Holmes Beach Vacation Rentals
528 rentals with 6,474 photos.Most Popular
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Holmes Beach
Meticously maintained 3 bed/3 bath home with two master suites. Gourmet kitchen with breakfast bar overlooking the pool. Over sized lot with large open pool area overlooking Bimini Bay with lush landscaping. Great cover...
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per night
3 beds
3 baths
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Holmes Beach
On Anna Maria Island, you hear a lot about visitors experiencing love at first sunset. By the time sun is setting on your first day, most people are hooked. But at this house, it might not even take you that long. With ...
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per night
3 beds
2 baths
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Holmes Beach
Just what you're looking for - a ground level villa value priced for vacationing in Florida for a month or more! Fabulous two bedroom and two bath Island vacation rental recently updated with new tile floors and new pai...
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per night
2 beds
2 baths
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Listings
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Holmes Beach
Meticously maintained 3 bed/3 bath home with two master suites. Gourmet kitchen with breakfast bar overlooking the pool. Over sized lot with large open pool area overlooking Bimini Bay with lush landscaping. Great cover...
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per night
3 beds
3 baths
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Holmes Beach
On Anna Maria Island, you hear a lot about visitors experiencing love at first sunset. By the time sun is setting on your first day, most people are hooked. But at this house, it might not even take you that long. With ...
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per night
3 beds
2 baths
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Holmes Beach
A lovely, two bedroom/two bathroom, modern, Gulf front penthouse apartment on Holmes Beach! This unit has a king bedroom with flat screen television and another bedroom with two twin beds. This great apartment has views...
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per night
2 beds
2 baths
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Holmes Beach
On Anna Maria Island, you hear a lot about visitors experiencing love at first sunset. By the time sun is setting on your first day, most people are hooked. But when you pull up the east side of this elevated vacation h...
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per night
2 beds
2 baths
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Holmes Beach
Just what you're looking for - a ground level villa value priced for vacationing in Florida for a month or more! Fabulous two bedroom and two bath Island vacation rental recently updated with new tile floors and new pai...
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per night
2 beds
2 baths
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Holmes Beach
Fabulous and gulf front, this vacation condo is located at 2700 Gulf Drive in Holmes Beach, right in the heart of Anna Maria Island. This two bedroom, two bathroom rental sits nestled in one of the island's most coveted...
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per night
2 beds
2 baths
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Holmes Beach
This Beach Cottage is in the preferred, northern end of Holmes Beach is an elegant, Gulf front, ground level home on a pristine beach. Walk for miles in either direction on the white, sugar sand and explore the island s...
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per night
2 beds
2 baths
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Holmes Beach
This Holmes Beach Vacation Rental, located in Holmes Beach is an extremely popular three bedroom, two bath home with a private heated pool, tropical landscaping, a double car garage and gulf views from the open deck. Th...
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per night
3 beds
2 baths
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Holmes Beach
(2) Bed: (2) Bath: Accommodates up to (4) people: 1 King, 2 twins Internet wireless No smoking: No Pets.
Enjoy a magical sunset in this updated Gulf of Mexico Direct beachfront Condo... Perfect family condo for a holid...
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per night
2 beds
2 baths
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Holmes Beach
Updated Holmes Beach Island home just steps to the Gulf of Mexico beaches. Enjoy this vacation rental with a new heated pool and a brand new paver area with propane grill. This vacation rental has everything to offer wi...
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per night
3 beds
2 baths
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Holmes Beach
Vacation Anna Maria Island in this magnificent elevated Mediterranean style three bedroom and three bath villa in a perfect location close to the pristine beaches, choice restaurants and fabulous shopping experiences. T...
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per night
3 beds
3 baths
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Holmes Beach
This is a gorgeous two bedroom, two bath direct Gulf front vacation rental unit situated in Holmes Beach. This much sought after complex features an elevator, heated pool, tennis court and a beach that is unparalleled. ...
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per night
2 beds
2 baths
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Holmes Beach
Welcome to Southern Comfort... Steps from the Gulf Beaches -- Holmes Beach, Anna Maria Island, FL -- (2) Bed: (2) Bath: Accommodates up to (6) people: 1 King, 2 Queens: Internet - Wireless: No Pets No smoking Enjoy this...
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per night
3 beds
2 baths
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Holmes Beach
Gracious Town Home Holmes Beach, Anna Maria Island, FL -- (2) Bed: (2.5) Bath: Accommodates up to (6) people: 1 Queen, 2 Twins & Sleeper Sofa: wirless internet, No smoking: No Pets.
Absolutely fabulous two bedroom and ...
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per night
2 beds
2 baths
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Holmes Beach
Wiggle your toes in the sand. relax with your morning coffee, afternoon tea or sunset drinks - or all three - on the white sandy beach which is just a short stroll from this luxury rental. Beach Retreat is a newly renov...
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per night
4 beds
2 baths
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Holmes Beach
This beautiful two bedroom, two bath Anna Maria Vacation home is situated on spring fed lake yet it's only three blocks to the beach. A beautiful heated pool and spa overlooks the lake and native landscaping and a large...
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per night
2 beds
2 baths
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Holmes Beach
These Anna Maria Island rentals are located within a charming beach side complex featuring eight units surrounding a heated pool, tropical landscaping, multi-level decks and built in BBQ area.
Perfect for your next Ann...
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per night
1 bed
1 bath
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Holmes Beach
This is a charming beachside complex featuring eight units surrounding a heated pool, tropical landscaping, multi-level decks and built in BBQ area. Anna Maria's white sandy beaches and the emerald green water of the Gu...
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per night
1 bed
1 bath
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Holmes Beach
This a charming Anna Maria beachside complex featuring eight units surrounding a heated pool, tropical landscaping, multi-level decks and built in BBQ area. Anna Maria's white sandy beaches and the emerald green water o...
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per night
1 bed
1 bath
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Holmes Beach
Fantastic three bedroom, two bath, recently remodeled island home with a brand new sparkling pool and dock access. Bring your family AND your boat on your vacation so you can enjoy all the activities Anna Maria Island h...
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per night
3 beds
2 baths
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Blog Posts
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November 08, 2011
Sarasota is working with boating community, which is good. A place boaters want to avoid is Holmes Beach on Anna Maria Island, just noryh of Longboat Key. The code enforcement officer [there] will har...
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August 18, 2011
LAURA AND MATT • HOLMES BEACH WEDDING • ANNA MARIA ISLAND, FL...
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