211 properties available

Located in Anna Maria, Florida, United States. Cute & cozy getaway at north end of Anna Maria Island. 5-min walk to the beach! Located at the quiet North end of Anna Maria Island, this charming 2-bedroom, 1-bath villa is a short walk to beautiful white sand beaches at Bean Point. The Rod-N-Reel Pier is right around the corner where you can enjoy a morning cup of coffee, evening cocktail, or simply watch the dolphins play. Visit a variety of shops and restaurants along Pine Avenue in downtown Anna Maria less than a mile from the villa. Enjoy the Gulf breezes from the screened lanai or patio area. Living room has a leather couch and armchair. The bedrooms have a King bed and 2 twin beds. Amenities include free wireless internet, cable TV, Roku, telephone, washer/dryer, dishwasher, microwave, gas grill, Mr. Coffee, and Keurig. Beach gear includes chairs, towels, beach wagon, umbrellas, and cooler. Occupancy limited to 4 persons, including children. We offer flexible check-ins and check-outs throughout the year, which makes i

Located in Anna Maria, Florida, United States. Sea Garden Cottage with Direct Beach Access,AC & WiFi - North End Anna Maria Fl This charming Sea Garden Cottage is a true island gem and escape. Sea Garden Cottage is located on North Shore Drive at the north end of the island. It’s charming decor and garden oasis are sure to make you lose yourself in your future get-a-way. This home rests on a 1.23 acre lot directly on the Gulf, a rarity on the island. The lot is surrounded by mature trees, tropical vegetation, and views of the Gulf and its sandy shores.The master bedroom has king size bed with half bath and TV. The guest bedroom has 2 twin beds. Both rooms open to a screened in porch where you can enjoy the beautiful surroundings. Keywords: CottageSingle StoryBeach CottageBeachBeach HouseAnna MariaAnna Maria IslandBungalowBeach BungalowGulf Front

Located in Anna Maria, Florida, United States. Anna Maria Guest House 401- 3 bedrooms in the middle of everything HighlightsLess than a 10-minute walk to the beachPrivate PoolSpacious 2,000 sq. ft. condo on Pine Avenue. Convenient location near beaches, Anna Maria Pier, shopping, dining, and ice cream. Free Trolly stop outside Minimum stay of 3 nights2 enormous decksThe front overlooks Pine Avenue, and the back overlooks the pool and yardAnna Maria Guest House 401 401 Pine AveAnna Maria, FL 34216Welcome to Anna Maria Guest House 401, where the shimmering white sand Gulf of Mexico beaches are two and a half blocks away. This three-bedroom and two-bathroom getaway is above a small, locally owned business with a staircase for privacy at the back of the building. Get ready to explore the local life by being right in the center of Anna Maria City. Friends and family can sit back in the living area to relax, watch tv, and discuss Anna Maria Island activities. The fully equipped kitchen is ready to please any level cook and has a beer and

Located in Anna Maria, Florida, United States. Canal Home with Private Dock and Heated Pool, Just 3 Houses to the Bay Wade 'N Sea by Anna Maria Island AccommodationsHome in Anna Maria, FL 342163 Minutes to BayHighlights:-Newly renovated and tastefully furnished-Located at the exclusive north end of Anna Maria Island-Located on the canal-Private Dock-Only 1.5 blocks to the beach -Generously sized heated pool-Warm-water outdoor shower-Full-size patio set with barbecue grill and deck chairs-High-speed internet-Telephone landline-Private washing machine and a dryer-Access 200+ cable channels or Roku TV streaming in the living room and master bedroom-Custom-made compact chef's kitchen, complete with high-end kitchen equipment and utensils-Rent or launch your own paddleboard, kayak, jet ski, or boat from the private dock-Outdoor parking space for up to three vehicles-Within walking distance to Pine Avenue which offers an assortment of shops and restaurants-Free Island trolley which runs daily from 8:00 AM to 10:00 PMRoom Details-Primary

Located in Anna Maria, Florida, United States. Bean Point Gem awaits your stay! Welcome to Castaway Cove, this beautiful residence is a Bean Point gem, a stunning 4 bedroom property and 2.5 bathroom on the exclusive Northern end of Anna Maria Island! Hide away from the world, relax and soak up the sun in the private backyard with heated pool and lush tropical landscaping.The downstairs game room provides an excellent 8ft Pool Table and Air Hockey table, perfect for adults and kids, or enjoy either of the 2 Smart HD TV's (internet only). Want to work on your beach body during your stay? Make use of the Bow-flex weights & treadmill in the Castaway Cove gym or stretch out your back on the inversion table! Have a refreshing outdoor hot or cold outdoor shower after the workout.We have 2 Adult Bikes, 2 Kids Bikes + one small Bike, all for you to use around the island at your leisure.Get the best of both worlds in a gorgeous home with fantastic amenities and a great location with the pristine white sandy beaches of Bean Point just a shor

Located in Anna Maria, Florida, United States. 4 FREE BIKES for new fall stays Sep 3-Nov 16 FALL SPECIAL: 4 FREE bikes for reservations *booked after 8/20/24* for stays *arriving between 9/3/24 and 11/16/24*. (Provided by our friends at Beach Bums at 427 Pine Ave, Anna Maria, FL 34216. Guests will need to pick up and drop off bikes.)You can’t imagine anyone not falling in love with the exquisite "Chillifish" - a peaceful gem, decorated with the utmost attention to details and surrounded by a garden full of palm trees, bromeliads and roses. Located just a short walk to the beach, this three bedroom, two bathroom cottage has all the amenities to make your stay an enjoyable one. The master bedroom, with a king bed, has a spa-inspired private bathroom. A guest room is furnished with a queen bed and has views of the garden. Another guest bedroom is just down the hall and is furnished with twin beds. The great room is breezy, airy, and easy with a streaming TV and comfy furniture. The kitchen is sparkling.**Please note: This property is

Located in Anna Maria, Florida, United States. On Point: Across Street from Bean Point Beach, Outdoor Games & Pool by Anna Maria Life 811 Jacaranda, Anna Maria, FL 34216What You'll Love About This Home:Location! 1 Block to Beach & Bean Point!4 Bedrooms / 3 Bathrooms3 Kings, Twin over Full BunkbedPrivate Heated PoolOutdoor ShowerPool Loungers & Deck ChairsPatio Dining under UmbrellaGas GrillVerandah with Outdoor Lounge Furniture & Dining Table for 6Foosball, Corn Hole & Giant Connect 4 GameBonus 2nd Living Area on Pool LevelProfessional Linen Service, Washer & DryerComplimentary WIFIBeach Towels, Beach Chairs & Beach WagonParking for 4 CarsDetails:With a premier location on the North End of Anna Maria, On Point is a one block walk from coveted Bean Point. Fantastic shelling and amazing sunsets are all yours!The kitchen, living and dining room space is located on the second level and includes a large verandah with lounge furniture and patio dining for six. Indoor dining includes a table for six with additional kitchen bar seating for

Located in Anna Maria, Florida, United States. BeachFront 4/3/ Amazing Views plus hot tub Beach front Bliss… Enjoy Swimming or relaxing in this 4 bedroom home on the North End of Anna Maria Island. Captivating Sunsets from your deck or steps away at the famous Bean Point. Elevator to all floorsFloor plan/Beds:Master Bedroom: King Bed with En-suite bathroomBedroom 2: King BedBedroom 3: King BedBedroom 4: King BedHall Bathroom has a tub/shower combination.Half Bathroom accessible from the hall as wellGround Floor 1/2 bath with outdoor shower Beach Side Hot TubNo Pool yet, but a new one is in the works…. 6 Adult Bikes, golf cart, 2 SUP’s and a tandem Kayak are all included

Located in Anna Maria, Florida, United States. Reel Deal: Water Views, Elevator, Pool Reel Deal by Anna Maria Life Vacation Rentals505 S Bay, Anna Maria, FL 34216What You'll Love About This Home:Location! On a Canal! Quick Walk to Bay!5 Bedrooms / 5 Bathrooms4 King Beds, 1 Set of Triple Bunkbeds (4 twin beds in this room)Private Heated PoolPool Loungers & Adirondack ChairsFurnished, Covered Poolside Lounge Area with TVPing Pong & Corn Hole2 Large Porches Overlooking Tampa Bay with Gorgeous Water ViewsPrivate Dock for Kayak & Paddle Board Launch (not large enough for boats)Elevator (to all floors)Gas GrillKeurig & Drip Coffee MakersProfessional Linen Service, Washer & DryerComplimentary WIFIBeach Towels, Beach Chairs, Beach Wagon, Umbrellas & CoolersParking for 3 Cars in Driveway & 1 Car in GarageDetails:With multiple balconies and lanais, including two overlooking Tampa Bay, this is the Reel Deal. Lovely outdoor spaces, spacious living areas, and a gorgeous pool and backyard on a canal! What more could you ask for?The main living l

Located in Anna Maria, Florida, United States. Vibrant Island Home w/ Pool, 1 Block to Beach A tropical paradise awaits when you book this stylish Anna Maria retreat! Ideally situated just 0.1 miles from the gorgeous Gulf beach and the Sandbar Restaurant, this 4-bedroom, 3-bath vacation rental comes complete with modern amenities, a newly renovated interior, and a screened-in pool and lanai that’s perfect for lounging with loved ones or grilling in the backyard. After days spent soaking up the sun, return home to rinse off in the outdoor shower and enjoy the sunset views from the porch!-- THE PROPERTY --Screened-In Pool & Lanai | Gas Grill | Keyless Entry | 1,908 Sq Ft | 0.1 Miles from Beach & SandbarIdeal for beach-lovers and snowbirds alike, 'AMI Du Soleil' - or ‘friend of the sun’ - offers at-home comforts and a prime location just steps from the shore and the island's best restaurants!Bedroom 1: King Bed | Bedroom 2: 2 Twin Beds | Bedroom 3: Queen Bed | Bedroom 4: King DaybedOUTDOOR LIVING: Large pool, sundeck w/ lounge chairs,

Located in Anna Maria, Florida, United States. 4 FREE BIKES for new fall stays Sep 3-Nov 16 FALL SPECIAL: 4 FREE bikes for reservations *booked after 8/20/24* for stays *arriving between 9/3/24 and 11/16/24*. (Provided by our friends at Beach Bums at 427 Pine Ave, Anna Maria, FL 34216. Guests will need to pick up and drop off bikes.)Welcome to Still Waters Beach House! Come rest and be refreshed in one of the most family friendly and spacious (3600+ SF) homes on the highly desirable north end of Anna Maria Island. Completely updated by new owners in February, 2021, this luxurious home is stocked with everything you need for the perfect beach vacation!Still Waters Beach House offers six bedrooms and sleeps 14 people, perfect for any size family or a multi-family group. The house offers two huge master bedroom suites with attached outdoor balcony seating, two king bedrooms with bathrooms, a queen bedroom and a bedroom with two twin trundle beds.When you wake up in the morning, head to the rooftop deck for gorgeous sunrise views of th

Located in Anna Maria, Florida, United States. Anna Maria North End Retreat, Private Pool, 250 feet from the beach The North Shore House is a clean and peaceful cottage, located in the desirable north end of Anna Maria Island, just 250 feet from the white sandy beach that stretches along the Gulf Coast. This ground level home is providing a fully equipped kitchen with stainless steel appliances, open floor plan with living room and dining nook. Linen and towels, beach chairs and beach towels are provided for your convenience. The property features 3 bedrooms and 2 full bathrooms, sleeping a maximum of 6 people. Two bedrooms have queen size beds, and one bedroom has 2 twin beds.A low wooden deck wraps around the side of the house and offers a sunny spot to relax and a fully heated outdoor shower to clean sandy feet and beach chairs.A small private pool with built-in jacuzzi jets is in the back of the house. The area is screened in to protect from “no-see-ums”, mosquitoes, and other biting insects, especially during hot summer days.

Located in Anna Maria, Florida, United States. Charming house with private heated pool, lanai. Great location to beach & shops Quaint Northshore Cottage a few blocks from the village of Anna Maria and the Gulf of Mexico beaches. Sapphire Surf is a “Old Florida” Ground Level House – No Stairs to Climb!Sapphire Surf is perfect for families, couples or a small group of friends. The house is located with an easy 4-minute stroll down Palmetto or Willow Avenue to the gorgeous white sand beaches of the Gulf of Mexico or four blocks on North Shore Dr. to historic Pine Avenue that has quaint shops, cafes, restaurants, including the General Store and Ginny’s and Jane E’s. When you’re ready to head to the beach, load up the supplied beach wagon, with the included umbrella, beach chairs, towels and sand toys for a fun day in the sun and surf.Each bedroom has a flat screen TV and plenty of dresser and closet space. The master bedroom has a king size bed and a bathroom next to it. Our second bedroom has two queen size beds with attached

Located in Anna Maria, Florida, United States. Sea 'Esta in Anna Maria, FL Welcome to Sea'Esta on gorgeous Anna Maria Island! Sea'Esta is a ground level Home that offers all the luxuries and comfort you will come to expect from staying at one of our vacation rentals on Anna Maria Island. This 2 Bed/2 Bath sweet and cozy beach home is located on North Shore Drive right on the North end of Anna Maria Island. Leave your car parked, two parking spaces are provided for this unit. This property offers a fantastic location, you are just a few flip flop steps away from the Rod and Reel pier, access to the Gulf Beach at Bean Point and all of the shops and restaurants of Pine Avenue. You are also only a very short walk away from one of our Island Trolley Stops that will take you all around the Island so you can explore with ease. Sea'Esta has been decorated and designed with relaxation and comfort in mind. Kick back and relax in the cozy living room and put on your favorite show or movie after a long day of soaking in the sun at the be

Located in Anna Maria, Florida, United States. The TipSea Turtle managed by Beach Retreats Bay Views!Contactless entryPrivate heated pool & spa3 hole mini-puttParking for 4Electric vehichle chargerFully Equipped KitchenJust over 3000 Sq feet of brand new luxury (completed March 2023)Close to Pine Ave- The Donut Experiment, The Waterfront, Popos, and all of the unique shops for souvenir searching!On our Professional Linen Service Program60' Flat Screen on LanaiWhole House Sonos Audio SystemLedge Loungers in PoolKeurigToasterToaster OvenJuicerGas GrillBeach and Pool ToysOverviewThe TipSea Turtle527 Blue Heron DriveAnna Maria, FL 34216 Brand new LUXE Property with sweeping views of Tampa Bay and the gorgeous Skyway Bridge.This custom home is nestled on a quiet, secluded dead end street in the prestigious City of Anna Maria on Anna Maria Island. No expense was spared and every detail was taken into account. This home was built with so many designer touches and features. This beautiful four-bedroom, four-and-a-half-bathroom custom

Located in Anna Maria, Florida, United States. Beachfront Home with Amazing Deck Views! Near Shops and Restaurants! -High Tide High Tide by AMI Locals Home in Anna Maria, Florida VR21-000077 Welcome to High Tide! This stunning three-bedroom and three-bath beachfront bungalow will become you and your loved one's new favorite spot. On the front deck, you can take in breathtaking sunsets and sunrises while lounging in Adirondack chairs or dining at the outdoor table while the group chef whips something up on the BBQ grill. Highlights • Beachfront • BBQ grill • Patio • Near restaurants and shops • Washer and dryer Inside is a delightful kitchen with an assortment of cookware and a dining room table set for four. From the comfortable living room sofa, you can watch TV or enjoy the beautiful beach view through the windows. Experience the ultimate comfort and relaxation in the primary bedroom with a premium mattress that guarantees a blissful night's sleep and enjoy the sparkling ensuite bathroom featuring a luxurious walk-in shower.

Located in Anna Maria, Florida, United States. Ideal Location, Stunning Villa! Close to beach, beach gear provided! ❗ Flexible check in days for most of the year--with the exception of holidays. Friday arrivals and departures during Peak Season. 🤩 If you love this rental but are not getting a quote with the dates you've selected contact us so we can check the availability for you!Seeking a private piece of Anna Maria Island charm? This Anna Maria rental is ideal for a small family, a romantic escape, or a long overdue, quiet catch-up with close friends. Palm Court is an updated villa which sleeps 4, making it perfect for smaller groups. But don’t let the small size fool you, Palm Court Villas has everything you need for the ultimate vacation.Palm Court is ideally situated in the heart of Anna Maria Village. Take a short walk to experience great shops, diverse restaurants, fishing piers and the Community Center. Beautiful white sand beaches are just one short block away and feature a wonderful row of Australian pine trees for sh

Located in Anna Maria, Florida, United States. Direct Beachfront Home, Steps to the Sand! Private Pool, Amenities for All! The Big Yellow House on Pine by Anna Maria Vacations Home in Anna Maria, FL 34216 A perfect beach getaway awaits at The Big Yellow House on Pine! This beachfront home has all the perfect amenities for a wonderful vacation, including a covered patio featuring a private pool and in-ground spa that overlook the Gulf of Mexico. With five bedrooms, four luxurious bathrooms, and multiple living areas plus a game area, you and your loved ones are guaranteed to have a memorable stay at this exquisite home. Highlights • Beachfront home • Pool and In-ground spa • Ping Pong table • BBQ grill • Washer and dryer Each floor has a spacious living area with comfortable seating, a TV, and a dining table where you can share meals with your loved ones. You'll find the main kitchen on the ground floor, while the second floor has a kitchenette for your convenience. There are two primary bedrooms, each with a premium King bed and a

Located in Anna Maria, Florida, United States. LOCATION, LOCATION, LOCATION. Great pool, close to beaches, twin family rooms! Location, Location, Location.... recently remodeled, surrounded by multi million dollar homes.....and three great beaches and the Rod and Reel Peir......this house contains 4 bedrooms, 2 baths. This four bedroom house - boasts 2 king bedrooms, two queens and a pull out couch-. Large heated pool w/sun shelf- large hot tub spa. TWIN FAMILY ROOMS, perfect for spreading the families out, washer & dryer, outdoor grill- all this is just steps from the northern most point on Anna Maria Island.

Located in Anna Maria, Florida, United States. 🏝AMI’s local LANDMARK🏖The BLUE HOUSE on PINE 🐬Casa Calienta🐬 🌀CASA CALIENTE 🌀 A spectacular and truly MAGICAL place to experience.🐬 AMI,fl This 2 bed , 2 bath home is a spectacular, and truly a special place to experience. Along with a queen size pull out couch. This local landmark, 🛏sleeps 6 very comfortably . Owner is willing to book less than 7 nights, upon request. ( if able )..CASA CALIENTE Talk about detail 🌞 This perfectly located, blue 💙 beach cottage, was built for entertaining. With it’s sprawling open floor plan, that opens up into the kitchen, dining, and living room. IT Is Sure to please guest of any size. As you enter this blue beauty, you will notice the detail and love it offers. The plush designer furnishings come with much comfort, as well as practicality. 🌴 ♨️CASA CALIENTE♨️Is detailed with only the finest upgrades. 🎼From the Niles Sound System, That allows you to stream from your own device, 📱through out the home, and the pool area, As well as the numerous flat scr

Located in Anna Maria, Florida, United States. Brand new luxury Home! Pool, Rooftop Deck, walk to the beach! -The James The James by AMI LocalsHome in Anna Maria, FL 34216The James is the ultimate beach getaway, featuring four bedrooms and four and a half baths, just moments from Anna Maria's renowned beaches. Enjoy incredible amenities, including a rooftop deck with breathtaking beach views, an array of games, and a picture-perfect backyard with a sparkling pool with swim-up bar seating, an in-ground spa, and a sunshelf.Highlights • Brand new construction home• Located on the coveted north end of Anna Maria Island• 5-minute walk to the beach (less than .2 miles)• Private pool with in-ground spa • Rooftop deck • Games • Outdoor living space • 6-minute walk to popular Rod and Reel PierAscend the stairs to your new modern oasis, where an open living space awaits with a chic seating area with a TV and a gorgeous fully equipped kitchen features stainless steel appliances, culinary essentials, and an island bar with barstools. This home

Located in Anna Maria, Florida, United States. 4 FREE BIKES for new fall stays Sep 3-Nov 16 FALL SPECIAL: 4 FREE bikes for reservations *booked after 8/20/24* for stays *arriving between 9/3/24 and 11/16/24*. (Provided by our friends at Beach Bums at 427 Pine Ave, Anna Maria, FL 34216. Guests will need to pick up and drop off bikes.)Treat yourself to the beachside vacation you’ve been dreaming of with this relaxing and dog-friendly Anna Maria vacation rental! You'll enjoy a premium location by the beach, a breezy atmosphere, and great amenities like a private pool.This home is only two blocks from some of the island's finest beaches. When you're not enjoying the soft sands, you can stroll to Anna Maria's Pine Avenue for shopping, dining, and art only three blocks away. When you're ready to explore the rest of the island, use the free trolley to visit Holmes Beach and Bradenton Beach. With parking for four cars, you're free to drive around the island if you'd prefer and always have a spot when you get back home.Back at the house, yo

Located in Anna Maria, Florida, United States. Anna Maria Northshore beauty !" Come for the sun, stay for the fun!" Enjoy The Good Life! In our unforgettable Beach Home.The property was built to standards for guests who demand the very best. The high ceilings, oversized windows, and light walls create a feeling of space, and with the addition of a spacious balcony at the front of the house, you can always grab a quiet moment alone with a favorite book. The pool area is surrounded by string lights that create a magical and lively evening environment. Your family can reunite in many places and enjoy our recliners, decks, family room, or pool area couches. Pick your spot. No matter what, you will always enjoy the house location and the many amenities provided. Every effort has been made to create something unique, from the sumptuous bed linens to designer bathrooms, to the tasteful decoration. BEDROOMS Offering flexible and spacious accommodation, the bedrooms are light and airy and all feature luxurious bed linens, sumptuous mat

Located in Anna Maria, Florida, United States. 4 FREE BIKES for new fall stays Sep 3-Nov 16 FALL SPECIAL: 4 FREE bikes for reservations *booked after 8/20/24* for stays *arriving between 9/3/24 and 11/16/24*. (Provided by our friends at Beach Bums at 427 Pine Ave, Anna Maria, FL 34216. Guests will need to pick up and drop off bikes.)Relax in this beautiful, bay view home! Bridgeview is the perfect vacation home for large family or multi-family getaways located on the charming northern end of Anna Maria Island. This beautiful home offers 4 bedrooms plus a bunk room and 5 full bathrooms which can accommodate up to 12 in beds. Wake up every morning with a cup of coffee to the sounds of the surf coming in, dolphin watching and enjoy the sunrise from your back patio or rooftop deck. You can take in the breathtaking views of the bay waters from the 2 decks in the back of the house, the Marina from the front deck and the island and ocean waters from your rooftop deck. Enjoy a swim in the private heated pool or relax in the hot tub after a