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Anna Maria, FL villas
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1465 Villa rentals in Anna Maria, FL

Browse Waterfront Vacation Homes in Anna Maria, FL

Experience relaxing coastal vibes at seaside vacation homes in Anna Maria, FL, located short distances from popular local shorelines.

Relaxed Luxury · Refined North-side 1 Bedroom - Anna Maria, FL
10 1 review

Relaxed Luxury · Refined North-side 1 Bedroom

cottage, Bradenton Beach
This one-bedroom cottage in Bradenton Beach is located minutes from Bradenton Beach and Coquina Beach, offering easy access to island trolley stops for exploration of local shops and restaurants.
This 540 square foot bungalow accommodates up to four guests, featuring a full kitchen, air conditioning, and access to shared amenities like a swimming pool and BBQ area, with a private patio for relaxation.

Find the Best Holiday Houses with Swimming Pool in Anna Maria, FL

Having a pool at your Anna Maria, FL vacation home lets you enjoy a dip to complement a day by the water without extra planning.

Cozy Cottage For 4 Located Steps From The Beach. Heated Pool In Private Patio. - Anna Maria, FL
10 20 reviews

Cozy Cottage For 4 Located Steps From The Beach. Heated Pool In Private Patio.

cottage, Holmes Beach
This charming cottage is just a short walk from the beautiful beaches of Bradenton Beach and Palmetto Avenue Beach, making it the perfect spot for a relaxing beach getaway. The cottage consistently receives excellent ratings from previous guests, ensuring a positive experience.
This cozy home features two bedrooms and one bathroom, comfortably accommodating up to four guests. You'll have access to a private pool, a fenced yard, and a well-equipped kitchen, along with a range of other amenities perfect for a comfortable and enjoyable stay.
Cozy 1-bed Cottage In Adorable Tradewinds Bradenton Beach, Steps To Beach/pool - Anna Maria, FL
10 19 reviews

Cozy 1-bed Cottage In Adorable Tradewinds Bradenton Beach, Steps To Beach/pool

cottage, Bradenton Beach
This newly renovated 1-bedroom, 1-bathroom cottage in Bradenton Beach is located mere steps from the Bradenton Beach shoreline and community pool, offering convenient access to Bridge Street Bistro, Anna Maria Oyster Bar, Mote Marine Laboratory & Aquarium, and Coquina Beach.
This 700 square foot rental accommodates up to 4 guests and features a full kitchen with a fridge, microwave, and dishwasher, air conditioning, internet, and private parking, with an option to book an adjacent unit for larger groups.
Bimini Bay: 3 Blocks To Beach! Private Pool! By Anna Maria Life Vacation Rentals - Anna Maria, FL
No reviews

Bimini Bay: 3 Blocks To Beach! Private Pool! By Anna Maria Life Vacation Rentals

house, Anna Maria
This Anna Maria vacation home is located 3 blocks from the beach and a 5-minute walk to Anna Maria Island, with Sarasota International Convention Center, John and Mable Ringling Museum of Art, and Sarasota Bradenton International Airport all within 16-18 miles.
This 1840 square foot house offers 4 bedrooms, 3 bathrooms, and can accommodate up to 8 guests, featuring a private swimming pool, full kitchen, air conditioning, free Wi-Fi, and on-site parking.
Two Bedroom Cozy Island Home Right Around The Corner From Gulf Beaches. Lots Of Amenities! - Anna Maria, FL
9.6 25 reviews

Two Bedroom Cozy Island Home Right Around The Corner From Gulf Beaches. Lots Of Amenities!

cottage, Holmes Beach
This two-bedroom, two-bathroom cottage is located in Holmes Beach, less than a mile from Bradenton Beach and Palmetto Avenue Beach.
The pet-friendly cottage features a private pool, a fully equipped kitchen, a patio with a barbecue grill, and can accommodate up to five guests.

Frequently Asked Questions about villa rentals in Anna Maria, FL

  • What are the must-see attractions in and around Anna Maria, FL?

    You definitely want to check out the Anna Maria Island Historical Museum, it's a great place to learn about the island's history. The City Pier is a classic spot for fishing or just enjoying the view. And if you're looking for something a little more adventurous, you can take a day trip to nearby Bradenton, which has the South Florida Museum and the Bishop Museum of Science and Nature.
  • What are the best villa rentals in Anna Maria, FL?

    Among the villa rentals in Anna Maria, FL, Standard 2 Bedroom B, Do You Love The Beach? and Bay Breeze Cottages #3 are the most popular ones.

  • What types of wildlife can travelers expect to see in the area of Anna Maria, FL?

    Anna Maria is a great place to spot dolphins, manatees, and even the occasional sea turtle. You can often see them from the beach or while kayaking or paddleboarding. Be sure to keep your distance and respect their space.
  • What are the best villa rentals with a pool in Anna Maria, FL?

    Standard 2 Bedroom B, Do You Love The Beach? and Bay Breeze Cottages #3 are the best villa rentals with a pool in Anna Maria, FL.

  • What is the best time to visit Anna Maria, FL?

    The best time to visit Anna Maria is during the spring or fall when the weather is mild and the crowds are smaller. You'll still get plenty of sunshine, but it won't be as hot and humid as during the summer months.
  • What are the best villa rentals with a jacuzzi in Anna Maria, FL?

  • When is it easiest to book a villa rental in Anna Maria, FL?

    The easiest time to book a villa rental is during the off-season, which is generally from May to October. You'll find better deals and more availability during these months.
  • What are the best villa rentals for families and kids in Anna Maria, FL?

  • What are the top hiking trails near Anna Maria, FL?

    Anna Maria itself doesn't have any hiking trails, but you can find some great trails nearby at Robinson Preserve in Bradenton. It's a beautiful place to hike, bike, or kayak, and you might even see some wildlife along the way.
  • What are the best pet friendly villa rentals in Anna Maria, FL?

  • What are the advantages of renting a house or a villa in Anna Maria, FL

    Renting a house or villa in Anna Maria gives you more space and privacy than a hotel. You can also enjoy amenities like a private pool and a fully equipped kitchen, which can save you money on dining out.
  • What are the best villa rentals with parking in Anna Maria, FL?

    Standard 2 Bedroom B, Do You Love The Beach? and Bay Breeze Cottages #3 are the best villa rentals with parking in Anna Maria, FL.

  • Are there popular destinations near Anna Maria, FL?

    Yes, there are many popular destinations near Anna Maria. You can visit the beaches of Siesta Key or Lido Key, or explore the historic downtown of Sarasota. There are also several state parks and nature preserves within a short drive.

Popular destinations

Best Anna Maria, FL villas and beach houses with jacuzzi

263 M² House ∙ 5 Bedrooms ∙ 12 Guests - Anna Maria, FL
9.8 43 reviews

263 M² House ∙ 5 Bedrooms ∙ 12 Guests

house, Anna Maria
This Anna Maria Island vacation home, located on the coveted north end, is a short 10-minute walk from Bean Point beach.
The 2,990-square-foot residence boasts five bedrooms, five bathrooms, and accommodates up to twelve guests, featuring a private heated pool, spa, and access to two cruiser bikes, two kayaks, and a private boat dock.
House ∙ 3 Bedrooms ∙ 8 Guests - Anna Maria, FL
No reviews

House ∙ 3 Bedrooms ∙ 8 Guests

house, Anna Maria
This newly renovated single-story beach house is located on Los Cedros, a short walk north of Pine Avenue in Anna Maria, offering proximity to dining, shopping, and the free island trolley.
Accommodating up to 8 guests, this premier beach house features 3 bedrooms and 3 bathrooms, a stunning saltwater pool with a heated spa, a screened lanai with a second dining area, a private exterior shower cabana, and direct access to Lake Marsha with a private kayak launch.
Luxury Waterfront - Sauna - Games - Minigolf - Gym - Anna Maria, FL
No reviews

Luxury Waterfront - Sauna - Games - Minigolf - Gym

house, Anna Maria
This luxury waterfront house in Anna Maria is an 18-minute walk from the island's beaches, 18 miles from the Sarasota International Convention Center, and 19 miles from The John and Mable Ringling Museum of Art.
This 2600 square foot residence accommodates up to 17 guests with 4 bedrooms and 4 bathrooms, offering amenities such as a private pool, jacuzzi, sauna, spa, fitness center, games, minigolf, and complimentary high-speed WiFi and on-site parking.
Beach Breeze West - Anna Maria, FL
8.0 1 review

Beach Breeze West

house, Bradenton Beach
Beach Breeze West is a vacation home in Ilexhurst, located a 3-minute walk from Bradenton Beach, 12 miles from Sarasota Bradenton International Airport, and 14 miles from Sarasota International Convention Center and the John and Mable Ringling Museum of Art.
This 1350 square foot villa accommodates up to 7 guests with 2 bedrooms, air conditioning, a full kitchen, and offers amenities like a swimming pool, jacuzzi, fitness center, tennis court, private patio, balcony, free WiFi, and accessible facilities.

Neighborhoods and points of interest in Anna Maria, FL

Best Anna Maria, FL houses with a kitchen

Minnow 1 - Anna Maria, FL
No reviews

Minnow 1

house, Anna Maria
Minnow 1 Cabin, a one-bedroom cottage in Anna Maria, Florida, is a 12-minute walk from Anna Maria City Pier and a 20-mile drive from The John and Mable Ringling Museum of Art.
This 620-square-foot Anna Maria Island rental sleeps three guests and features a full kitchen, air conditioning, free Wi-Fi, and a separate bedroom.
Green Jacaranda /Bean Point Beach 5 Min Walk/pool - Anna Maria, FL
9.9 175 reviews

Green Jacaranda /Bean Point Beach 5 Min Walk/pool

house, Anna Maria
This Anna Maria Island apartment is situated on the north end of the island, just steps away from Bean Point Beach.
The 990-square-foot duplex features two bedrooms, one bathroom, and can accommodate up to four guests, offering amenities such as a heated pool, grilling areas, and bicycles.
Beach N Bay 204 Villa - Anna Maria, FL
9.7 30 reviews

Beach N Bay 204 Villa

house, Anna Maria
Beach N Bay 204 villa is a pet-friendly (dogs up to 50 lbs, fee applies) Anna Maria Island vacation rental, a six-minute walk from Anna Maria Island's beaches and a seven-minute walk from the Anna Maria City Pier.
This 830-square-foot, two-bedroom, one-bathroom villa offers a fully equipped kitchen with a dishwasher, a Jacuzzi, free Wi-Fi, and in-unit laundry; it's close to Sarasota Bradenton International Airport (17 miles).
South Bay Inn 2 - Anna Maria, FL
No reviews

South Bay Inn 2

house, Anna Maria
This Anna Maria condo is located at South Bay Inn 2, a 13-minute walk from Anna Maria Island and 18 miles from Sarasota International Convention Center and the John and Mable Ringling Museum of Art.
This 900-square-foot apartment accommodates up to 7 guests and features air conditioning, a swimming pool, a restaurant, a fully equipped kitchen with a dishwasher, and a TV with satellite channels.

Check Out 5-Star Holiday Houses in Anna Maria, FL

Upscale finishes and prime locations define these luxury vacation homes in Anna Maria, FL, ensuring every detail of your stay is considered.

Colorful Beach Cottage W Heated Private Pool & Grill Area - Dog-friendly - Anna Maria, FL
No reviews

Colorful Beach Cottage W Heated Private Pool & Grill Area - Dog-friendly

cabin, Anna Maria

Compare Family Vacation Homes in Anna Maria, FL

Choosing a family vacation home in Anna Maria, FL provides plenty of room to spread out and the perfect space to plan your day with the kids.

276 M² House ∙ 5 Bedrooms ∙ 8 Guests - Anna Maria, FL
10 1 review

276 M² House ∙ 5 Bedrooms ∙ 8 Guests

house, Anna Maria
Coastal Luxe Villa - Anna Maria, FL
9.5 2 reviews

Coastal Luxe Villa

house, Cortez
Heated Pool And Putt-putt Golf - Stunning Coastal Retreat - Anna Maria, FL
No reviews

Heated Pool And Putt-putt Golf - Stunning Coastal Retreat

house, Anna Maria
167 M² House ∙ 3 Bedrooms ∙ 8 Guests - Anna Maria, FL
No reviews

167 M² House ∙ 3 Bedrooms ∙ 8 Guests

house, Anna Maria

Guest-Favorite Pet-Friendly Vacation Homes in Anna Maria, FL

Traveling with a pet to Anna Maria, FL is easy in these vacation homes, featuring dog-friendly amenities.

Caribbean Surf By Beach Retreats - Anna Maria, FL
9.6 58 reviews

Caribbean Surf By Beach Retreats

house, Holmes Beach
Sea Esta - Anna Maria, FL
10 1 review

Sea Esta

house, Anna Maria
Furnished Sunroom W/ Tv! Canal-front Bradenton Gem - Anna Maria, FL
10 1 review

Furnished Sunroom W/ Tv! Canal-front Bradenton Gem

house, Cortez
Cottage In The Shade, 3 Min Walk To Beach, Restaurants, And Pickleball Crt. - Anna Maria, FL
9.8 19 reviews

Cottage In The Shade, 3 Min Walk To Beach, Restaurants, And Pickleball Crt.

cottage, Bradenton Beach

Discover Vacation Homes with Spa in Anna Maria, FL

Choosing a vacation home with a spa in Anna Maria, FL makes wellness effortless. Enjoy included spa bath access just steps from the water.

2 Mi To Bradenton Beach: Water-view Home W/ Bbq - Anna Maria, FL
9.6 13 reviews

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

house, Cortez

Best Anna Maria, FL houses with air conditioning

Waterfront Anna Maria Oasis - Anna Maria, FL
No reviews

Waterfront Anna Maria Oasis

house, Anna Maria
Southern Breeze 6 - Anna Maria, FL
9.5 2 reviews

Southern Breeze 6

house, Anna Maria
Beach N Bay Home - Anna Maria, FL
9.9 53 reviews

Beach N Bay Home

house, Anna Maria
Ami 1 Block 2 Beach, Big Heated Saltwater Pool - Anna Maria, FL
10 2 reviews

Ami 1 Block 2 Beach, Big Heated Saltwater Pool

house, Anna Maria
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