Holiday Rentals in Anna Maria, FL

1981 available vacation rental offers

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

1981 Holiday rentals and Airbnb in Anna Maria, FL

Best family friendly Anna Maria, FL holiday rentals

Among the 1981 accommodations in Anna Maria, FL, here are the 4 best family friendly rentals

70 M² House ∙ 2 Bedrooms ∙ 6 Guests - Anna Maria, FL
10 3 reviews
Anna Maria, FL
27/06 – 04/07
525 â‚¬/nightTotal: 3675 â‚¬ (7 )

70 M² House ∙ 2 Bedrooms ∙ 6 Guests

2 5
house , Holmes Beach
Hidden Treasure Unit A, a Holmes Beach holiday home, is situated 0.16 km from Holmes Beach centre and 0.32 km from Manatee Public Beach, offering easy access to shops and restaurants including Hurricane Hanks and The Ugly Grouper.
This two-bedroom, one-bathroom apartment, boasting 69 square metres of floor space, sleeps six guests and features a fully equipped kitchen, shared heated pool, smart TVs, and high-speed Wi-Fi.
Designer 5br For Groups | 10-min To Ami - Anna Maria, FL
9.7 56 reviews
Anna Maria, FL
05/07 – 11/07
533 â‚¬/nightTotal: 3198 â‚¬ (6 )

Designer 5br For Groups | 10-min To Ami

1 11
apartment , Bradenton
This luxurious five-bedroom house, sleeping 16-19 guests, is situated near Bradenton, Florida, a 6.4km drive from pristine beaches and a 19.3km drive from Anna Maria Island.
The property boasts a fully equipped kitchen, laundry facilities, a swimming pool, fitness centre, and family-friendly amenities including a pack 'n play and high chair, alongside an electronic front door lock for convenient access.
House ∙ 3 Bedrooms ∙ 7 Guests - Anna Maria, FL
10 6 reviews
Anna Maria, FL
21/06 – 26/06
324 â‚¬/nightTotal: 1620 â‚¬ (5 )

House ∙ 3 Bedrooms ∙ 7 Guests

3 3
house , Bradenton
Sunset Seacret, a condo within One Particular Harbour Resort on a private island in Bradenton, Florida, is a two-minute drive (approximately 1.6km) from Manatee Beach.
This three-bedroom, three-bathroom property sleeps seven, boasting a spacious layout with a light-filled kitchen, screened lanai, and access to resort amenities including a heated pool, children's play area, and BBQ facilities; longer stays grant access to a waterfront Beach Club, fitness centre, and sky bar.
The Poop Deck: *Pet-friendly *Canalfront *Heated Pool *Sleeps 8 - Anna Maria, FL
10 2 reviews
Anna Maria, FL
15/07 – 17/07
1315 â‚¬/nightTotal: 2630 â‚¬ (2 )

The Poop Deck: *Pet-friendly *Canalfront *Heated Pool *Sleeps 8

4 5
apartment , Anna Maria
This five-bedroom Anna Maria Island waterfront property is situated less than 1.6km from Bay Boulevard Beach and Anna Maria Beach, and within a 15-minute drive of Anna Maria City Pier and Bayfront Park.
This 197 square metre holiday home boasts a private pool, tennis court, and accommodates up to eight guests, offering a fully equipped kitchen, four bathrooms, and a terrace with stunning views.

Best Anna Maria, FL holiday rentals with a pool

Among the 1981 accommodations in Anna Maria, FL, here are the 4 best rentals with a pool

Anna Maria Beach Cottage 110  Traditional Beach Cottage, Moments From The Sand! - Anna Maria, FL
9.8 44 reviews
Anna Maria, FL
15/07 – 17/07
819 â‚¬/nightTotal: 1638 â‚¬ (2 )

Anna Maria Beach Cottage 110 Traditional Beach Cottage, Moments From The Sand!

3 5
apartment , Anna Maria
This Anna Maria Island property is just a 10-minute walk from Bradenton Beach and Palmetto Avenue Beach, offering easy access to the Gulf of Mexico and the island's relaxed atmosphere. It has received excellent guest reviews, highlighting its comfortable and convenient stay.
The house is a spacious 105 square metres, comfortably accommodating up to 7 guests across its three bedrooms and two bathrooms. Guests can enjoy amenities such as a swimming pool, a spa, a terrace and a garden, as well as a fully equipped kitchen and free Wi-Fi.
Anglers Bay At One Particular Harbour 392-103 · Lagoon Views · 5-night Min - Anna Maria, FL
10 36 reviews
Anna Maria, FL
24/07 – 01/08
313 â‚¬/nightTotal: 2504 â‚¬ (8 )

Anglers Bay At One Particular Harbour 392-103 · Lagoon Views · 5-night Min

3 7
apartment , Bradenton
This three-bedroom, three-bathroom condo in One Particular Harbour, Bradenton, offers stunning lagoon views and is located minutes from Anna Maria Island's beaches.
The 155 square metre (1667 square foot) property features a spacious open-plan living area, a fully equipped kitchen, and a private screened balcony, accommodating up to six guests and providing access to resort-style amenities including a heated pool and private beach club perks for stays of 30 nights or more.
Low Tide Beach House On Ami - Anna Maria, FL
Anna Maria, FL
27/06 – 04/07
369 â‚¬/nightTotal: 2583 â‚¬ (7 )

Low Tide Beach House On Ami

2 5
apartment , Holmes Beach
This Holmes Beach cottage is located by the sea, a 365-meter walk from the white sand beaches of Anna Maria Island, and is close to local dining and shopping.
This two-bedroom, two-bathroom property accommodates up to six guests, includes a pull-out sofa, in-unit laundry, free parking with a private garage, provided beach gear, and a downstairs games room, with pets permitted for an additional fee.
Near Beaches & Img Academy, Mins To Downtown - Anna Maria, FL
10 21 reviews
Anna Maria, FL
03/07 – 06/07
201 â‚¬/nightTotal: 603 â‚¬ (3 )

Near Beaches & Img Academy, Mins To Downtown

2 3
apartment , Bradenton
This Bradenton flat offers excellent access to Anna Maria Island beaches (12.8-20.9 kilometres) and IMG Academy (8 kilometres), with shops, restaurants, and entertainment within walking distance.
This two-bedroom, two-bathroom flat accommodates four guests and features a fully equipped kitchen with new stainless steel appliances, a 4K HD television, complimentary Wi-Fi, and an attached lanai/game room with a foosball table and dart board.

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.

Destinations nearby

Best Anna Maria, FL holiday rentals with a balcony

Americana Ami Lighthouse 3br W/pool + Rooftop Deck - Anna Maria, FL
9.8 68 reviews
Anna Maria, FL
27/06 – 04/07
441 â‚¬/nightTotal: 3087 â‚¬ (7 )

Americana Ami Lighthouse 3br W/pool + Rooftop Deck

3 5
apartment , Holmes Beach
This Holmes Beach holiday home boasts direct beach access and is less than 1.6km from Bradenton Beach and Island Gallery West, with AMI Paddleboard Adventures and Palmetto Avenue Beach within 3.2km.
This three-bedroom, three-bathroom property offers 166 square metres of living space, sleeping up to six guests and featuring a private pool, a fully equipped kitchen, free WiFi, and outdoor barbecue facilities.
The Sea Grape, End Unit, Walk To Beach And Steps To The Community Pool/spa - Anna Maria, FL
9.6 35 reviews
Anna Maria, FL
21/06 – 26/06
259 â‚¬/nightTotal: 1295 â‚¬ (5 )

The Sea Grape, End Unit, Walk To Beach And Steps To The Community Pool/spa

3 3
apartment , Bradenton Beach
This Bradenton Beach apartment is situated in the Bradenton Beach Club complex, a short walk from the beach, boardwalk, and the free trolley, making it easy to explore the island's shops and restaurants. The apartment consistently receives excellent ratings for its cleanliness, location, and overall user experience.
The apartment features an open-plan layout spanning 118 square metres, providing ample space for families or groups. Amenities include a fully equipped kitchen, a private balcony, a washer and dryer, and access to a shared swimming pool and jacuzzi, ensuring a comfortable and enjoyable stay.
Coastal Cottage W/ Pickleball And Outdoor Oasis 2 Mi To Beach - Anna Maria, FL
10 104 reviews
Anna Maria, FL
28/07 – 03/08
575 â‚¬/nightTotal: 3450 â‚¬ (6 )

Coastal Cottage W/ Pickleball And Outdoor Oasis 2 Mi To Beach

4 11
apartment , Cortez
This family-friendly holiday home is located in Bradenton, just 5 kilometres from Anna Maria Sound, Fish Hole Adventure Golf and arcadeland, offering a peaceful and relaxing atmosphere. The property has consistently received excellent ratings from previous guests for its cleanliness, location and overall experience.
The 139 square metre property sleeps up to 12 guests in its three bedrooms and two bathrooms. It offers a range of amenities including a private pool, a games room, a terrace, a garden and free Wi-Fi, ensuring a comfortable and enjoyable stay for families and groups.
Seashell Oasis: 2.5 Blocks To Gulf! Dog Friendly, Pool By Anna Maria Life - Anna Maria, FL
10 34 reviews
Anna Maria, FL
05/07 – 11/07
756 â‚¬/nightTotal: 4536 â‚¬ (6 )

Seashell Oasis: 2.5 Blocks To Gulf! Dog Friendly, Pool By Anna Maria Life

4 11
apartment , Bradenton Beach
This Bradenton Beach holiday home, situated between the Gulf of Mexico (0.4 km) and the Bay (0.16 km), offers unparalleled access to both stunning beaches and Bradenton Beach's local amenities.
This spacious 243 square metre property boasts four king-size bedrooms, five bathrooms, a private heated pool, and ample parking for six cars, comfortably accommodating up to nine guests and including a fenced yard for pets.

Best Anna Maria, FL holiday rentals with parking

Beachwalker Apartment:  Duplex Within 100 Steps To The Sand. - Anna Maria, FL
9.2 61 reviews
Anna Maria, FL
27/06 – 04/07
270 â‚¬/nightTotal: 1890 â‚¬ (7 )

Beachwalker Apartment: Duplex Within 100 Steps To The Sand.

1 2
apartment , Holmes Beach
This holiday home is located in Holmes Beach, just a short walk from Bradenton Beach and within a 16km drive of Manatee Public Beach and Anna Maria Sound. The property has received excellent ratings for location, cleanliness, and overall guest experience.
The 42 square metre house has one bedroom and one bathroom, comfortably accommodating two guests. It offers a range of amenities including a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, and parking.
The Palms #3   Beach, Pool & Trolley  No Car Needed - Anna Maria, FL
9.6 58 reviews
Anna Maria, FL
27/06 – 04/07
255 â‚¬/nightTotal: 1785 â‚¬ (7 )

The Palms #3 Beach, Pool & Trolley No Car Needed

2 2
apartment , Holmes Beach
This holiday home is located in Holmes Beach, just under a kilometre from Bradenton Beach, Anna Maria Sound, and AMI Paddleboard Adventures, offering easy access to the area's many attractions. The property has consistently received excellent user ratings for its location, cleanliness, and overall experience.
The two-bedroom house spans 70 square metres and comfortably accommodates up to six guests. It features a fully equipped kitchen, a private swimming pool, a spa, a garden, and a terrace, providing everything you need for a relaxing and enjoyable stay.
Manatee Haven Pool Games Hot Tub Firepit - Anna Maria, FL
Anna Maria, FL
05/07 – 11/07
519 â‚¬/nightTotal: 3114 â‚¬ (6 )

Manatee Haven Pool Games Hot Tub Firepit

4 11
apartment , West Bradenton
This 4-bedroom residence is situated in the Palma Sola district of West Bradenton, offering proximity to Anna Maria Island and the Gulf beaches, with the De Soto National Memorial and Palma Sola Botanical Park nearby.
This spacious 158 square metre holiday home accommodates up to 12 guests, featuring a fully equipped chef's kitchen, a dedicated workspace, a games room with pool and foosball, an outdoor entertainment area with a heated swimming pool and hot tub, and parking for up to five vehicles.
232 M² House ∙ 6 Bedrooms ∙ 12 Guests - Anna Maria, FL
9.9 47 reviews
Anna Maria, FL
27/06 – 04/07
1413 â‚¬/nightTotal: 9891 â‚¬ (7 )

232 M² House ∙ 6 Bedrooms ∙ 12 Guests

6 9
house , Holmes Beach
This six-bedroom, six-bathroom Holmes Beach holiday home is situated on 42nd Street, a short distance from the beach, restaurants, and shops, offering easy access to Bean Point and Bridge Street via the free trolley.
Sleeping up to twelve guests, this luxurious property boasts a private heated saltwater pool, a spa, fitness centre, tennis court, and all mod cons including a fully equipped kitchen, free Wi-Fi, and flat-screen TVs; beach towels are provided.
©2026 cozycozy.com