211 properties available

Located in Anna Maria, Florida, United States. Updated bayside condo with heated pool - across the street from the beach South Bay Inn 1Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This romantic getaway is a great place to spend some time on Anna Maria Island. Located right across the street from the bay, this rental is just a short stroll from the beach! It comes with a shared heated pool and comfortable outdoor furniture for relaxing in the island breeze.Located within walking distance of Pine Avenue and its many attractions, this unit is close to some of the best dining and shopping the island has to offer. Directly across the street is a great view of the bay, as well as a short sandy path to the beach. Bayfront Park, featuring picnic areas, sandy beaches, and great fishing, is nearby, as well. The famous beaches of Bean Point are also within your reach, just a short, one mile drive up-island.THINGS TO KNOWAll guests occupying this prop

Located in Anna Maria, Florida, United States. Luxury bungalow with pool and spa! Canal front with dock! Bamboo Bungalow by AMI Locals Home in Anna Maria VR19-000043Welcome to the Bamboo Bungalow, a canal-front home where you can fish off the canal dock and dip in the modern pool nestled in the bamboo garden. With three-bedrooms and two-bathrooms, this home is located on the canal at the north end of Anna Maria Island, just two blocks from shops and restaurants on Pine Street, explore the small, local businesses and enjoy a fresh meal before heading to the pristine Gulf of Mexico beaches!Highlights• Canal Front with dock• Less than a 15-minute walk from the Beach• Private Pool and Hot Tub• Outdoor dining area• Less than a 5-minute walk to Pine AveWhen you open the front door, you will be greeted by the inviting great room with a large sectional sofa, a dining room table, and a sunroom that overlooks the pool and has a TV. The spacious updated kitchen has ample space for meal preparation and is equipped with culinary essentials. The

Located in Anna Maria, Florida, United States. Casa de Playa Cozy, ground-level cottage, across the street from the beach! Located at the quiet North end of Anna Maria this 2BR/2BA home is located just across from the Gulf of Mexico. Interior has Interior has a newly remodeled kitchen with quartz counters and stainless appliances , Mexican tiled floors, updated furnishings, an open floor plan with living and family room. Enjoy the gulf breezes on the large brick paver patio. King bed and twin beds. Sleeps 4. Washer/dryer and dishwasher. Non smoking unit. Beach access is at Cypress Ave just a few doors away.Wireless Internet, Digital Cable TV and Free long distance calling in the U.S, Canada and Puerto Rico.❌🐶 Please note that pets are not allowed in this rental.

Located in Anna Maria, Florida, United States. Naut 2 Shabby Cottage Next-Level Pool Area, Darling FL Cottage - Best of Both! Welcome to Naut 2 Shabby Cottage! This 1922 Old-Florida-style cottage pool home is the front unit on the property, located on Pine Avenue just half a block from the Anna Maria City Pier and Tampa Bay, and within walking distance to shops and restaurants. Rent a bike or catch the free Island Trolley to explore the Gulf end of Pine Avenue in just a few minutes' ride!At the home, you'll be charmed by the eclectic and homey decor. The backyard was made for fun in the sun! The private heated pool sports a basketball hoop, there's a hot tub nestled next to the gorgeous tropical landscaping and soft, springy turf surrounds the pool. Complete with Adirondack chairs, loungers, and a 4-top table with umbrella, you'll have everything you need right at the house! The interior is nice and cozy and includes updated amenities such as a large flat-screen SmartTV, ice maker, and dishwasher. The dining area in the sunny encl

Located in Anna Maria, Florida, United States. Anna Maria Beach Cottage 110B | Updated studio beach cottage, steps to the sand! This rental is part of the Anna Maria Beach Cottages. More information on this charming property below!Cottage 110B is perfect for couples on a romantic Anna Maria Island vacation! One of the charming Anna Maria Beach Cottages, this is a studio vacation rental with a trellised entry deck and is only moments from the gorgeous white sands Anna Maria Island is famous for.The picturesque patio includes a sun-dappled table for two under a beautiful trellis, surrounded by tropical landscaping. Large windows let in the natural light, making this a bright and inviting place to relax, read a book, or watch a movie. This little studio includes everything you might need for a comfortable and memorable beach vacation, including a full kitchen, lounge area, queen bed, and full bathroom.You’ll also have access to all the amenities the Anna Maria Beach Cottages has to offer, including a heated pool with a lounge area, as

Located in Anna Maria, Florida, United States. Resort-Style Ground Floor Suite Heated Pool/Spa 🐢 Resort-Style Ground Floor Suite, Prime Location, Lakefront, Heated Pool & Spa 🐢In our lakefront luxury resort (12,500 sqft) we offer three separate ground level apartments with a large outdoor area that can be rented together or separately. Enjoy the privacy of your own entrance, fully equipped kitchen and outside seating area or spend time as a group at the large, Mickey Mouse-shaped, heated salt water pool or spa. Our lakefront property is situated at 604 North Shore Drive, the prime location in Anna Maria, close to Bean Point. The most beautiful part of the white sandy beach is only a few steps away across the street. Go fishing, observe Manatees or use one of our kayaks for a trip from the private dock on Vista Lake right behind the house. Spend precious time with your family while enjoying a barbeque or lounging in one of several outdoor seating areas. Guest amenities like grills, pool, spa, putting green, giant chess, beach carts

Located in Anna Maria, Florida, United States. Spacious Home with Private Pool, Just 1 Block to Beach! Starfish Beach by AMI AccommodationsHome in Anna Maria, FL 1 Block to BeachHighlights:- Private pool surrounded by tropical landscaping- Comfortably furnished living room- Living room is outfitted with a wall of sliding glass doors that open up to the front porch/deck- Outdoor dining table on the deck- Spacious kitchen with bar seating- The perfect choice for those looking to be close to the beach and in close walking distance to all that the north end of the Island has to offerRoom Details -Primary Bedroom, 2nd floor: King bed, tv, and ensuite bathroom. -Second Bedroom, 2nd floor: Queen bed. -Third Bedroom, 2nd floor: Twin beds and tv. -Living Area: Queen Sleeper SofaThere are no pets allowed in this home.*Please note: 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. This home is managed by A

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.)Sea grape trees, hibiscus bushes and palm trees surround this pretty white-roofed daffodil-colored cottage that is just a short walk to the gulf beaches. The heart of Anna's Cottage is the great room, with French doors that open to a heated pool and a patio.. Another comfortable couch, wireless internet, free long distance calls and flat screen TV will keep everyone connected, comfy and entertained. The sunny kitchen is stocked with everything the chef in your group needs. The private upstairs master bedroom sparkles and is generously proportioned with an ensuite bathroom and a view of the pool below. Porches are back! Enjoy evenings filled with the creaking of white wicker easy chairs, the rustle of l

Located in Anna Maria, Florida, United States. Welcome to Go with the Flow Go with the Flow by AMI LocalsHome in Anna Maria, FloridaWelcome to Go with the Flow! This brand-new five-bedroom, five-and-a-half-bath getaway offers an array of amenities, including an incredible and unique Lazy River-style pool and spa, a rooftop deck, and a versatile 3-in-1 game table; it's the epitome of vacation living!Highlights5-minute walk to the beachLazy river style pool with in-ground spaRooftop deck3-1 game tableNear restaurants and shoppingInside is just as impeccable, with a chef's dream kitchen boasting a full suite of appliances, cookware essentials, and a convenient bar area with a wine fridge and a formal dining room table. Relaxation takes center stage in the spacious seating area, tastefully furnished with modern sofas, side chairs, and a Smart TV.A spacious haven awaits in each guest room, with every room featuring crisp linens, ample storage space, and televisions. The main bedroom has high-end furnishings and a king-sized bed envelope

Located in Anna Maria, Florida, United States. Heated Pool, FREE WiFi, Close to Beach, Dock your Boat, Dog* Friendly (See... **ASK ABOUT LAST MINUTE DEALS! A contemporary aesthetic combined with a top-notch location is sure to make Pelican Bay a favorite part of your Anna Maria vacation! Tucked away at the north end of the Island just a bit beyond the shops and restaurants of Pine Avenue, this lovely two bedroom, two bath home is nestled on the banks of Lake LaVista and sports a new dock ready for your boating or fishing pleasure! It is best to launch at High tide as the water levels can make a difference. Travel under two humpback bridges out to Tampa Bay and you can go anywhere in the world! A quick walk of two blocks will take you to the wonderful Bayfront Park, a perfect spot to hit the beach with the kids, or walk just a little further is access to the beaches at Bean Point at the Island's very northern tip. Between it all is the famous Rod & Reel Pier, where you can fish, eat and drink

Located in Anna Maria, Florida, United States. Upscale waterfront home, private pool, beautiful views! Paradise on Pine by AMI LocalsHome in Anna Maria, FLFeatures:• Waterfront home with private dock• Elevator for guest use• Private pool• beach chairs, beach cart and umbrella for guest use• great location on Pine Avenue, close to shops and dining• Tesla Universal Wall Connector, both NACS and J1772 compatible, up to 48 AmpsRoom Details-Primary Bedroom, 3rd floor: King bed, private balcony, and an ensuite bathroom with a walk-in shower, double vanity, and stand-alone tub.-Second Bedroom, 2nd floor: King bed and ensuite bathroom with walk-in shower.-Third Bedroom, 3rd floor: King bed and shares hallway bathroom with walk-in shower-Fourth Bedroom, 3rd floor: Two twins over twin bunk beds and shares hallway bathroom with walk-in showerWelcome to Paradise on Pine!A beautiful waterfront 4 Bedroom, 3.5 Bath home on Pine Avenue, this spacious property will accommodate everyone! Recently remodeled with fine details and finishes, this home

Located in Anna Maria, Florida, United States. Drop Inn: Pine Ave, Pool, Game Room, 1.5 Blocks to Beach Drop Inn by Anna Maria Life Vacation Rentals305 Pine Ave, Anna Maria, FL 34216What You'll Love About This Home:Location! 2 Blocks to the Beach!4 Bedrooms / 3 Bathrooms2 Kings, Queen, Full over Twin Bunkbed Private PoolPool LoungersOutdoor ShowerGas GrillCovered Patio DiningCorn Hole, Ping PongKeurig & Drip Coffee MakersProfessional Linen Service, Washer & DryerComplimentary WIFIBeach TowelsParking for 4 CarsDetails:Drop Inn is in a prime location on Pine Ave and 2 blocks from the sparkling clear waters of the Gulf of Mexico.The bright kitchen overlooks a dining room with seating for eight and additional seating for four in the breakfast nook. The living area is a comfortable spot for the family to gather and relax after a day in the sun and sand.Two of the bedrooms feature king beds and ensuite bathrooms and one has access to a balcony. The 3rd guest room includes a queen bed and the final bedroom has a set of full over twin bun

Located in Anna Maria, Florida, United States. Mermaid House Rooftop deck, Gulf views, beautiful home, steps to the sand! 🤩 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! Flexible check in days every day except Sundays during Non- Peak dates._______________________________☀️ Summed Up in a SentenceMermaid House is a three-bedroom Anna Maria Island home with a rooftop deck, only four houses to the beach! ✨ Hitting the Highlights- Be at the beach in a one-minute walk- Rooftop deck with gorgeous views of the Gulf- Updated home with beachy-chic decor- Spacious bedrooms, renovated kitchen and bathrooms🌅 Painting a PictureLocationBeing only four houses to the beach, you can have your toes in the sand in a short one-minute walk! Excellent dining, snacks, and shopping are well within walking distance, too. Check out The Porch (for finer fare), Anna Maria Island Creamery, Ginny’s and Jane E’s (for coffee, casual dining, and shopping!), or plan a spa d

Located in Anna Maria, Florida, United States. Summer Strand: Resort like pool, close to beach, kayak w/ manatees, Rooftop Deck Welcome to Summer Strand on Anna Maria Island.This brand new luxury vacation home is perfectly situated a short 5 minute walk to the pristine white sands of Anna Maria Island’s North Shore. This luxury getaway is ideal for groups of families & friends. If this home is not available be sure to check out our other property, successful 5-star Amie House (VRBO # 2013436). The Summer Strand is sure to exceed your expectations.HIGHLIGHTS:- Heated Pool with spa - Automated botanical insecticide to control mosquitos and No-See-Ums- Easy 5 minute walk to beach- Spacious Open concept Kitchen, Dining, Living Area- bar area with dual zone fridge and icemaker- Large kitchen with subzero fridge and wolf range- 1 King bedroom with private bathroom and balcony- 1 King bedroom with private bathroom and balcony- 1 bunk room with twin over queen bed and private bathroom- top floor king bedroom retreat with gorgeous bathroom

Located in Anna Maria, Florida, United States. Flirty Flamingo Cottage | Updated beach cottage, moments from the sand, w/pool! This rental is part of the Anna Maria Beach Cottages. More information on this charming property below!Flirty Flamingo Cottage is your fun and funky ticket to a fabulous Anna Maria Island vacation experience! Cottage 112 of the charming Anna Maria Beach Cottages is a 3 bed/2 bath standalone vacation home with a bonus bedroom on Oak Avenue, just three houses from the beach.This cottage was recently redecorated with beachy chic décor for a bright and cheerful atmosphere throughout. For soaking up the sunshine and fresh Florida air, there’s a beautiful deck just off the dining room with a table for four under the vine covered trellis. Featuring a full kitchen, separate dining area, spacious living room, two full bathrooms, and a private charcoal grill, you’ll have everything you need for a fun-filled and comfortable stay. Enjoy room for a group of up to 8 guests with 3 bedrooms and a bonus sleeping room. The m

Located in Anna Maria, Florida, United States. Custom Home Walking Distance from the Gulf ! NOT LISTED ON FACEBOOK This large home was constructed in 2009. It is a decorator furnished, pool home and considered top of the line in vacation rental homes. With approximately 3200 square feet of conditioned space and over 2000 square feet of covered balconies, poolside dining and lounging areas, there is plenty of room for a family to spread out and relax in this Florida lifestyle home.Soak in the sparkling pool after a day at the beach and then gather for dinner at the table for eight in the dining room, or, if you prefer, outdoors on the balcony amid the sea breezes, or down by the heated pool.We also added a Tesla car charger for electric vehicles to save you on gas and are offering 1-2 golf carts for rent located on premise for rental (4 seater or a 6 seater with doors). All in all, a perfect vacation paradise.Feel free to text me at (586) 872-6187. Patrick——————Please note, you can save with us as we have a Tesla Wall Charger

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 Rose Quartz, your haven of warmth and comfort nestled in the heart of Anna Maria Island. Step inside, and you'll instantly feel the embrace of a cherished friend's home. This delightful three-bedroom retreat, boasting a detached master bedroom, offers ample space for your entire family to unwind and reconnect. Embrace the joys of modern living with amenities like flat-screen TVs and wireless internet, ensuring everyone stays entertained and connected.Outside, a glistening private heated pool and soothing hot tub beckon, promising endless relaxation and rejuvenation. Retreat to the covered pool patio, where comfortable seating invites you to enjoy a meal and sip your favorite drinks as you soa

Located in Anna Maria, Florida, United States. Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point! CAST AWAY your stress and worries at this adorable piece of old Florida near BEAN POINT. Charming vintage cottage with LUSH TROPICAL HEATED POOL & SPA area. 💦Two bedrooms with queen beds, well equipped kitchen, flat screen TVs mounted in each room, full sized washer & dryer, and large front porch with mini fridge all combine as your home base in paradise. Enjoy relaxing moments poolside, 🏖 beachfront, or exploring the whimsical boutiques in the SUNNY QUAINT VILLAGES on Anna Maria Island. 🤩Everything you need to enjoy your days on the island is at the cottage - just add food & drink + swimsuit & flip flops. We provide a street legal golf cart (4 seats), beach chairs, beach umbrellas, Wheeleez beach wagon, bicycles 🚲, four stand up paddle boards, two-seat kayak, private outdoor shower/changing room with hot & cold water, two gas grills, coolers, and more! 🍔 After a day at the beach or sightseeing, the priva

Located in Anna Maria, Florida, United States. Reef Romance managed by Beach Retreats It's all about location on vacation, and Reef Romance does not disappoint! Sail away to this beautiful four-bedroom, four-and-a-half-bathroom custom-built home for a dose of luxury at the beach. Located on the prestigious north end of Anna Maria Island, you're just a few houses away from the beach with no busy road to cross.Stunning inside and out, Reef Romance features only the best amenities for your beach vacation. From the gourmet kitchen to the primary suite, every detail has been meticulously planned. Stainless steel kitchen appliances, flat-screen TVs, hand-tiled walk-in showers, and more are all waiting for you. Enjoy floor-to-ceiling sliding glass doors on both sides of the primary suite, leading you out to the spacious open-air decks. Each room is professionally decorated with custom finishings.After you have explored Reef Romance inside and out, head to the back of the home and discover your tropical oasis. A private heated pool, large

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.)Come join us at Mykonos on Anna Maria Island! This beautifully decorate, two bedroom, two bathroom home has the perfect location for you and your family. You are a quick 2 minute walk to Gulf beaches and 5 minutes to Pine Avenue where you will find shopping, restaurants, and the Free Anna Maria Trolley. The property has plenty of sleeping space for everyone! The master suite has a king bed, TV, and private ensuite bathroom. The guest bedroom has a queen bed with a twin trundle and TV. The shared bathroom has a tub/shower and is located directly across from the in house washer and dryer. The homeowners have recently complete construction on a brand new heated pool, astro-turf covering the entire backyard

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.)Sorgenfrei South has everything you need for a perfect beach getaway. This stunning 3 bedroom, 3.5 bath home is located less than a block from the gorgeous gulf beaches and just a few blocks from the fabulous shopping and dining on Pine Avenue. Not only does this home have plenty of space for the whole family, it is meticulously decorated and has all the comforts of home. Book your vacation today. You're sure to fall in love with Sorengfrei South and Anna Maria Island.Floor 2 (main living level): Living room, kitchen, dining room, and front-facing balconyHalf bathWet BarFloor 3 (All bedrooms)Bedroom 1: King w/ TV and office area. Double sinks, walk-in shower and separate tub.Bedroom 2: King w/ TV and e

Located in Anna Maria, Florida, United States. Large Private Beach Home. Private Pool and Spa, Outdoor Lighting Southern Exposure by Anna Maria VacationsHome in Anna Maria, FLVRC16-000065Highlights • Less than a 10-minute walk from Anna Maria Island Beach• Private Pool and Hot Tub• Ping Pong Table• Elevator and Multiple Balconies• 1 block from Pine AveWelcome to Southern Exposure, a luxury beach home tucked away on the prestigious north end of Anna Maria Island with a large private heated pool, spacious outdoor living area, and is just a stone’s throw from the Gulf and Bay beaches and Pine Avenue. This newly-constructed getaway boasts five bedrooms and four bathrooms and many features that enhance comfort and convenience so you can unwind, including an elevator and ping pong table. Coastal vibes flow through the fully-equipped kitchen, with generous counter space, stainless steel appliance, countertop seating, and there is a colorful indoor dining room and a dining table under the covered pool deck. Relax in the comfortable living

Located in Anna Maria, Florida, United States. Resort-Style Ground Floor Suite On Vista Lake, Heated Pool & Spa 🦤🦤🦤 Welcome to the Pelican Suite of AMI Beach Lagoon on Anna Maria Island!In our lakefront luxury resort (12,500 sqft) we offer three separate ground level apartments with a large outdoor area that can be rented together or separately. Enjoy the privacy of your own entrance, fully equipped kitchen and outside seating area or spend time as a group at the large, Mickey Mouse-shaped, heated salt water pool or spa. Our lakefront property is situated at 604 North Shore Drive, the prime location in Anna Maria, close to Bean Point. The most beautiful part of the white sandy beach is only a few steps away across the street. Go fishing, observe Manatees or use one of our kayaks for a trip from the private dock on Vista Lake right behind the house. Spend precious time with your family while enjoying a barbeque or lounging in one of several outdoor seating areas. Guest amenities like grills, pool, spa, putting green, giant chess, be

Located in Anna Maria, Florida, United States. Ground-floor duplex with fast WiFi, central AC & grill 21 Palms Unit BOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Come and enjoy Anna Maria's postcard-perfect beaches at this ground-floor duplex! Inside, you'll be surrounded by colorful beach-themed decor anywhere you go. The living area features two comfortable sofas, a ceiling fan, and a wall-mounted flatscreen TV. Right there is a small, but convenient four-person dining table. The kitchen may also be small, but it boasts all the essentials to prepare meals, snacks, delicious and warm coffees, and basically everything that comes to mind. There is a dishwasher that will take care of the dishes once mealtime is over. Additionally, the breakfast bar offers three dining spaces for quick meals on the go.The bedroom available is at the end of the hall and offers that much-needed privacy. It also has a ceiling fan and a flatscreen TV. There's centra