Top 10 Monthly Rentals In Anna Maria Island, Florida - Updated 2024

Stephen
Stephen 
Updated
| 5 min read

Discover a hidden gem in the state of Florida–Anna Maria Island. Some of the world’s best beaches and beach parks are found on this island. Whether you’re visiting for a honeymoon or a family vacation, the island surely has a lot to offer. Admire the breathtaking scenery at Coquina Beach while enjoying a family picnic. Take your spouse to Bean Point Beach to go for a romantic stroll and watch a spectacular sunset. Bayfront Park features a playground, picnic facilities, and sweeping views of the ocean. If you’re on the island for a month, you will need a comfortable holiday home. Check below for the top monthly rentals in Anna Maria Island, Florida.

We handpicked these listings carefully, considering (wherever possible) Superhost status. recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on February 08, 2024.

1. Cute abode with one bedroom in Bradenton Beach (from USD 118)

You will enjoy a peaceful stay at this one-bedroom condo that’s like a boutique hotel room. Its location means you can spend your afternoons dipping your feet on the white sand of the beach. Indulge in some refreshments by the pool as you admire the crystal blue waters. The rental is bright, and it features a beautiful, flower-themed décor on the walls and furniture.

If your plan is to stay for a month, the host will be delighted to offer you a discount on your accommodation. You will also be given access to high-speed Wi-Fi.

Stayed at this property?
Bradenton Beach, Florida, United States
79 reviews   Superhost Wifi Available
ENTIRE CONDO 1 Bed 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

2. Spacious condo with a fully appointed kitchen in Holmes Beach (from USD 289)

Sitting at a lush compound, just a short stroll from the beach, this spacious haven offers fantastic views of palm trees dancing beautifully to the blowing sea breeze. The availability of a large heated swimming pool and beach accessories makes it even more appealing to water activities enthusiasts.

To make guests feel at home, the condo is fitted with Wi-Fi, Smart TVs, coffee-making facilities, and a fully appointed kitchen. You will have ample space to park your car. If you spend at least 30 days, you’ll enjoy a monthly discount.

Stayed at this property?
Holmes Beach, Florida, United States
84 reviews   Superhost Wifi Available
ENTIRE CONDO 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

3. Colorful beachfront home in a tree-lined compound in Bradenton Beach (from USD 245)

Set in a tree-lined compound, this colorful beachfront home is ideal for five travelers. It sits a stone’s throw away from a pristine beach and is within walking distance of a world-class spa. The neighborhood is quiet and peaceful, offering a good atmosphere to stay with your four-legged friend.

There’s air conditioning and free Wi-Fi throughout the house. A well-equipped kitchen is provided too. In the afternoons, you can relax in the backyard and enjoy the lovely coastal breeze. One-month vacationers will enjoy a discount on their accommodation fee.

Stayed at this property?
Bradenton Beach, Florida, United States
45 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 5 Guests 2 Bedrooms 1 Bathrooms

Accommodates: 5

4. Beautiful haven with gulf views in Holmes Beach (from USD 450)

You can marvel at the breathtaking views of the turquoise waters of the gulf from the front yard of this beautiful two-bedroom haven. If you’re planning a beach retreat with your friends, the monthly rental is the perfect option. In addition to accessing world-class facilities, you will enjoy a reasonable discount on your accommodation fee if you book for one month.

The house boasts a stylish swimming pool with a hot tub for unwinding. You can use the free Wi-Fi while enjoying drinks by the pool. The beach is only steps away.

Stayed at this property?
Holmes Beach, Florida, United States
93 reviews   Wifi Available
ENTIRE HOME 4 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

5. Tranquil cottage with an outdoor pool in Holmes Beach (from USD 259)

Featuring a large outdoor pool and a tropical-inspired compound with lush palm trees, this one-bedroom paradise is a good place to enjoy a family getaway. It is close to a beach, spots for family-friendly activities, and a number of fantastic nightclubs. You can pay a surcharge if you wish to stay with your dog. If you plan to stick around for a month, you will enjoy a discount on your accommodation fee.

You can unwind on the balcony and admire spectacular pool views. Other features of the home include a cable TV, complimentary Wi-Fi, and free parking.

Stayed at this property?
Holmes Beach, Florida, United States
181 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 3 Beds 6 Guests 1 Bedroom 1 Bathroom

Accommodates: 6

6. Elegant residence near shops in Bradenton Beach (from USD 220)

Set on the shore of the Gulf of Mexico, this unit is a great place for visitors who wish to spend their vacation indulging in water sports and outdoor activities. It is only a few minutes from the local restaurants and shops. You can spend your leisure time kayaking, fishing, scuba diving, and enjoying nature hikes.

The interiors of the residence are eye-catching. The home features an ocean-themed décor and elegant furnishings. Take advantage of the monthly discount to enjoy a longer vacation filled with fun and adventures.

Stayed at this property?
Bradenton Beach, Florida, United States
251 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 2 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

7. Pet-friendly retreat with a patio in Holmes Beach (from USD 215)

You will enjoy a romantic getaway at this one-bedroom home with a stylish design and a lovely outdoor pool. The rental has a fenced compound, which means that your four-legged friend can also enjoy a safe stay. It features a chic design and provides air conditioning and two flat-screen TVs. There’s also a full chef’s kitchen for preparing your favorite delicacies.

You can take advantage of the patio to enjoy some fresh breeze as you dine and wine. By the end of the month, you will receive a discount on the rental fee. Security cameras are available too.

Stayed at this property?
Holmes Beach, Florida, United States
154 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

8. Cozy apartment with two bedrooms in Holmes Beach (from USD 148)

You will admire the wonderful décor of this cozy two-bedroom apartment that is a stone’s throw away from the beach. You will be able to walk to the local shops and restaurants and will enjoy a discount on any monthly reservations you make. With a queen-sized bed and two single beds, the home offers ample space to host up to four guests.

You can watch movies on the HDTV with premium channels or surf the internet, using the free Wi-Fi. You can also meditate in the bathtub or unwind by the pool.

Stayed at this property?
Holmes Beach, Florida, United States
107 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 3 Beds 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4

9. Gorgeous hideout with a backyard in Bradenton Beach (from USD 145)

Once you step inside this gorgeous hideout, you will marvel at the lovely design and beach-themed décor reflected on the walls. The home features an open floor plan with a dining table for four people and a cozy living area with comfortable sofas and a TV. There’s a sleek kitchen equipped with top-notch appliances and granite countertops.

Outside, there’s a spectacular pool to dive into when the afternoons are hot. You can relax in the backyard, enjoying a barbecue. The rental is owned by an accommodating host who offers guests a discount when they book one-month stays.

Stayed at this property?
Bradenton Beach, Florida, United States
125 reviews   Wifi Available
ENTIRE CONDO 3 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

10. An island getaway

Anna Maria Island is a great destination where you can have an unforgettable getaway. What will make your trip even more amazing is staying at a monthly vacation rental.

Stayed at this property?

Spectacular beach house with security cameras in Bradenton Beach

Oozing with a peaceful, tropical vibe, this place is one of the top rentals on the island. You will get to enjoy a reasonable weekly rental discount if you book it. The beach is just a short walk from the house. To ensure the property is secure, the owner has installed state-of-the-art security cameras.

The home has air conditioning, a bathtub, and a TV with your favorite programs. Take advantage of the well-equipped kitchen to fix something to eat. There’s a balcony where you can relax and read a book.

Stayed at this property?
Bradenton Beach, Florida, United States
74 reviews   Superhost Wifi Available
Entire townhouse 3 Beds 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Stephen is an avid content writer with a passion for adventure. He enjoys traveling and has visited several countries around the world. So far, South Africa stands out as his most exciting...Read more

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