Anna Maria Island, FL vacation rentalscozycozy

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Best Vacation rentals and Airbnb offers in Anna Maria Island, FL

Cozy Haven Near Manatee Memorial And Great Beaches - Anna Maria Island, FL
9.1 8 reviews
Anna Maria Island, FL
6 3
$297/nighttotal: $594 (2 )

Cozy Haven Near Manatee Memorial And Great Beaches

house - Bradenton
This Bradenton house is located 6.2 miles from Sarasota Bradenton International Airport and 7.6 miles from the Sarasota International Convention Center, offering convenient access to the John and Mable Ringling Museum of Art (8 miles) and Manatee Memorial Hospital.
This 1370 sq ft, 1-bedroom accommodation comfortably sleeps 13 guests and features air conditioning, free Wi-Fi, a full kitchen with a dishwasher and oven, a terrace, and parking, making it suitable for families and pet owners.
Oasis Backyard With Hot Tub 4/2 Close To The Beach - Anna Maria Island, FL
9.6 18 reviews
Anna Maria Island, FL
6 4
$577/nighttotal: $4039 (7 )

Oasis Backyard With Hot Tub 4/2 Close To The Beach

house - West Bradenton
This West Bradenton home is conveniently located near the beach, just 11 miles from the John and Mable Ringling Museum of Art and 9.3 miles from Sarasota Bradenton International Airport. The house has received excellent ratings for location, cleanliness, and overall user experience.
This 4-bedroom house is perfect for families or groups of friends. The home offers a variety of amenities, including a swimming pool, hot tub, outdoor fireplace, and a fully equipped kitchen, making it a great place to relax and enjoy the Florida weather.
Mycataleya Comfy Condo Near Beach (Bradenton) - Anna Maria Island, FL
9.5 41 reviews
Anna Maria Island, FL
2 2
$208/nighttotal: $624 (3 )

Mycataleya Comfy Condo Near Beach (Bradenton)

apartment - Bradenton
This 2-bedroom, 2-bathroom apartment is located in the heart of South Bradenton, within walking distance of IMG Academy and Smugglers Cove Adventure Golf. The apartment is rated "excellent" for its location, cleanliness, and user ratings. It can accommodate up to 4 guests and features a fully equipped kitchen, a private balcony, and access to a fitness center and a spa tub.
Enjoy relaxing in the garden, swimming in the pool, grilling in the barbecue area, or simply enjoying the views from your private balcony. The apartment is also pet-friendly and offers parking, making it the perfect home away from home for your vacation in South Bradenton.
Starfish House - 2bed/2bad - Anna Maria Island, FL
9.9 55 reviews
Anna Maria Island, FL
2 2
$201/nighttotal: $1407 (7 )

Starfish House - 2bed/2bad

house - Holmes Beach
Starfish Beach #4, a two-bedroom, two-bathroom villa in Holmes Beach, Anna Maria Island, is located 50 yards from Anna Maria Public Beach access and a short walk from local shops and restaurants.
This Holmes Beach vacation rental sleeps six guests comfortably, boasting a king bed, queen bed, sleeper sofa, full kitchen with dishwasher, air conditioning, private pool access, and baby accessories available for rent.
Paradise Cove - Anna Maria Island, FL
9.9 420 reviews
Anna Maria Island, FL
2 3
$263/nighttotal: $1841 (7 )

Paradise Cove

apartment - Bradenton
This family-friendly vacation rental is located in Bradenton, just a short distance from attractions like Smugglers Cove Adventure Golf, arcadeland, and The Bishop Museum of Science and Nature. The property has received excellent ratings for its location, cleanliness, and overall experience.
This 3-bedroom home with a sofa bed offers ample space for families or groups of friends. It features a private pool and patio, a fully equipped kitchen, a fireplace, and outdoor amenities like a garden and barbecue grills for enjoying the Florida sunshine.
Beaches Anna Maria Island Img Tennis Bradenton - Anna Maria Island, FL
9.8 10 reviews
Anna Maria Island, FL
2 2
$183/nighttotal: $732 (4 )

Beaches Anna Maria Island Img Tennis Bradenton

apartment - Bradenton
This Bradenton apartment rental is conveniently located near IMG Academy and Sarasota Bradenton International Airport (SRQ), 7.9 miles from the Ringling Museum.
The 1100-square-foot unit features two bedrooms, two bathrooms, accommodates up to nine guests, and includes a fully equipped kitchen, swimming pool, jacuzzi, free parking, and Wi-Fi.
Spacieuse Maison, Piscine Chauffee, Pres Ana Maria - Anna Maria Island, FL
9.8 79 reviews
Anna Maria Island, FL
7 4
$356/nighttotal: $712 (2 )

Spacieuse Maison, Piscine Chauffee, Pres Ana Maria

apartment - West Bradenton
This West Bradenton vacation home, a 15-minute drive from Anna Maria Island, is situated in a quiet residential area near Warner East Bayou.
The newly renovated house features four bedrooms, two bathrooms, and can comfortably accommodate eight guests, boasting a spacious open-plan layout with two living rooms, a full kitchen, and a large heated pool within a tropical garden.
Bayview Beach Retreat - Island Charm & Water Views - Anna Maria Island, FL
9.9 53 reviews
Anna Maria Island, FL
2 1
$197/nighttotal: $591 (3 )

Bayview Beach Retreat - Island Charm & Water Views

apartment - Bradenton Beach
This Gulf-front condo in Bradenton Beach offers direct beach access and is a short walk to Historic Bridge Street and its pier, shops, and dining.
This one-bedroom, one-bathroom unit accommodates up to four guests and includes air conditioning, a full kitchen, complimentary beach chairs, two bikes, and on-site parking for exploring the 7-mile island via the free trolley.
Sunshine Retreat With Heated Saltwater Pool.  Minutes To Gulf Beaches And Img - Anna Maria Island, FL
10 131 reviews
Anna Maria Island, FL
6 4
$445/nighttotal: $890 (2 )

Sunshine Retreat With Heated Saltwater Pool. Minutes To Gulf Beaches And Img

apartment - Bradenton
This Bradenton vacation home is located near the sea, just 1.1 miles from Blake Medical Center and 2.7 miles from Arcadeland. It has been rated excellent by previous guests.
This 4-bedroom, 2-bathroom rental offers 1910 square feet of space and can comfortably accommodate up to 8 guests. You'll enjoy a private pool, a fenced yard, barbecue grills, a fully equipped kitchen, free Wi-Fi, and a terrace.
4br Private Coastal Retreat: Heated Pool, Near Ami - Anna Maria Island, FL
9.8 119 reviews
Anna Maria Island, FL
7 4
$581/nighttotal: $1162 (2 )

4br Private Coastal Retreat: Heated Pool, Near Ami

apartment - West Bradenton
This West Bradenton vacation home, located less than 2 kilometers from De Soto National Memorial and Palma Sola Botanical Park, offers easy access to Robinson Preserve and other local attractions.
This 2,350-square-foot property boasts four bedrooms, 2.5 bathrooms, a private pool, and can comfortably accommodate up to 16 guests, featuring a fully equipped kitchen, BBQ grills, and an on-site game room.
Captain America Dream - Anna Maria Island, FL
9.6 102 reviews
Anna Maria Island, FL
2 3
$348/nighttotal: $1392 (4 )

Captain America Dream

house - Bradenton
This Bradenton vacation rental is conveniently located just 8.9 miles from the John and Mable Ringling Museum of Art and 6.8 miles from Sarasota Bradenton International Airport. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience.
The 3-bedroom home comfortably accommodates up to 6 guests. Enjoy a private pool, a children's playground, a fully equipped kitchen, air conditioning, free Wi-Fi, a garden, and convenient access to nearby cycling trails.
Dolphin Cabin! Available For Summer! Screened Pool, Dock & More! - Anna Maria Island, FL
Anna Maria Island, FL
6 3
$770/nighttotal: $5390 (7 )

Dolphin Cabin! Available For Summer! Screened Pool, Dock & More!

cabin - Cortez
Dolphin Cabin, located in Bradenton, Florida, offers convenient access to Sarasota attractions, including the Ringling Museum of Art, approximately 12 miles away.
This 1980-square-foot vacation home features three bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, screened pool, private dock, free Wi-Fi, and air conditioning.

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

Heated Salt Poolmini Golfarcadespaami 6miimg - Anna Maria Island, FL
10 86 reviews
Anna Maria Island, FL
7 3
$511/nighttotal: $1022 (2 )

Heated Salt Poolmini Golfarcadespaami 6miimg

apartment - South Bradenton
This South Bradenton vacation rental, located minutes from Anna Maria Island (8 miles), IMG Academy (4 miles), and the Bradenton Riverwalk (6 miles), offers a quiet neighborhood setting close to major attractions.
The three-bedroom, two-bathroom home sleeps nine guests and features a private heated pool, mini golf course, hot tub, outdoor movie theater, backyard arcade shed with shuffleboard and air hockey, a fully equipped kitchen with beach essentials, and smart TVs in each bedroom.
Shorewalk Rental By Owner/condo 2bed/2bath/img Academy /Anna Maria Island - Anna Maria Island, FL
9.6 143 reviews
Anna Maria Island, FL
2 2
$222/nighttotal: $444 (2 )

Shorewalk Rental By Owner/condo 2bed/2bath/img Academy /Anna Maria Island

apartment - Bradenton
This two-bedroom, two-bathroom apartment is in the heart of Bradenton, near major tourist attractions, shopping, dining, and entertainment options. The condo has excellent user ratings and offers a convenient location for travelers visiting Bradenton.
The apartment has a floor area of 910 square feet and can accommodate up to four guests. It features a fully equipped kitchen, a living area, a balcony or patio, and access to resort-style amenities such as two swimming pools, two whirlpools, a playground, BBQ grills, tennis and basketball courts, and free parking.
Img Lake & Beach Home With Pool White Sand Beaches May 16-10, Oct, Nov Specials! - Anna Maria Island, FL
9.8 140 reviews
Anna Maria Island, FL
7 1
$367/nighttotal: $734 (2 )

Img Lake & Beach Home With Pool White Sand Beaches May 16-10, Oct, Nov Specials!

apartment - South Bradenton
This South Bradenton house is located just 8 minutes from Anna Maria Island beaches, offering a prime location for exploring the area's beautiful coastline and nearby attractions. The property has received excellent user ratings, suggesting a comfortable and enjoyable stay for guests.
The house spans 2000 square feet and comfortably accommodates up to 8 guests. Amenities include a private pool, a fully equipped kitchen, and a range of activities like fishing, cycling, and access to a nearby LA Fitness gym and spa.
Close To Beaches And Img, Heated Pool, Minigolf - Anna Maria Island, FL
10 38 reviews
Anna Maria Island, FL
7 3
$302/nighttotal: $604 (2 )

Close To Beaches And Img, Heated Pool, Minigolf

apartment - Bradenton
This Bradenton residence is located 5 miles from Anna Maria Island and 4 miles from IMG Academy, offering a modern coastal living experience near Bradenton's sandy shores, Bradenton Riverwalk, and dining options. This family-friendly 3-bedroom, 2-bathroom condo accommodates up to 8 guests and features a heated pool, putting green, cornhole, a game room with Pac-Man, and a dedicated workspace with 500 Mbps Wi-Fi.

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

Beach Castle Resort #17 - Anna Maria Island, FL
9.2 4 reviews
Anna Maria Island, FL
2 1
$319/nighttotal: $957 (3 )

Beach Castle Resort #17

house - Longboat Key
This vacation rental in Longboat Key is located 4 minutes on foot from Longboat Key Beach and 14 miles from the John and Mable Ringling Museum of Art.
This 640 square foot bungalow accommodates up to 7 guests and features air conditioning, a swimming pool, a jacuzzi, a private patio, a balcony, and a fitness center.
Heated Pool! Beautiful Condo, Close To Beach - Anna Maria Island, FL
9.5 28 reviews
Anna Maria Island, FL
6 2
$466/nighttotal: $3262 (7 )

Heated Pool! Beautiful Condo, Close To Beach

apartment - Holmes Beach
This Holmes Beach condo is located just a 15-minute walk from Bradenton Beach, close to Island Gallery West and within 2 miles of other popular beaches. It has received excellent ratings for user experience, location, and cleanliness.
The condo offers two bathrooms and a full kitchen with a fridge, microwave, dishwasher, and stovetop. Guests can enjoy a private balcony, a swimming pool, a spa, and a garden, along with free WiFi in public areas.
Basque Bungalow With Pool, Minutes To Beaches - Anna Maria Island, FL
10 2 reviews
Anna Maria Island, FL
6 3
$379/nighttotal: $758 (2 )

Basque Bungalow With Pool, Minutes To Beaches

house - Bradenton
This Basque-style bungalow in Bradenton, Florida, is located 8.3 miles from the Sarasota International Convention Center and 8.8 miles from the Ringling Museum of Art, offering easy access to Sarasota's cultural attractions and Bradenton's beaches.
This 1,580-square-foot vacation rental boasts three bedrooms, two bathrooms, and accommodates up to 13 guests, featuring a private pool, terrace, garden, and free Wi-Fi; private parking is also available.
Family Oasis--private Pool & Hot Tub-near Anna Maria Island, Beaches, Parks, Shops - Anna Maria Island, FL
9.4 30 reviews
Anna Maria Island, FL
6 3
$460/nighttotal: $920 (2 )

Family Oasis--private Pool & Hot Tub-near Anna Maria Island, Beaches, Parks, Shops

apartment - Bradenton
This Bradenton vacation rental is conveniently located 1.1 miles from Blake Medical Center and within 6 miles of IMG Academy and De Soto National Memorial, offering easy access to area attractions.
This 1,270-square-foot house features three bedrooms, two bathrooms, and accommodates up to six guests, boasting a private pool, hot tub, tennis court, and fully equipped kitchen.

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! The Bean Point is a must-see for its stunning sunsets and views. The Anna Maria City Pier is a great place to fish or just relax and watch the Gulf. Historic Bridge Street in Bradenton Beach offers unique shops and restaurants. And don't forget to explore the nature preserves like the Anna Maria Island Nature Preserve and the Leffis Key Preserve.
  • What are the best Airbnb and vacation rentals in Anna Maria Island, FL?

    Standard 2 Bedroom B, 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?

    The island's location on the Gulf Coast means you'll see amazing sunsets. The beaches are known for shelling, with a variety of shells washing ashore. You might even spot dolphins playing in the waters near the shore. Birdwatching is also popular, with various species frequenting the island's natural areas.
  • 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, sunglasses, a hat, and comfortable walking shoes. Don't forget insect repellent, especially for evenings. A beach umbrella and beach chairs will make your beach days more enjoyable. And of course, a camera to capture those amazing sunsets!
  • What are the best vacation rentals with a pool in Anna Maria Island, FL?

    Standard 2 Bedroom B, 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 famous events or festivals are happening on Anna Maria Island, Florida?

    Anna Maria Island doesn't have large-scale, internationally known festivals. However, throughout the year, smaller local events take place, including the annual Christmas boat parade and various art walks. Check local event listings closer to your travel dates for the most up-to-date information.
  • What are the best rentals for families and kids 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 can vary greatly depending on your travel style. For a comfortable trip, expect to spend around $150-$300 per person per day. This includes mid-range accommodation, meals, some activities, and local transportation. Budget-conscious travelers could likely manage on less, while luxury travelers will spend significantly more.
  • What are the best rentals or Airbnbs with a jacuzzi 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 fresh seafood. Rod & Reel Pier offers casual dining with waterfront views. Many restaurants feature fresh seafood, which is a local specialty. Key lime pie is a must-try dessert, reflecting Florida's citrus heritage.
  • What are some less-famous attractions on Anna Maria Island, Florida that are worth the visit?

    The Anna Maria Island Historical Society Museum offers a glimpse into the island's past. Exploring the quieter beaches away from the main tourist areas provides a more peaceful experience. Take a leisurely bike ride along the island's scenic paths. Consider kayaking or paddleboarding through the mangroves.
  • What are the best activities for engaging with locals and understanding their culture on Anna Maria Island, Florida?

    Visiting local shops and art galleries allows you to interact with business owners. Attending smaller community events offers opportunities to meet residents. Simply striking up conversations with people you meet on the beach or in restaurants can provide insights into island life. The laid-back atmosphere makes it easy to connect with people.
  • What unique natural landscapes and terrain features can travelers explore on Anna Maria Island, Florida?

    Anna Maria Island features beautiful beaches with soft, white sand. The mangrove forests provide unique ecosystems to explore via kayak or paddleboard. The island's relatively flat terrain makes it easy to explore on foot or by bike.
  • How many days are ideal for visiting Anna Maria Island, Florida, and what are some itinerary suggestions?

    Three to five days is a good amount of time to explore Anna Maria Island at a relaxed pace. Spend a day relaxing on the beach, another exploring Bridge Street, and perhaps a day kayaking or visiting the nature preserves. Consider a sunset cruise for a memorable experience.

Nearby regions

Best Anna Maria Island, FL vacation rentals with a balcony

Pool Access, Walk To Manatee Beach: Coastal Condo - Anna Maria Island, FL
8.7 97 reviews
Anna Maria Island, FL
6 2
$640/nighttotal: $4480 (7 )

Pool Access, Walk To Manatee Beach: Coastal Condo

house - Holmes Beach
This Holmes Beach condo is conveniently located just a short walk from Bradenton Beach and less than a mile from Anna Maria Island's main attractions. It has received very good user ratings for cleanliness and overall experience, along with an excellent location rating.
The two-bedroom apartment offers 1000 square feet of space, comfortably accommodating up to 6 guests. Enjoy the private pool, direct Gulf access, fully equipped kitchen, and a host of other amenities for a relaxing and enjoyable stay.
Tropical Haven B - 4505   Anna Maria Island - Anna Maria Island, FL
10 18 reviews
Anna Maria Island, FL
6 2
$414/nighttotal: $828 (2 )

Tropical Haven B - 4505 Anna Maria Island

apartment - Cortez
This Bradenton condo, located within three miles of Anna Maria Sound, Bradenton Beach Marina, Fish Hole Adventure Golf, Bridge Street, and the Historic Bridge Street Pier, offers convenient access to area attractions.
This 1100-square-foot, two-bedroom, two-bathroom unit sleeps six and features a fully equipped kitchen, private balcony, free WiFi, a swimming pool, and on-site barbecue grills.
Bay Retreat, Huge Yard & Fire Pit, Near Beach - Anna Maria Island, FL
Anna Maria Island, FL
7 1
$153/nighttotal: $306 (2 )

Bay Retreat, Huge Yard & Fire Pit, Near Beach

house - Bayshore Gardens
This spacious house in Bayshore Gardens is located 4.3 miles from the Sarasota International Convention Center and 2.5 miles from Sarasota Bradenton International Airport.
This 1360 square foot holiday home accommodates up to 15 guests and features 1 bedroom, 2 bathrooms, a fully equipped kitchen, air conditioning, complimentary WiFi, and on-site private parking.
Gulf Coast Getaway Pool Mini Putt Fenced Yard - Anna Maria Island, FL
10 1 review
Anna Maria Island, FL
7 3
$387/nighttotal: $774 (2 )

Gulf Coast Getaway Pool Mini Putt Fenced Yard

house - Palmetto
This house is located in Palmetto, 11 miles from Sarasota International Convention Center and 12 miles from the John and Mable Ringling Museum of Art.
This 1800 square feet accommodation features 3 bedrooms, 2 bathrooms, a private outdoor swimming pool and garden, a fully equipped kitchen, and on-site parking with free WiFi, accommodating up to 14 guests.

Best Anna Maria Island, FL vacation rentals with parking

Charming And Updated 1 Bedroom In Runaway Bay - Anna Maria Island, FL
9.7 136 reviews
Anna Maria Island, FL
2 1
$138/nighttotal: $966 (7 )

Charming And Updated 1 Bedroom In Runaway Bay

apartment - Bradenton Beach
This Bradenton Beach condo, located directly across the street from the beach with deeded access and a free trolley stop outside, offers unparalleled convenience.
The 1-bedroom, 1-bathroom unit sleeps 4, features a king-sized Serta mattress, Samsung flat-screen TVs, in-unit laundry, and access to a large heated pool, kayaks, bikes, a fishing pier, fitness center, and more.
Privacy Lockoff Units 4/5 Beach Club Ami Rva - Anna Maria Island, FL
9.5 1544 reviews
Anna Maria Island, FL
2 1
$255/nighttotal: $1020 (4 )

Privacy Lockoff Units 4/5 Beach Club Ami Rva

apartment - Bradenton Beach
Beach Club At Anna Maria Island #12 Resort By Rva is located on Bradenton Beach, just a short walk from both Bradenton Beach and Cortez Beach, and a five-minute walk from Anna Maria Sound. The smoke-free apartment building has earned excellent ratings for location, cleanliness, and user experience.
This vacation rental features a full kitchen, a TV with a DVD player, a washing machine, and a coffee/tea maker. Guests can enjoy the on-site spa tub, swimming pool, fitness center, tennis court, and garden, as well as the direct access to the beach.
Coastal Comfort  Beach Castle #26 By Rva - Anna Maria Island, FL
9.6 53 reviews
Anna Maria Island, FL
2 1
$437/nighttotal: $27531 (63 )

Coastal Comfort Beach Castle #26 By Rva

apartment - Longboat Key
This waterfront resort, the Beach Castle Resort #26 By Rva, is conveniently located within 1 mile of Longboat Key Beaches and Cannons Marina. It has excellent user ratings for its location, cleanliness, and overall experience.
The condo has 1 bedroom and 1 bathroom, and can accommodate up to 4 guests. It features a fully equipped kitchen, a spacious living area with a TV and DVD player, and a private spa tub. Guests can also enjoy access to a swimming pool, Jacuzzi, tennis court, and free self parking.
Private Resort:pool, Game Room, Near Img & Beaches - Anna Maria Island, FL
9.9 30 reviews
Anna Maria Island, FL
6 3
$431/nighttotal: $862 (2 )

Private Resort:pool, Game Room, Near Img & Beaches

apartment - Bradenton
This resort-style rental is located in Bradenton, offering a 10-minute drive to IMG Academy and Bradenton Beach, and a 15-minute drive to Anna Maria Island.
This 3-bedroom, 2-bathroom villa accommodates up to 8 guests and features a private, heated saltwater pool, a screened lanai, a fully updated modern interior with luxury vinyl plank flooring, and a fenced backyard.
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