Book Direct & Save - No Booking Fees
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
This beautiful property offers a perfect blend of indoor and outdoor living, with welcoming accommodations for a maximum of 6 guests, all just a short walk to the pristine white sand beaches and centrally located on Anna Maria Island!The decor is a perfect blend of coastal elegance and comfort, featuring...
Key Amenities
About this property
Escape to this beautifully decorated beachfront retreat, a 3-bedroom, 2-bathroom vacation rental just steps from the pristine white sands.The living area invites you to unwind after a day at the beach, with comfortable seating and coastal decor that soothes the senses.The fully equipped kitchen has...
Key Amenities
About this property
Welcome to “Barefoot Mermaid 4” a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria Island. The serene location of this property is just amazing. Located steps, less than 50 ft to white powder sand beaches of the Gulf of Mexico and less than a few flip flop...
Featured review
Perfect 1-bedroom apartment, only a steps away from the beach! Perfect location within walking distance to everything on Pine Street.
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...
Why Choose FloridaRentals.com?
No Booking or Service Fees
Save up to 25% compared to other websites - no hidden costs.
Connect Directly with Hosts
Book with confidence and get the best rates.
Florida's #1 Vacation Rental Site
Trusted by millions - your go-to for the perfect Florida getaway.
Key Amenities
About this property
WELCOME to "Paradise on Pine" – a stylish island retreat perfectly situated in the heart of Anna Maria! This charming 3-bedroom, 2-bath vacation home is nestled right on Pine Avenue – just 1.5 blocks to the stunning Gulf beaches and only a few blocks from the bay, City Pier, and...
Key Amenities
About this property
Have the best of both worlds with the bay & the gulf beaches at this new 4 bed/3.5 bath luxury home. Enjoy the quiet, laid back way of life on the north end of the island being only steps to the gorgeous bayside beach with city park or a 5 minute walk to the world renowned Bean Point! You are also...
Featured review
The entire stay was above all expectations. It was my wife's birthday. We invited friends from out of town to celebrate with us. The place was roomy and very comfortable. The kitchen is fantastic with the...
Key Amenities
About this property
Indulge in the ultimate beach escape to “Mary’s Place” located on Los Cedros, a *premier location* just north of Pine Avenue in the city of Anna Maria. Mary’s Place is a very short walk to the gorgeous, white sandy beaches of Anna Maria Island. This *ultimate beach house* has been...
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
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
Welcome to West O’ Gulf. This property suffered minimal damage from hurricanes Helene and Milton and is better than ever! If you are ready for a relaxing stay on beautiful Anna Maria Island, then this is the beach house for you! This exceptional custom-built 4 Bedroom 3-bathroom house makes it easy...
Key Amenities
About this property
Welcome to “Pineapple Cottage” – a beautifully updated ground-level beach cottage located in the heart of Anna Maria City and just 1 block from all the shops, restaurants, and fun on Pine Avenue. This charming cottage has been completely restored after hurricanes Helene and Milton. This...
Featured review
This house is in a great location, three blocks to the beach, restaurants, and three blocks to the pier, and many other amenities. It is beautiful, spacious and has everything you need to make your stay...
Key Amenities
About this property
Discover island paradise at “Magnolia” located on Magnolia Ave., a *premier residential street* just south of Pine Ave. in Anna Maria. Magnolia is just 2 blocks from the gorgeous, white sandy beaches of Anna Maria Island, 1 ½ blocks from the charming Ginny & Jane E’s Café,...
Distance to beach: 0.1 miles to 30 seconds to your left
Key Amenities
About this property
This newly redesigned elevated pet friendly 3 Bedroom, 2 Bathroom home is beautifully appointed throughout, with state of the art quartzite counter tops, stainless steel appliances and driftwood style hardwood floors and ceilings. Relax on the covered porch with direct views of the Gulf of Mexico and...
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...
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 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
WELCOME to “Island in the Sun” ...this newly renovated home on AMI offers charm, comfort, and luxury. No damage from hurricane Helene or Milton. This Anna Maria Island vacation rental is located just one block south of Pine Ave and just a few flip flop steps away from the City Pier Bay Beach...
Featured review
We stayed 6 nights and had a great time. The property was clean and had everything we needed. The Florida Rental staff checked on us after we arrived to make sure everything was good. Very caring staff....
Key Amenities
About this property
VRC22-000083 Welcome to "Beach Escape" on beautiful Anna Maria Island. Appropriately named, this Mediterranean-inspired beach house offers all the charm and luxury you expect from a memorable vacation on AMI.Find ease and relaxation the moment you arrive, this charming multi-level home...
Featured review
Everything was Perfect. The only thing I would change is to Stay Longer! Everything was wonderful. Location was perfect, the Beach, the Pool and the Restaurants.
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...
Featured review
Beautiful, outstanding home with unbelievable views from every window! The water is right outside your door. Plus there's a hot tub out back and a pool out front. It was a very memorable trip that I'll...
Key Amenities
About this property
Welcome to Sweet Home Anna Maria! Walk to Manatee Public Beach, Grocery Stores, Restaurants, Shopping & More! Private Heated Pool & Hot Tub with Plenty of Seating for the Whole Family! Game Room with Ping Pong, Dart Board, Extra Fridge & Bathroom Every Bedroom has an Ensuite Bathroom!...
Key Amenities
About this property
Welcome to "Barefoot Mermaid 2" a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria Island. The serene location of this property is just amazing. Located steps, less than 50 ft, to white powder sand beaches of the Gulf of Mexico and less than a few flip flop...
Featured review
We booked last minute for a long weekend to get out of the COLD Midwest. Location was exceptional! Literally STEPS to the beach where Pine Avenue dead ends at the GULF. Beach chairs and towels provided....
Key Amenities
About this property
Welcome to “Salty Sunsets” on beautiful Anna Maria Island. This luxurious property is located north of Pine Ave with easy access to Bean Point. This Anna Maria Island vacation rental home offers all the goodies to make sure your vacation does not skip a beat. This beautiful property offers...
Key Amenities
About this property
This luxurious property offers a perfect blend of indoor and outdoor living, with spacious accommodations for large groups or families, all while staying steps from the pristine white sand beaches and centrally located on Anna Maria Island!As you step through the front door, you enter a bright and...
Featured review
I’d give it a 10 star! Absolutely perfect vacation rental! About a block and a half from beach no busy road to cross to get there! We could see the ocean from the front porch. The home is clean, fully...
Key Amenities
About this property
New Paint, Furniture and Decor as part of our mini makeover! King in primary bedroom and queen in second bedroom!When you come to Anna Maria Island for vacation, make this charming and inviting two-bedroom condo your home away from home! You're sure to love the relaxed island attitude with amenities...
Featured review
Sandy Point condo was the perfect spot for our getaway! It was clean, comfortable, and in a great location—close to everything but still nice and quiet. We loved the easy beach access and relaxing by...
Key Amenities
About this property
Welcome to Sailfish Nest, a beautifully remodeled 2-bedroom, 2-bath duplex located in the heart of Holmes Beach—just a short stroll from the pristine white sands of Anna Maria Island.Step inside to discover a thoughtfully designed, open-concept living space with all-new furnishings. Relax in...
Key Amenities
About this property
VRC24-000077 Come experience Unit 201 at Sun Plaza West on beautiful Anna Maria Island. This 2 bedroom 2 bathroom Condo is located in the heart of Holmes Beach within walking distance to restaurants, shopping and the Islands Free Trolley. Sun Plaza West complex offers a secure entry, an elevator, heated...
Key Amenities
About this property
Create unforgettable memories at “Mia Bella” located on Hammock Road, just north of Pine Avenue, in a *premier deep water canal location* in Anna Maria. Mia Bella is a short walk to the gorgeous, white sandy beaches of Anna Maria Island. This *very spacious beach house* has been fully renovated...
Featured review
Salty Mermaid Vacation Rental in Anna Maria Island- Even before arriving to Mia Bella, the communication with both Bella and David was incredible. They both go above and beyond to make you feel comfortable...
Key Amenities
About this property
Welcome to “Barefoot Mermaid 3” a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria Island. The serene location of this property is just amazing. Located steps, less than 50 ft to white powder sand beaches of the Gulf of Mexico and less than a few flip flop...
Featured review
We were so pleased with Barefoot Mermaid 3. Everything was so clean and well cared for. The kitchen was stocked with the things we might need. We were so close to all our favorites like The Sandbar, Mademoiselles...
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
Discover island paradise at “North Shore” located on the *premier corner* of North Shore & Palmetto in Anna Maria, only 2 blocks from the gorgeous, white sandy beaches of Anna Maria Island and a few steps from very popular Slim’s Place restaurant and sports bar. This *ultimate beach...
Featured review
This house was great we have been coming to the island for about 10 years! This was the best house and so close to the beach!! We will be back
Key Amenities
About this property
Create unforgettable memories at “Crescent Palms”. This *perfect island house* has been fully renovated in 2025. Crescent Palms is centrally located, just north of Pine Avenue in Anna Maria. This home is steps away from the gorgeous white sandy beaches of Bayfront Park, having captivating...
Featured review
We were looking for a quiet spot for the family and hit the bullseye at Max and Denise's place on Northern Anna Maria island. Centrally located, 3 blocks either way, between the Gulf of Mexico or Tampa...
Key Amenities
About this property
Welcome to “Barefoot Mermaid 1” a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria Island. The serene location of this property is just amazing. Located steps, less than 50 ft to white powder sand beaches of the Gulf of Mexico and less than a few flip flop...
Key Amenities
About this property
Welcome to Sea Site Unit A! 100 Steps to the World Class Beaches of Anna Maria Island Close to Restaurants, Shopping, and More Water Views from Balcony King, King, & Two Full Beds High speed Wi-Fi & Smart lock for Self-Check-inWaking up to a view of the coast with your morning cup of...
Key Amenities
About this property
Welcome to Sea Site Unit B! 100 Steps to the World Class Beaches of Anna Maria Island Close to Restaurants, Shopping, and More Private Patio for Beach Equipment and Grilling King, King, & Two Full Beds High speed Wi-Fi & Smart lock for Self-Check-inWelcome, too Sea Site Retreat Unit B!...
Key Amenities
About this property
Welcome to Ocean Star! .01 Miles to Amazing Gulf Coast Beaches Private Heated Pool/Spa with Outdoor Seating & BBQ Beach Equipment Available for Use Every Bedroom Has a Private Bathroom Fully stocked kitchen for all of your favorite home-cooked meals High-speed Wi-Fi, Smart lock for Self Check-in...
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
Escape the Madness to the serenity of Anna Maria's north end. This single family, two bedroom, 2 bathroom, ground level house is located on the far north end of Anna Maria Island near Bean Point. The property is only 250 feet from the sugar sand beaches where you can walk for hours or sit and...
Featured review
My family and I stayed at the cottage. House was perfect. It was nice that beach chairs and towels, etc. were available. We also enjoyed using the backyard and grill. The house is literally across the street...
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
We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most flexible cancellation policy in Anna Maria Island! 100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.Experience 24/7...
Featured review
Love this property, loved the location and could not have had a better experience. Owner as great to work with and the communication was outstanding.
Key Amenities
About this property
Bring your family and guests to this 2-unit house! About 40 steps to the beach entrance of Anna Maria white, sandy beach, this home combined boasts 5 bedrooms, a sleeper sofa and 5 bathrooms. Bean Point Unit A boasts 3 bedrooms/3 bathrooms, while Unit B has 2 bedrooms/2 bathrooms. Both units feature well-equipped...
Key Amenities
About this property
Welcome to La Isla Bonita!- Steps to Anna Maria Island's powdery-white sandy beaches - Private heated pool, ping pong table, and basketball game - Impressive deck with breathtaking views - 4 spacious bedrooms & 4 bathrooms - 3-story home with elevator - Close proximity to local dining,...
Featured review
Great accommodations..good location to shopping, marina, Anna Maria Island, restaurants.. quick response from Mgmt Team for minor issue.. quiet area, carport, security gate.. enjoyed our time there..
Key Amenities
About this property
A few things that make Bay Breeze Bungalow special: - North end of Anna Maria - private home on cul-de-sac - Pool (not heated) - Canal front with 15 ft dock (6 ft clearance) - Enclosed screened-in patio - Grill (propane included) - Professional Linen Services - Complimentary WiFi - Beach chairs,...
Key Amenities
About this property
Approximately 40 steps and you'll be at the beach entrance to Anna Maria's sandy, white beach. This property offers convenient access to one of the island's main attractions. As the upper level of a two-unit home, Bean Point Residence Unit A boasts 3 bedrooms/3 bathrooms, providing ample...
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
Come enjoy this 4 bedroom/4 bath duplex that can sleep up to 12 people with the add-on of the sleeper sofas. Blue Lagoon is located on North Shore which is just a few blocks from the renowned shopping and dining of Pine Avenue and features a large, shared heated pool, and an EV Charger. Upon entry in...
Key Amenities
About this property
Welcome to Sunrise Vista on gorgeous Anna Maria Island. Pack up the family car and head to Anna Maria Island's perfectly located beach house, one of the last remaining generation-owned single-family cottages located directly on the beach.This is the place to put down your iPhones and reset your...
Key Amenities
About this property
Casa Amiga by Beach Retreats Vacation Rentals 144 Crescent Dr. Anna Maria, FL 34216 City of Anna Maria | 4 Bedrooms | 4.5 Bathrooms | Sleeps 10 | Heated Pool + Jacuzzi | Rooftop Deck | Shared DockLuxury Island Living Near Bean Point Welcome to Casa Amiga, a beautifully designed 4-bedroom, 4.5-bath...
Key Amenities
About this property
NO CANCELLATION FEES: $500 deposit due at time of booking; balance due 60 days prior to arrival Cancel 60+ days before arrival → Full refund (no fees). Cancel within 60 days of arrival → No refund. Cancellations must be made in writing and received by Beach Retreats on or before the...
Featured review
This house was incredible! Absolutely beautiful, well stocked, an amazing pool and outdoor setup, and so conveniently located! While it's not beach-front, it's just a house or two away from the beach entrance...
Key Amenities
About this property
If you're looking for the perfect spot to drop anchor on Anna Maria Island— look no further than this spacious four-bedroom oasis. Located on the idyllic north end, Anchor Splash is a short stroll from the white sandy beaches and warm, aquamarine gulf waters. It's also within walking distance...
Featured review
House is bigger then it looks with the main bedroom/bathroom feeling like its a whole other unit. Had 10 quests 6 being kids under 12. With the pool right there and the beach and bridge street within a...
View on map
List view