
Happy Place
Holmes Beach · 6 bedrooms · Up to 12 guests
A canalfront home with a private pool and a separate guest apartment. The beach is approximately 0.4 miles away.
30-night minimum
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A pool for the kids. A quiet patio for your morning coffee. Enough space for everyone to sit down together. Start with the things that will make this trip yours.
AnnaMariaRentals.com brings together Anna Maria Island vacation rentals managed by Florida Vacation Homes and homes managed by other professional local rental companies. Compare the properties, choose your dates and check the details that matter to your group.
Bring family or friends together in a waterfront home with a private pool. Take a closer look at Happy Place and Island Life Villa.

Holmes Beach · 6 bedrooms · Up to 12 guests
A canalfront home with a private pool and a separate guest apartment. The beach is approximately 0.4 miles away.
30-night minimum
Explore this property
Holmes Beach · 5 bedrooms · Up to 10 guests
Two kitchens, room to spread out and a pool overlooking the water. The beach is approximately 0.2 miles away.
7-night minimum; seasonal arrival rules apply
Explore this propertyAvailability, minimum stays and amenities vary by property and travel dates. Check the current listing and rental terms before booking.
The address shapes your day. Think about the beach you’ll use, where you’d like to eat and how much driving you want to do.
Island overview · not to scale
Look toward the north end if Pine Avenue’s shops and places to eat are part of your plans. Compare the exact address: a home near the bay offers a different beach routine from one near the Gulf.
Explore Anna Maria diningA central base for exploring the island, with Manatee Public Beach and everyday stops nearby. Check the walking route from each rental; “Holmes Beach” covers more than the few blocks around the beach entrance.
Explore Holmes Beach diningConsider the south end if you’d like Bridge Street’s restaurants and shops within reach. Cortez Beach and Coquina Beach are also in this part of the island. Distance to each depends on your rental’s address.
Explore Bradenton Beach diningOur collection includes properties managed by Florida Vacation Homes alongside rentals managed by other professional local companies. The company looking after your stay depends on the home you choose.
Look beyond the bedroom count. Photos, floor plans where available, amenities and rental terms help you decide whether a property works for your group.
Unsure about a pool, a beach route or the company managing a home? Contact our reservations team so you can clarify the details before making a booking.
Review the manager’s details and arrival instructions in your booking confirmation. Use the contact provided for that property when you need help during your stay.
Beachfront, beach view and near the beach describe different settings. Look for the actual beach entrance and walking route, including any roads you’ll cross with chairs and a cooler.
A canalfront or bayfront home can be lovely for watching the water. It does not necessarily have a sandy beach. If you’re bringing a boat, confirm dock access, restrictions and suitability before booking.
Is the pool private or shared? Is heating included, optional or seasonal? A spa may have separate operating rules. Confirm those details for your dates rather than relying on a photo.
Check bed sizes, stairs and where everyone will sleep. A separate guest suite may suit two families, while a group with young children may prefer bedrooms together in the main home.
Start with what you want nearby. Anna Maria puts you toward Pine Avenue and the north end; Holmes Beach is a central base; Bradenton Beach puts you toward Bridge Street and the southern beaches. Then check each home’s precise location, beach access and route to the places you plan to visit.
No. We market homes managed by Florida Vacation Homes and homes managed by other professional local rental companies. Management, arrival arrangements and booking terms vary by property. Review the listing and rental agreement, and ask us to clarify the managing company if it is not clear before you book.
No. Waterfront can mean a bay or canal setting. Beachfront usually describes a location along the beach, while a beach view does not necessarily mean direct access. Check the property description and the route to a public beach entrance before deciding.
Read the amenities and pool information for the specific property. A shared community pool is different from a pool reserved for your home. Heating arrangements, extra charges and temperature expectations can vary, so confirm them for your travel dates before booking.
Pet policies are specific to each home, and many properties do not allow pets. Do not assume a rental accepts dogs unless the listing and rental terms confirm it. Ask about approval, size or number limits and any charges before making a reservation.
Minimum stays vary. Some listings require seven nights; others require 30 nights, and seasonal arrival-day rules may apply. Enter your dates and check the individual property. For a condo, also look for association applications and any advance approval deadlines.
Review the full quoted total, including taxes, cleaning charges and any optional extras you select. Check the payment schedule, deposit requirements and cancellation terms in the agreement for your chosen property. These may differ between homes and managing companies.
That depends on your address and plans. Compare the walking route to the beach, restaurants and transport stops before deciding. Our island trolley and bus guide and bike and golf cart rental guide are useful starting points; check current services and rental rules when planning your trip.
Work out how you’ll get from your rental to the places you want to visit.
Trolley and bus guidePick a few nearby options for the evenings when nobody feels like cooking.
Holmes Beach restaurantsMake space in the week for a boat trip or a different view of the island.
Boat tours and water sportsGuest support for a better experience
Availability Calendars are live & up to date for Instant Booking
Call our vacation planners to book your vacation to Anna Maria Island
Start with your dates and the number of guests, then compare the homes and condos available for your trip. Before booking, review the property’s amenities, total price, cancellation terms and check-in details.
Planning to explore without driving every day? Our island trolley and bus guide and bike and golf cart rental guide can help you plan how to get around.
Leave room in your plans for a beach morning, a shopping stop and dinner close to your rental. Browse Holmes Beach restaurants or Bradenton Beach restaurants to compare menus and settings.
Our Anna Maria Island shopping guide covers local shops and beach supplies. Check current hours and reservation policies with each business before heading out.
Start with your dates and guest count, then compare the homes and condos available for your trip.
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