72,107 properties available

Located in Holmes Beach, Florida, United States. Newly Remodeled-Island Chic Island Chic by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 Welcome to Island Chic, a beautifully renovated home featuring four bedrooms and four bathrooms. This incredible home is packed with all the vacation amenities you’ll want, including a private pool and hot tub, putting green, corn hole, and a ping pong table! Feel the warm sunshine on your smiling face and the sand underneath your feet at the Gulf of Mexico beaches, just a short stroll away. Highlights• Newly Remodeled• Less than a 5-minute walk from the beach • Private Pool and Hot Tub• Putting Green, Corn Hole, and Ping Pong Table• Outdoor ShowerWhen you first walk in the front door, you’ll be welcomed into the great large room with a gourmet kitchen, dining table, and a great living space for movie nights. The primary bedroom is outfitted with luxuriously plush bedding, an ensuite bathroom with a gorgeous vanity and standalone tub, and this suite even has access to the bac

Located in Holmes Beach, Florida, United States. Waterfront home with heated pool + spa, patio, grill, & free WiFi - dog-friendly 3 OarsOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.The stunning canal front Holmes Beach vacation rental 3 Oars Oasis is the perfect destination for a luxury getaway. Spacious and elegant, as well as dog-friendly, this rental has a heated pool and spa, boat dock, designer furnishings and a location in the exclusive Key Royale neighborhood. Key Royale is a desired area for both vacationers, families, and retirees alike. This quiet portion of Holmes Beach is off the main path and offers a high-end coastal suburban feel. Key Royale juts off into Tampa Bay making this a boaters paradise! In just a short ride you can cruise under the stoic Sunshine Skyway Bridge and find excelle

Located in Anna Maria, Florida, United States. H2O Bungalow by Beach Boutique Rentals H2O Bungalow is a 3 bed, 3 bath stunning vacation home that is unique and unlike any others. *Features include* * Private lazy river pool with hot tub! * 3 bedrooms, 3 full bathrooms * 2 master king suites * Fun bunk bedroom for the family * Gourmet kitchen and spacious dining room * Washer and dryer * Massive outdoor space with loungers, tables + charcoal grill * Patio dining table for 6 * Beach chairs, umbrellas and cart * Less than 2 blocks to the beach * Dog Friendly! There is nothing else on the island quite like the Polynesian inspired backyard at H2O Bungalow! You will have your own private retreat complete with a spectacular lazy river, waterfalls, a stone bridge and Easter Island statues. The amazing pool also features fountains and a large hot tub for relaxing. While the family enjoys the pool, cookout on the charcoal grill and and then dine outside amidst the tropical landscaping. We won't blame you if you never want to leave this bac

Located in Holmes Beach, Florida, United States. Holmes Sweet Holmes by SeaBreeze Vacation Nestled in a tranquil coastal community in beautiful Holmes Beach, the aptly named Holmes Sweet Holmes is the ideal spot for your family's next escape to the shore. Featuring three blissful bedrooms and lots of communal living space, this picture-perfect home base allows everyone to have their own private time, while still keeping everyone close as well. Located near the beach and lots of local activities and featuring a large community swimming pool too, Holmes Sweet Holmes is simply the ideal family oasis.The main level living space is airy and open, featuring a wall of glass doors that allow plenty of bright Florida sunshine inside. Luxurious leather sofas sit on bleached wood flooring and face the large HDTV, while lots of dramatic, coastal-inspired artwork adds an elegant style to the space. The glass door leads outside to a generous screened-in porch, where you'll want to sit while sipping your morning mug of coffee or frozen happy hour m

Located in Holmes Beach, Florida, United States. Cozy 'Day' Side Cottage with Heated Pool Pet Friendly No size restrictions VRC# 19-000218Cozy 'Day' Side Cottage is located in Holmes Beach on Anna Maria Island. It offers 2 bedrooms and 1 1/2 baths. This pet friendly cottage has everything you need to relax and enjoy the island life style! Open floor plan includes kitchen with new stainless steel appliances and table for 4. Updates include white cabinetry, granite counters and new food pantry. Light and bright, the Kitchen/Dining/Living room is full of windows and a sliding glass door to your own balcony, the perfect place for that first cup of coffee while enjoying the sun rise!There is also a covered patio with propane grill to prepare your meals while soaking in the heated pool. Our unique pool design is child friendly offering a shallow lazy river, connecting two deeper pools, where younger children can play. We have water toys, life jackets, floaties, etc to keep kids having fun! Adult supervision required while children

Located in Holmes Beach, Florida, United States. Spacious family home with heated Pool and Spa - Shamrock Palms Shamrock Palms by Anna Maria Island AccommodationsHome in Holmes Beach, FL 34217VRC16-000106Welcome to Shamrock Palms, a delightful ground-level home featuring three bedrooms and two bathrooms. This vacation haven boasts a splendid backyard, complete with a sparkling pool, rejuvenating spa, BBQ grill, and luxurious lounge chairs perfect for soaking up the Florida sunshine. Highlights • Private pool with in-ground spa• Less than a 10-minute walk from the beach• BBQ grill• Near the Free Island trolley stop• Outdoor showerUnwind in the spacious front living area with very comfortable sofa seating and a 55" HDTV. The fully-equipped kitchen has all the essential cookware to prepare a feast, an island bar, and opens to the dining room table. Relax and refresh in the primary bedroom with sea-life themes, a luxurious King bed, pool deck access, and an ensuite bathroom that features an exquisite vanity and walk-in shower. The second

Located in Holmes Beach, Florida, United States. Unwind Sunshine - heated pool, steps to the local's favorite beach, free bikes ***WEEKLY RENTAL**** This Luxury beach chic cottage home has it all....location, fully stocked luxury kitchen, and beach bikes. 4 minute walk to the beach and near the free trolley stop. This boutique property is not your average rental. We are blessed to have multiple repeat visitors year after year. Come see why!THE HOME - Pristine 4 bedroom, 3 bath charmer sleeps 8 guests. Dual King Ensuite bedrooms. Luxury mattresses and black out shades for a good night sleep. Automated home with electronic locks, 4 smart TV's, WIFI, a nest system, and bluetooth stereo, so you can enjoy tropical tunes poolside. The ranch style floor plan with open concept kitchen and living room is a perfect layout for family fun. THE BEACH - Our beach access is known by the locals as one of the BEST beaches on the island due to the gentle sloping ocean floor, no high rise condos, and a wide sand bar to look for sand dollars.

Located in Holmes Beach, Florida, United States. Anna Maria Hideaway by SeaBreeze Vacation In the heart of Holmes Beach on Anna Maria Island rests this charming home just steps to the beaches. The home creates fun Florida island vibes with two bedrooms perfect for a family or a small group getaway. Anna Maria Hideaway lies within a stone's throw of the trolley stops for guests to hop on for a ride and enjoy all the nearby shopping and restaurants. With spots for three cars, this coastal home allows guests to enjoy the ocean and town's attractions within walking distance without the hassle of having to park anywhere else! As you open the front door, the fully-equipped kitchen and spacious living/dining room area invite you inside. With granite countertops, any guest would feel enchanted to cook up something delicious. The breakfast bar serves as the ideal spot to enjoy french toast and orange juice in the morning while the dining room table gathers everyone together for dinner and conversation. The living room provides ample options

Located in Holmes Beach, Florida, United States. Beautifully outfitted home with a heated pool and tropical backyard! Seahorse Paradise2.5 Blocks to BeachHighlights:• Heated Pool• Tropical Backyard • Large Covered Patio• Poolside Dining TableBeautifully outfitted and maintained is this 3 bedroom/2 bath home with a Heated Pool in a very tropical backyard setting. All of the bedrooms and the spacious open concept living area are on the second level. The downstairs contains the garage and pool area which is accompanied by a large covered patio area outfitted with an outdoor living room set, poolside dining table, a small bistro table, and wall mounted flat screen TV. The fully stocked kitchen boasts very nice Granite Countertops and Stainless Appliances. The beachy feel is further accentuated by the tall white-washed wood planked vaulted ceilings and coastal decor. This is a great location in a quiet neighborhood, just a couple of short blocks to the beach access and a half block to the Free Island trolley. This Paradise sleeps up to 6

Located in Holmes Beach, Florida, United States. Ground level home with pool, spa and lanai! - Coastal Breeze Coastal Breeze by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217VRC17-000063 Welcome to Coastal Breeze! This four-bedroom, three-bathroom retreat features an outstanding backyard! You'll love the private pool with an in-ground spa, the comfy and colorful outdoor seating, and the unique tiki bar where you can enjoy tropical drinks and soak up the island lifestyle!Highlights • 2-minute walk to the beach • Private pool with in-ground spa• Tiki-bar• Outdoor shower• Washer and dryerThis beach-themed house has cozy seating in the living room, family room, and screened lanai, so every guest has a comfortable space to unwind. The galley kitchen is fully equipped with stainless steel appliances, granite countertops, and cooking utensils. There are three dining areas, including an outdoor dining area with a grill that's perfect for cooking fresh seafood.Experience ultimate relaxation in any of the four bedrooms, each a

Located in Holmes Beach, Florida, United States. Peaceful Holmes by Beach Boutique Rentals Peaceful Holmes is your perfect and tropical home away from home. *Features include* * Private heated pool * Totally updated home * 3 bedrooms, 3 full bathrooms * Cable or Roku TV in each room * Washer and dryer * Lounge chairs by the pool * Ground level home, no stairs * Outdoor dining * Gas grill * Hot and cold outdoor shower* Beach chairs, cart, umbrella and cooler* Steps to the beach! Located west of Gulf drive, this immaculate home is only steps away from the white sandy beaches of Holmes Beach, without any streets to cross. You are sure to feel right at home, as this house was lovingly furnished and decorated to make sure guests wouldn't miss a thing. This 3 bedroom, 3 bath home is the perfect place to spend a family vacation on Anna Maria Island. Your group will appreciate the spacious layout, which includes two master king suites with private attached bathrooms. A full size bed with additional trundle in the third bedroom will afford e

Located in Holmes Beach, Florida, United States. West Bay Point Moorings 155 West Bay Point Moorings 155 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 4 people. VRC#20-000123Distance to the Beach: 6 blocksCommunity pool. Nice and bright, this Holmes Beach condo is located one level above ground, with a few easy steps up. Facing south, this end unit allows you to enjoy all the nice sunshine coming in through the enclosed sunroom. Open up the sliders to let the fresh breezes in. This complex offers several pools, tennis courts, and a jacuzzi. Great community of Island people to enjoy as well with social activities. Full size washer and dryer for your convenience right at your front screened lanai.*This condo association does not permit motorcycles, trailers, large trucks, or RV parking on their property. 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 the entire island. It is one of the finest

Located in Holmes Beach, Florida, United States. Pool, Spa, Games, and Tiki Bar! - View of the Gulf View of the Gulf by Anna Maria VacationsHome in Holmes Beach, FL 34217VRC16-000749Welcome to View of the Gulf, a magnificent villa with a rooftop deck with gorgeous Gulf views just mere steps away from the stunning white sands of Holmes Beach. This seven-bedroom, four-full, two-and-a-half-bath home features a sparkling pool, hot tub, a tiki bar, and shuffleboard, making this home a dream beach vacation getaway! Highlights • Rooftop deck with Gulf views• Short block from the beach • Hot tub and pool with built-in seating• Tiki bar, grill, and outdoor seating• Shuffleboard Guests can relax on the oversized leather sectional in the living room and have a movie night, unwind in the smaller den with comfortable sofas and tropical views, or have a family game night in the downstairs living space. The elegant kitchen has stainless steel appliances, gorgeous countertops and is well-equipped to prepare and serve delicious meals. Gather guests f

Located in Holmes Beach, Florida, United States. Gone Coastal by Beach Boutique Rentals Welcome to Gone Coastal! No detail was spared when this fabulous vacation rental was designed.*Features include* * Private saltwater pool * 2 bedrooms and 2 full bathrooms * 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 getaway. Inside the

Located in Holmes Beach, Florida, United States. Wish Upon a Starfish by Beach Boutique Rentals A Wish Upon a Starfish, where all your island dreams come true! This elevated Key West style 3 bedroom home is truly paradise found. *Features include* * 3 bedrooms with 3 full attached baths * Private heated saltwater pool * Beach chairs and wagon and toys * Washer and dryer * Ping pong table * Bicycles * Outdoor shower * Family friendly, stocked with children's supplies * Large family dining table in the poolside lanai * Rooftop deck * 2 blocks to the beach! This beautiful home is located in a quiet and peaceful Anna Maria Island neighborhood. Too many wonderful features to list including vaulted ceilings, open floor plan and huge ground floor lanai with French doors opening up to the private heated pool. You will enjoy your coffee on the spacious front deck. Relax with one of the many books provided in the library or a cocktail in the evening. The fully equipped kitchen has everything you need to prepare a quick snack for your family

Located in Holmes Beach, Florida, United States. Blue Haven Beach House - Peek at Gulf, Heated Pool, Elevator, 4 Min Walk to Beach, Games! Welcome to Blue Haven Beach House!On Anna Maria Island (Holmes Beach, FL)Recently updated & AMAZING LOCATION!This LOVELY two story elevated island home has been recently updated with fresh coastal colors, new furniture, and decor. This home is in a SUPERB location just steps to the white sands of the gulf-side pristine beaches, nearby trolley stop, and shops of Holmes Beach. You can literally peek at the blue waters of the Gulf of Mexico from one of your two screened-in lanais on the front porch of this home!HIGHLIGHTS:- Open Concept Kitchen, Dining Area, Island Seating, Living w/ TV & Sleeper Sofa- 1 King Bedroom w/ TV & En-Suite Bath- 1 Queen Bedroom & En-Suite Bath- 2 Twins Bedroom (can be converted into a king bed by advance request)- Hall Full Bath- Screened-in Lanais- Peek-A-Boo Gulf Views & Quick Walk to Beach- Elevator *Please note this home is not wheelchair accessible and is maintained a

Located in Holmes Beach, Florida, United States. Ebb Tide by Duncan Real Estate Come to this Island home and have a vacation of a lifetime! Totally remodeled, this 3-bedroom, 3-bath pool home is well appointed with designer finishes throughout. The living area has plenty of seating for the whole family. The kitchen is outfitted with gorgeous granite countertops and stainless-steel appliances. Start your day with your favorite morning treat at the breakfast bar. There is also a large Florida room with a dining table for six to gather around the family. A sofa and chair provide an additional seating area. This spacious and serene getaway sleeps up to six people. Hop on the close by, free Trolley and explore the quaint Island shops and restaurants. Take a short stroll to the Ugly Grouper in Holmes Beach for a little live music in their tropical, open-air venue. The Gulf of Mexico is in walking distance with a beach access at the end of 65th St. HIGHLIGHTS - 1361 sq ft. - Pet friendly - Private

Located in Holmes Beach, Florida, United States. Private Beach Home with Pool, Two Primary Suites, Close to Beach - Coral Retreat Coral Retreat by Anna Maria VacationsHome in Holmes Beach, FL 34217VRC16-000353 Welcome to Coral Retreat, a vibrant coral beach home with five bedrooms and three and a half bathrooms just a five-minute walk from the pristine Gulf of Mexico beaches! Designed for family and friend getaways, this home has an incredible backyard with a sparkling pool and an in-ground spa, and inside, you'll find a ping pong table and arcade game. Highlights• Private Pool and In-ground Spa• 5-minute walk to the beach • Ping Pong table and Arcade game• Near restaurants and shops• Outdoor Entertainment AreaThe main seating area has a TV and is elegantly decorated with a coastal-inspired decor. You'll find sweeping white granite countertops in the kitchen area, a beautiful light green tiled backsplash, a full suite of stainless steel appliances, a large island with a breakfast bar for three, and a rustic-chic table with seating fo

Located in Holmes Beach, Florida, United States. Private Ground Level Beach Paradise 3 bedroom, 2 bath, spacious deck with lovely heated swimming pool. Great for grilling and enjoying the lovely, spacious, lush, tropical landscaping. Located on 2 corner lots affords great privacy. Outdoor, warm water shower. 1 block from the incredible white sands of the Gulf of Mexico. All ground level home. Great laundry room, spacious kitchen and sit down bar. High speed Internet connection and 2 cable TV 's with HD flat screen TV. This is a tobacco-free property. No pets.

Located in Holmes Beach, 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.)If you are looking to enjoy Anna Maria Island in a beautiful home, look no further than "Sunny Side of the Beach" on 66th Street. This five bedroom, 3 bathroom island paradise, nestled into the city of Holmes Beach, is equipped with a beautiful, state of the art kitchen fully supplied with all the cookware, appliances and other kitchen supplies to allow for the full expression of your inner gourmet chef. The home is beautifully decorated with understated beach house elegance throughout. The five bedrooms-each of them comfortable, cozy and bright-are arranged for maximum privacy, with flat screen TVs and cable access. Conveniences abound here: the washer and dryer are top of the line, and Wi Fi gives

Located in Holmes Beach, Florida, United States. Lakefront 3BR Duplex with Private Pool - Anna Maria Island - Island Real Estate If you’re looking to enjoy the beaches of Anna Maria Island, as well as relaxing island life, look no further than “Sugar Sands”. This duplex style home sports stylish and calming décor, with a fun and sophisticated feel. The high ceilings lend to a spacious layout, something to be enjoyed by family and friends. This home, located in a quiet Holmes Beach neighborhood, easily accommodates six with 3 bedrooms and 2 baths.During your stay at Sugar Sands, you’ll find the amenities just as enjoyable as the home itself. Spend some time in the living area, where you can make use of the WIFI or watch your favorite shows on the flatscreen TV. When it’s time to eat, the fully equipped kitchen comes with stainless steel appliances for preparing meals. Or if you’d rather grill, the property comes with a propane barbeque grill. Either way, feel free to enjoy your meals in the outdoor dining area. Sugar Sands also has a

Located in Holmes Beach, Florida, United States. Cozy Night Side Cottage with Heated Pool on quiet street on Anna Maria Island VRC# 19-000219This cozy 2 bedroom 2 full bath cottage is half of our A Lazy River Day and Night duplex. You will feel right at home the minute you walk in! The home is open and airy and it welcomes you to relax on the comfy new sofa and love seat. Here you can check the boating forecast on your cable TV or face time with your loved ones using the high speed wireless internet. A Roku is included for your entertainment as well as a Nintendo Switch for game nights. There are some fun board games as well. The kitchen has been just outfitted with brand new stainless steal appliances as well as cooking and baking ware to help out on those meals you may prepare inside. New white cabinetry and Granite counters and new food pantry complete the workable kitchen. We keep oils and spices for your amazing meals! Outside we have outdoor couches to rest while cooking the latest catch on the propane grill. Or swim in th

Located in Holmes Beach, Florida, United States. West Bay Point Moorings 85 West Bay Point Moorings 85 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. VRC21-000195Distance to the Beach: 7 blocksCommunity pool. Relax and enjoy the tranquility of West Bay Point Moorings with its panoramic view of Tampa Bay. Your vantage point for these spectacular views is a condo located in the unique Anna Maria Island resort style complex of West Bay Point & Mooring. This community is tucked away in the City of Holmes Beach. Your spacious Island retreat hosts a coastal flair throughout with master and guest bedrooms featuring luxury linens and en suite baths. Open your floor-to-ceiling rear slider doors and a soft breeze will flow through your master suite and beyond! The gourmet kitchen with its full array of items and view-line of the waterfront will enhance your cooking experiences. In addition, you will enjoy your own boat slip plus the complex's amenities that include lush tropical landscaping, a heated swimm

Located in Holmes Beach, Florida, United States. Beautiful Beach House with Heated Pool and Fenced Backyard! Sol y Mar by Anna Maria Island LocalsHome in Holmes Beach, FLHighlights:• Outdoor Shower• 2 Paddle Boards • 1 Kayak• Cornhole game• Dog friendly with host approval and $250 pet feeHome Layout:Bedroom #1- King bedBedroom #2- Queen bedBedroom #3- Queen bedBonus: Twin Day bed and Twin pull out sofa sleeperThis bright, newly refreshed 3 Bedroom beach house oasis features the perfect mix of modern decor mixed with touches of mid-century inspired furnishings and original terrazzo floors. Guest will love the BRAND NEW heated pool with private fenced in backyard lined with tropical palms. Kick back and relax "Palm Springs" style or enjoy a day of paddle boarding or kayaking. With 2 levels, Sol y Mar offers privacy for all parties, featuring 2 bedrooms, 2 full baths plus adorable half bath all on first floor and Master bedroom and sun lit bathroom equipped with large soaking tub and shower on the 2nd floor. Kids will love the bonus