Vacation Rentals on Anna Maria Island Florida

Anna Maria 4/4.5 Beach Front Cottage - Best Location Ever!

Amazing, newly redone 1912 bungalow on beautiful Anna Maria Island beach. Sleeps 10! 4/4.5 - bathrooms in each room! Incredible sunsets from the porch, comfy decor with awesome amenities with coffee stations in each room, huge flat screens, streaming video, and gourmet kitchen items. Majestic vacation rental located in the best spots on the island, close to local shopping, the best eatery's and much more. Come stay in our home and enjoy it as you.......read more

4 Bedroom(s)
5 Bath(s) - Sleeps 10 House Rentals

Vacation Home

Found Your Sol Mate! Gorgeous Home w/ Pool, Spa, Steps to Bean Point, Dogs OK!

Welcome to Sol Mate! On Anna Maria Island (Anna Maria, FL) Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency. Beautifully updated, fresh, and clean elevated 3 Bed, 2.5 Bath which sleeps up to 8 within easy walking distance to Bean Point beaches & Close to Anna Maria's Beloved Pine Avenue 1500 square feet HIGHLIGHTS - Kitchen, Dining Area, Living w/ TV - 1 King Bedroom w/ TV and ensuite .......read more

4 Bedroom(s)
4 Bath(s) - Sleeps 8 House Rentals

Vacation Home

Tarpon Pointe in Anna Maria

Tarpon Pointe is a gorgeous, newly remodeled 2 bedroom 2 bath Island home located on the North end of Anna Maria Island. You’ll enter the elevated home from a large front deck with sliding glass doors into the living area. The open concept living area features a large 65" flat screen HDTV with plenty of seating for the whole family. The kitchen is fully stocked and outfitted with granite counter tops, all modern appliances. There is a fo.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 House Rentals

Vacation Home

Welcome to the Jungalow! Luxury 3 bedroom Tropical Paradise with Private Pool

Welcome to the Jungalow. Your Anna Maria Island adventure awaits you in this unique, modern Bohemian and Polynesian paradise located on the North end of the island and surrounded by one of Anna Maria's most mature tropical landscapes! *Features include* * 3 bedrooms, 3 bathrooms * Private tropical heated pool * Outdoor living and dining spaces * Poolside bar, TV and gas grill * Foosball and games * Peloton^ and yoga room * Spacious scre.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 8 House Rentals

Vacation Home

AMG 317: Beautiful Cottage w/Private Heated Pool on Pine Ave Close to Everything

******Please Read our Property Manager Notes Below ****** BEFORE YOU BOOK: We rent Saturday to Saturday…Usually. If you are interested in starting or ending on a different day other than Saturday, then Please contact us before you book by clicking the “Ask Manager a Question” button to send us a message with your desired dates. We’ll let you know if we can accommodate within 24 hours Monday through Saturday. Messages received Saturday eve.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Villa Rentals

Vacation Home

Beach You To It: Heated Pool, Hot Tub, Close to Everything, 1 Block to Beach!

******Please Read our Property Manager Notes Below ****** BEFORE YOU BOOK: We rent Saturday to Saturday…Usually. If you are interested in starting or ending on a different day other than Saturday, then Please contact us before you book by clicking the “Ask Manager a Question” button to send us a message with your desired dates. We’ll let you know if we can accommodate within 24 hours Monday through Saturday. Messages received Saturday eve.......read more

4 Bedroom(s)
2 Bath(s) - Sleeps 8 House Rentals

Vacation Home

Canal Front Home With Private Heated Pool

Fantasea is a gorgeous ground level home located on the end of a cul de sac street in Anna Maria. This home includes the following features: • 1 King bed, 1 Queen, & 2 Twin bunks – Sleeps up to 8 • Private heated pool (during the winter months) overlooking the canal • Professional Linen Service includes - Bath towels, beach towels, and bed linens. • Close to local shops and restaurants on Pine Avenue-4 adult and 2 kid bikes available .......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 8 House Rentals

Vacation Home

Come relax at Manatee Lookout relax on the dock and private heated pool

Manatee Lookout is a charming 3 bedroom 3 bath home with private heated pool located on the sought after north end of Anna Maria Island. This home has everything you need for the perfect vacation and is only a short walk to the white sandy beaches. Upon entry you have the living room where you can relax and read to book or watch TV after a long day in the sun. Adjacent to the living room you have the dining area and full kitchen. The kitchen wi.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 8 House Rentals

Vacation Home