Vacation Rentals on Anna Maria Island Florida

Luxury waterfront home w/ heated private pool & dock only three blocks to beach

Casa Bonita Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' Surround yourself with elegance and luxury at this four-bedroom Anna Maria home, where you'll enjoy a private heated pool, a canal-front dock, and a wonderfully convenient location mere blocks from sugar sand beaches. You'll find this upscale home on a quiet street in Anna Maria, where it sits alo.......read more

5 Bedroom(s)
4 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Charming island home with WiFi & heated private pool - close to it all

Mon AMI Beach House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' Welcome to your new vacation home away from home on Anna Maria Island! Offering four parking spots and a private, pristine pool, this home is perfect for the whole crew to come enjoy! Located on bustling Pine Avenue, you’ll be in the heart of Anna Maria's shopping, dining, and sightseei.......read more

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

Vacation Home

Dreamy Beach Condo w/Incredible Location, Shared Pool, Washer/Dryer, Free WiFi

Sunrise Garden #12 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' The beach escapade you've been waiting for is right here, at Sunrise Garden condos! This incredibly convenient home away from home boasts a fully-equipped kitchen with all the cooking essentials (no dishwasher), access to a shared swimming pool, laundry facilities on-site, and free WiFi so y.......read more

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

Vacation Home

Welcome Jungalow Bay! Luxury 3 bedroom Tropical Paradise with Private Pool

Welcome to Jungalow Bay. 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* * Private tropical heated pool * Plenty of outdoor furniture including Ledge Loungers in the pool * Outdoor living and dining spaces and tiki bar * Poolside bar, TV and gas grill * Foosbal.......read more

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

Vacation Home

Budget-Friendly Beach Condo w/Shared Pool, Washer/Dryer, Free WiFi, Full Kitchen

Sunrise Garden #14 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' The beach escapade you've been waiting for is right here, at Sunrise Garden condos! This incredibly convenient home away from home boasts a fully-equipped kitchen with all the cooking essentials (no dishwasher), access to a shared swimming pool, laundry facilities on-site, and free WiFi so y.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

Luxurious home with private pool, hot tub, WiFi, central AC, W/D, & grill

Mer-Vue Abode Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' Surrounded by leafy tropical plants and a gorgeous private pool and hot tub, this charming home is full of upscale touches that are sure to delight. Central air conditioning and all-white walls make it easy to stay cool and refreshed, while balconies both private and common mean that everyone can.......read more

3 Bedroom(s)
4 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Convenient & Well-Located Condo w/Shared Washer/Dryer, Pool, and Free WiFi

Sunrise Garden #2 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' Located on the bottom floor, these poolside suites are ideal for a refreshing and rejuvenating beach escapade. They are well-appointed to meet every guest's expectations no matter what! Featuring a fully-equipped kitchen with all the needed appliances and cooking essentials (no dishwasher), a.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park

Harmony House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' Come to historic Anna Maria Island and remember days gone by when you stay in this three-bedroom Key West-style cottage. With a sparkling cocktail-style pool, close proximity to the beach, dining, and Bayfront Park, you'll soon see why this beautiful rental is such a special place! You'll also ha.......read more

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

Vacation Home

Ground-Floor Duplex w/Free High-Speed WiFi, Enclosed Yard, Central A/C, & Grill

21 Palms Unit B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' Come and enjoy Anna Maria's postcard-perfect beaches at this ground-floor duplex! Inside, you'll be surrounded by colorful beach-themed decor anywhere you go. The living area features two comfortable sofas, a ceiling fan, and a wall-mounted flatscreen TV. Right there is a small, but convenient .......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 2 Apartment Rentals

Vacation Home

Bay-facing condo with amazing views, heated pool, & beach across street

South Bay Inn 2 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' This spacious condo with spectacular views of Tampa Bay offers wonderful access to some of the best attractions in Anna Maria! Located right across the street from the beach and the bayshore, this property comes equipped with a shared swimming heated pool, a full kitchen, a game table for fun-f.......read more

3 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

Updated bayside condo with heated pool - across the street from the beach

South Bay Inn 1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' This romantic getaway is a great place to spend some time on Anna Maria Island. Located right across the street from the bay, this rental is just a short stroll from the beach! It comes with a shared heated pool and comfortable outdoor furniture for relaxing in the island breeze. What's nearby.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 2 Condo Rentals

Vacation Home

High-end home w/ heated private pool/spa, courtyard, & floor-to-ceiling windows

Dream Maker Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' This home's backyard is your ticket to island life, whether you're lounging in the saltwater pool, soaking in the private spa, relaxing under the palm trees, or firing up the gas grill. Access the bedrooms and living room via the windowed walkway that surrounds the house. Dream Maker has an extraor.......read more

3 Bedroom(s)
4 Bath(s) - Sleeps 6 House Rentals

Vacation Home