1981 Vacation rentals and Airbnb in Anna Maria, FL
9.8 17 reviews
Anna Maria, FL
03/07 – 06/07
₹22668/nighttotal: ₹68004 (3 )
Ks-near Beaches And Img, Pool, Tennis, Pickleball, Shorewalk Condo 2 Bedroom/2 Bath
2 3
apartment , Bradenton
This beachfront apartment, near Bradenton, Florida, is located approximately 2.7 kilometres from Smugglers Cove Adventure Golf and the IMG Academy. The 109-square-metre property boasts two bedrooms, two bathrooms, a fully equipped kitchen, and a private balcony; it comfortably sleeps four guests and offers access to a swimming pool, Jacuzzi, and tennis court.
9.4 66 reviews
Anna Maria, FL
31/10 – 10/11
₹29908/nighttotal: ₹299080 (10 )
North End Duplex With Pool On Anna Maria Island! Near Bean Point
2 2
apartment , Anna Maria
Southern Breeze #3, a ground-floor duplex in Anna Maria, Florida, is less than 1.6km from Bean Point Beach and Bayfront Park. This 73 square metre, two-bedroom Anna Maria holiday flat sleeps six, boasting a fully equipped kitchen, shared pool, and a professional linen service; king-size beds and TVs in each bedroom are additional features.
9.2 48 reviews
Anna Maria, FL
31/10 – 10/11
₹27423/nighttotal: ₹274230 (10 )
Dog Friendly Cottage - One Block To The Bay!
2 2
apartment , Anna Maria
This Anna Maria Island beachfront property is steps from Historic Green Village and Anna Maria City Pier, a short 2.4km walk from Bay Boulevard Beach and Bradenton Beach. This 50 square metre holiday home offers two bedrooms, a sofa bed, one bathroom, and amenities including a swimming pool, terrace, garden, parking, and Wi-Fi, accommodating up to four guests and featuring gas grills and an on-site water park.
10 15 reviews
Anna Maria, FL
27/06 – 04/07
₹44388/nighttotal: ₹310716 (7 )
Americana Ami Lighthouse 3br W/pool + Rooftop Deck
3 5
apartment , Holmes Beach
This Holmes Beach holiday home, a six-minute walk (approximately 0.96km) from the Gulf beach, offers a family-friendly escape near Anna Maria Island's attractions. Sleeping six guests across three bedrooms and two-and-a-half bathrooms, this property features a private pool, garden, and full kitchen including a dishwasher, plus Wi-Fi; enjoy its open-plan living space and vintage Americana aesthetic.
9.3 37 reviews
Anna Maria, FL
15/08 – 17/08
₹41162/nighttotal: ₹82324 (2 )
Quiet Beach Cottage. Shared Community Pool And Grill. Close To Beach!
2 4
apartment , Anna Maria
This two-bedroom apartment is located in Anna Maria, just a short walk from Bradenton Beach, Bayfront Park, and Anna Maria Beach, and within a 1.5 km walk of Bean Point Beach and Anna Maria City Pier. The apartment has received excellent ratings for location, user experience, and cleanliness. The property features a well-equipped kitchen, a private patio, and a swimming pool. Guests can enjoy the convenience of air conditioning, a washing machine, and a dishwasher, as well as the opportunity to relax in the garden or prepare a barbecue meal.
10 66 reviews
Anna Maria, FL
24/07 – 01/08
₹158640/nighttotal: ₹1269120 (8 )
2 Min Walk To Gulf~3 King+bunk~pool+spa+golf+bikes
1 7
apartment , Anna Maria
This three-bedroom, three-bathroom house on Anna Maria Island's north end is a two-minute walk from the Gulf beach and a three-minute cycle from Bean Point and Pine Avenue. Sleeping eight guests, this luxurious property boasts a heated saltwater pool, jacuzzi, extensive outdoor space with a propane grill and smoker, and plentiful amenities including bikes, beach gear, and games; making it ideal for families.
Anna Maria, FL
27/06 – 04/07
₹38075/nighttotal: ₹266525 (7 )
Sand And Sea 113 B
2 2
apartment , Anna Maria
Sand And Sea 113B, a beachfront property in Anna Maria, Florida, offers direct beach access and is a 2-kilometre walk from Anna Maria City Pier. This two-bedroom, one-bathroom house sleeps eleven guests and boasts a fully equipped kitchen, air conditioning, a private pool, free Wi-Fi, and proximity to Sarasota Bradenton International Airport (27 kilometres).
9.6 87 reviews
Anna Maria, FL
10/09 – 13/09
₹39172/nighttotal: ₹117516 (3 )
Duplex With Heated Pool! 2 Blocks To Beach! - Turtle Crawl
2 4
apartment , Anna Maria
This Anna Maria Island beachfront property is less than 1km from Bradenton Beach and Anna Maria Beach, and within a 1km radius of Bean Point Beach and Bayfront Park, offering easy access to the island's best attractions. This 102 square metre holiday home sleeps four guests in two bedrooms and boasts a fully equipped kitchen, including a dishwasher, in-house laundry facilities, air conditioning, a swimming pool, and parking; plus access to an on-site water park.
9.8 37 reviews
Anna Maria, FL
05/07 – 11/07
₹45627/nighttotal: ₹273762 (6 )
New Poolhouse/4bdr/3bath/9 Beds /Dog/outdoorkitchen/heatedpool/fireplaces/golf
4 11
apartment , Bradenton
This spacious Bradenton holiday home, located near LECOM Park baseball stadium and Smugglers Cove Adventure Golf (both within a 5-minute drive, or approximately 3km), offers convenient access to local attractions. The 158 square metre property boasts three bedrooms, two bathrooms, sleeps up to twelve guests, and includes a fully equipped kitchen, swimming pool, garden, spa, and parking, alongside in-unit amenities such as Wi-Fi, a smart TV, and laundry facilities.
Anna Maria, FL
27/06 – 04/07
₹155597/nighttotal: ₹1089179 (7 )
Villa La Concha~west Of Gulf Steps To The Beach!
6 9
apartment , Anna Maria
This six-bedroom, four-and-a-half-bathroom holiday flat is located just 100 metres from Anna Maria Beach and within easy walking distance of Pine Avenue's shops and restaurants, with the AMI trolley service also available. This property offers a private heated pool and spa, a games room with Ping Pong and Foosball, multiple outdoor living spaces including a covered patio with a BBQ grill, and balconies with seating, accommodating up to twelve guests.
9.5 203 reviews
Anna Maria, FL
03/07 – 06/07
₹29115/nighttotal: ₹87345 (3 )
Beach Loft - Heated Pool & Spa, Slide, Fire Pit
1 3
apartment , Bradenton
This one-bedroom flat is located in Bradenton, directly opposite Publix, a short walk from Palma Sola beaches, and under 8 kilometres from Anna Maria Island beaches. This apartment offers accommodation for up to four guests and features a full kitchen, air conditioning, a private entrance, and parking, with access to a shared outdoor area containing a heated saltwater pool, spa, rock water slide, and playground.
10 4 reviews
Anna Maria, FL
24/07 – 01/08
₹86581/nighttotal: ₹692648 (8 )
Blue Sky Day Beach Bungalow
1 7
apartment , Anna Maria
This Anna Maria beach cottage is situated directly across Gulf Drive from the Gulf of America, offering immediate beach access within 96 meters, and is a short stroll from Pine Avenue's boutiques and eateries. This holiday home accommodates up to eight guests with three bathrooms, a fully equipped kitchen featuring a fridge, freezer, microwave, and dishwasher, air conditioning, a garden, and a private pool available from Summer 2026, complemented by an outdoor living space with a grill and an outdoor TV.
Best family friendly Anna Maria, FL vacation rentals
Among the 1981 accommodations in Anna Maria, FL, here are the 4 best family friendly rentals
8.8 93 reviews
Anna Maria, FL
10/09 – 13/09
₹20142/nighttotal: ₹60426 (3 )
Bay View Inn 202
1 4
apartment , Bradenton Beach
Bay View Inn 202 is located in Bradenton Beach, just a short walk from Cortez Beach and less than a kilometre from Coquina Beach, offering a peaceful setting close to the beach. The hotel has received very good user ratings, with excellent location and cleanliness scores. The apartment is 51 square metres and can accommodate up to four guests. It features a kitchen, a terrace, a garden, a swimming pool, parking, and free Wi-Fi, as well as a comfortable seating area and a private bathroom.
Anna Maria, FL
29/06 – 30/06
₹129272/nightfor 1 night
New!~heated Pool! Steps To The Beach! Sailfish
2 2
apartment , Holmes Beach
Villa 1 Sailfish is a dog-friendly holiday flat located in Holmes Beach, just 180 metres from Manatee Beach and within the Islands West Resort. This holiday flat offers two bedrooms and two bathrooms, sleeping up to six guests with a king suite, twin bunks, and a queen sofa bed, and features a shared heated salt pool, on-site barbecue, and includes beach gear.
9.9 27 reviews
Anna Maria, FL
24/07 – 29/07
₹55732/nighttotal: ₹278660 (5 )
Luxury ~ Heated Pool ~ Games ~ Near Ami, Img, Srq
1 9
apartment , Bradenton
Palma Paradise, a five-bedroom Bradenton villa, is situated a short drive (approx. 16km) from Anna Maria Island and 24km from Longboat Key, offering easy access to local beaches and attractions. This self-catering property sleeps eleven guests and boasts a private heated saltwater pool and spa, a fully equipped games room with air hockey and arcade games, and provides beach equipment including chairs, umbrellas, and coolers.
9.9 103 reviews
Anna Maria, FL
24/07 – 29/07
₹49638/nighttotal: ₹248190 (5 )
Coquina Haus Stylish Home Steps Away From Private Bay Inlet!
5 9
apartment , West Bradenton
This five-bedroom apartment is located in West Bradenton, a short walk from Riverview Point Park and within a few kilometres of several beaches including Coquina, Holmes, Manatee, and Bradenton, as well as the popular Anna Maria Island. This property consistently receives excellent ratings for its location, cleanliness, and overall experience. The apartment comfortably accommodates up to 14 guests and includes a fully equipped kitchen, two bathrooms, and a screened-in veranda with an outdoor shower. Guests can enjoy access to a heated pool, a kids' playset, a pack 'n play, a high chair, and a queen air mattress for additional sleeping arrangements, along with a Weber charcoal grill, beach chairs, a cooler, sand toys, pool toys, and a full-size washer and dryer.
Best Anna Maria, FL vacation rentals with a pool
Among the 1981 accommodations in Anna Maria, FL, here are the 4 best rentals with a pool
9.2 37 reviews
Anna Maria, FL
10/09 – 13/09
₹44250/nighttotal: ₹132750 (3 )
Getaway On Gladiolus
2 4
house , Anna Maria
Getaway on Gladiolus is a holiday home in Anna Maria, Florida, situated a short walk (approximately 1.9km) from Anna Maria City Pier and Anna Maria Island, and within 32km of The John and Mable Ringling Museum of Art. This 111 square metre property offers two bedrooms, two bathrooms, two living areas, a private garden with outdoor dining, a swimming pool, tennis court, and free Wi-Fi; it sleeps up to four guests and is close to cycling routes and a children's playground.
9.4 13 reviews
Anna Maria, FL
27/06 – 04/07
₹75184/nighttotal: ₹526288 (7 )
Canario Cottage By Duncan Real Estate
1 5
apartment , Anna Maria
This Anna Maria holiday flat is centrally located near Pine Avenue, offering easy access to the bay just 400 metres away and the beach a 0.6-mile walk. This elevated property provides accommodation for up to six guests, featuring a private 20x10 ft swimming pool, multiple outdoor decks, a propane grill, and five reserved parking spaces.
Anna Maria, FL
27/06 – 04/07
₹94066/nighttotal: ₹658462 (7 )
Beach View Retreat
5 9
house , Holmes Beach
Beach View Retreat, a beachfront property in Holmes Beach, Florida, is situated 5.5km from Anna Maria City Pier and 27km from The John and Mable Ringling Museum of Art. This five-bedroom, four-bathroom holiday home boasts 269 square metres of floor space, accommodating up to 19 guests and offering a private pool, free Wi-Fi, and parking; nearby attractions include Holmes Beach, Anna Maria Island, and Bradenton Beach.
Anna Maria, FL
29/06 – 30/06
₹76367/nightfor 1 night
149 M² House ∙ 3 Bedrooms ∙ 6 Guests
3 2
house , Holmes Beach
This Holmes Beach holiday home is situated a short 0.9-kilometre walk from the beach and close to Anna Maria Island's restaurants. The 148-square-metre property boasts three bedrooms, three bathrooms, sleeps six guests, features a private boat dock, heated pool, Tesla EV charger, and full kitchen with stainless steel appliances.
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 full of charm! You can visit the historic City Pier, explore the Anna Maria Island Historical Museum, or take a stroll along the beautiful beaches. If you're looking for a bit more adventure, you can head over to the nearby Mote Marine Laboratory & Aquarium in Sarasota, or visit the Ringling Museum of Art, also in Sarasota.
What are the best Airbnb and vacation rentals in Anna Maria, FL?
Which walking or cycling routes are the best in Anna Maria, FL?
The Pine Avenue Trail is a great option for a leisurely stroll or bike ride, offering scenic views of the Gulf of Mexico. For a more challenging ride, try the Anna Maria Island Nature Trail, which winds through a beautiful, protected natural area. You can also explore the many quiet side streets in Anna Maria, which are perfect for a peaceful bike ride.
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 outdoor enthusiasts. You can enjoy swimming, sunbathing, and fishing at the beautiful beaches. There are also plenty of opportunities for kayaking, paddleboarding, and boating. If you're looking for something more adventurous, you can try parasailing or jet skiing. And don't forget to visit the Anna Maria Island Beach Cafe for a delicious meal after a day of fun in the sun.
What are the best vacation rentals with a pool in Anna Maria, FL?
What other towns or cities can be easily accessed from Anna Maria, FL?
Anna Maria is conveniently located near other popular destinations. You can easily drive to Sarasota, which is known for its beautiful beaches, vibrant arts scene, and delicious restaurants. Bradenton, just a short drive away, offers a more laid-back atmosphere with plenty of shopping and dining options. You can also take a day trip to St. Petersburg, which is home to the Salvador Dali Museum and other cultural attractions.
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 offer a variety of amenities to make your stay comfortable. Most rentals include a fully equipped kitchen, laundry facilities, and a private balcony or patio. Many also have access to a pool, hot tub, or other community amenities. You can find rentals with different sizes and configurations to suit your needs, whether you're travelling with family, friends, or a romantic getaway.
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 depends on your preferences. If you're looking for warm weather and sunshine, the months of March to May and September to November are ideal. These months offer pleasant temperatures with fewer crowds. If you prefer cooler weather, you can visit during the winter months, but you may experience occasional rain.
What are the local dishes in Anna Maria, FL region?
The local cuisine in Anna Maria reflects the area's rich seafood tradition. You can find fresh, local seafood dishes at many restaurants, including grouper sandwiches, shrimp scampi, and stone crab claws. You can also enjoy other local specialties like Key lime pie and Florida orange juice. Don't forget to try the fresh oysters from the nearby oyster farms.
Destinations nearby
Best Anna Maria, FL holiday rentals with a balcony
9.8 8 reviews
Anna Maria, FL
29/06 – 30/06
₹262820/nightfor 1 night
Tortuga Bay~canal & Waterslide Putt Putt! Tiki Hut
5 2
apartment , Anna Maria
This five-bedroom Anna Maria Island house is conveniently located near Bean Point Beach, offering easy access to other Anna Maria Island attractions. The property boasts a private pool and hot tub, a fully equipped kitchen, laundry facilities, free high-speed Wi-Fi (500 Mbps or more), and can comfortably accommodate large families or groups.
Anna Maria, FL
03/07 – 06/07
₹245674/nighttotal: ₹737022 (3 )
Bridgeview - Amazing Bay Views! Roof Top Deck, Pool & Spa By Anna Maria Life
1 3
house , Anna Maria
This Anna Maria holiday home is situated in Anna Maria, 2.9 kilometres from Anna Maria Island and 30.5 kilometres from Sarasota International Convention Centre. Boasting 365 square metres of living space, this property accommodates up to 23 guests across 4 bedrooms and 5 bathrooms, featuring a private outdoor swimming pool, hot tub, rooftop deck with bay views, and a well-equipped kitchen.
9.5 35 reviews
Anna Maria, FL
03/07 – 06/07
₹22668/nighttotal: ₹68004 (3 )
Fm-near Beaches And Img, Pool, Tennis, Pickleball, Shorewalk Condo 2 Bedroom/2 Bath Lake View
2 3
apartment , Bradenton
This two-bedroom apartment is located in Bradenton, just over 1.5 kilometres from both Arcadeland and IMG Academy, making it ideal for families and sports enthusiasts. The property has received excellent ratings for location, cleanliness, and overall user experience. The apartment is 116 square metres in size and can comfortably accommodate up to four guests. It features a fully equipped kitchen, two bathrooms, a washing machine, a patio, a TV, parking, internet access, and table tennis, ensuring a comfortable and enjoyable stay.
10 86 reviews
Anna Maria, FL
27/06 – 04/07
₹33277/nighttotal: ₹232939 (7 )
Gulf Beach Apartment - With Pool & Beach Access
2 2
apartment , Holmes Beach
This one-bedroom flat is situated just 500 metres from Anna Maria Sound and Bradenton Beach, offering easy access to the beautiful beaches and waterfront activities. The property has consistently received excellent reviews from previous guests. The 65 square metre flat comfortably sleeps four guests and features a fully equipped kitchen, a spacious living area with a sofa bed, and a private balcony. Guests can enjoy amenities like a swimming pool, on-site parking, and free Wi-Fi, as well as a range of entertainment options including a TV, DVD player, and a music library.
Best Anna Maria, FL holiday rentals with parking
9.6 250 reviews
Anna Maria, FL
15/08 – 17/08
₹61065/nighttotal: ₹122130 (2 )
Newly Renovated Sea Breeze Cottage With Private Dock, Easy Access To Bimini Bay
2 4
cottage , Anna Maria
This charming waterfront cottage is situated just 1.6km from Bay Boulevard Beach, the Anna Maria City Pier, and Bayfront Park, offering easy access to the island's attractions. The cottage has received excellent ratings for its location, cleanliness, and overall experience. This two-bedroom, two-bathroom property spans 102 square metres and comfortably accommodates up to six guests. The cottage is equipped with a kitchen, a Jacuzzi, a terrace, a garden, and a barbecue grill, ensuring a relaxing and enjoyable stay.
9.6 11 reviews
Anna Maria, FL
24/07 – 29/07
₹49925/nighttotal: ₹249625 (5 )
Palma Sola Bay Gem Heated Pool Near Img!
4 9
apartment , Bradenton
This Bradenton holiday home, near Palma Sola Bay, is conveniently located within a 9.6km radius of Anna Maria Island beaches, Holmes Beach and Manatee Public Beach. This spacious 178 sq m property boasts four bedrooms, two bathrooms, sleeps up to ten guests, and includes a private heated pool (optional extra charge), a fully equipped kitchen, beach gear, and high-speed Wi-Fi.
9.2 10 reviews
Anna Maria, FL
03/07 – 06/07
₹22668/nighttotal: ₹68004 (3 )
Lp-near Beaches And Img, Pool, Tennis, Pickleball, Shorewalk Condo 2 Bedroom/2 Bath Lake View
2 3
apartment , Bradenton
This Bradenton seaside apartment, near IMG Academy and other attractions within 5km, offers stunning ocean views. The 109 square metre property boasts two bedrooms, four bathrooms, a private balcony, and access to a swimming pool, jacuzzi, tennis court, and garden; accommodating up to four guests.
9.3 45 reviews
Anna Maria, FL
27/06 – 04/07
₹32262/nighttotal: ₹225834 (7 )
Sea Spray 3: *Steps To The Beach *Close To Shops, Restaurants *Quiet Street
2 2
apartment , Anna Maria
This Anna Maria holiday home is perfectly situated, just a 10-minute walk from both Bradenton Beach and Palmetto Avenue Beach, and close to the Island Players theatre, making it ideal for exploring the island's beautiful beaches and cultural offerings. The property has received excellent ratings for its location, cleanliness, and overall experience. This two-bedroom property offers 74 square metres of space and can comfortably accommodate up to four guests. The house is equipped with a range of amenities, including a swimming pool, terrace, garden, barbecue grills, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.