Owner Direct Vacation
Rentals in Anna Maria Island
The Best Owner Direct Vacation Rentals in Anna Maria Island. Explore thousands of vacation home rentals, large cabins, and villas near Anna Maria Island
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Explore the Best Anna Maria Island Vacation Homes
Looking for the perfect place to stay in Anna Maria Island? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Anna Maria Island character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
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Find Anna Maria Island Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Anna Maria Island
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Popular Neighborhoods for Anna Maria Island Vacation Rentals
What are the best areas to stay in Anna Maria Island
Discover the top neighborhoods in Anna Maria Island and choose a place that suits your stay.
Sunday Jan 25
Anna Maria Island, Florida
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Anna Maria Island vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Anna Maria Island
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How to Reserve Your Anna Maria Island Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Anna Maria Island Vacation Rental FAQs
1. What are the top vacation rentals in Anna Maria Island?
There are a lot of options in Anna Maria Island. If you plan on staying in the Anna Maria Island area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Anna Maria Island:
- Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
- Best Little Beach House on Anna Maria Island! With a pool & steps to the beach!
- Sea Pirate Cottage By The Sea on Anna Maria Island, Smart TV in every room.
- Beautiful, Gulf-Front Home on Bean Point-Halcyon House
- Beachfront Condo, Newly renovated! Heated Pool on the beach. GulfView 102.
- Cozy Cottage w private Beach Access,AC&WiFi -Quiet North End AMI. Tropical Oasis
- Blue Sky: Luxury 5 Bdrm/4 bath with heated pool - 1 block to beach!
- AMI Sunset Beach - Gulf View Retreat w/Pool+Decks
- Blue Water Beach House: 5+ bdrm, 4.5 bath, Heated Pool/spa, 1.5 blocks to beach
- Dragonfly - Southern charm on the North end of Anna Maria Island
2. How many vacation rentals have private pools in Anna Maria Island?
There are 2184 vacation rentals with private pools near Anna Maria Island. Top-rated homes that have access to a swimming pool include:
3. Which vacation homes in Anna Maria Island are best for families?
If you are looking for a family-friendly vacation home in Anna Maria Island, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Anna Maria Island:
4. How many vacation rentals are available in Anna Maria Island?
Currently, the total number of properties listed in 2026 is over 5956 in the Anna Maria Island area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Anna Maria Island.