Holmes Beach Vacation Rentals
Holmes Beach is a small beach town on Anna Maria Island with that charming Old Florida Town feel that vacationers crave. Holmes Beach is a year-round vacation destination with some of the best sunsets anywhere in the country. There’s miles of soft, white, sandy beaches to explore and gorgeous emerald green water to swim in. With around 5,000 residents, Holmes Beach is the largest of the three communities that make up Anna Maria Island.
You’ll find the perfect Holmes Beach vacation rental at Island Real. Whether you’re looking for a luxury rental with private pool access, a rental with its own canal access, or a beachfront house rental big enough for the whole family - we have you covered! If you’re traveling with a canine companion, be sure to check out our pet friendly rentals.
Check out our favorite things to do in Holmes Beach, read our “Top 10” guides, and more on our blog!
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“dreAMI” 12 Palm Harbor Drive is perfect for a fun and memorable vacation, one of the best rental homes that Anna Maria Island has to offer. “dreAMI” 12 Palm Harbor Drive is a gorgeous home, with three bedrooms three and a half baths this home sports two king beds, and two twin beds and is able to accommodate up to 6 guests. Only monthly stays are
DreAMI
Home- 3
- 3 Full Baths , 1 Half Baths
- Pool
- Dogs Allowed
- Sleeps 6
- 19 Views
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“Martinique” is directly on the coast providing the quintessential beach experience complete with powder white sand, blue water, fresh gulf breezes and amazing sunsets. You’ll want to spend all day soaking up the sun and salt water! Relax with a good book, cool drink or chat with friends around the heated community pool. Enjoy premium linen service
Martinique404N
Condominium- 2
- 2
- Pool
- Dogs Allowed
- Sleeps 6
- 45 Views
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Nestled into a gorgeous resort style setting, Anna Maria Island vacation rental home “Blue Lagoon 5 – Sandpiper” is a fun vacation destination with endless character. Accommodating up to 6 guests this 2 bedroom 2 bathroom vacation rental home offers 1 king bed, 2 twin beds and a 1 queen sleeper sofa and all the amenities of a beachy home away from
Blue Lagoon 5
Condominium- 2
- 2
- Pool
- Dogs Allowed
- Sleeps 6
- 24 Views
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Staying at Buena Vista unit 4 is a fun and memorable experience. Including comfortable furniture, smart televisions in all rooms with HBO and Showtime, and a custom chefs kitchen with induction stove as well as a double door wine fridge; vacationers love celebrating their stay in the spacious living room perfect for entertaining. The open floor pla
Buena Vista 4
Condominium- 4
- 3 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 8
- 26 Views
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"Flip Flop Oasis" Two Single Family Homes with Adjoining Yards and TWO Heated PoolsFirst Home 201 57th Street "Flip Flop Inn" If you are searching for luxury on your Island vacation, this home is your dream come true. Tucked away on a quiet street on Anna Maria Island, this Mediterranean-style Townhouse is your perfect family vacation destination.T
Flip Flop Oasis
Multi-Family- 6
- 6
- Pool
- No Pets
- Sleeps 12
- 15 Views
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With stunning direct Bimini Bay views, the stylish “High Tides and Good Vibes Westbay Point and Moorings Unit 265” is a fine example of a luxury island vacation getaway. Comfortably rooming up to 4 guests this 2 bedroom 2 bathroom Holmes Beach vacation rental condominium offers two king beds and a queen sleeper sofa in a beautiful coastal inspired
High Tides and Good Vibes
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 4
- 21 Views
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Welcome to the freshly updated Spacious Oasis! Spacious Oasis is a Mediterranean style 3-bedroom, 3-bathroom pool home located just blocks away which is a short stroll from the gorgeous beach of Anna Maria Island! This home has everything you need to feel like you are on vacation every day. This home also has an elevator for your convenience. Spaci
Spacious Oasis
Home- 3
- 3
- Pool
- Dogs Allowed
- Sleeps 6
- 84 Views
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This Poolside condo offers direct access to the Pool Area, creating a dreamy atmosphere reminiscent of living atop the beautiful blue waters of the Gulf of Mexico. Memorable sunsets and the soothing sound of calm waves will leave you feeling refreshed and rejuvenated during your stay on Anna Maria Island. The kitchen, living, and dining areas boast
Coconuts 119
Condominium- 1
- 1
- Pool
- No Pets
- Sleeps 4
- 15 Views
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Inside this Holmes Beach vacation rental you’ll find a well-appointed condominium to kick your feet up in island style. The living room offers a flat screen television, comfortable furniture and the dining area seating four. In the kitchen you’ll find all the basics including a dishwasher. Off the kitchen there is a private balcony.Accommodating up
Casa Sierra 205B
Condominium- 2
- 2
- Pool
- Dogs Allowed
- Sleeps 6
- 29 Views
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For a laid back beach vacation you won’t soon forget, visit “EverLasting Sunsets A” in the city of Holmes Beach! <br /><br />“EverLasting Sunsets A” offers accommodations for three guests in a premium beach bound location. This cozy duplex is just a short block walk from some of Anna Maria Island’s most coveted beaches in Holmes Beach. These beach
EverLasting SunSets A
Multi-Family- 1
- 1
- Pool
- No Pets
- Sleeps 3
- 17 Views
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"La Casa Marie" - Luxurious Gulf-Front Vacation Condo in Holmes BeachWelcome to "La Casa Marie," a stunning waterfront vacation condo situated in the picturesque La Casa Costiera complex at 7320 Gulf Drive, Holmes Beach. This exquisite 3-bedroom, 2.5-bathroom retreat can comfortably accommodate up to 6 guests, featuring a King bed, a Queen bed, and
La Casa Marie
Condominium- 3
- 2 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 6
- 51 Views
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Experience the Tropical beach paradise vacation of a lifetime when you stay at Holmes Beach vacation rental condominium “Vista Grande Sul Mar”. This gorgeous beach front condo, located within the Vista Grande complex, rooms up to 6 guests with 1 king bed, 1 queen bed and 2 twin beds in this 3 bedroom 3 bathroom spacious vacation destination.<br /><
Vista Grande 1 Sul Mare
Condominium- 3
- 3
- Pool
- No Pets
- Sleeps 6
- 27 Views
