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Ana Maria Island Vacation Rentals

Where Is Bean Point

Blue Oasis | Vacation Rentals | Anna Maria Island

Bean point is located in Anna Maria City where the Tampa Bay and the Gulf of Mexico meet. The main beach entrance is found at the crossroads of North Bay Blvd and North Shore drive. Parking for sure can be a challenge so if you can bicycle ride up to the beach access that would be best. The City has several spots where you can lock up your bicycle if you are looking to spend a good portion of the day on the beach. The beach access is beautiful as it takes you over a wooden footbridge and the path is through some wonderful Florida native vegetation. Be careful if you drive up to Bean Point as parking can be challenging and there are a great deal of guidelines when parking in Anna Maria City to avoid receiving a parking ticket.

Write The Next Chapter Of Your Vacation Story With Once Upon A Beach

As frequent visitors to Anna Maria Island, Florida, we quickly fell in love with the small town feel of this beach island paradise. We relocated here for the purpose of being able to enjoy this gem full time and make a business of our passion to share the island with others. It is our utmost goal to make every one of our guests instantly feel at home as a true local in one of our unique, pristine, meticulously designed and luxurious accommodations. From two bedroom beach bungalows to a premier waterfront homes to sprawling multi-story single family homes. We take great pride in ensuring our homes are maintained with the highest standards in quality and care. We know planning a vacation can be stressful so we are dedicated to providing a personalized and stress free rental experience from booking to departure for all of our guests. As a boutique short term vacation rental & property management company, our guests experiences are everything and we look forward to helping you write the next chapter of your vacation story with us and welcome you back for years and years to come.

What Are The Top Vacation Rentals In Anna Maria Island

Whether you’re organizing your next exciting adventure with friends or a romantic escape with your darling, one of these top vacation rentals in Anna Maria Island is sure to tempt you:

  • “Best Little Beach House On Anna Maria Island. . . With A Pool”: If you’re after somewhere in Ilexhurst with 1 bedroom and plenty of home comforts, consider this escape. Amenities include a heated pool and heating.
  • “New Completely Renovated Beach Front With Heated Pool Gulf View #102”: Located in Bradenton Beach, this home away from home has 2 bedrooms and lots of handy amenities. A blender and a microwave oven are among them.

For even more great options, use the search bar at the top of the page to find the perfect Anna Maria Island vacation rental for you.

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Vacation Rentals On Anna Maria Island

We are the Flip-Flop Company. The Anna Maria Island Accommodations team exudes the laid-back Island vibe. With many years of Anna Maria Island vacation rental property management under our belts, we are resident experts and are always ready to share our vast wisdom of all things AMI. We invite you to relax and enjoy an extraordinary vacation experience. So lose the shoes and live life like a local in one of our many amazingly appointed Island vacation homes.

Awesome Attractions On Anna Maria Island

Anna Maria Island Vacation Rental Management

1. Anna Maria Island Historical Museum

Learn about the island’s history in this lovingly cared-for museum. Among photographs and artefacts, you can also send the kids on a scavenger hunt.

2. Anna Maria City Pier

Enjoy delicious seafood and views over the ocean in the enclosed deck or out in the open air right next to Bayfront Park. Dolphins can commonly be spotted here, too.

3. Manatee Public Beach

Relax on beautiful white sands and go swimming or boating here. There are a range of handy facilities including changing cabins and local eateries.

4. Bradenton Beach

This is a tranquil spot where you can spend the day sunbathing by the water or exploring the local boutiques near the seafront.

5. Bean Point

The beach area at the very tip of the island is a must-see, with wonderful views and the best of the laid-back Floridian atmosphere. Its a popular spot to collect beautiful seashells.

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What Are The Best Houses For Rent With A Pool In Anna Maria Island

In Anna Maria Island, you’ll find plenty of house rentals where a pool day can be every day. Having a splashing good time will be your highest priority at one of these superb escapes:

  • Mum, dad, kids, grandparents everyone will love relaxing by the pool at “Best Little Beach House On Anna Maria Island. . . With A Pool”. Take the whole family on a vacation at this Ilexhurst rental home which also comes with a separate dining area and a barbecue grill.
  • “Spectacular Beachfront House With Pool” in Southeastern United States is another popular pick. There’s plenty to love about this place apart from its pool, such as a DVD player and a swimming pool.

What Are The Best Large Group Vacation Rentals In Anna Maria Island

If your idea of the perfect trip away is to bring along your nearest and dearest, you’ll be needing a whole lot of space. Luckily, there are plenty of vacation rentals in Anna Maria Island that will house large groups, starting with these sprawling sensations:

  • “Blue Water Beach House: 5+ Bedroom”: This popular retreat is a great choice for larger groups wanting to stay in Bradenton Beach. It has 6 bedrooms and conveniences that include a swimming pool and an ocean view.
  • “Family Fun Close To Beach, Pool Slide Spa And Elevator”: Located in Bradenton Beach, this spacious option has 4 bedrooms and is another top pick for a fun family vacation. There’s a whole lot to keep guests both entertained and comfortable, such as a swimming pool and a water park.

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City Of Anna Maria Vacation Accommodation Rentals

Located in the North of Anna Maria Island off the Gulf Coast of Florida, Anna Maria City is a small, friendly and charming Old Florida town, with a wonderful all year climate and beautiful sunsets perfect for your vacation escape!

With a population in the region of 2,000 residents a blend of permanent and seasonal, Anna Maria City is one of three island communities on Anna Maria Island, neighbored with the small island cities of Bradenton Beach and Holmes Beach.

In Anna Maria City you will find your perfect vacation rental accommodation. Here at Anna Maria Vacations we specialise in luxury rentals throughout Anna Maria City and across the Island. Whether you are seeking a small intimate villa for your romantic getaway, a beautiful beach front condo rental, bay front rentals with docks, or a large villa with pool and elevator we have 1-8 bed vacation accommodation to suit, with plentiful beach front rentals.

The city of Anna Maria itself provides everything you will need for your vacation stay, our small, quaint town offering restaurants, bars and retail outlets with some local history culture, parks and wildlife thrown in!

Because of its position in the North of the island, Anna Maria City is blessed with wonderful views and sunsets over the Gulf, which serves as inspiration for budding artists. Several boutique art galleries can be found in the city. Bottle nose dolphins and manatees are also common sightings!

Anna Maria Island Monthly Rentals

Key Largo Cottage | Vacation Rentals | Anna Maria Island

Anna Maria Island monthly rentals are the perfect choice for those looking to enjoy the beautiful beaches and comfortable weather. Whether you are looking for winter snowbird stays or spending a summer month on the beach, we have properties for you! With our monthly vacation rentals ranging from stunning canal front homes and charming beach bungalows to bayfront condos, youll find the perfect property to accommodate your party. These vacation properties require stays of 1-month minimum and come fully furnished with all utilities included.

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Ami Locals Does Anna Maria Island Property Management And Anna Maria Island Vacation Rentals A Little Differently

Some members of our team were born and raised here, others migrated here, but all of us are now Locals. This area is incredibly special, so we want to make sure your experience on Anna Maria Island, Bradenton Beach, and Holmes Beach is better than anyone else could offer.

Guest Reviews

Thanks Airbnb for cancelling our reservation. Otherwise we would have missed out on enjoying this great property. Although its a duplex and close to the house next door, its very private. The pool in the front was wonderful and having the outdoor space in the back on the channel was a bonus for those of us who enjoy fishing. The beach, Pine Ave. shops and restaurants, and both piers were within walking distance. We had an issue with the upstairs air conditioner which was addressed as soon as we reported it. Would definitely vacation here again and found the staff to be wonderful! Thanks from all of us!~ Kathy S.

Christmas on Bridge Street and Outdoor Movie

Bridge Street Bradenton Beach, FL

12/17/2022 – 12/17/2022

Prepare To Fall In Love With Providenciales

With its sugar-white sand, crystal azure waters and lazily-swaying palms, Providenciales is straight from the pages of a glossy vacation brochure. So it’s no surprise that in the island epicenter of the Turks and Caicos archipelago, life is all about sun, sea, rest and recreation. Here, you can dive into fast-paced watersports, glide alongside sea turtles through enchanting coral reefs, explore the island’s colonial past or stretch out on spacious beaches with a fruity cocktail in hand. Whatever pace you choose, a lavish Providenciales vacation rental will help you enjoy your days in style.

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Fun In The Sun In Anna Maria Island

Vacation homes in Anna Maria Island are close to unique venues and landmarks for any interest, whether you enjoy history, art, or the natural environment. The Robinson Preserve is perfect for animal lovers and outdoor enthusiasts, thanks to its boating, hiking, biking, and native wildlife, while the Island Gallery West features masterpieces of painting and sculpture for art lovers. The DeSoto National Memorial is of interest to history buffs, due to its living-history camp dedicated to the famous explorer, and the Perico Preserve is a serene location for strolling through marshlands.

All Our Anna Maria Island Vacation Rentals

Anna Maria Island Luxury Vacation Rentals

If you are looking for a wide variety of choices in Anna Maria Island Rentals then our list of all Anna Maria Island Vacation Rentals is the perfect place to search. Our vacation rentals range from Multifamily, Condominiums, Private homes, pools, and pools with spas. We list our property amenities in easy to understand web architecture. Looking for a specific location, no problem. We provide all our Anna Maria Island, Holmes Beach, Bradenton Beach and Anna Maria City rentals on an Anna Maria Island map that shows your location. Bayfront, Gulf Front, Intercoastal, near shopping or restaurants, we have tons of choices for your perfect Anna Maria Island Vacation. Be sure to visit our things to do page where you can review shopping, restaurants and other activities all while checking the location as compared to vacation rentals on our program. Look no further, you have found a huge variety of Anna Maria Island vacation rentals that will satisfy the most discerning Anna Maria travelers.

90 properties listed.

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Central Ontario Golf Vacation Rentals

Sorry, there is no rental accommodation currently available in Central Ontario for your search criteria. Please change your search preferences or try a nearby region to increase the number of properties displayed.

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Get Back To Nature In Providenciales

With its turquoise lagoons, lush vegetation and kilometers of pristine beaches, Providenciales, like many islands in the archipelago, is a haven for tropical wildlife. Alongside Smith’s Reef and Bight Reef, Chalk Sound National Park is a great place to spot some of the island’s marine creatures. The park’s centerpiece is a 5-kilometer protected lagoon, known for its luminous turquoise color, and inhabitants that include barracudas, bonefish, stingrays and lemon sharks. For birdwatchers, Providenciales offers endless opportunities, especially within its sprawling marine wetlands.

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What Do I Need To Know To Rent A Vacation Home On Anna Maria Island

Anna Maria Island Vacation Rental Information

There are three distinct villages on the island and each have their own vacation rental rules and regulations depending on the zone the property is situated in. There are very few small hotels and motels on the island so a vacation rental is the primary choice for accommodation on Anna Maria Island, Florida.

Typical Stay Periods

Anna Maria Island vacation rentals can be rented as follows depending on the area of the island and the host’s preference.

Typical Turnover Day

Anna Maria Island vacation rentals most often have a Saturday turnover date during high season. Although this turnover date can vary by host.

Anna Maria Island Vacation Rental Price Information

Low range from $81 per night – $535 per week – $3,000 per month

High range from $1,000 per night – $8,500 per week – $20,000 per month

Booking Window

Anna Maria Island is a very popular location. The best vacation rentals book 1 year in advance. On average the booking window for this region is 5 – 6 months in advance. Plan ahead to secure your favorite property!

Guest Retention

Many Anna Maria Island visitors fall in love with this location and return to it every year with their families which also increases the demand to book early.

High Season
Anna Maria Island High Season – February to August
Low Season
Anna Maria Island Low Season – September to January
Anna Maria Island Monthly Stays – Snowbird Rentals
Anna Maria Island Pet Friendly Rentals

Dont Miss Out On Anna Maria Island Vacation Rentals Deals

Hidden Cove 2 | Vacation Rentals | Anna Maria Island

Make sure to browse our Online Specials. Duncan Deals are changing often and you do not want to miss a good deal! If you like to keep up to date with all Duncan Real Estate and Anna Maria Island news, sign up for our newsletter. Be the first one to know what is happening on beautiful Anna Maria Island!

New properties join our program all the time, so be sure to check out our Featured Vacation Rentals for the latest additions. Oftentimes introductory rates with special pricing are offered on the brand new Anna Maria Island vacation rental properties.

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Can I Find Studio Apartments For Rent In Anna Maria Island

Easy to keep tidy and with everything you need close by, studio apartments are an excellent choice if you’re traveling solo or with a friend. If you’re looking for someplace small and comfy to call home while you’re away, have a look at these studio apartments for rent in Anna Maria Island:

  • “Best Little Beach House On Anna Maria Island. . . With A Pool” is a cozy escape in Ilexhurst. You’ll have lots of amenities to take advantage of here, including a kitchen and outdoor furniture. When it’s time to get out and explore some of the area’s cultural sights, Art Center Sarasota and Players Theatre should be among your first stops.
  • Located in Holmes Beach, “Tranquil Anna Maria Island Resort” is another terrific base for your adventure. When you’re not out exploring hot spots like Florida Studio Theatre and Historic Spanish Point, make use of a microwave oven and air conditioning back at your apartment.

What Cities Are Found On Anna Maria Island

Anna Maria

Anna Maria is a city located on the northernmost tip of the island in Manatee County, Florida. The population is a little over 1,800. Known for its picturesque Key West-style main street on Pine Avenue and its historic 100+ year-old fishing pier. Walkable from east to west and north to south it’s the perfect backdrop for island living. It’s the perfect place for couples, snowbirds, and families to relax and enjoy a sleepy small-town atmosphere.

Holmes Beach

Holmes Beach is a city located in the center of the Anna Maria Island. The population is close to 5,100 people. Holmes Beach is known for being the heart of the island, supplying the island with a grocery store, pharmacy, many restaurants, and stores. It’s the perfect place for active couples, teens, and families with an abundance of volleyball nets and beach activities provided at the lively Public Beach.

Bradenton Beach

Bradenton Beach is a city located on the southernmost tip of the Anna Maria Island. The population is a little over 1,500. Known for its beautiful Bridge Street Pier it has a down to earth vibe. Bridge Street has many shops and restaurants to enjoy. Coquina Beach has an incredibly scenic bike path of 1.5 miles to enjoy on the Gulf. It’s the perfect place for couples families and snowbirds. This city has the most condos and townhomes offered on the island.

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What Are The Top Vacation Rentals In Or Near Providenciales

Whether you’re organizing your next exciting adventure with pals or a romantic trip with your sweetheart, one of these top vacation rentals in Providenciales is sure to attract you:

  • “White Osprey: Spectacular Views From Every Room And Pool Overlooking The Ocean”: If you’re after a comfy space in Caicos Islands, this escape won’t disappoint. It comes with 2 bedrooms and quality amenities including wheelchair accessibility and beach towels.
  • “Casa De Isle, Taylor Bay, Chalk Sound Area”: Put your suitcase down and your weary feet up at this pick of the bunch in Chalk Sound Drive. It comes with 3 bedrooms, a nearby casino, towels and more.

For even more great options, use the search bar at the top of the page to find the perfect Providenciales vacation rental for you.

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