Book Direct & Save - No Booking Fees
Key Amenities
About this property
Steps to Beach + Heated Pool + Putting Green + Golf Cart | WavesWelcome to Waves, your beautifully remodeled coastal retreat on Anna Maria Island — where modern luxury, effortless beach access, and resort-style outdoor living create the ultimate island escape.Perfectly positioned just across...
Key Amenities
About this property
Steps to Beach + Heated Pool + Golf Cart & Bikes | North End RetreatThis beautifully remodeled 4-bedroom, 4-bath Anna Maria Island vacation home is perfectly situated on the coveted north end — just steps from the Gulf of Mexico. With a convenient beach access path directly across the street,...
Key Amenities
About this property
Salt + Sol | Canal-Front Oasis + NEW Heated Pool + Golf Cart | North End RetreatWelcome to Salt + Sol, your serene canal-front escape on the coveted north end of Anna Maria Island. This bright and breezy 4-bedroom home blends relaxed coastal elegance with modern comfort — all just minutes from...
Key Amenities
About this property
This rental is part of the Anna Maria Beach Cottages. More information on this charming property below!Cottage 110A is a beautifully beachy place to call home on your next Anna Maria Island vacation! One of the charming Anna Maria Beach Cottages, this is a 2 bed/2 bath second-floor vacation home,...
Key Amenities
About this property
Waterfront Pool Retreat + Dock & Boat Lift + Golf Cart | Beach BlissWelcome to Beach Bliss, your waterfront escape on Anna Maria Island — where relaxed luxury, boating adventures, and effortless island living come together for an unforgettable stay.This beautifully designed 4-bedroom,...
Key Amenities
About this property
Limefish Luxury | Premier Gulf-Front Living & Iconic SunsetsTrue beachfront luxury with a private heated pool. Wake up to unobstructed Gulf views, step directly onto the sand, and enjoy total privacy in this stunning 3BR/3BA coastal retreat. Perfect for romantic escapes, work-from-the-beach stays,...
Key Amenities
About this property
Location, Location, LocationStaying near the Holmes Beach public beach means you get the best of the island without the hassle:Easy, stress-free beach access (no long walks or parking) Nearby public amenities like restrooms, showers & lifeguards Walk to restaurants, cafes & beach...
Key Amenities
About this property
Sandcastle – Beachside Escape with Heated Pool, Golf Cart & Island Adventure Gear3 Bedrooms | 2.5 Bathrooms | Heated Pool | Golf Cart | Bikes | Paddle Boards | Kayaks | Steps to the BeachWelcome to Sandcastle, your perfect Anna Maria Island beach retreat. Ideally located just across...
Key Amenities
About this property
Private Pool Oasis + Beach Volleyball Court + INCLUDED Golf Cart | Fanta-SeaEscape to Fanta-Sea, your private tropical retreat on the coveted north end of Anna Maria Island — where backyard fun, beachside relaxation, and effortless island exploring come together.Step through your back gate...
Key Amenities
About this property
Bayfront Pool Retreat + Walk to Pine Ave + Golf Cart | TripletailWelcome to Tripletail, your bayfront escape on the coveted north end of Anna Maria Island — where peaceful waterfront views, walkability to Pine Avenue, and resort-style outdoor living come together for an unforgettable stay.Perfectly...
Distance to beach: 50 feet to across the street
Key Amenities
About this property
Key Lime Cottage | Hot Tub + Fenced Yard + Golf Cart | North Shore Retreat 3 Bedrooms | 2 Bathrooms | Sleeps 8 | Pet Friendly | Private Hot Tub | 6-Passenger Golf CartWelcome to Key Lime Cottage, a charming north-end escape tucked along coveted North Shore Drive on Anna Maria Island. Just a short...
Key Amenities
About this property
True Beachfront Escape + Elevator + Hot Tub + Golf Cart | Serendipity Anna MariaWelcome to Serendipity, your pet-friendly beachfront sanctuary on the coveted north end of Anna Maria Island — where quiet mornings, spectacular sunsets, and the rhythm of the Gulf create the perfect island escape.Perfectly...
Key Amenities
About this property
Beachfront boho escape on Anna Maria Island NEW heated Gulfside pool + hot tub with sunset views 4BR layout with private cottage for extra space & privacy Steps to the sand + paddle boards, bikes & INCLUDED 6-passenger golf cart Serene north-end location — the island retreat guests...
Key Amenities
About this property
Shangri-La | Gated Bean Point Estate — Anna Maria Island’s Most Coveted LocationWelcome to Shangri-La, a rare and extraordinary beachfront estate perched on the exclusive tip of Anna Maria Island at Bean Point — widely considered the island’s most breathtaking and sought-after...
Key Amenities
About this property
Beachfront Luxury + Pool Deck + Complimentary Golf Cart | Cloud 9Welcome to Cloud 9, a stunning beachfront retreat where modern luxury meets relaxed coastal living. Perfectly positioned on the quiet north end of Anna Maria Island, this beautifully designed 5-bedroom home offers everything your group...
Featured review
This home was perfect for our family vacation- great views, clean, well stocked, we will definitely be back! Thank you!
Key Amenities
About this property
Luxury Coastal Retreat + Elevator + Complimentary Golf Cart | Serendipity DeuxWhere luxury meets effortless island living, you’ll find Serendipity Deux — a beautifully designed 4-bedroom retreat offering refined interiors, premium beach access, and an unbeatable Anna Maria Island location.From...
