The house offers a range of amenities and features, including a private pool, a fully equipped kitchen, a laundry room, a terrace, a garden, a tennis court, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
9.8 71 reviews
Anna Maria Island, FL
11/07 – 25/07
A$362/nighttotal: A$5068 (14 )
Stylish House Near Manatee River & Anamaria Island
3 7
apartment , West Bradenton
This newly renovated three-bedroom, two-bathroom house is located in Northwest Bradenton, Florida, a short distance (within a few kilometres) of Anna Maria Island, Cortez Fishing Village, and Manatee Village Historical Park. The single-storey property, sleeping up to eight guests, offers a fully equipped kitchen, spacious living areas, a private patio, and backyard with fire pit, plus amenities including Wi-Fi, Roku TV, beach equipment, and cruiser bikes.
9.8 100 reviews
Anna Maria Island, FL
27/07 – 29/07
A$462/nighttotal: A$924 (2 )
King Suite! Heated Pool! 5 Miles To Beach!
1 5
apartment , West Bradenton
This West Bradenton holiday home, situated approximately 8km from Anna Maria Island's beaches, offers easy access to local shops and restaurants. Sleeping eight guests, this three-bedroom, two-bathroom property boasts a private heated saltwater pool, expansive backyard with gas grill, fully equipped kitchen with stainless steel appliances and a custom coffee bar, plus smart TVs, a washer/dryer and keyless entry.
9.5 40 reviews
Anna Maria Island, FL
03/08 – 07/08
A$384/nighttotal: A$1536 (4 )
Coastal Cheer
1 3
apartment , Bradenton Beach
This recently renovated one-bedroom apartment is situated in Bradenton Beach, just a 1.1 kilometre walk from Cortez Beach and 1.1 kilometres from Coquina Beach. The 55 square metre self-catering property features a private terrace, a fully equipped kitchen with a dishwasher and oven, and a private parking space, and can accommodate up to seven guests.
9.9 30 reviews
Anna Maria Island, FL
27/06 – 28/06
A$609/nightfor 1 night
Modern Coastal Quiet & Comfy
1 6
apartment , Cortez
This Cortez apartment is situated approximately 3.2 kilometres from Anna Maria Island's beaches and offers easy access to Longboat Key and Sarasota. The two-bedroom, one-bathroom flat sleeps six guests and includes a kitchen, air conditioning, parking, and internet access; enjoy nearby beach access and the modern coastal design.
10 3 reviews
Anna Maria Island, FL
02/07 – 05/07
A$1852/nighttotal: A$5556 (3 )
Near Img & Ami! Sleeps 10 Heated Pool Pickleball Tiki Bar Luxury Home
3 6
apartment , Bradenton
This Bradenton holiday home is centrally located, offering easy access to Anna Maria Island beaches, Robinson Preserve, Cortez Fishing Village, and IMG Academy, all within a 10-15 minute drive. This spacious 3-bedroom, 2-bathroom apartment, covering 177 square metres, accommodates up to 10 guests and boasts a resort-style private backyard with a heated saltwater pool, a tiki-style bar, a games room with multiple activities, and a private pickleball and basketball court.
10 14 reviews
Anna Maria Island, FL
27/06 – 04/07
A$273/nighttotal: A$1911 (7 )
Near Beaches & Outdoor Activites! Relaxation And Fun! 2 Br/ba/lr & Kitchen
1 2
apartment , Bradenton
This Bradenton condo, ideally located near Bradenton Beach, is within walking distance of shops (including Aldi and Publix supermarkets) and IMG Academy. The 116 square metre (1248 square feet) first-floor apartment boasts a newly renovated open-plan layout, sleeping four guests, and offers access to two swimming pools, tennis courts, and a fully equipped kitchen; beach equipment is also provided.
9.4 70 reviews
Anna Maria Island, FL
17/07 – 24/07
A$307/nighttotal: A$2149 (7 )
Cozy Seashore! Only 15 Min From Ami Beaches, Relaxing Pond Views, Free Wifi
2 2
apartment , Bradenton
This two-bedroom apartment is situated in the Shorewalk resort in Bradenton, just a short distance from IMG Academies, shops, restaurants, and the beaches of Anna Maria Island. The property is highly rated, with guests consistently praising its excellent facilities and comfortable accommodation. The apartment has a floor area of 109 square metres and can comfortably accommodate four guests. It offers a range of amenities including a swimming pool, Jacuzzi, tennis courts, and a fully equipped kitchen, as well as access to a variety of activities such as jet skiing, scuba diving, hiking, and hunting in the surrounding area.
9.8 203 reviews
Anna Maria Island, FL
06/11 – 08/11
A$297/nighttotal: A$594 (2 )
2br Corner Condo W/ Lanai · Dual Pools & Hot Tubs · Img Academy · Gulf Beaches
1 2
apartment , Bradenton
This waterfront apartment is located just 1.8 km from Arcadeland and 2.4 km from IMG Academy, offering easy access to popular attractions in Bradenton. The apartment has received excellent user, location, and cleanliness ratings, making it a popular choice for travellers. The two-bedroom, two-bathroom apartment spans 116 square metres and comfortably accommodates up to four guests. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, terrace, garden, tennis court, and free parking.
9.9 43 reviews
Anna Maria Island, FL
28/06 – 03/07
A$709/nighttotal: A$3545 (5 )
Nautical Escape! Private Pool Home With A Tropical Backyard Oasis!
4 8
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.
9.3 3 reviews
Anna Maria Island, FL
28/06 – 03/07
A$741/nighttotal: A$3705 (5 )
Bloom Lagoon! Tropical Home With Heated Pool And Grill! Pet Friendly!
3 8
house , Bradenton
This Bradenton holiday home is situated 2.6km from Palma Sola Causeway Park, offering easy access to Sarasota Bradenton International Airport (15km) and is within a 48km radius of attractions including The Ringling Museum of Art. The 177 square metre property sleeps up to 15 guests, boasting three bedrooms, two bathrooms, a private pool, free Wi-Fi, and a fully equipped kitchen including a dishwasher; nearby activities include golfing at Greens of Manatee Golf Club (10km).
Anna Maria Island, FL
28/06 – 03/07
A$756/nighttotal: A$3780 (5 )
Blue Chill! Heated Pool Home With Grill! 15 Min Drive To The Beach!
3 8
house , Bradenton
This Bradenton holiday home, situated 15 minutes' drive from the beach and 13 kilometres from Sarasota Bradenton International Airport, offers convenient access to local attractions including the John and Mable Ringling Museum of Art, 16 kilometres away. This spacious property boasts 172 square metres of living space, encompassing three bedrooms, three bathrooms, and a swimming pool, comfortably accommodating up to 15 guests with amenities including a fully equipped kitchen, free Wi-Fi, and a children's playground.
Best family friendly Anna Maria Island, FL holiday rentals
Among the 6231 accommodations in Anna Maria Island, FL, here are the 4 best family friendly rentals
8.2 10 reviews
Anna Maria Island, FL
11/07 – 25/07
A$256/nighttotal: A$3584 (14 )
Dog-friendly Home W/ Patio & Bbq In Bradenton
3 7
apartment , Bradenton
This Bradenton seaside property, a three-bedroom house, is conveniently located 2.9km from Blake Medical Center, 4.5km from IMG Academy, and 4.3km from Smugglers Cove Adventure Golf. The 188 square metre holiday home sleeps seven, boasting three bathrooms, a fully equipped kitchen including dishwasher, a terrace, garden, parking and Wi-Fi, all within easy reach of Bradenton's attractions.
9.2 28 reviews
Anna Maria Island, FL
17/07 – 20/07
A$312/nighttotal: A$936 (3 )
Mycataleya Comfy Condo Near Beach (Bradenton)
2 2
apartment , Bradenton
This Bradenton apartment is conveniently located just 10 kilometres from Sarasota Bradenton International Airport and 13.7 kilometres from the John and Mable Ringling Museum of Art. The 100 square metre property boasts two bedrooms, two bathrooms, sleeps seven guests, and features a private balcony with river views, a full kitchen, and access to on-site amenities including a swimming pool, hot tub, tennis court, and table tennis.
9.8 465 reviews
Anna Maria Island, FL
27/06 – 04/07
A$657/nighttotal: A$4599 (7 )
Beachfront - Bradenton Beach Club 226 By Seabreeze Vacation
3 2
apartment , Bradenton Beach
This Bradenton Beach Club condo is located just 0.8 kilometres from the sandy white beaches of Bradenton Beach, offering a prime location close to the action. The property has received excellent ratings for its location, cleanliness, and overall user experience. This three-bedroom apartment sleeps up to eight people and includes a fully equipped kitchen, two heated pools (one on the beach), a jacuzzi, private beach access, and a pier with a porch swing. Guests can enjoy breathtaking views of the Gulf of Mexico and the bay from the screened balcony, and take advantage of the free trolley service that runs every 20 minutes from 6 a.m. to 11 p.m., connecting the north end of Anna Maria Island to Coquina Beach.
10 3 reviews
Anna Maria Island, FL
27/06 – 28/06
A$3564/nightfor 1 night
Bradenton Oasis - Pool, Hot Tub, Mini Golf - Ami, Img
5 8
apartment , Bradenton
This detached house in Bradenton offers a 5-minute walk to Palma Sola Bay and a 22-minute drive to Tampa Bay. This spacious 279 square meter residence accommodates up to 16 guests with 5 bedrooms, 3 bathrooms, a private swimming pool, hot tub, garden, and balcony, featuring a fully equipped kitchen and on-site parking.
Best Anna Maria Island, FL holiday rentals with a pool
Among the 6231 accommodations in Anna Maria Island, FL, here are the 4 best rentals with a pool
Anna Maria Island, FL
28/06 – 03/07
A$485/nighttotal: A$2425 (5 )
My Seaside Escape
4 8
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.
9.3 73 reviews
Anna Maria Island, FL
27/07 – 29/07
A$602/nighttotal: A$1204 (2 )
Private Pool Home- Near Beaches-room For Boat Or Jet Ski Parking
3 5
apartment , Bradenton
This Bradenton property is conveniently situated just 5km from Blake Medical Center, De Soto National Memorial and Robinson Preserve, offering easy access to both the beach and local attractions. The house has received excellent user ratings and very good ratings for location and cleanliness. This 3-bedroom, 2-bathroom home is ideal for families or groups of up to 6 guests, offering 143 square metres of comfortable living space. The property includes a private pool, a fully equipped kitchen, laundry facilities, a garden and parking, ensuring a relaxing and enjoyable stay.
9.8 60 reviews
Anna Maria Island, FL
08/07 – 15/07
A$256/nighttotal: A$1792 (7 )
Top Floor Corner Unit 2 Bedroom Condo In Shorewalk Anna Marie Island 15 Min
2 2
apartment , Bradenton
This Bradenton golf condo is situated within 5 kilometres of IMG Academy, IMG Golf Academy, and Smugglers Cove Adventure Golf, with Manatee Golf Course and IMG Soccer Academy also nearby. This two-bedroom, two-bathroom apartment offers 101 square metres of space, sleeping up to four guests and boasting a fully equipped kitchen, free Wi-Fi, a private terrace, and access to a swimming pool and tennis court.
9.7 50 reviews
Anna Maria Island, FL
27/06 – 04/07
A$519/nighttotal: A$3633 (7 )
Home With Private Backyard And Heated Pool - Gulf Breeze Villa B
1 2
cottage , Holmes Beach
This Holmes Beach holiday home is situated near Bradenton Beach, a 15-minute walk away, and within 3.2km of Holmes Beach and Manatee Public Beach. The 52-square-metre property offers one bedroom, one bathroom, sleeps two guests, and includes a private pool, fully equipped kitchen, and fenced yard; nearby amenities include a water park and barbecue grills.
Frequently asked questions about holiday 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 views and iconic lighthouse. The Anna Maria City Pier offers great fishing and sunset views. For a bit of history, explore the historic Anna Maria City and its charming cottages. The Island's nature preserves, like the Anna Maria Island Nature Preserve, are also worth exploring.
What are the best Airbnb and holiday rentals in Anna Maria Island, FL?
Are there any unique natural phenomena on Anna Maria Island, Florida?
The island's location means you'll see incredible sunsets over the Gulf of Mexico. The beaches themselves are a unique natural phenomenon – the soft, white sand and the diversity of seashells are something special. Keep an eye out for the diverse birdlife in the mangroves and nature preserves.
What are the most popular Airbnbs in Anna Maria Island, FL?
What essentials should you bring to Anna Maria Island, Florida?
Pack light clothing, swimwear, sunscreen (essential!), sunglasses, a hat, insect repellent, and comfortable walking shoes. Don't forget your reusable water bottle to stay hydrated in the Florida sun. A beach towel and beach bag are also a must.
What are the best holiday 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 budget around £150-£300 per day for a couple, covering accommodation, meals, some activities and local transport. Budget accommodation and self-catering can significantly reduce costs.
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 popular choice for fine dining. Rod & Reel Pier offers casual waterfront dining with fresh seafood. For more casual options, explore the many cafes and restaurants along Pine Avenue in Anna Maria. Fresh seafood is a must-try, especially the stone crab claws (seasonal) and grouper sandwiches.
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 a visit?
The Leffis Key Preserve offers beautiful nature trails and is less crowded than some of the more popular spots. Exploring the quieter sections of the beaches away from the main access points can offer a more secluded experience. Take a bike ride along the island's many scenic paths.
What are the best activities for engaging with locals and understanding their culture on Anna Maria Island, Florida?
Visiting local shops and markets is a great way to interact with residents. Many smaller restaurants and cafes offer a more intimate setting to chat with locals. Attending smaller, community events (check local listings) can provide opportunities to meet people.
What unique natural landscapes and terrain features can travellers explore on Anna Maria Island, Florida?
Anna Maria Island features beautiful beaches, of course, with the Gulf of Mexico on one side and Tampa Bay on the other. The mangrove forests and the various nature preserves offer unique ecosystems to explore. The island itself is quite flat, making it easy to walk or cycle around.
How many days are ideal for a visit to Anna Maria Island, Florida, and what are some itinerary suggestions?
Three to four days is a good amount of time to enjoy the island at a relaxed pace. A possible itinerary could include beach time, exploring Anna Maria City, visiting the Anna Maria Island Nature Preserve, and enjoying some water activities. Consider a sunset cruise or a dolphin watching tour.
Nearby regions
Best Anna Maria Island, FL holiday rentals with a balcony
Anna Maria Island, FL
03/07 – 05/07
A$2030/nighttotal: A$4060 (2 )
Sports Court Playground Putt Putt Spa Pool
4 10
apartment , Bradenton
This oceanfront apartment in Bradenton offers sea views and is conveniently located 4 kilometres from LECOM Park and 5 kilometres from Smugglers Cove Adventure Golf. This spacious 196 square metre holiday home accommodates up to 12 guests across 4 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, in-unit laundry, Wi-Fi, a swimming pool, hot tub, garden, balcony, and barbecue facilities, with pets welcome.
Anna Maria Island, FL
28/06 – 03/07
A$6499/nighttotal: A$32495 (5 )
600 M² House ∙ 6 Bedrooms ∙ 17 Guests
6 8
house , Cortez
This private waterfront estate is located in Bradenton, Florida, on Sarasota Bay, offering direct access to the Gulf via a private dock and situated less than 5 kilometres from the beaches of Anna Maria Island. This spacious villa, covering 599 square meters, accommodates up to 17 guests across multiple independent living structures, boasting a resort-style heated pool, spa, tiki hut, kayaks, paddleboards, and on-site recreational facilities including a putting green and bocce ball court.
10 1 review
Anna Maria Island, FL
17/07 – 24/07
A$595/nighttotal: A$4165 (7 )
Relax And Unwind! 2 Convenient Units, Walk To Dining, Entertainment, And Golf
4 7
apartment , Bradenton
This apartment complex is situated in a gated community in Bradenton, just a short drive from the beautiful white sand beaches and a range of attractions including golf courses, museums, restaurants, and shopping malls. It boasts excellent user ratings, making it a popular choice for travellers. The property offers two spacious apartments, each with four bedrooms and four bathrooms, accommodating up to 10 guests. Guests can enjoy a range of on-site amenities including two swimming pools, a hot tub, BBQ area, tennis courts, a basketball court, a clubhouse with a pool table, and weekly activities.
Anna Maria Island, FL
03/08 – 07/08
A$295/nighttotal: A$1180 (4 )
85 M² Condo ∙ 2 Bedrooms ∙ 4 Guests
2 3
apartment , Bradenton
This West Bradenton condo is situated near IMG Academy, 11km from Anna Maria Island beaches and 13km from Sarasota Bradenton International Airport. The 84 square metre apartment sleeps four, offering two bedrooms, two bathrooms, a fully equipped kitchen, a private screened lanai, and access to community pools, a hot tub, tennis courts, and a clubhouse with billiards and other amenities.
Best Anna Maria Island, FL holiday rentals with parking
10 63 reviews
Anna Maria Island, FL
02/07 – 05/07
A$16328/nighttotal: A$48984 (3 )
Charming Cottage With Heated Pool, Tropical Landscaping In Prime Location.
2 6
apartment , Anna Maria
This Anna Maria Island property enjoys a prime waterfront location, less than 1.6km from Bradenton Beach and Anna Maria Beach, and under 5 minutes' drive from the Island Players theatre and Palmetto Avenue Beach. The two-bedroom, two-bathroom holiday home sleeps six guests and boasts a private pool, patio, barbecue, fully equipped kitchen, free Wi-Fi, and ample parking.
Anna Maria Island, FL
17/07 – 24/07
A$472/nighttotal: A$3304 (7 )
Riverbend Cottage
2 7
house , Bradenton
Riverbend Cottage, a detached house in Bradenton, is located approximately 16 kilometres from the John and Mable Ringling Museum of Art and 15 kilometres from the Sarasota International Convention Centre. This property offers accommodation for eight guests, featuring two bedrooms and two bathrooms, with amenities including air conditioning, a swimming pool, jacuzzi, terrace, garden, and Wi-Fi, alongside a fully equipped kitchen and a fireplace.
10 11 reviews
Anna Maria Island, FL
27/06 – 28/06
A$1569/nightfor 1 night
Gulf Coast Escape/pool, Hot Tub, Sleeps 12, Pets
4 8
apartment , Bradenton
This Bradenton apartment, near IMG Academy, offers easy access to Anna Maria Island (13km) and Siesta Key Beach (24km). Sleeping up to 12 guests, this single-storey property boasts a private heated pool, outdoor kitchen, fully equipped kitchen, and numerous family-friendly amenities including a pack 'n play, stroller, high chair and baby monitor.
9.6 22 reviews
Anna Maria Island, FL
27/06 – 28/06
A$1072/nightfor 1 night
Beach Sunrise Villa! Outdoor Dining, Beach Cart And Gulf Breezes
2 6
apartment , Bradenton Beach
This Bradenton Beach duplex, a one-minute walk from the Gulf of Mexico beach, offers convenient proximity to attractions such as the John and Mable Ringling Museum of Art and Fish Hole Adventure Golf. The 88-square-metre (947 square feet) property sleeps six guests in two bedrooms and one bathroom, and includes a fully equipped kitchen, washer/dryer, outdoor dining area with BBQ, beach chairs, and a beach cart; pet-friendly with prior approval and additional fee.
