Anna Maria Island, FL holiday rentals

Holiday Rentals in Anna Maria Island, FL

5676 available vacation rental offers

2 1
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Best Holiday rentals and Airbnb offers in Anna Maria Island, FL

Island Living - Walk To The Beach - Anna Maria Island, FL
9.6Excellent 111 reviews
Anna Maria Island, FL
2 2
£190/nighttotal: £380 (2 )

Island Living - Walk To The Beach

apartment - Bradenton Beach
This two-bedroom flat is situated on Anna Maria Island, just a short stroll from the beach, offering a tranquil escape in a relaxed, island setting. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The flat comfortably accommodates four guests and features a well-equipped kitchen with a fridge, microwave, and dishwasher. Enjoy the sunny weather with a dip in the pool, or explore the island's beauty by bike. This pet-free property provides everything you need for a relaxing beach getaway.
The Cannon - Anna Maria Island, FL
9.2Excellent 162 reviews
Anna Maria Island, FL
5 2
£501/nightfor 1 night

The Cannon

apartment - Bradenton Beach
The Cannon apartment is situated in Bradenton Beach, just a short distance from the Anna Maria City Pier and the beautiful beaches of Bradenton Beach, Cortez Beach, and Coquina Beach. It enjoys excellent user, location and cleanliness ratings, making it a popular choice for visitors.
The apartment is a spacious three-bedroom property with a living room and fully equipped kitchen, covering 93 square metres. Guests can enjoy modern amenities such as free Wi-Fi, private parking, air conditioning, and a garden, as well as the convenience of being close to the Greens of Manatee Golf Club and just 12 miles from Sarasota Bradenton International Airport.
Sea 'Esta - Two Bedroom House, Sleeps 6 - Anna Maria Island, FL
10Excellent 38 reviews
Anna Maria Island, FL
6 2
£390/nighttotal: £1950 (5 )

Sea 'Esta - Two Bedroom House, Sleeps 6

house - Anna Maria
This Anna Maria holiday home is located just a five-minute walk from the beach and close to Bayfront Park, Bean Point Beach, and Bradenton Beach. The property has excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The two-bedroom property comfortably sleeps six guests. It comes equipped with a kitchen, air conditioning, free Wi-Fi, and a garden with a barbecue.
Anna Maria Beach Place 6 Directly Across The Street From The Beach With Pool - Anna Maria Island, FL
9.7Excellent 281 reviews
Anna Maria Island, FL
4 1
£319/nighttotal: £2233 (7 )

Anna Maria Beach Place 6 Directly Across The Street From The Beach With Pool

apartment - Holmes Beach
This apartment is located in Holmes Beach, a short 10-minute walk from Bradenton Beach and Manatee Public Beach, offering easy access to the area's beautiful beaches and attractions. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment provides a comfortable and convenient stay with a fully equipped kitchen and a private balcony. Enjoy a range of amenities including a swimming pool, spa, fitness centre, and restaurant, as well as the added benefit of a pet-friendly environment.
Great Cottage With Private Pool, So Close To Beach! - Anna Maria Island, FL
9.5Excellent 252 reviews
Anna Maria Island, FL
2 2
£294/nighttotal: £2058 (7 )

Great Cottage With Private Pool, So Close To Beach!

apartment - Holmes Beach
This apartment is located in Holmes Beach, just a short stroll from paddleboarding and surfing opportunities, with two popular beaches within a 5-minute walk. It has excellent user, location, and cleanliness ratings, making it a great choice for travellers looking for a comfortable and convenient stay.
The apartment has two bedrooms, a sofa bed, and a patio, accommodating up to 6 guests. You can enjoy a private pool, barbecue grills, a garden, and a fully equipped kitchen, as well as access to a nearby water park.
Inn At The Beach Units, MI CASA ES TU CASA - Anna Maria Island, FL
9.2Excellent 820 reviews
Anna Maria Island, FL
5 2
£759/nightfor 1 night

Inn At The Beach Units, MI CASA ES TU CASA

house - Bradenton Beach
This one-bedroom house is located in Bradenton Beach, just a short walk from popular attractions like Fun and Sun Parasail and Bradenton Beach Parasailing. The property has excellent user, location, and cleanliness ratings.
The house offers 48 square metres of space and can accommodate up to four guests. Amenities include a private terrace with city views, a well-equipped kitchen, free Wi-Fi, and a private bathroom.
Dolphin Dance Both Side Across From Beach With Panoramic Beach Views - Anna Maria Island, FL
8.0Very good 101 reviews
Anna Maria Island, FL
10 4
£384/nighttotal: £3072 (8 )

Dolphin Dance Both Side Across From Beach With Panoramic Beach Views

apartment - Bradenton Beach
This charming holiday home is situated just a short stroll from the beautiful sands of Bradenton Beach, providing easy access to both Bradenton Beach and Coquina Beach. The property consistently receives positive feedback, with guests praising its excellent location and very good overall experience.
This spacious property offers 163 square metres of comfortable living space. Guests will enjoy a range of amenities, including a fully equipped kitchen, a private balcony, a swimming pool, a fitness centre, and a barbecue area.
Charming Beach House Sits Amongst Huge Banyan Trees, Walk To Beach & Pine Ave. - Anna Maria Island, FL
9.6Excellent 206 reviews
Anna Maria Island, FL
4 2
£363/nighttotal: £726 (2 )

Charming Beach House Sits Amongst Huge Banyan Trees, Walk To Beach & Pine Ave.

house - Anna Maria
This charming two-bedroom apartment is situated on the northern tip of Anna Maria Island, a short stroll from historic Pine Avenue with its shops and restaurants. It boasts excellent ratings for location, cleanliness, and overall user experience.
The apartment offers 218 square metres of living space, including a private suite downstairs. Guests can enjoy a spacious tropical garden, a charming porch, and a fully equipped kitchen with a fridge, microwave, and dishwasher.
Sea Pirate 7  2/1 Condo Pool Just Steps To Beach - Anna Maria Island, FL
9.1Excellent 63 reviews
Anna Maria Island, FL
2 2
£240/nighttotal: £1680 (7 )

Sea Pirate 7 2/1 Condo Pool Just Steps To Beach

apartment - Holmes Beach
This apartment is conveniently located in Holmes Beach, just a short walk from Bradenton Beach and within a 15-minute reach of Manatee Public Beach and Anna Maria Sound. With excellent user, location, and cleanliness ratings, this property offers a comfortable and enjoyable stay. The apartment is spacious, with a floor area of 68 square meters and features two bedrooms and one bathroom. Amenities include a well-equipped kitchen, a private patio, a swimming pool, a spa, a fitness centre, and access to a water park, ensuring a relaxing and enjoyable stay.
Tradewinds 2 Bedroom Bay Front - Anna Maria Island, FL
8.3Very good 4 reviews
Anna Maria Island, FL
2 1
£323/nighttotal: £1292 (4 )

Tradewinds 2 Bedroom Bay Front

apartment - Bradenton Beach
This apartment is located in Bradenton Beach, just a short walk from the beautiful white sand beaches and a few blocks from the lively Bridge Street with its shops and restaurants. The property has excellent location and cleanliness ratings and a very good user rating.
The apartment sleeps up to six guests comfortably and has two full bathrooms with walk-in showers. Guests can enjoy a private deck with bay views, a fully equipped kitchen, a washer and dryer, central air conditioning, Wi-Fi, and cable TV.
Canalfront Anna Maria Cottage with Pool & Hot Tub! - Anna Maria Island, FL
9.8Excellent 194 reviews
Anna Maria Island, FL
4 2
£425/nighttotal: £850 (2 )

Canalfront Anna Maria Cottage with Pool & Hot Tub!

house - Anna Maria
This canalfront cottage is located in Anna Maria, Florida, a short walk from Anna Maria Island and a 9-minute walk from the Anna Maria City Pier, offering easy access to the area's attractions and amenities. The property has received excellent ratings for user experience, location, and cleanliness.
This two-bedroom house, with a floor area of 119 square metres, can comfortably accommodate up to six guests. The cottage features a private pool and hot tub, a balcony, a fully equipped kitchen, air conditioning, free Wi-Fi, and a garden.
Beautiful Pool Home With Private Deck 250 Steps Beach! - Anna Maria Island, FL
9.9Excellent 280 reviews
Anna Maria Island, FL
2 1
£216/nighttotal: £1512 (7 )

Beautiful Pool Home With Private Deck 250 Steps Beach!

house - Holmes Beach
This holiday home is situated in Bradenton Beach, just a short walk from the beach and within a mile of Holmes Beach Beaches and Manatee Public Beach. The property has received excellent ratings for its location, cleanliness, and overall experience.
The accommodation has a spacious layout and can comfortably sleep up to 6 guests. Enjoy a range of amenities including a private pool, a spa, a garden, and access to a water park, perfect for a relaxing and fun-filled holiday.

Other types of accommodation in Anna Maria Island, FL

Best Anna Maria Island, FL holiday rentals with a pool

Among the 5676 accommodations in Anna Maria Island, FL, here are the 8 best rentals with a pool

Sweet Retreat Cottage: Ground Level Cottage Across The Street From The Beach - Anna Maria Island, FL
9.2Excellent 31 reviews
Anna Maria Island, FL
2 3
£1150/nighttotal: £2300 (2 )

Sweet Retreat Cottage: Ground Level Cottage Across The Street From The Beach

cottage - Anna Maria
This charming three-bedroom house is located in Bradenton Beach, just a short walk from both Bradenton Beach and Bean Point Beach, making it the perfect base for exploring the beautiful surroundings. The property has received excellent ratings for location, cleanliness, and overall user experience, ensuring a comfortable and enjoyable stay.
The 129 square metre house comfortably sleeps eight guests and boasts a fully equipped kitchen, a private pool, a garden, and a tennis court. Enjoy al fresco dining on the terrace, relax by the pool, or take a dip in the nearby water park, all within the comfort of this well-equipped holiday home.
A Wright Place 2/2 Private Pool Duplex Short Block To Beautiful Beaches - Anna Maria Island, FL
9.6Excellent 98 reviews
Anna Maria Island, FL
6 2
£245/nighttotal: £1960 (8 )

A Wright Place 2/2 Private Pool Duplex Short Block To Beautiful Beaches

apartment - Holmes Beach
This two-bedroom holiday home is situated in a peaceful neighbourhood close to Bradenton Beach, just a 15-minute walk from the sand and surf. Guests consistently rate this property as excellent, highlighting its convenient location and comfortable amenities.
The property spans 223 square metres and includes a fully equipped kitchen, a private pool, and a relaxing patio. Enjoy a range of amenities including air conditioning, free Wi-Fi, and parking, as well as a fitness centre and a garden.
Silver Surf Gulf Beach Resort - Anna Maria Island, FL
9.2Excellent 1702 reviews
Anna Maria Island, FL
4 2
£421/nighttotal: £842 (2 )

Silver Surf Gulf Beach Resort

hotel - Bradenton Beach
The Silver Surf Gulf Beach Resort is located on Bradenton Beach, just under 15 miles from Sarasota-Bradenton International Airport, making it a convenient option for travellers. The 2-star hotel has consistently received excellent user ratings, suggesting a positive experience for guests.
The resort offers a range of amenities and activities for a relaxing beach getaway, including a swimming pool, a spa, and a restaurant. Guests can enjoy direct beach access, water sports, a daily continental breakfast, and comfortable rooms.
Great Home Close To The Beach With Private Pool! 5 Bedrooms, Close To Pine Ave! - Anna Maria Island, FL
9.3Excellent 130 reviews
Anna Maria Island, FL
10 5
£582/nighttotal: £4656 (8 )

Great Home Close To The Beach With Private Pool! 5 Bedrooms, Close To Pine Ave!

house - Anna Maria
This five-bedroom house is located on Anna Maria Island, just a short walk from Island Players and Anna Maria Beach, and within a five-minute drive of the Anna Maria Island Museum and Historical Park and Bradenton Beach. The property has received excellent ratings for location, cleanliness, and user experience.
The house comfortably sleeps 11 guests and features a fully equipped kitchen, a private pool, and a peaceful garden. Guests can enjoy al fresco dining on the patio, access to a water park, and a fitness centre.
Spacious Beach House, Friends And Family Will Love! Pool And Spa, Rooftop Deck! - Anna Maria Island, FL
9.6Excellent 159 reviews
Anna Maria Island, FL
10 6
£706/nighttotal: £5648 (8 )

Spacious Beach House, Friends And Family Will Love! Pool And Spa, Rooftop Deck!

house - Bradenton Beach
This Bradenton Beach property is located just a short walk from Cortez Beach and the Bradenton Beach Marina, offering easy access to the area's top attractions. The property has received excellent ratings for its cleanliness, location, and user experience.
The six-bedroom house offers 350 square metres of living space. This spacious holiday home features a private pool, a rooftop terrace with a spa tub, a fully equipped kitchen, multiple bathrooms, a garden, and barbecue facilities.
Bridgeview Retreat - Anna Maria Island, FL
9.0Excellent 130 reviews
Anna Maria Island, FL
7 4
£670/nighttotal: £2680 (4 )

Bridgeview Retreat

house - Bradenton Beach
Bridgeview Retreat is situated just a short walk from Cortez Beach in Bradenton Beach, offering a peaceful escape with easy access to the vibrant beach and local amenities. This property has received excellent ratings for its location, cleanliness, and overall user experience, ensuring a comfortable and enjoyable stay.
The four-bedroom, three-bathroom property spans 249 square metres, providing ample space for families or groups of friends. Guests can enjoy a private pool, a terrace with sea views, a fully equipped kitchen, and air conditioning throughout the house, along with a garden and parking.
Bridgewalk A Landmark Resort - Anna Maria Island, FL
9.2Excellent 760 reviews
Anna Maria Island, FL
5 2
£359/nightfor 1 night

Bridgewalk A Landmark Resort

resort - Bradenton Beach
Bridgewalk A Landmark Resort is situated directly on Bradenton Beach, just steps from Fish Hole Adventure Golf and close to Bradenton Beach Marina and Cortez Beach. It has received excellent ratings for its location, cleanliness and overall experience.
The resort offers spacious apartments with kitchenettes, washers and dryers, and private lanais. Guests can enjoy a swimming pool, bar, coffee shop, spa, and a business centre, as well as free parking and Wi-Fi.
Anna Maria Island Bay Watch Bungalow - Anna Maria Island, FL
9.5Excellent 1238 reviews
Anna Maria Island, FL
2 2
£313/nighttotal: £2191 (7 )

Anna Maria Island Bay Watch Bungalow

apartment - Bradenton Beach
This beachfront flat is conveniently located in Bradenton Beach, close to Bradenton Beach, Cortez Beach, and Coquina Beach. It has received excellent ratings for location, cleanliness, and user experience.
The accommodation features two bedrooms, a fully equipped kitchen, and a TV with satellite channels. Guests can enjoy a private heated pool, a garden, a playground, free parking, and Wi-Fi.

Best family friendly Anna Maria Island, FL holiday rentals

Among the 5676 accommodations in Anna Maria Island, FL, here are the 8 best family friendly rentals

Elegant Beachfront Condo W/pool!  Walking Distance To Many Restaurants And Shops - Anna Maria Island, FL
9.8Excellent 322 reviews
Anna Maria Island, FL
6 3
£582/nighttotal: £2910 (5 )

Elegant Beachfront Condo W/pool! Walking Distance To Many Restaurants And Shops

apartment - Bradenton Beach
This Bradenton Beach apartment is conveniently located just a 5-minute walk from both Bradenton Beach and Cortez Beach, with popular attractions like Historic Bridge Street Pier and Fish Hole Adventure Golf also within easy reach. The apartment has received excellent ratings for location, cleanliness and overall user experience.
The apartment has 3 bedrooms and 2 bathrooms, comfortably accommodating up to 8 guests. It comes equipped with a fully fitted kitchen, air conditioning, a swimming pool, a jacuzzi, a terrace, a garden, a spa, a fitness centre, parking, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
The Anchor - Anna Maria Island, FL
9.3Excellent 107 reviews
Anna Maria Island, FL
2 2
£597/nighttotal: £1194 (2 )

The Anchor

apartment - Bradenton Beach
The Anchor is a two-bedroom apartment located just a short walk from Cortez Beach and a mile from Coquina Beach, offering easy access to the best of Bradenton Beach. This property has received excellent ratings for location, cleanliness, and overall experience.
The apartment features a fully equipped kitchen, a comfortable living area with a flat-screen TV, and private parking. Guests can enjoy amenities such as air conditioning, free Wi-Fi, a Jacuzzi, a garden, and a spa.
Beachfront! The Diamond Star-summer Dates Released - Anna Maria Island, FL
10Excellent 17 reviews
Anna Maria Island, FL
2 3
£989/nighttotal: £3956 (4 )

Beachfront! The Diamond Star-summer Dates Released

apartment - Anna Maria
This beachfront property is situated on Anna Maria Island, a short walk from Anna Maria City Pier and a 15-minute drive from the John and Mable Ringling Museum of Art, offering a peaceful and tranquil setting. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This three-bedroom house, spanning 300 square metres, comfortably accommodates up to six guests. The property features a private garden, a balcony, a swimming pool, and free parking, ensuring a comfortable and enjoyable stay.
Runaway Bay 275 - 1845189 - Anna Maria Island, FL
9.2Excellent 362 reviews
Anna Maria Island, FL
2 1
£162/nighttotal: £1134 (7 )

Runaway Bay 275 - 1845189

apartment - Bradenton Beach
Runaway Bay 185 - 1357300 is situated in Bradenton Beach, just a two-minute walk from the beach and less than a mile from Cortez Beach, making it ideal for those seeking a relaxing beach getaway. The property has been highly rated by guests, receiving excellent reviews for its location, cleanliness, and overall experience.
The apartment is spacious, with a floor area of 100 square metres, and offers a range of amenities to ensure a comfortable stay, including a fully equipped kitchen, a terrace, a swimming pool, a fitness centre, and a tennis court. Guests can also enjoy the on-site restaurant, garden, and sauna.
The Anna Maria Island Beach Paradise 6 - Anna Maria Island, FL
9.6Excellent 167 reviews
Anna Maria Island, FL
2 2
£269/nighttotal: £1883 (7 )

The Anna Maria Island Beach Paradise 6

apartment - Holmes Beach
The Anna Maria Island Beach Paradise 6 is a short walk from the beach in Holmes Beach, a peaceful area close to the Anna Maria City Pier. This apartment has excellent user, location, and cleanliness ratings.
The apartment has a kitchen with a fridge, freezer, microwave, and dishwasher. Guests can enjoy the pool, terrace, garden, spa, restaurant, bar, fitness centre, tennis court, and parking facilities.
Luxury Waterfront Home With A Heated Pool And Spa! - Anna Maria Island, FL
9.9Excellent 57 reviews
Anna Maria Island, FL
10 1
£655/nighttotal: £5240 (8 )

Luxury Waterfront Home With A Heated Pool And Spa!

apartment - Anna Maria
This waterfront property is situated in Anna Maria, within a mile of the Anna Maria Island Museum and Historical Park, Bean Point Beach, and Anna Maria Beach. It has received excellent ratings for its location, cleanliness, and overall user experience.
The house has four bedrooms and can accommodate up to ten guests, providing ample space for a large family or group. It comes equipped with a private pool, a Jacuzzi, a spa, a terrace, a garden, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.
Seaclusion At Island Getaway - Anna Maria Island, FL
9.7Excellent 138 reviews
Anna Maria Island, FL
4 2
£392/nighttotal: £784 (2 )

Seaclusion At Island Getaway

apartment - Bradenton Beach
This two-bedroom apartment is located just steps from Cortez Beach and a short walk from the lively downtown area of Bradenton Beach, offering easy access to the island's attractions. It consistently receives excellent ratings for its location, cleanliness, and overall guest experience.
The apartment is comfortably sized at 46 square metres and can comfortably accommodate up to six guests. Guests can enjoy a range of amenities, including a private courtyard, shared outdoor spaces, and access to beach equipment, making it a perfect choice for families or groups looking for a relaxing beach getaway.
Spectacular Beach & Dolphin Views!  Huge Private Balcony! 2br/2ba Upstairs Villa - Anna Maria Island, FL
9.8Excellent 1089 reviews
Anna Maria Island, FL
4 1
£313/nighttotal: £626 (2 )

Spectacular Beach & Dolphin Views! Huge Private Balcony! 2br/2ba Upstairs Villa

apartment - Bradenton Beach
This apartment is situated directly on the beach in Bradenton Beach, just a short walk from the marina and the heart of the town. The property has received excellent ratings for its location, cleanliness, and overall experience.
The spacious two-bedroom apartment is perfect for families or groups of friends. Guests can enjoy a fully equipped kitchen, a private balcony, and access to a range of on-site amenities including a tennis court, spa, and jacuzzi.

Frequently asked questions for the holiday rentals in Anna Maria Island, FL

Popular regions

Best pet friendly Anna Maria Island, FL holiday rentals

Among the 5676 accommodations in Anna Maria Island, FL, here are the 3 best pet friendly rentals

Ohana Hale North 2 Bedroom - Anna Maria Island, FL
9.4Excellent 188 reviews
Anna Maria Island, FL
4 2
£285/nighttotal: £570 (2 )

Ohana Hale North 2 Bedroom

apartment - Holmes Beach
This two-bedroom apartment is situated just a 7-minute stroll from the beautiful white sand beaches of Anna Maria Island, offering a tranquil escape in a popular holiday destination. The property consistently receives excellent ratings for its cleanliness, location, and overall user experience.
The apartment offers a comfortable living space for up to six guests and features a well-equipped kitchen, a spacious living area with access to a private garden, and a private backyard with a gas grill. Amenities include beach chairs, an umbrella, towels, and high-speed Wi-Fi, ensuring a relaxing and enjoyable stay.
A+ Location! Steps To Beach, Walk To Bridge St! #1 - Anna Maria Island, FL
9.7Excellent 202 reviews
Anna Maria Island, FL
4 2
£231/nighttotal: £462 (2 )

A+ Location! Steps To Beach, Walk To Bridge St! #1

apartment - Bradenton Beach
This charming two-bedroom apartment is located on Anna Maria Island, just a short walk from the Cortez Bridge and Bridge Street, offering easy access to restaurants, shops, and the pier. The property boasts excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The apartment comfortably accommodates up to four guests and features a fully equipped kitchen, a garden, and parking. Enjoy the convenience of an outdoor shower, beach chairs, towels, and an umbrella, all provided by the owner, making your beach days even more relaxing.
Beach Front 2 Bedroom B - Anna Maria Island, FL
9.6Excellent 1420 reviews
Anna Maria Island, FL
2 2
£1043/nighttotal: £2086 (2 )

Beach Front 2 Bedroom B

house - Holmes Beach
This beachfront property is located just a short walk from Anna Maria Island, with the town centre a convenient 1.7 miles away. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The home features a fully equipped kitchen, comfortable bedrooms, and a balcony offering stunning sea views. Guests can enjoy a range of amenities including a private swimming pool, a Jacuzzi, a fitness centre, and a garden, all within a short distance of the beach.