Anna Maria Island Vacation Rentals
1-24 of 143 rentals
Bay-facing condo with amazing views and heated pool - beach across the street
Condo in Anna Maria, FL
4Persons
2Bedrooms
1Bathrooms
$281/night

Luxury Gulf-front condo with beach access, heated pool, sunset views, & balcony
Condo in Bradenton Beach, FL
4Persons
2Bedrooms
2Bathrooms
$502/night

Anna Maria Island condo with heated pool, short walk from the beach
Condo in Holmes Beach, FL
4Persons
2Bedrooms
1Bathrooms
$311/night

Breezy condo with WiFi & pool - minutes from beach, shopping, & dining
Condo in Bradenton Beach, FL
4Persons
1Bedrooms
1Bathrooms
$173/night

Beachfront condo with WiFi, two decks, Gulf views & pool - walk to the trolley
Condo in Holmes Beach, FL
4Persons
2Bedrooms
3Bathrooms
$442/night

First-floor condo with pools, hot tubs & tennis - near IMG & Gulf beaches
Condo in Bradenton, FL
6Persons
2Bedrooms
2Bathrooms
$151/night

Cozy Beachfront Villa | Direct Gulf Access | Free Parking, W/D
Villa in Holmes Beach, FL
4Persons
2Bedrooms
1Bathrooms
$224/night

Ground-floor home with fast WiFi, shared pool, & central AC - close to beach
House in Holmes Beach, FL
4Persons
1Bedrooms
1Bathrooms
$204/night

Suite near the beach & restaurants with covered deck & shared grill
Apartment in Holmes Beach, FL
6Persons
3Bedrooms
1Bathrooms
$207/night

Old Florida-style cottage w private heated pool - walk to the beach - dogs OK
House in Anna Maria, FL
6Persons
2Bedrooms
2Bathrooms
$545/night

Serene oceanfront suite with Gulf view, grill, patio, central AC, & WD
Apartment in Holmes Beach, FL
4Persons
2Bedrooms
1Bathrooms
$190/night

Steps away to beaches and the Gulf, snowbird friendly, AC, free WIFI and parking
House in Anna Maria, FL
4Persons
2Bedrooms
2Bathrooms
$290/night

2nd-floor condo with heated pool - walk to beach & Bridge Street
Condo in Bradenton Beach, FL
4Persons
1Bedrooms
1Bathrooms
$216/night

Dog-friendly home with amazing backyard, pool, spa, putting green & game room
House in Anna Maria, FL
6Persons
2Bedrooms
2Bathrooms
$381/night

Duplex near beach with heated pool, grill, washer-dryer, patio, AC
Condo in Bradenton Beach, FL
6Persons
2Bedrooms
1Bathrooms
$202/night

Charming 3BR Home w Private Lanai & Pool Near Anna Maria Beaches & IMG Academy
House in Bradenton, FL
6Persons
3Bedrooms
2Bathrooms
$214/night

2nd Floor OceanView Home Steps to Beach - Shared Pool & Putting Green - On-Site Parking
Condo in Bradenton Beach, FL
6Persons
3Bedrooms
3Bathrooms
$424/night

Beachview balconies with pool, steps from the beach
House in Bradenton Beach, FL
12Persons
6Bedrooms
6Bathrooms
$1,253/night

Ground-floor duplex with fast WiFi, central AC & grill
Apartment in Anna Maria, FL
2Persons
1Bedrooms
1Bathrooms
$160/night

Waterfront condo with pool and easy access to sugar sand beach
Condo in Holmes Beach, FL
4Persons
1Bedrooms
2Bathrooms
$278/night

3rd Floor OceanView Condo Steps to Beach - Shared Pool & Putting Green - On-Site Parking
Condo in Bradenton Beach, FL
6Persons
3Bedrooms
3Bathrooms
$444/night

Updated bayside condo with heated pool - across the street from the beach
Condo in Anna Maria, FL
2Persons
1Bedrooms
1Bathrooms
$205/night

Dog-friendly house w beautiful upstairs deck and grill, steps from the beach
House in Anna Maria, FL
8Persons
3Bedrooms
2Bathrooms
$319/night

Dog-friendly seaside home - heated private pool & spa, great location near beach
House in Holmes Beach, FL
6Persons
3Bedrooms
2Bathrooms
$333/night