58,368 properties available

Located in Holmes Beach, Florida, United States. North Beach Village 63 Beautiful Professionally Decorated Villa with community pool, 3 minute walk to beach. 6250 Holmes Boulevard - North Beach Village - Anna Maria Island Condo 2 Bedroom /2.5 Bath, maximum occupancy of 6 people. VRC16-000850Community pool, PET FRIENDLYSaturday to Saturday bookings during the months of January through March (high season), or monthly. Freshly renovated, this beachy, airy villa is located in the North Beach Village community, a peaceful oasis only 3 minute walk from the soft white sands of the Gulf of Mexico. Steps away from the property is a heated, community pool for you to refresh and relax in. Every aspect of this professionally designed villa has a beach-themed yet elegant flair, from the relaxing color palette to the breezy window treatments. The first-floor open-concept living area features a kitchen with quartz countertops and stainless-steel appliances leading into a cozy living area with a large flat screen TV. The living room opens onto a sc

Located in Holmes Beach, Florida, United States. Holmes Beach- Fall Sale! The Palms, AMI- 2BR/2BA vrc 000075 ** Sale! Falls rates in effect for reservations in Sept, Oct, Nov and Dec! The PALMS at Anna Maria Island is the perfect getaway locale for the entire family. This 2 bedroom 2 bathroom villa is in the heart of Holmes Beach, AMI. Just mins from the beach (10 minutes walk to beach access), and steps to local restaurants, bars, shops, and the free AMI trolley to take you all across the island! Enjoy a bright and modern home furnished in a bright and airy modern coastal style. Book now and get ready to start your perfect island vacation!

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 Holmes Beach, Florida, United States. 209 83rd unit B in Holmes Beach 209 83rd Street, Unit B - Anna Maria Island -Duplex with your Private Pool -2 Bedroom / 2 Bath, maximum occupancy of 4. (Pool is not shared with the other A side - private pool only for unit B)Distance to the Beach: 3 blocksSaturday to Saturday bookings during the months of January through March (high season), or monthly. Unit B is a lovely ground level unit (east unit) with private pool, walking distance to pristine gulf beaches. The unit's open concept is great for families. This property has lush tropical landscaping, with a secluded, fenced backyard. Play in your own private pool with plenty of deck space for relaxing in the chaise lounges. Take a break from the sun on the large screened in porch, just perfect for game night. When it's time for sleeping, the primary bedroom has a king bed, with an en-suite bathroom with a tub. The 2nd bedroom is just around the corner with 2 twin beds and an en-suite bathroom with a shower. The spacious kitche

Located in Holmes Beach, Florida, United States. Flip Flops Forever by SeaBreeze Vacation Flip Flops Forever is a traditional Florida home just steps from the beach nestled in the quiet residential area in the heart of Holmes Beach. Offering 5 bedrooms/3 bathrooms, Flip Flops Forever is located in the perfect location for a great family vacation. Only a few seconds walk (around 200 steps) from the world-renowned white sandy beaches of the Gulf of Mexico. This home offers enough space for everyone to have their privacy while still enjoying quality time together. Sit back and relax - you are on vacation! Flip Flops ensures you have it all. Make memories as a family that will last a lifetime! Vacations are for fun and relaxation. The outdoor area at Flip Flops Forever provides just that. Have fun in the pool which is heated year round for your enjoyment or play on the mini golf hole. The family dogs are welcome to join you here. The weight limit per dog is 30 lbs. The entire family, including the dogs, are sure to have a great time and

Located in Holmes Beach, Florida, United States. ANNA MARIA ISLAND COTTAGE Original, Quaint and Quiet Island Beach Cottage in Holmes Beach on Beautiful Anna Maria Island only minutes from the Island’s finest white sandy beaches. Enjoy swimming in the Gulf, snorkling for sanddollars and shells, fishing or just listening to the waves as you relax and soak up some Florida Sunshine, just remember the sunscreen. Don't miss our amazing sunsets in the evening as they are truly breathtaking. Our special Island Trolley makes getting around easy. The Trolley Stop bench is just steps away in front of house next door and passes every 20 to 30 minutes. It will take you to the finest restaurants and shops on the Island, Coquina Beach and Famous Bridge Street with great food, drinks and nightly entertainment. If you'd rather bike this beautiful seven mile island, Beach Bums Bike Rentals makes it convenient and will deliver and pick up when you are done. This Original 1050's Island Cottage has been totally updated and remodeled and has all new app

Located in Holmes Beach, Florida, United States. Three Bedroom Ground Floor Home with Retro Finishes and many Amenities! Welcome to Lime Cottage located just 2 blocks from the Gulf beaches of Anna Maria Island. Lime Cottage is a ground level half duplex with 3 bedrooms and 2 bathrooms and its own private patio surrounded by tropical landscaping where you can enjoy the heated pool and outdoor shower. Inside you will find a spacious living area with entry to the patio as well as the retro style kitchen with diner style booth seating for meal times. For your day at the beach, we have provided a beach wagon, chair and umbrella. In the evening you can retreat to the bedrooms where you will enjoy our comfortable beds complete with 600 thread count prima cotton wrinkle free sheets. This home includes a fully equipped kitchen, linens, towels, beach towel, and a Weber grill.Lizzie Lu's Island Retreat is a full service property manager on Anna Maria Island to ensure our guests enjoy some of the nicest, well stocked homes on the island. For an

Located in Holmes Beach, Florida, United States. Golf cart Inc + 4bd/2bth + private pool! Recent Review: "This is an incredible place to stay. The location is awesome, the communication is phenomenal and the house is gorgeous. We can’t wait to come back again!!"Urban Oasis too is a privately owned home on Anna Maria Island. It has 4 bd, 2 bth plus outdoor shower with a large pool, 10,000 sq foot yard, two large decks, outdoor bar and dining space AND a brand new 6 seater electric golf cart included! This private home features coastal hues, driftwood accents and comfortable furniture to enjoy your vacation. You will have premium linen service including all towels and linens changed with each stay. Urban Oasis too is truly a turnkey Vacation Rental! 5 minute walk to walk to the beach or take the golf cart and park at the beach access point! . This home features grey blue hues, coastal furniture, driftwood accents and designer touches. This home has been fully renovated in the fall 2019 with a brand new kitchen, flooring etc. This home

Located in Holmes Beach, Florida, United States. Anna Maria Island gem w/ private pool | Near beach Welcome to Waves, a Tstays Island Living Property. With only a small distance separating us from the shore, our guests have access to all kinds of enthralling activities and attractions. While staying at Waves, make sure to take full advantage of our new and improved saltwater heated pool, deck furniture and grill. And rest assured, our standards for cleanliness are unmatched. Guests will be receiving the ultimate 5-star experience. Add this listing to your Wishlist by clicking "save" in the top right corner. This is a DUPLEX LISTING that can fit up to 12 people. It is offered as two units right next to each other. * Duplex for larger families. * 6 Minutes Walking to world-renowned white sands of Anna Maria Island. * Spacious outdoors with parking, fitting up to 4 cars.* Balcony Sitting Area. * Quiet, SAFE, FAMILY-FRIENDLY neighborhood. * In-Unit Washer and Dryer ( 2 Washer and 2 Dryers!). * Wireless Fast Internet. * Cold AIR CONDITIO

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 Holmes Beach, Florida, United States. Villa Verde-4 bedroom with private pool with restaurants and boutiques nearby 311 61st Street is a lovely elevated 4 bedroom and 3.5 bathroom tucked away in the heart of Holmes Beach just a short two blocks from the Gulf beaches. Its incredible location puts you close to it all for the best Anna Maria Island getaway. Not to mention all of the amazing amenities! Spend your days lounging by the tropical private heated pool, sip a refreshing drink under the covered pool-side deck or enjoy a friendly game of foosball in the game room. Local restaurants and boutiques are just around the corner for your convenience–rent a golf cart, bicycles, take advantage of the free Island Trolley or simply explore by foot. You’ll absolutely fall in love with the location and its easy access to all the best that AMI has to offer. This home away from home has everything you need to make the best of your vacation. From the fully stocked kitchen to the open floor living area. You’ll find there is room enough

Located in Holmes Beach, Florida, United States. Serenity Now - Newly Listed Holmes Beach Beauty. Heated Pool with Sun Shelf Welcome to Serenity Now!On Anna Maria Island (Holmes Beach, FL)HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV, Covered Porch/Balcony off living area- 1 King Bedroom w/ TV, En-Suite Full Bathroom (shower, tub, double sink), Walk-in closet, Private balcony/porch- 1 King Bedroom w/ TV, En-Suite Full Bathroom (shower, double sink)- 1 Queen Bedroom- 1 Bunk Room with Twin over Full Bunk Bed with Twin Trundle- 1 Additional Full Bath (tub/shower combo)- 1 Hall Half Bath- Additional Seating area/office nook- Covered Porch- Heated Pool- Laundry RoomKitchen:Stove, Oven, Dishwasher, Microwave, Refrigerator w/ Ice Maker & Water, Garbage Disposal, Coffeemaker (12 cup), Blender, Crock Pot, Toaster, KitchenwarePool Area:Heated Private Pool w/ Sun Shelf, Covered Outdoor Space, Outdoor Dining & Loungers, Outdoor Shower, Gas GrillApproximate Pool Size:12' x 20'Parking:1 Car Garage, 2-3 Additional Cars in Driv

Located in Holmes Beach, Florida, United States. Stay Salty: Dog Friendly, Pool with Waterslide, 2 Blocks to Beach by Anna Maria Life 6906 Holmes Blvd, Holmes Beach, FL 34217What You'll Love About This Home:Location! 2 Blocks to the Beach!6 Bedrooms / 4.5 Bathrooms5 King Beds, Bunkbeds - Twin over QueenPrivate Heated Pool & Hot TubWaterslideOutdoor ShowerCovered Poolside Lanai with Bar, Patio Dining for 10, Lounge Furniture & TVGas GrillGame Room with Foosball & Ping Pong TablesProfessional Linen Service, Washer & DryerComplimentary WIFIBeach Towels & Beach Chairs & Beach WagonDog Friendly (with pet fee - see below) Max - 50lbsParking for 4 CarsDetails:Located 2 blocks from the sugar sand beaches of Anna Maria and in the heart of Holmes Beach, Stay Salty is the vacation home of your dreams!Our elevated home features a bright and comfortable living, dining and kitchen, in an open concept on the main living area. The deck with Adirondack chairs overlooks the lush tropical landscaping and is perfect for relaxing with a morning cup of co

Located in Holmes Beach, Florida, United States. Coral Beach by Duncan Real Estate Welcome to Coral Beach! This beautiful 4-bedroom, 3-bathroom pool home comfortably accommodates eight guests. From the quality quilts and linens on the beds, to the TVs in the two living rooms and the fully equipped kitchen, nothing has been spared when decorating this home. You will not want for anything when it comes to the amenities and the quality vacation that you will experience. HIGHLIGHTS - 1908 sq ft. - screened lanai 600 sq ft. - Luxury Rental Property - Private heated pool and spa - Centrally located near Holmes Beach Skate Park - 0.4 miles from bay access - 0.3 miles from beach access BEDROOMS - Sleeps 8 - Primary Bedroom: King Ensuite - Second Bedroom: King Ensuite - Third Bedroom: Queen - Fourth Bedroom: 2 Twins BATHROOMS - Primary Bathroom: Walk-in Shower - Second Bathroom: Shower/

Located in Holmes Beach, Florida, United States. Sand Of Times-Beautiful 6 bedrooms with private pool/spa with a water slide Sands of Time6908 Holmes BlvdHolmes Beach, FL 34217Sands of Time is a newly built 6 bedroom, 4.5 bathroom vacation home located less than two blocks from the white sand beaches in the heart of AMI. The home sleeps 12 and is the perfect choice for a multiple family vacation! The home is professionally decorated to create the perfect luxury beach atmosphere! High-speed internet and Spectrum TV will keep you connected, or choose to escape from it all on the four private decks, tropical pool, or on a beach bike ride with the 4 adult cruisers. The kitchen is fully stocked with all of the amenities of home. High capacity washer and dryer are located on the main floor to clean those sandy swimsuits.This house is conveniently located on Holmes Blvd, providing a quiet retreat located in the heart of the island. The home is centrally located with access to the charm of the Pine Ave shops and easy to access shops, restau

Located in Holmes Beach, Florida, United States. A Shore Thing by Beach Boutique Rentals A Shore Thing is a beautifully renovated key west style 3 bedroom beach house. Plenty of room for the whole family and friends. *Features include* * Private heated saltwater pool * Seating ledge with jacuzzi jets * Pet friendly! * Elevator for easy access to all 3 levels^* 3 bedrooms including queen size bunk room * Sleeper sofa in living room * Master bedroom with ensuite bath * Washer and dryer * Beach chairs, wagon, toys and cooler * Patio with outdoor dining * Ping pong table, bicycles, surfboard * Outdoor shower * Tiki bar and plenty of lounge space by the pool * 3 blocks to the beach! Located on a central and quiet street in Holmes Beach, A Shore Thing has everything you need for a dream vacation. Your group can explore the island on the bikes included with the rental or ride just 3 blocks to the beach where you'll find powder white sand and blue waters. If you decide to spend a day by the pool, you will never have to leave the comfort of

Located in Holmes Beach, Florida, United States. Golf Cart, Dream Weaver by SeaBreeze Vacation 6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 23, 2023!All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle InsuranceDream Weaver is an amazing, custom luxury home nestled in the quiet residential area in the heart of Holmes Beach. This oversized home offers 3 bedrooms/2.5 luxury bathrooms. You will find that this home has everything you need for your perfect Anna Maria Island vacation! From the luxurious, resort-style infinity pool that features a separate infinity spa to the putting green. There is also an elevator from the garage to all floors and a full gourmet kitchen. Dream Weaver has it all - from a whole house (indoor/outdoor) professional high-speed WiFi system, outdoor 4K TV for movies on the patio or watch it from the pool or spa. The list goes on with the amazing amenities - what more could you possibly need to make your tropical island

Located in Holmes Beach, Florida, United States. Ground Level Cottage Steps to the Beach – No Streets to Cross - Heated Pool AWESOME LOCATION! Only 3 Houses to the BEACH! The Tangerine House is a quaint ground level 1940's Beach Cottage with plantation shutters nestled in a quiet island neighborhood. Located just steps to the white sandy beaches with no streets to cross and a private heated pool!Enjoy the perfect beach getaway only 500 feet to the beautiful beaches of Anna Maria Island. This well-kept 1950’s Beach Cottage has tile flooring throughout with tile counter tops and beachy décor throughout. The eat in kitchen has French Doors that open to the private heated pool and is a great place for your morning coffee or reading your favorite book. The split design offers 2-bedrooms, 3-bathrooms, a spacious den with laundry room and bathroom which provides all the comforts of home and space for all guests. The King Suite has French Doors opening to the private heated pool and the Queen Suite is a spacious beachy theme both suites have

Located in Holmes Beach, Florida, United States. 8 houses to the beautiful white sand! Come get your beach on! Welcome to "Tropical Treehouse". This property is zoned for 7 nights minimum. Beautifully updated vacation rental in Anna Maria Island (Holmes Beach) presents an incredible option for those needing beach therapy at its best! Spend your days lying on white sandy beaches soaking up the sun. This 3 bedroom 2 1/2 bath townhome is just 8 houses from the beach. Three spacious bedrooms are all on the top floor - one king, one queen, and one w/twin beds - with two additional baths and one additional balcony for privacy. Each bedroom has its own TV and DVD player so that you can get away - the kids even have their own gaming unit in bed #3. We have a pack-n-play, baby gate and a portable high chair. Will give you all the comforts of a real beach home - not just a rental! Beach chairs, beach towels, beach cart and cooler provided. PLEASE NOTE: *Due to new code enforcement stricter golf cart rules are being implemented July 2022 an

Located in Holmes Beach, Florida, United States. Luxury House with Temperature-controlled Pool in Private Oasis! Welcome to Coconut Ranch - You will walk into an island lovers paradise when you walk into this Stunning BRAND-NEW build. Even the most design-oriented individuals will love the custom details spread throughout the house. There is plenty of room for the entire group with 4 bedrooms and 4.5 bathrooms. Relax in the private backyard on the balcony or in the nook overlooking the tropical landscaping where you can enjoy the heated (and chilled!) pool, outdoor shower, and Weber grill. Beach chairs, a beach wagon, and beach umbrellas are located in the garage to help make your trip to the beach a little more convenient. Start your morning with coffee under the canoe in the kitchen, breakfast under the crab trap in the dining room, or brunch out on the balcony overlooking the private backyard. The main living area features a fully stocked open concept kitchen and living room. On this floor you will find a master bedroom with an e

Located in Holmes Beach, Florida, United States. 7310 Holmes Blvd in Holmes Beach 7310 Holmes Boulevard, Unit B - Anna Maria Island - Duplex - 1 Bedroom / 1 Bath, maximum occupancy of 4 people. VRC16-000060No Pool - Distance to the Beach: 3 blocksSaturday to Saturday bookings during the months of January through March (high season), or monthly. Ground level, Holmes Beach, duplex that's fun and adorable. This cozy unit has a private outdoor patio area. Having been renovated, it is perfect for visiting with family and friends. Anna Maria Island is a tropical barrier island seven and one half miles long. Its fine white sugar sand beaches are open to the public with convenient accesses along the entire island. It is one of the finest beaches in the United States. Unlike some tourist areas of Florida that are typified by endless rows of high rise apartment buildings and hotels, Anna Maria is an island of homes and small resorts. Enjoy many activities on your visit: swimming, snorkeling, beautiful sunsets, fishing, boating, shopp

Located in Holmes Beach, Florida, United States. Charming 2Bdrm Coastal Cottage 3 min from Beach! Welcome to Southern Cross, your idyllic coastal escape nestled in the heart of Anna Maria Island! This charming cottage offers a perfect blend of comfort, convenience, and coastal charm, just a stone's throw away from the pristine beaches of the Gulf of Mexico!🏡 Property Highlights:✨3 minute walk to the beach✨2 full bedrooms with King beds and 2 bathrooms✨Screened balcony with outdoor dining✨Washer and dryer in unit✨Brand new heated pool with private fenced yard✨Premier Holmes Beach Location✨Beach Essentials Included🏖️ Beachside Bliss: Located 3 minutes from the sugar-white sands and azure waters, this cozy cottage is a beach lover's paradise. Spend your days soaking up the sun, swimming in the surf, or simply strolling along the shoreline as the gentle waves lap at your feet.🏠 Coastal Comfort: Step inside to discover a beautifully appointed living space adorned with coastal-inspired décor and furnishings. The open-concept layout creates

Located in Holmes Beach, Florida, United States. Newly Updated 4 Bedroom 3 Bath Duplex with 2 Pools Bring your bikinis and board shorts to this lovely 4 bedroom, 3 bath duplex, a short block to the gorgeous white sand beaches of Anna Maria! Updated furnishings and amenities abound at this quaint vacation destination, sure to be loved by the whole group. Enter through the front door to find yourself in the bright and beachy open concept living area, perfect for spending quality time with the family as they enjoy home prepared meals compliments of the fully stocked kitchen. Each unit has its own living area and full kitchen creating a full private space. Unit A features a king bed with TV in the first bedroom, and 2 twins in the second and Unit B features a king bed with TV and en-suite bath in the first bedroom, and 2 twins in the second bedroom. Units A and B have a private heated pool, outdoor shower, propane grill, stainless-steel appliances, cable TV, wireless internet, nationwide calling, and private laundry facilities are includ

Located in Holmes Beach, Florida, United States. Beautiful New Home! Exceptional outdoor and pool area with swim up bar The Blue Crab by Anna Maria VacationsHome in Holmes Beach FL 34217VRC-000057Welcome to The Blue Crab, a spectacular island gem with an unbelievable tropically landscaped backyard with a covered deck, a serene outdoor firepit with seating, a hot tub, and a pool with easy access to the swim-up bar with a wet bar and a wine fridge. Only two blocks from the sparkling, pristine Gulf of Mexico, this four-bedroom, four-and-a-half-bathroom home is the perfect spot for your next getaway. Start packing now!Highlights• Private pool with build-ins and spa• Swim-up bar• Outdoor firepit• BalconyThe nautical farmhouse theme carries throughout the home’s open layout. There is a dry bar in the living room for refreshments, plenty of seating, and amenities designed for a large family or group of friends. The spacious functional kitchen has stainless steel appliances, including a Wolf oven and induction stovetop, a huge wine fridge, a