58,368 properties available

Located in Anna Maria, Florida, United States. Beachology: 1 Block to Bean Point Beach, Pool, Game Room by Anna Maria Life Vacation Rentals 749 Jacaranda, Anna Maria, FL 34216What You'll Love About This Home:Location! Bean Point Across the Street! 2 Min Walk To Beach!5 Bedrooms / 3.5 Bathrooms4 Kings, Set of Queen over Queen BunkbedsElevator (access to all 3 levels)Private Heated PoolPool LoungersOutdoor ShowerGas GrillCovered Poolside Lounge Area with FurnitureGarage Game Room with TV, Ping Pong & Foos BallCornholeBalcony with Lounge FurnitureProfessional Linen Service, Washer & DryerComplimentary WIFIBeach Towels, Beach Chairs & Beach WagonParking for 4 CarsDetails:Located on the coveted North End of Anna Maria and one block to Bean Point, Beachology is your beach vacation retreat. Magical sunsets, sun, surf and the sugar sand beach will welcome you home.The open and spacious floor plan features seaside and beach decor. The dining room has seating for eight with additional kitchen counter stools for four. Relax together with your

Located in Anna Maria, Florida, United States. Bikini Bottom: One Block to Pine,3 Blocks to Beach, Dog Friendly, Pool, by Anna Maria Life 302 Spring Ave, Anna Maria, FL 34216What You'll Love About This Home:Location! 5 Min Walk to Gulf! 5 Min Walk to Bay!4 Bedrooms / 4.5 BathroomsHeated Pool & SpaPool LoungersOutdoor ShowerPoolside Lounge Area with Swings & FurniturePool Level Indoor Living Room & Game Room with Foos Ball & Ping Pong TableOutdoor Patio Dining (4 Top)Gas GrillFurnished Roof Top Deck with Amazing Views of Gulf & Bay!Keurig & Drip Coffee MakersDog Friendly (with fee - see notes below)Fenced YardBeach Towels, Beach Chairs & Beach WagonDriveway Parking for 4 CarsDetails:Located in the heart of Anna Maria, Bikini Bottom is a block from Pine Ave and two blocks to the City Pier. A quick walk to the end of Spring Ave leads you to the shimmering waters of the Gulf of Mexico. You have found paradise!Our three-level beach retreat provides guests with lovely gathering places inside and out. The main living level on floor two co

Located in Anna Maria, Florida, United States. Sea Star by Beach Boutique Rentals Ideally located just steps from the beach, Sea Star offers a unique 3 bedroom vacation home with carriage house for a perfect family getaway.*Features include* * Private yard with sparkling heated pool * Gourmet kitchen * 3 bedrooms, 3 luxurious full bathrooms * 2 master suites, one located in the carriage house* Fun bunk bedroom for the kids* Sleeper sofa* Washer and dryer * Expansive patio with loungers and covered recreational area* Outdoor dining and gas grill* Ping-pong and cornhole* Beach chairs, umbrellas, beach toys * Steps to Bayfront Park and the bay beachNestled in the heart of Anna Maria, Sea Star awaits. This beachside sanctuary offers the perfect blend of comfort, style, and convenience, with direct beach access to Bayfront Park.Sea Star is a unique 3 bedroom, 3 bathroom home. The entire house is elevated, providing a huge outdoor covered area below for playing games or taking in some shade by the pool. Upstairs, you will find a main 2

Located in Anna Maria, Florida, United States. AMI Retreat: 200 Steps to Beach, Dog Friendly Pool Home by Anna Maria Life Vacation Rentals AMI Retreat by Anna Maria Life Vacation Rentals746 Jacaranda, Anna Maria, FL 34216What You'll Love About This Home:Location! AMI North End! 200 steps to Beach!3 Bedrooms / 2 Bathrooms2 Kings, 1 Queen, 1 TwinPrivate Heated Pool & Spa*Pool LoungersOutdoor ShowerGas GrillCovered Poolside Patio DiningOutdoor Patio Dining on Upper DeckBumper Pool, Air Hockey, CornholeProfessional Linen Service, Washer & DryerComplimentary WIFIDog Friendly - with pet fee - see info belowBeach Towels, Beach Chairs, Beach WagonParking for 4 CarsDetails:AMI Retreat is located 200 steps to the sugar sand beaches and sparkling clear waters of the Gulf of Mexico. With a prime location on the North End of Anna Maria, AMI Retreat is close to Bean Point and Pine Ave.The main level includes the kitchen, dining and living rooms. The living room is a comfortable spot for the family to relax. The dining room features a table for s

Located in Anna Maria, Florida, United States. Beach Escape: Pool, 1.5 Blocks to Bay, Walk to Bean Point 236 Gladiolus St, Anna Maria, FL 34216What You'll Love About This House:Location! 1.5 Blocks to Bay & Bayfront Park. Walk to Bean Point3 Bed / 2.5 BathKing, 2 Fulls, Queen, Queen Sofa BedPrivate Heated Salt Water PoolOutdoor ShowerPool Loungers & Adirondack ChairsPool Level Screened Patio with Dining Table & Bar & TVSeparate Entrance In-law Bedroom on First Level (queen bed), 1/2 bath also on this levelScreened Furnished Wrap Around PorchGas GrillKeurig & Drip CoffeeFenced YardProfessional Linen Service, Washer & DryerComplimentary WIFIBeach Towels, Chairs & WagonParking for 4 CarsDetails:Located on the coveted north end of AMI, Beach Escape is a quick walk to Bayfront Park, Bean Point, Pine Ave and the City Pier. Location is everything!Our elevated beach house invites you to relaxation and family fun! With a wraparound screened in porch, the comfortable living room is bathed in natural light. The kitchen features counter bar se

Located in Anna Maria, Florida, United States. North end canal front home ,tiki hut, dock, heated pool, spa,beaches.... Single family quiet vacation home on Lake La Vista has it all... Incredible view with Roser Church across the canal. This home is tucked away on an incredibly landscaped lot that had winding paths around the home leading to tikis and the pool area and the dock. Listen to the church bells ringing on Sunday Morning or walk to church, numerous restaurants, and beaches. Bring your boat for the week... This home has a heated pool, jacuzzi, two tiki areas for eating or relaxing with a card game, an indoor pool table and a private dock. We rent Saturday to Saturday most of the time. Please let us know if you wish to book outside these days. We try to make all happy...... please let us know and we will get back with you as soon as possible. This is a seven night minimum Saturday to Saturday stay.Boaters.... A humpback bridge spans the canal before you can access Tampa Bay with a clearance of approximately 7’ at high

Located in Anna Maria, Florida, United States. Private pool, 1 Block to beach, Putting Green - Lady from the Sea Highlights • Less than a 10-minute walk from the beach • Private pool • Putting Green• Outdoor living space• Near restaurants and shopsLady From The Sea by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR18-000156 Welcome to Lady From the Sea, a fantastic north-end vacation home on Anna Maria Island with a private pool and putting green that is a six-minute walk to Bean Point Beach! This rental has three bedrooms and three and a half bathrooms. Friends and family can gather and connect on the oversized sectional in the welcoming living room, where conversations flow smoothly, and plans for island adventures are made. The modern, updated coastal kitchen is a centerpiece where guests can easily prepare meals and snacks. It is fully equipped and has countertop seating for quick snacks before heading to the beach. Serve home-cooked meals or Anna Maria Island take-out at the dining room table, outside on th

Located in Anna Maria, Florida, United States. BEST LOCATION! NORTH END OF ANNA MARIA, FL , STEPS TO BEACH & DINING , UNIT B Location, Location, Location! The home located on the very desirable quiet north end of Anna Maria, Florida . This charming two story duplex- each unit has two bedrooms , one bathroom. Rent one unit or both. Perfect for a group of extended family and friends who want their own place but still be right together as a group. Heated inground pool, steps to the Bean Point Beach and everything you need for your perfect Anna Maria Vacation. Parking is right at the front of the property. Very short walk to the white sandy north end beach. Close enough to run for lunch and return for the most amazing sunsets. Includes beach chairs, umbrellas, coolers and all you need for a perfect day at the beach!If you like to fish, grab your fishing pole and walk few minutes to the Rod and Reel Pier. Heated pool , private seating and grilling areas. The house is fully equipped with all linens, kitchen equipment, WIFI and more. Low

Located in Anna Maria, Florida, United States. Bean Point Beachfront- Beachfront 4 bedroom private home with pool/spa At A GlanceGulf-Front, Beach side HomeSpacious Backyard Deck with Covered Dining Area, TV & Gas BBQ GrillNEW Private Heated Pool with SpaUpstairs Master Suite with Private BalconyIncredible Views of the Gulf From All 3 LevelsShort Walk to Bean Point and Rod-n-Reel PierNEW and Fully-Equipped Kitchen + Washer/Dryer3 Parking SpacesCable TV, Unlimited Local & Long Distance, WIFI, and 5 TV'sOn our Professional Linen Service ProgramOverviewBean Point Beachfront795 North Shore Dr.Anna Maria, Fl. 34216With an exterior that matches the crystal clear, teal waters of the Gulf of Mexico and literally located on Bean Point Beach, Bean Point Beachfront is a highly sought-after rental perfect for Florida beach-goers. With newly updated interior features, a brand new private pool, and views to die for, there is no question that this home is everything you’d need for a memorable Florida vacation.When pulling up to Bean Point Beachfr

Located in Anna Maria, Florida, United States. 4 Bed 4.5 Bath Family Friendly, 3 Blocks to Gulf You won't be disappointed with this brand home! This home has 4 bedrooms each with an en-suite washroom, home is located in the heart of ANNA MARIA ISLAND! When you come up the stairs you are greeted by beautiful coastal decor in soft hues of light blues and corals. The open living, dining, and kitchen areas are the perfect spot to host a family meal, game night, or just relax and take a load off. The kitchen has Jenn-Air appliances that are accented by a beautiful white backsplash and white custom cabinets! The living room opens up to a spacious back porch that overlooks the spacious freeform swimming pool! The entire home was professionally decorated with luxury and comfort in mind. The dining room seats 8 comfortably, and the kitchen island seats 4. The home is a few blocks walking from Anna Maria's famous shopping district, Pine Ave. If you ever want to leave your private oasis, the home is a short five-minute walk to the white sandy

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.)8 palms is a beautiful 3 bedroom 2 bath home on the North end of Anna Maria Island. The property is newly renovated and has a gorgeous boho beach theme. The standout is the oversized pool area! The backyard is your mini oasis with a large pool, hot tub, turf throughout, putting green, and covered patio with TV. The property has indoor laundry with a stacked washer and dryer. The kitchen includes everything needed to cook and enjoy meals at home! 8 Palms has the perfect location! A quick 5 minute walk to Pine Avenue where you can enjoy visiting boutiques and restaurants and a 10 minute walk to the Gulf Beach. Bedroom 1: King BedShared Bath 1: Combination Tub/ShowerBedroom 2: King BedBedroom 3: 2 Bunks (2

Located in Anna Maria, Florida, United States. Sea Whisper in north-end Anna Maria with private dock and pool Welcome to Sea Whisper, our brand new renovated home with 3 bedrooms / 3 bathrooms, private dock, swimming pool, and spacious backyard. Located at the tranquil north end of Anna Maria Island but still just two blocks from Pine Ave, our private bungalow has everything you need for a perfect beach getaway! Sailboat directly to Bimini Bay, walk to the gulf side of the island or the City Pier. Has large screened porch; full kitchen with cooking essentials; Smart TV, WiFi; central air; washer/dryer.Get the most out of your vacation by enjoying our spacious backyard that connects directly to our private dock and swimming pool. Fire up the grill or enjoy a relaxing drink on the screened porch; take a dip in the pool, which can be heated; boat or kayak directly from the dock into Bimini Bay. The private dock is also a great way to experience the plentiful island wildlife; you'll be sure to see fish, birds, and even manatees from t

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.)"Emma's Cottage" is located on the north end of Anna Maria Island in the City of Anna Maria. It is offered exclusively through Sato Vacation Rentals. Rich history and beautiful antiques await you. Built in 1912, one of four Gulf front Anna Maria homesteads known as the "Painted Ladies", Emma's boasts a spectacular view of the sand and sea which beckons the soul.Relax on the wraparound front porch with your morning coffee, refresh your spirit in the very private backyard tropical oasis, stroll to delightful North End restaurants such as Ginny and Jane E's and The Sandbar, or experience the boutique, local flavor of Pine Street. No matter how you decide to make Emma's your home away from home, you will

Located in Anna Maria, Florida, United States. Quiet North End Home Only 2 Blocks to Beach with Private Pool Highlights• 5-minute walk from the beach• Private Pool• Outdoor showerOur Place By The Sea761 Jacaranda RdAnna Maria, FL 34216VR16-000359Welcome to Our Place By The Sea, an inviting vacation home with a private pool on the quiet north end of Anna Maria Island just a five-minute walk from secluded Bean Point Beach! This ground-level home has three bedrooms and two and a half bathrooms. You and your guests can gather and connect in the welcoming living area and in the second living area where conversations flow and Anna Maria Island plans are made. The fully-equipped kitchen has an island that makes meal and snack preparation easy and has countertop seating for quick snacks. Guests can enjoy home-cooked meals or the best Anna Maria Island takeout in the dining room or at the patio table. Catch up on the much-needed sleep primary bedroom that has coastal colors, a private deck perfect for morning coffee and evening drinks, and

Located in Anna Maria, Florida, United States. Canary Cottage Perfect modern cottage, quiet street, short walk to the beach! The Canary Cottage has 2 bedrooms and 2 full baths and will Sleep up to 6. Located in the heart of Anna Maria City- This Key West charmer is elevated and has been updated with a new kitchen,  new tile, fixtures, plus a new tub/shower! Updated furnishings, and appliances, which add to the charm plus it has been painted (exterior and interior) with updated cheerful island colors! The outside deck is great for enjoying your morning coffee or evening margarita! Its quiet location is perfect and it is just a short flip flop stroll to several quaint cafes (Just 2 short blocks to Ginny & Jane-E's and the Sandbar Restaurant), shops, ice cream parlors, and the most pristine beaches the island has to offer. The community center is across the street with tennis courts, and community events all year long.Sleeps 6. The Master bedroom has a king size bed. The guest bedroom has a Queen size bed. There is a sleeper sofa i

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 Sundowner Beach! This luxury gulf-front property offers everything you need to enjoy the perfect beach getaway! Take in the beautiful panoramic views of the white sand beach from the large balcony while you dine al fresco in the sunset.This modern beach house is filled with gorgeous furnishings creating a chic and comfortable home for your stay. Located in a quiet neighborhood at the north end of the island, Sundowner Beach has its own private gate directly to the beach. The property is ideally located just 10 minute beach walk from beautiful Bean Point. The shops of Pine Avenue and The Sandbar, one of Anna Maria's most popular beachfront restaurants, are also within 10 minutes beach walk t

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.)What more could you want from a vacation rental then a beautiful Mediterranean inspired canal home nestled into the private North End of Anna Maria Island? Mediterranean Canal Retreat is the perfect escape for those looking to relax enveloped in the simplicity and peacefulness that is Anna Maria. This four bedroom, two bathroom home has a spacious and fully equipped kitchen and large area for entertaining or relaxing, a heated pool and dock with gorgeous views of our luscious mangrove landscape. Too much sun by the beach or pool? Relax under one of the covered porches and let your worries fade away. In the mood for a little entertainment? You are just a short trip to Anna Maria's newest boutique distric

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 The Salty Beach Cottage, a comfortable and inviting family vacation home. Decorated with a refreshing palette of crisp whites, warm reds and ocean blues, this island-styled home has the power to enchant the eye and soothe the soul. The Salty Beach Cottage is brimming with an eclectic mix of art from full-color vintage Florida travel advertisements to original artwork. The large mirrors are covered with shells that the owners children found on our own beaches. Try shelling for yourself as just a short walk away are some of the very best Gulf Coast beaches. Upon your return from the beach, take a dip in your own heated pool or enjoy kayaking through the canals with the 2 kayaks available. Sleep

Located in Anna Maria, Florida, United States. Unique Island Home on the beach block! Private pool! Blue Crush by Anna Maria Island Accommodations Home in Anna Maria, Florida Welcome to Blue Crush, a fantastic vacation home with a sparkling pool near Pine Avenue’s shops and restaurants and a quick walk to the sugar-white sands of the Gulf of Mexico. This four-bedroom and three-bathroom getaway features a second kitchen off the pool deck, making it perfect for hosting family and friends with island style. Highlights • Less than a 5-minute walk from the beach • Private pool • Two kitchens The comfortable living area has pocket sliding doors that open onto the large outdoor deck, perfect for having drinks and delighting in the breeze. There are two fully equipped kitchen, with stainless steel appliances, and broad countertops with island seating. The sun-kissed primary bedroom is your dream oasis, with a private balcony, plush seating, and a fabulous walk-in closet. The luxurious ensuite bathroom has a double vanity, a spa-l

Located in Anna Maria, Florida, United States. Luxurious Private Canal Front Home with Resort Style Pool! - Banyan Manor Banyan Manor by AMI AccommodationsHome in Anna Maria, FL Welcome to Banyan Manor! This stunning four-bedroom, four-bath canal-front rental on Anna Maria Island is a dream retreat. Just a five-minute walk from the Gulf of Mexico and near popular restaurants and shops on Pine Ave, this home offers an unforgettable getaway.Highlights • Canal front home • Private 50ft dock • 5-minute walk to the beach • Pool with in-ground spa • Pool Table • Ping Pong table • Elevator • Built-in BBQ grill • Resort-style backyard The main living area exudes modern excellence with professional decor, naturally brightened by floor-to-ceiling windows and doors leading to furnished balconies. You’ll love the gourmet kitchen, dining area, and spacious seating area with a large sectional couch, side chairs, and smart TV. Use the elevator or stairs to access the second living space with premium seating and a table for four.Each bedroom feat

Located in Anna Maria, Florida, United States. Anna Maria Island, NORTH END 3 bedroom, pet friendly, private pool home! Paradise found in this 3 bedroom, 2 bath pet friendly, home on Anna Maria Island! This family home is just 1 block from the pristine white sandy beaches on the Gulf of Mexico and has a private heated pool. Fully furnished in coastal style and with all the luxuries of home for a stress free vacation. Located in the prestigious North End of the Island.The home offers a tropical pool with a lounging and dining area for enjoying a late afternoon snack or a sunset meal. The master bedroom leads to the pool area and its lush tropical surroundings.The master bedroom offers a king size bed overlooking the pool. The second guest room offers a full size bed and the final guest room offers a set of twin size beds. The living room has a pull our couch for additional sleeping. There are two full size bathrooms with bath tub and shower.You can't beat the accommodations this home offers! Fully furnished kitchen with all the comf

Located in Anna Maria, Florida, United States. Back To Blue: Amazing Bean Point Location, Resort Style Backyard with Pool by Anna Maria Life 850 North Shore Drive, Anna Maria, FL 34216What You'll Love About This Home:Location! AMI North End! Walk to Bean Point! Across the Street from Bay!4 Bedrooms / 4 BathroomsFour King Beds / One Queen Sofa SleeperPrivate Heated Pool & SpaIn Pool Lounge ChairsPrivate Outdoor Shower & Foot Wash StationsPool Level Covered Lounge & Recreation Room with Foosball & TVPing Pong & CornholePuzzles, Games & BooksGas Grill2nd Level Deck - Patio Dining for 6Outdoor Patio Dining & Picnic Table (Pool level)Guest House with Separate Entrance - Studio with King Bed, Full Bathroom & KitchenBeach Towels, Beach Chairs, Beach WagonParking in Driveway for Four CarsDetails:Located on Anna Maria's coveted North End, Back to Blue is walking distance to Bean Point & the Rod & Reel Pier.Our elevated home features luxury living and dining spaces with panoramic views of the bay. The full kitchen is available to create a ho

Located in Anna Maria, Florida, United States. Perfect Family-Friendly Home with Putting Green, Pool, and Games The 19th Hole by Anna Maria Island Accommodations 238 Gladiolus St, Anna Maria, FloridaVR21-000087Welcome to The 19th Hole! This family-friendly vacation home features three bedrooms and two bathrooms. Just a short walk from stunning Bay beaches and less than fifteen minutes to the pristine Gulf beaches, it's perfectly located. Anna Maria Island's famous Pine Avenue is less than a 10-minute stroll away, offering shops, restaurants, and the historic City Pier.Highlights • 7-hole putting green • Private pool with in-ground spa • 3-minute walk to bay beaches • 12-minute walk to Gulf of Mexico beaches • Ping pong table • Outdoor bar • BBQ grill • Convenient location near dining and shopping • Outdoor living space • Washer and dryer Adorned with chic decor and high-end furnishings, the great room is designed for relaxation. The spacious kitchen boasts stainless steel appliances, a wine fridge, and island seating for six. Just

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.)Gorgeous and spacious is this 4 Bedroom/3 Bath Home in a desirable north-end location, just steps to Historic Pine Avenue and all of its great shops, eats, and treats. As large of a home as this is, it is not to be out done by its expansive back yard. Ultra private and densely landscaped with heated pool, hot tub, garden area, and tons of seating to include plenty of loungers, multiple outdoor dining options, umbrellas galore, and an outdoor sound system. After a long day at the beach rinse off in the full outdoor shower. The main living level offers an open concept floor plan with kitchen, living room, family room, one of the King bedrooms, and a full bath. The uppermost level contains the master bedro