Top 10 Holmes Beach Vacation Rentals on Anna Maria Island

Holmes Beach is one of the three communities that make up Anna Maria Island, full of charm and a classic “Old Florida” feel. From historic sights to beautiful and clean beaches, there’s something to consume you every second of your vacation. At the end of a busy day exploring the area and making the most of your getaway, you’ll want a space to relax and unwind. We are proud to have Anna Maria vacation rentals that are ideal for any size party and any special need.

Gulf views from living room in Holmes Beach vacation rental

1. Island Paradise 1

This 2-bed, 2-bath home is perfect for your family of 4. Enjoy amenities like a shared heated pool, a fully equipped kitchen, and multiple TVs with DVD players throughout the home. You’re just steps from the beach and shops, and thanks to our Professional Linen Service Program, you won’t have to lift a finger!

Outdoor and pool view of Holmes Beach vacation rental in Anna Maria Island

2. Under The Tuscan Sun

With 3 bedrooms and 3 bathrooms, this rental puts your party of 6 in the lap of luxury. You have a tropical heated pool and the beach is just a few blocks down. You are centrally located on the island, so it is only a short walk to shopping and dining or the island’s free trolley.

Backyard of Holmes Beach vacation rental

3. Casa del Playa

Parties of 8 will love this 4-bed, 3-bath option. Large kitchen and living areas are great for socializing while providing enough room for everyone to spread out. Each bedroom has its own TV, and the outdoor area is a tropical paradise with a private heated pool, grill, and more!

Front yard view of Holmes Beach Vacation Rental

4. Sand Palace

Sand Palace is a 3-bed, 2.5-bath unit perfect for 6 people. This home is luxurious and welcoming with amenities like an elevator, open living spaces, flat screen TVs, and a private heated pool. You’ll have access to our Professional Linen Service Program and will be just 2 minutes from the beach.

Back yard of Holmes Beach vacation rental

5. Island Retreat

Enjoy privacy and luxury in this 4-bed, 3-bath home. Your party will adore features like the heated pool, Tiki bar, game room, flat screen TVs, full kitchen, and double garage. The view of the Gulf is breathtaking, and it’s a quick stroll to reach the sand.

Front view of gorgeous Holmes Beach vacation home

6. Gulfside Oasis

Larger parties love Gulfside Oasis, a 6-bed, 5-bath house that leaves no detail unnoticed. Relax and unwind with a meal in your gourmet kitchen, a glass of wine on your balcony overlooking the Gulf, or a movie on your 60” flat screen TV! You’ll also find Internet access, a game room, and more.

Holmes Beach vacation rental pool

7. Dolphin House

This 3-bed, 2.5-bath option is great for making the most of your downtime. Enjoy 4 TVs, Internet access, laundry facilities inside, a jacuzzi tub, and an eat-in breakfast bar, giving you the convenience of an Anna Maria Island hotel but with much more privacy. When it’s time to explore the town, you have 4 adult bikes available during your stay.

Front drive of vacation rental in Holmes Beach, Florida

8. Key Largo Cottage

Parties of up to 6 people will be comfortable in this 3-bed, 3-bath home. This is an ideal option for enjoying the outdoors, with features like a private heated pool, outdoor shower, beach equipment, and a BBQ grill. You’ll also be close to the free Anna Maria Trolley to help you explore the rest of the island.

Boardwalk and gulf view from patio at vacation rental in Holmes Beach

9. Coastal Sunrise

You’ll find breathtaking Gulf views all throughout this 3-bed, 2.5-bath home. Take your private staircase right onto the beach! You’ll also have access to a gourmet kitchen, laundry facilities inside the home, and luxurious finishes and furniture. Finally, having our Professional Linen Service Program means you’ll have one less thing to pack!

Beachbreeze rental on Holmes Beach

10. Beachbreeze

This luxurious 6-bed, 4.5-bath home is fit for the entire family. Walk just a minute down the street to the Gulf Beach. Situated on a quiet residential street you don’t have to worry about hearing the hustle and bustle of Anna Maria Island.

Take in the sunset on the rooftop deck. Looking for a place to chill at the end of the day? Take a dip in the heated pool and spa or cook dinner in the outdoor kitchen. Later, challenge everyone to a game of foosball or one of the multiple available video games!

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