211 properties available

Located in Anna Maria, Florida, United States. Canal front home with a pool and boat dock! Highlights• Canalfront with dock• 5-minute walk to the beach • Private pool• Putting green • Pool Table and Ping Pong TableShore Bet by AMI Locals 220 Periwinkle PlzAnna MariaVR21-000037Welcome to Shore Bet, a spectacular canalfront vacation home with a private pool and dock just five minutes from the beach! This rental has three bedrooms and three bathrooms. The open modern living area has large windows that let in the bright Florida sun and gives guests a relaxing place to connect with friends and family or have a movie night. Additionally, the living space opens up to the screen-in patio with stunning views of the canal for guests to enjoy while relaxing and discussing Anna Maria Island activities. The fully equipped kitchen has plenty of space for making homemade island-inspired meals and snacks for the beach. Guests can enjoy a quick bite to eat at the kitchen island and enjoy homemade meals and the best Anna Maria Island take-out at the

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.)Experience the ultimate beachfront luxury at the Beach House! This stunning home, meticulously crafted and adorned in 2022, sits proudly on the northern end of Anna Maria Island. With every lavish amenity imaginable, it promises to delight the entire family.Step through the entryway to be greeted by your own private beachfront oasis. Dip into the heated pool or unwind in the hot tub, all while soaking in panoramic views of the Bay. Adventure awaits with included paddle boards and a tandem kayak for exploring the glistening waters.Indulge in 3,000 sq ft of open-concept living space on the main level, perfect for post-sun relaxation. Watch dolphins frolic in Tampa Bay from your balcony or cozy up for a mo

Located in Anna Maria, Florida, United States. Golf Cart, Bimini Cove by SeaBreeze Vacation A 6-person electric golf cart is included with any new reservation for this property! You must be 21 years old and show proof of US driver's license and vehicle insurance.You'll fall in love with this incredible bay front 5 bedroom/6 full bathrooms home with a separate suite, having 2 full-size kitchens on the sought-after north end of Anna Maria Island! Short distance to the white sandy beaches and only minutes to restaurants and shops. The space is very modern and airy, with high ceilings and upscale furnishings. Heated pool, private dock, gas BBQ grill, and all the amenities you need to live a VIP island experience!The entry leads you to either the main home or the separate suite off to the left. Upon entry to the main home, you will find a sitting area complete with a wet bar, fridge, and wine cooler where you can make and enjoy an evening cocktail. The fully-equipped kitchen features a gas stove and everything you will need to make a f

Located in Anna Maria, Florida, United States. FREE WiFi & Trolley ONLY STEPS to Pristine Sandy Beach NO Roads to Cross! **ASK ABOUT LAST MINUTE DEALS! Island fun is easy in this 2 unit charming cottage located two houses from the beach. Enter through a screened-in porch to a Newly remodeled seaside haven. Coastal charm throughout, Sun and Seadar South, features 2 bedrooms and 1.5 bath. Rest in comfort with a King bed in one bedroom, and a trundle with a twin bed in the second bedroom. Prepare your meals on the gas grill or stroll a few blocks for a meal at on of the many family owned restaurants on Pine Ave and Gulf Drive. No worries about traffic on this quiet dead end street. Play at the beach all day and be close enough to come home for lunch. Outdoor shower for easy clean up before entering. This unit has a connecting door to Sun and Seader North if you want to rent both sides for extended family or visiting friends. While we know you love your furry friends

Located in Anna Maria, Florida, United States. Pine Ave Hideaway: Secluded Bungalow on Anna Maria`s North End! Pine Avenue HideAway is a secluded Beach Bungalow tucked away on Historic Pine Avenue on Anna Maria's North End. Conveniently located in the heart of it all, and just a short stroll to the beach, restaurants, boutiques, Anna Maria City Pier and a trolley stop to explore Anna Maria the islanders way!This modern and stylish, two bedroom, two bathroom beach bungalow offers wood floors throughout, stainless appliances, and granite counter tops giving you a cozy coastal feel! The kitchen is fully-equipped but if you prefer to cook outdoors; there is a propane grill available along with outdoor dining for four on the over-sized private deck with a hot tub to relax in after a day of shopping the Boutiques and Restaurants nearby. There are also three Flat Screen TV’s with cable access, Wi-Fi, and a full-size washer and dryer to make your stay enjoyable!

Located in Anna Maria, Florida, United States. AMI Boathouse:Dog Friendly Canal Front Pool Home North End of AMI by Anna Maria Life AMI Boathouse by Anna Maria Life Vacation Rentals520 Loquat, Anna Maria, FL 34216What You'll Love About This Home:Location! AMI North End! On Canal! Bring the Boat!3 Bedrooms / 2 BathroomsCalifornia King, 2 Kings, 2 QueensPrivate Heated Pool & Spa*Pool LoungersOutdoor ShowerCovered Poolside Lounge Area with TV & Patio Dining55' Boat Dock - No Bridges to get out to Tampa BayPing Pong, Oversized Connect Four Game, Corn HoleGas GrillProfessional Linen Service, Washer & DryerComplimentary WIFIDog Friendly - with pet fee - see info belowBeach Towels, Beach Chairs, Beach WagonParking for 4 Cars & Room for the Boat TrailerDetails:AMI Boathouse is a canal front home on Anna Maria's coveted North End. Bring the Boat! The dock can accommodate a 55' boat and the canal provides easy access to Tampa Bay.The main level includes the kitchen, dining and living rooms. The dining room features a table for eight with fou

Located in Anna Maria, Florida, United States. Island Breeze: Steps to Beach, Heated Pool & Spa, Huge Verandah by Anna Maria Life Vacation Rentals 119 Beach Ave, Anna Maria, FL 34216What You'll Love About This Home:Location! 5 Houses to the Beach!2 Bedrooms / 2 Bathrooms1 King Bed, 2 Twin BedsHeated Pool & Spa (Spa only heats to the temp of the Pool)Pool LoungersCovered Poolside Lounge with Adirondack Bar Chairs & TVFenced YardCharcoal GrillVerandah with Rocking Chairs & Patio Dining Table for FourKeurig Coffee MakerProfessional Linen Service, Washer & DryerComplimentary WIFIBeach TowelsParking for 4 Cars (2 Driveway & 2 Covered Carport)Details:Island Breeze is our elevated beach house on Beach Ave located 5 houses to the beach! That's a lot of beach in one sentence! With such a great location, it's worth repeating.The perfect balance of indoor and outdoor spaces await your family vacation. The main living space is on level two and includes kitchen, dining area and living room and two bedrooms. Enjoy your morning coffee in one of t

Located in Anna Maria, Florida, United States. Hidden Oasis - DIRECT BEACHFRONT DUPLEX - 1BR/1BA Anna Maria - By Island Real Es Hidden Oasis is beautiful 1-bedroom 1-bathroom duplex that’s perfect for an island stay. The décor will make you feel right a home, while giving you a sense of island living with Gulf colors throughout. This home has everything needed to make your stay on Anna Maria Island a vacation to remember. Prepare meals in the spacious kitchen, loaded with a full range of appliances. You can enjoy those meals with your family and friends in the dining area, or out on the covered balcony. From the covered balcony you can enjoy splendid views of the Gulf of Mexico, as well as the Bean Point Beach. When you aren’t taking in the breath-taking views of Anna Maria Island feel free to lounge and relax in the living area. There you can catch up on your favorite shows on the flat-screen TV.Some of the best views and places that Anna Maria Island has to offer surround Hidden Oasis. The cerulean waters of the Gulf of Mexico ar

Located in Anna Maria, Florida, United States. Coconut Lagoon - Lovely Historic Renovated Cottage w/Huge Heated Pool & Backyard Oasis/Cabana/Bar Welcome to Coconut Lagoon!On Anna Maria Island (Anna Maria, FL)Ground Level Completely Updated Luxury Historic Home3 Bed (sleeps 6), 2 1/2 Bath with Heated Pool easy walking distance to Pine Avenue and Gulf side beachesHIGHLIGHTS:- Kitchen, Dining Area, Living w/ TV- 1 Queen Bedroom w/ TV and ensuite full bath- 1 Queen Bedroom- Loft Bedroom with 2 Twins (can be converted into King with advance notice)- Hall Full Bath- Loft Half Bath- Covered Screened-in Front Porch- Covered Cabana in Pool Area w/ TVKitchen:Stove, Oven, Microwave, Refrigerator/Freezer, Coffeemaker (12 cup), Blender, Crock Pot, Toaster, KitchenwareOutdoor Area:Heated Private Pool, Grill, Outdoor Shower, Outdoor Seating, Outdoor Covered Cabana w/ TV & BarLaundry:Washer/DryerParking:2-3 Cars in DrivewayAMENITIES:A/C, Heat, Cable Television, Wireless Internet, Linens, Towels, TV's, Hair Dryers, Iron/Ironing Board, Beach Towels*

Located in Anna Maria, Florida, United States. Cottage with Private Pool, Tropical Landscaped Backyard, Near Beach Highlights• 7-minute walk to the beach • Private Pool• 1-minute walk to Pine Ave • Outdoor showerCovey Cottage418 Spring AveAnna Maria, FL 34216VR16-000292Welcome to Covey Cottage, an inviting vacation home in the heart of Anna Maria Island, with a tropical landscaped backyard and a swimming pool just a one-minute walk to shopping and restaurants on Pine Ave and a seven-minute walk to the beach! This vacation getaway has three bedrooms and three-and-a-half bathrooms. Friends and family can relax in the welcoming living room, enjoy conversation, watch movies, and discuss Anna Maria Island activities. The fully equipped kitchen has stainless steel appliances and granite countertops that make snacks and island meals a breeze. Use the island to make beach snacks, prepare your family’s favorite recipe, or set up delicious Anna Maria Island take-out. Additionally, there is a Florida room where you and your guests can deligh

Located in Anna Maria, Florida, United States. Private Bungalow with Pool, Perfect for Family Vacations! - Hav'Anna Daydreamin Hav'Anna Daydreamin by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR16-000403 Welcome to Hav'Anna Daydreamin, where you can unwind and have a great time! This vibrantly blue-themed vacation home has three bedrooms and two well-equipped bathrooms. You and your guests will love the spacious backyard, which features a sparkling pool and ample comfortable seating for guests to soak up the Florida sunshine. Highlights • Less than a 5-minute walk to the beach • Private Pool (Heated seasonally) • BBQ grill • Near Anna Maria Island trolley stop • Outdoor shower As you step inside, you will be transported into a vibrant, nautical-themed living space with cozy seating, a TV, and a rustic table. The kitchen has a full suite of stainless steel appliances and culinary essentials that make cooking a breeze. In addition to the kitchen island seating, there is a formal indoor dining room table. The pri

Located in Anna Maria, Florida, United States. Island Home with Private Pool, Oversized Front Porch, and Poolside Dining! Highlights • Less than a 10-minute walk to the beach • Private pool • Ping pong table • Outdoor shower • Washer and dryerBeachcombers by AMI Locals 317 Spring Ave Anna Maria, FL 34216 VR16-000284 Welcome to Beachcomber, a centrally located home on Spring Avenue where you can find activities in every direction to unwind and indulge in the local Anna Maria Island style. With easy access to Gulf Beaches, Bay Piers, shopping, and restaurants just a few short blocks away, your guests will find endless possibilities. Whether relaxing in the backyard pool, enjoying refreshments on the oversized front porch, or dipping your toes in the sandy beaches of Anna Maria Island Beach, you will find this home a perfect place for your guests to experience the best Anna Maria Island has to offer. Beachcomber is a three-bedroom and two-bathroom vacation home. As you enter, the open concept living space welcomes you with coastal d

Located in Anna Maria, Florida, United States. Dog Friendly Cottage - Near the Beach and Shopping! Aquaville B by AMI Locals Home in Anna Maria VR18-000018Welcome to Aquaville B, a three-bedroom and one bath beach-style cottage, nestled in a quaint, coastal neighborhood that is just a quick stroll from Anna Maria Island Beach and Palmetto Ave Beach! The backyard has lush landscaping that surrounds the pool and outdoor seating to create a private oasis. Aqua Ville B is located on the north end area of Anna Maria Island and is surrounded by lovely boutiques, locally owned restaurants that serve delicious meals, and activities for the whole family! Highlights• 5-minute walk from Anna Maria Island Beach and Palmetto Ave Beach• Private Pool • Pet Friendly • Less than a 5-minute walk from Pine Ave shops and restaurants• Outdoor seating areaFall in love with your new home away from home that features a kitchen with cooking essentials including pots, pans, and utensils, a dining table, and a lovely living area with a sofa and a tv. The pri

Located in Anna Maria, Florida, United States. Bayou Breeze | Amazing Waterfront Condo on Pine Ave with Dock and Water Views Amazing Waterfront Condo at the North end of Anna Maria! Tucked away off of Pine Ave just before the Historic Anna Maria City Pier you will find the Bayou Condos. This secluded waterfront community is located on Lake LaVista waterway which has direct access to the Gulf of Mexico. The City Pier, Bayfront Park and Rod and Reel Pier are just a short paddle away. Unit 4B is a completely remodeled unit located on the ground level and has awesome water views from the Dining area and Living room. Just out your living room through the sliding doors is a brick paver patio and just beyond that is your private dock. This unit features tile floors, new kitchen cabinets, granite counters, stainless appliances (featuring a super quiet Bosch dishwasher) and a remodeled bathroom. A full-size washer/dryer was added to this unit so there is no need to use the onsite laundry facility! You will love the location on Pine Ave as

Located in Anna Maria, Florida, United States. FALL 2024 SPECIAL: FREE bikes and a kayak or paddleboard! For arrivals between July 13, 2024 and November 16, 2024, enjoy complimentary bikes and either a paddleboard or kayak for your stay!Welcome to Pelican Lagoon, your ultimate beachside haven on the desirable north end of Anna Maria Island! Just a 5-minute stroll to the pristine sandy shores and mere steps from the tranquil bay beach, this charming canal front retreat offers the perfect blend of convenience and coastal comfort. All furnishings and decor are brand new and ready for your comfort and enjoyment!Pelican Lagoon boasts three beautifully appointed bedrooms and two full bathrooms, making it an ideal getaway for families or small groups. The master bedroom features an ensuite bathroom, creating a private oasis for relaxation. There is also a desk for any work needs. Gather in the spacious, open-concept kitchen, dining and living areas. Whether you're whipping up a delicious meal or enjoying a cozy movie night, this space is

Located in Anna Maria, Florida, United States. Beach Front and Close to Bean Point Azure Seas Azure Seas is thoroughly cleaned and sanitized prior to your arrival. We pay special attention to high touch areas like remotes, light switches and doorknobs, etc... All bedding is professionally laundered and sanitized with fresh clean comforters or duvets. This property has keyless, no-contact check in for your convenience.The Azure Seas is a three bedroom, two bath Gulf front home in the much desired and tranquil northern end of Anna Maria Island. Tropical paradise found!! This is the perfect place to forget your troubles and soak in the unbelievable views of the Gulf of Mexico. A large, 16 x 60 foot open deck at beachside is perfect for sunbathing, watching for birds and dolphins or just enjoying a good book and an afternoon siesta. A covered deck is just outside your door if you would rather sit in the shade. This charming and updated home has a nautical flair and lovely furnishings. All of the amenities to make your stay more pleasan

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