58,368 properties available

Located in Holmes Beach, Florida, United States. Beautiful bungalow with private pool! Close to beach! Day Break Bungalow by Anna Maria Island LocalsHome in Holmes Beach, FLFeatures:• Pool• BBQ grill, Backyard patio pool deck• 5 minute walk to the beach, beach chairs and cart for guest use• Ping Pong table• Dog friendly with host approval and $250 pet feeHome Layout:Main level (2nd Floor)• Bedroom 1 - King bed, ensuite bathroom with walk-in shower• Bedroom 2 - Twin over Twin Bunk bed with Trundle, ensuite bathroom with walk-in showerThere is also a half bath on this levelUpper level (3rd floor)• Bedroom 3 - Master with King bed, ensuite bathroom with double vanity sinks, shower and soaking tubClose to beach beauty! Experience the stunning view from the balcony at this newly remodeled 3 bedroom, 3.5 bathroom home. Centrally located to shopping, dining and fun summer activities in the heart of Anna Maria Island, Day Break Bungalow has it all.The home features elegant furnishings throughout. The comfortable living room is well equipp

Located in Holmes Beach, Florida, United States. Hart of the Gulf: Dog Friendly, 2.5 Blocks to Beach, Pool & Spa by Anna Maria Life Vacation Rentals 305 67th St, Holmes Beach, FL 34217What You'll Love About This Home:Location! 2.5 Blocks to the Beach!3 Bedrooms / 2 Bathrooms2 Kings, Bunkbed (Full over Twin), Queen Sofa SleeperPrivate, Heated Pool & SpaPool LoungersGas GrillPoolside Patio Dining for 6Fenced BackyardEnclosed Florida RoomKeurig & Drip Coffee MakersProfessional Linen Service, Washer & DryerComplimentary WIFIBeach Towels, Beach Chairs, Beach WagonDog Friendly! (with pet fee - see notes below)Parking for One CarDetails:Welcome to our delightful one level ranch home located 2.5 blocks from the sugar sand beach of Anna Maria. Hart of the Beach has everything needed for your beach vacation.The kitchen includes a Keurig and a regular coffee maker and is tucked away from the main living space. The living room and dining room are open and bright and the enclosed Florida room is the perfect place to enjoy a peaceful view of the b

Located in Holmes Beach, Florida, United States. Ideal Family Getaway: Private Pool 2 Mins from the Beach - Lay'By, Too Lay'By, Too by AMI LocalsHome in Holmes Beach, Florida VRC16-000175Welcome to Lay'By, Too! This vibrant ground-level vacation home features four bedrooms and three bathrooms just a short 2-minute walk from the stunning beaches of Anna Maria Island. Enjoy easy access to nearby attractions like the shops and restaurants of Pine Avenue, plus a free trolley stop just up the street for exploring the island.Highlights• 2-minute walk to the beach• 4-minute walk to Anna Maria Island Trolley stop• Private pool • Ourdoor dining and Grill• Dog friendly with approval and additional feeThe backyard boasts a private pool perfect for refreshing swims and lounging in the sun, along with an outdoor BBQ area for memorable cookouts. Inside, you'll find a bright open living room with colorful furnishings and a galley-style kitchen equipped with stainless steel appliances and an island for additional seating. The chic primary bedroom in

Located in Holmes Beach, Florida, United States. Private paradise w/ all the beach supplies & toys! Casa Laguna is a privately owned home with private amenities and entry via smart locks. The home is surrounded by lush palms ands vegetation offering. Creating a feeling of your own private paradise. We welcome you and your family to take a break, relax and feel safe in your own private paradise. Anna Maria Island is a family-oriented vacation destination with a laid-back feel. The island has a very relaxing atmosphere. The beautiful, world-famous white beaches and friendly character of the island will make you want to come back again and again.BEDROOMS5 Bedrooms/ 8 Beds & Upstairs retreatOur home has 5+ bedrooms that are all comfortably apart from each other in the house, accommodating for the privacy of members of your group. ALL BEDROOMS HAVE FLAT SCREEN TVs & CABLE. Three TV's are Smart TVs, Netflix, or HULU ready. The master suite has a Purple Mattress king bed, and a master bath equipped with two shower heads, and penny tiled fl

Located in Holmes Beach, Florida, United States. Spacious coastal home with private pool and jetted spa - Blue Coral Beach House Blue Coral Beach House by AMI Locals Home in Holmes Beach, FL 34217 VRC23-000024 Welcome to Blue Coral Beach House, a charming four-bedroom, three-bathroom coastal casita nestled in a quaint neighborhood of Holmes Beach that is close to the pristine Gulf beaches! In the tropical backyard is a sparkling pool, a jetted spa, a ping pong table, fabulous seating areas, and a great BBQ area perfect for soaking up the Florida sunshine with friends and family. Highlights• Less than a 10-minute walk to the beach• Private Heated Pool with In-ground Spa• Ping Pong Table• Outdoor living space• 1 house from free Anna Maria Island trolley stopAs you walk in you will be greeted into a seating area that is brightened by the large windows with two sofas, a comfy side chair, and mounted flat screen. Adjacent is the rustic chic kitchen with stainless steel appliances, a wet bar, and has essentials including pots, pans, and

Located in Holmes Beach, Florida, United States. Beautiful home near the beach with pool and hot tub! Beachside Paradise by Anna Maria Island AccommodationsHome in Holmes Beach, FL 34217VRC16-000088Welcome to Beach Paradise, an adorable three-bedroom and three-bathroom home plus a private suite totaling four bedrooms. Just a quick walk from the pristine Gulf of Mexico beach, you'll love spending your days in the sun!Highlights• 2-minute walk to the beach• Private pool and In-ground spa• Outdoor Seating and BBQ grill• Outdoor Shower• Near Anna Maria Island Trolley stopThe kitchen is fully equipped with essentials for preparing delicious meals and has stainless steel appliances. The open living area has two seating areas designed to make every guest comfortable. One has a large mounted TV, and the second is in the Florida-style room with plush wicker seating; this is also where you will find the home’s formal dining room table. Unwind in the primary bedroom with beautiful blue décor, storage space, and a King bed. The two Queen guest

Located in Holmes Beach, Florida, United States. Easy walk to beach, enjoy private splash pool, super clean! Custom built this three bedroom, two bath home is beautifully designed for six guests. Come to Island Breeze and relax with all the amenities to make your vacation a truly memorable experience. From your first step into the oasis you will feel yourself decompress. Eleven foot ceilings welcome you with an open spacious feeling. The kitchen has been stocked with everything you need to prepare your meals when your not experiencing one of our island restaurants. Two full baths with large showers and tasteful decor await you. The master suite has a new king size bed & guest bedroom is a queen size bed with comfy mattress and linens. The third bedroom is equipped with two twin beds designed for comfort. All three bedrooms have plasma flat screen TV's in addition to a new 75" smart TV in the living room for your entertaininment. We have WiFi and cable so you can bring your lap top or iPad if you choose to stay contacted to the outsi

Located in Holmes Beach, Florida, United States. New to rentals! 3 bedroom, private pool home! Pet friendly w/a golf cart! VRC22-000165Poolside Palms is now available so grab your suit and shades and come poolside!This spacious 3 bedroom/ 2.5 bath single-family home is nestled on a quiet street in northern Holmes Beach and ready for the entire family! This well-appointed home features a screened in lanai, an open patio with a gas grill, fenced yard and updated kitchen. A full-size laundry room with washer and dryer. Poolside Palms will accommodate six people with a king size bed, a queen size bed, a set of twin beds in the third bedroom and two sleeper sofas in the living room. The updated kitchen is stocked with everything you need to make your favorite family meals. Poolside Palms is a one month minimum.Parking is limited to four cars.You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the

Located in Holmes Beach, Florida, United States. Pet Friendly Private Duplex. Fenced Yard with Private Pool Short Walk to Beach Hawaiian Tide by Anna Maria VacationsHome in Holmes Beach, Fl 34217VRC17-000059Welcome to Hawaiian Tide, a tropical escape just minutes from the beach with three bedrooms and two bathrooms. This home has a fabulous backyard featuring a private pool with built-in seating, a BBQ grill, and plenty of outdoor seating for friends, family, and pets to relax and soak up the Florida sunshine! Highlights• Less than a 5-minute walk to the beach• Private Pool• Close to Anna Maria Island Trolley stop• BBQ grill and Outdoor Seating• Near restaurantsInside is a bright, open living space with an updated with sofas and a TV, and a fully equipped kitchen with a full suite of stainless-steel appliances and a chic dining table. The primary bedroom boasts coastal vibes. It has a TV, closet space, and an ensuite bathroom with a granite vanity and a walk-in shower. The second bedroom boasts a King bed, and the third bedroom is

Located in Holmes Beach, Florida, United States. Island Vibe 2: Close to Beach with Private Heated Pool Rent with attached duplex Island Vibe 3 (VRBO# 1307973) if you need 5 bedrooms!Welcome to Island Vibe 2, a renovated 3-bedroom, 2-bathroom home with a private, heated pool, tropical landscaping, and a private back yard. Located in Holmes Beach, this lovely property is convenient to the beach and in a very quiet Holmes Beach residential neighborhood. It has one shared wall with the unit next door. From here, it's just a short walk to the many shops and restaurants of downtown Holmes Beach, as well as the Island’s only dog park. This beautiful property will sleep 6 people with 1 King bed, 1 Queen bed, and 2 Twin beds. Plus, there is a pullout couch in the living room! You can park up to 2 cars in the driveway.In the backyard, you'll find a large open deck and a covered, shaded area overlooking the pool. We've added solar string lights on the lower patio for enjoying the outdoors during those great Florida evenings.You'll never miss a

Located in Holmes Beach, Florida, United States. Starfish Cove managed by Beach Retreats 302 60th Street Holmes Beach, FL 34217VRC19-000274At 3 bedrooms and 2 full bathrooms, this is a beautiful choice for your next Anna Maria Island getaway! Two short blocks to the beach, and around the corner to restaurants, pubs & stores. Featuring a heated pool to relax in after your busy day, Starfish Cove is a luxurious and welcome retreat in the perfect location on Anna Maria Island. This home is completely new and has been built with no expense spared. The 4 Flat screen TV's, Sonos multiroom audiosystem, stainless steel appliances, beautiful tile floors, granite counter tops, free phone/cable/wireless Internet, and a great outdoor living area with pool, spa & patio will exceed the expectations of even the most discerning vacationers. (1 Master Suite, one room with two twin beds and an additional room with a queen sized bed. Take the trolley to Bean Point, or historic Bridge St. Have a bite at Chateau Anna Maria, or the Beach Bistro or grab

Located in Holmes Beach, Florida, United States. Canal Front Old Florida Charmer! 2BDRM 2 Full Bath Welcome to Westbay 203 at Westbay Point & Moorings located Bayside in Holmes Beach! Make yourself at home at this Old Florida charmer with 2 bedroom, 2 bathroom canal front unit!🏡 Property Highlights:✨ Heated community pool✨ Tennis courts and outdoor "living room" with lounge chairs and dining tables✨ Just a 10-minute walk to the beach!✨ Unbeatable central location close to grocery store and shops✨ Primary bedroom: King bed, full bathroom with shower/tub combo✨ Bedroom 2: Two twin beds, full bathroom with shower onlyWelcome to Westbay 203 at Westbay Point & Moorings! Make yourself at home at this beautiful 2 bedroom, 2 bathroom canal front condo! This top-notch home is beautifully decorated and has all the feels of the old Florida lifestyle and charm. Inside you will find a cozy main living space that consists of a kitchen with brand new stainless steel full-size appliances, a dining area that seats four and a breakfast bar with addit

Located in Holmes Beach, Florida, United States. Your Own Oasis: A Tropical Retreat with Lagoon Style Pool Holmes Beach and Anna Maria Island await you and your family with this custom built island retreat. The large, central great room is a wonderful place to gather to share a meal or play a game, while the split bedroom configuration creates privacy. Hand scraped hardwood floors and 11' ceilings complete the homes appeal. The fully equipped kitchen boasts top of the line appliances and a washer/dryer combo to make your stay easy. There is also a full house water filtration system.Behind the fenced back yard is a private lagoon pool, with plenty of patio for relaxing after a day of fun on AMI. The central location make this home the perfect base for all your island adventures.  It is close to the island trolley (1 block), right behind the marina to launch your kayak on the bay and it is an easy walk to the beach.  You are close to the many chef owned restaurants so famous on the island.You are vacationing in a residential area. Plea

Located in Holmes Beach, Florida, United States. Golf Cart, Surfer's Dream by SeaBreeze Vacation 6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS MADE AFTER April 29, 2024!All Drivers must be over the age of 21. Drivers must provide valid US Driver's License and US Vehicle InsuranceSurfer's Dream boasts 4 bedrooms, 6 full bathrooms, and 1 half bath, and is also pet-friendly! This splendid home is fully equipped for your vacation needs, so grab your bags and get ready to embark on your getaway! Plus a loft with 4 twin beds for extra sleeping accommodations!The main living area features an open-concept design with a stunning, well-equipped kitchen. Enjoy dining around the island for a quick snack, or opt for a meal in the dining room conveniently located adjacent to the kitchen. Witness breathtaking sunsets from your rooftop deck, unwind by the private pool and hot tub, take a nap in the hammock swing, or relax in the indoor/outdoor space. The possibilities are endless, with even a gaming console available on the 3rd-floor loft.Expl

Located in Holmes Beach, Florida, United States. Day Dream: Pool, Spa, Waterslide, 1.5 Blocks to Beach by Anna Maria Life Vacation Rentals 207 77th St, Holmes Beach, FL 34217What You'll Love About This Home:Location! 1.5 Blocks to the Beach!4 Bedrooms / 4 Bathrooms2 Kings, 1 Queen, Queen over King BunkBed, Twin over Twin BunkBedPrivate Heated Pool & SpaIn Pool Bistro Table with Umbrella & SunshelfWaterslidePool LoungersOutdoor ShowerGas GrillCovered Tiki Hut Patio Dining for 8Professional Linen Service, Washer & DryerComplimentary WIFIBeach TowelsParking for 3 CarsDetails:Day Dream is a single-story pool home located 1.5 blocks from the shimmering soft sands of the beach and sparkling clear waters of the Gulf of Mexico.The ranch style home features a colorful living area and kitchen with counter island dining for four and a dining room with seating for eight. The living area is a comfortable spot for the family to gather and enjoy the pool view from the patio doors.Two of the bedrooms feature a King Bed with ensuite bathrooms and one

Located in Holmes Beach, Florida, United States. New Luxe Home with Rooftop Deck, Pool, Spa, Air Hockey - Annabella by the Sea Annabella by the Sea by AMI LocalsHome in Holmes Beach, FloridaWelcome to Annabella by the Sea! This stunning four-bedroom, four-bathroom house is newly built and boasts a resort-style backyard complete with a sparkling pool, an in-ground spa, ladder golf, and a game room with a pool table. We are excited to offer your friends and family the ultimate vacation experience on Anna Maria Island!Highlights• 5-minute walk to the beach• Private pool with in-ground spa• Rooftop deck • Brand new luxury home• Air Hockey tableThis house has been meticulously designed with numerous living spaces, including a spacious modern seating area, a fully-equipped kitchen with high-end appliances and essential amenities, and a formal dining room table. There is even a wine fridge! Upstairs, there is a den area with a sleeper sofa, TV, and a wet bar. Additionally, the furnished balconies and rooftop deck offer great spots to hang o

Located in Holmes Beach, Florida, United States. Gone Coastal Too by Beach Boutique Rentals Welcome to Gone Coastal, Too! This sister property to Gone Coastal has all the comforts of home.*Features include* * Private saltwater pool * 2 full bedrooms and 2 bathrooms * Brand new queen sleeper sofa - sleeps 6 total* Stainless appliances * Keurig coffee maker and regular drip coffee maker * Flat screen TV * Laundry room * Ping Pong and Corn Hole! * Video game console for the kids (or the kids at heart!) * Outdoor shower * Beach cart, chairs, and umbrellas Centrally located in Holmes Beach, this elevated two bedroom/two bath half duplex is the perfect retreat! It has its own private heated salt water pool and outdoor bbq area with gas grill! The beach is a short 2 1/2 blocks away. Beach chairs, umbrellas and a cart are provided. Just load up and go! There is also an outdoor shower for rinsing off after your trips to the beach.Updated throughout and furnished in bright, coastal colors, you will feel right at home here for your beach getaw

Located in Holmes Beach, Florida, United States. Charming cottage with Pool, close to the Beach! Don't Miss Out! Island Escape by AMI Locals Home in Holmes Beach, FLFeatures:• Private heated pool• Ground-level home, very accessible• Lovely outdoor space, very private, with BBQ grill and dining table• Washer + Dryer• Just a 4-minute walk to the beach!• Beach chairs and Beach cart for guest useSleeping Arrangements:• Bedroom 1 - two Twin beds, shares hallway bathroom with shower/tub combination• Bedroom 2 - Master bedroom with King bed, ensuite bathroom with dual vanity sinks and walk-in shower*Please note: this home is strictly an animal-free zone due to severe allergies. Due to this homeowner allergy, we are unable to welcome any animals including service and/or emotional support animals. No pets are allowed in this property. Please see our AMI Locals Rental Policies for full details.This home is managed by AMI Locals, an Anna Maria Island property management company.We do not accept reservations from anyone under 25 years of age. W

Located in Holmes Beach, Florida, United States. Island Girl East & West - Heated Pool, Porches, Walk to Beach! Welcome to Island Girl East & West!On Anna Maria Island (Holmes Beach, Florida)Introducing Island Girl East & West, an extraordinary duplex that guarantees an unforgettable escape to Anna Maria Island.HIGHLIGHTS:- Expansive tropical patio and heated saltwater pool- Four bedrooms and four bathrooms- Two master suites with attached baths- Accommodates up to 10 guests- Outdoor dining tables- Chaise loungers- Two Propane grills- Provided bicycles- Short walk to the beachNestled a brief stroll from the white sands of Holmes Beach, Island Girl offers a captivating retreat with a wraparound deck overlooking the lush private yard and vibrant pool area.With both sides of this spacious duplex at your disposal, you'll find ample room for up to 10 guests, boasting two of everything – living rooms, dining rooms, kitchens, and more!Craft culinary delights in either of the fully equipped, gourmet kitchens. With generous space, meal prepar

Located in Holmes Beach, Florida, United States. Island Pineapple: 5 min to Beach, Screened Pool, Waterfalls, Game Room by Anna Maria Life 404 80th Street, Holmes Beach, FL 34217 What You'll Love About This Home:Location! 5 Minute Walk to the Beach!4 Bedrooms / 4 Bathrooms3 King Beds / 2 Sets of Twin over Twin BunkbedsPrivate, Heated, Screened Pool with Waterfalls & Ambient LightingPoolside Air Hockey TableWrap Around Balcony Overlooking PoolCovered Lanai with Outdoor SeatingOutdoor Kitchen with Gas Grill & TVGame Room with Ping PongWhole Home Air Purification SystemProfessional Linen Service and Washer & DryerComplimentary WIFIBeach Towels, Chairs, WagonParking for 5 CarsDetails:Island Pineapple will delight the beach vacation in you! Located a quick, five minute walk to the sugar sand beaches of Anna Maria, our home is made for vacation!With the main living space on the second floor and many oversized windows, the home is bathed in natural light. Have the chef in your family create your favorite meal in the modern kitchen. The larg

Located in Bradenton Beach, Florida, United States. Meant to Bee on AMI managed by Beach Retreats 310 60th street Unit B- Holmes Beach - 34217"You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property”You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that time, or for reservations made on or less than 60 days in advance of check-in, your reservation is non-refundable.Written notice is required to cancel a reservation; an email from the address associated with the reservation is acceptable as written notice.For canceled reservations with a check-in date equal to or less than 60 days away: We will open the property back up to the rental market and if the property re-rents we will

Located in Holmes Beach, Florida, United States. Close to Gulf of Mexico with Pool -Serenity at Bay Palms Serenity at Bay Palms by AMI Locals Home in Holmes Beach, FL 34217 Welcome to Serenity at Bay Palms, a newly updated chic vacation home with a private pool and just a few minutes walk to the spectacular Gulf of Mexico beaches. This home features four bedrooms, and each bedroom has an ensuite bathroom! Enjoy the nearby restaurants and shopping that are just a bike ride or a fun trolley ride away.Highlights • Newly Updated Home • Private Pool with heated in-ground Spa• Less than a 10-minute walk from the beach • Near Restaurants and Boutiques on Pine Ave • Outdoor Patio with exterior Sonos SpeakersThis piece of paradise offers a bright and open layout with an inviting living room, a stunning fully equipped kitchen, and an adorable dining room table with access to the backyard through the sliding glass doors. This home has a split bedroom floor plan with a primary bedroom and guest bedroom on each side, making it the perfect hom

Located in Holmes Beach, Florida, United States. Lakeside Beach House 3/2 Pool Home Outdoor Kitchen Close to Beach VRC16-000807The Lakeside Beach House is a wonderful newly renovated three bedroom, two bath home with a private heated pool. Located at 6935 Holmes Blvd. in Holmes Beach, this lovely property is convenient to the beach and in a very quiet, Holmes Beach residential neighborhood. This home faces natural canal area. Although boat access to the bay is not available, rumor has it that this canal is loaded with snook for fishing enthusiasts. There is a small fishing pier facing the water so bring your rods and reels! It’s also a quick walk to the library and restaurants in the preferred northern end of Holmes Beach. It features a washer and dryer, wireless internet with expanded cable and free domestic long distance calling. There is a large open deck at poolside and a covered deck overlooking the pool. There is a very nice outside kitchen at poolside complete with an outdoor stereo system. There is also one car garage. There

Located in Holmes Beach, Florida, United States. Island Serenity: North Beach Village, Dog Friendly, Short Walk to Beach by Anna Maria Life 6250 Holmes Blvd. #54, Holmes Beach, FL 34217What You'll Love About This Home:Location! 2.5 Blocks to the Beach!3 Bedroom/ 2.5 Bathroom1 King bed, 1 Queen bed, 1 Bunkbed - Twin over DoubleFully Equipped KitchenHeated Community PoolGas BBQ GrillProfessional Linen Service, Washer & Dryer, Complimentary WIFIBeach Chairs & Beach TowelsDog Friendly! (with pet fee - see notes below) - 1 Dog Max3 Parking SpacesDetails:Relax in lush tropical island style in this Anna Maria Island condo! Island Serenity is beautifully decorated, and well equipped featuring a shared pool, lush island views, and dog-friendly accommodations just a short walk from legendary white sandy beaches!Conveniently located in Holmes beach you'll be close to several excellent dining options, Leave your cars in the driveway and garage and take the free trolley anywhere else on the island you wish to go, or rent a golf cart and explore o