Holmes Beach Florida Vacation Rentals and Vacation Homes


Island Real Estate Of A...
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Island Real Estate is Anna Maria Islandís leading full service Real Estate Agency and Vacation Rental Company, specializing in waterfront properties, rentals, investment property, beac...

IslandVacationPropertie...
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Island Vacation Properties is located on beautiful Anna Maria Island on Florida\'s Central Gulf Coast, at the entrance to Tampa Bay, and offers the finest in Florida Gulf Coast vacatio...

Anna Maria Vacations
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Hello, and welcome to Anna Maria Vacations.We are truly a unique rental company specializing in only the finest vacation rentals on Anna Maria Island.

A Paradise Vacation Ren...
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Looking for a little piece of paradise on Anna Maria Island? The Island Specialist's at A Paradise Realty can help. Browse our website to find your perfect vacation accommodation, and ...

 297 Rentals in Holmes Beach

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Property 91488

Blue Dolphin Inn Flamingo

  • Blue Dolphin Inn - Anna Maria Island
  • Inn in Anna Maria Island (Near Holmes Beach)
  • 9 Bedroom(s), Sleeps 26
  • 5 Bathroom(s)
Property 96069

Garden Villas all units

  • Garden Villas all units
  • Anna Maria Island (Near Holmes Beach)
  • 8 Bedroom(s), Sleeps 20
  • 4 Bathroom(s)
  • Weekly Rates from $2,646 - $5,315
Property 108418

Surf View

  • The home is lavish and bold - it offers everything you would expect out of a luxury home and more!
  • House in Holmes Beach (Near Anna Maria Island)
  • 8 Bedroom(s), Sleeps 18-20
  • 5 Bathroom(s)
Property 108432

Summer House

  • Come and enjoy your next family reunion in style - this versatile home offers something for everyone to enjoy!
  • House in Holmes Beach (Near Anna Maria Island)
  • 8 Bedroom(s), Sleeps 16-18
  • 5 Bathroom(s)
  • Islands West Resort All units
  • Resort in Anna Maria Island (Near Holmes Beach)
  • 7 Bedroom(s), Sleeps 24
  • 6 Bathroom(s)
  • Weekly Rates from $3,244 - $6,993
Property 42187

Almost GulfFront

  • Holmes Beach Beautiful Private Vacation Home
  • House in Holmes Beach (Near Anna Maria Island)
  • 6 Bedroom(s)
  • 4.5 Bathroom(s)
  • Weekly Rates from $1,950 - $4,540
  • 529 Key - 529 Key Royale Drive
  • Holmes Beach
  • 6 Bedroom(s), Sleeps 12
  • Weekly Rates from $3,395 - $3,900
Property 82975

Sans Souci Both units

  • Anna Maria Island 6 Bedroom Vacation Rental
  • House in Anna Maria Island (Near Holmes Beach)
  • 6 Bedroom(s), Sleeps 14
  • 4 Bathroom(s)
Property 108441

South Seas

  • South Seas is a new luxury island tropical home with 6 bedrooms, 4.5 bathrooms and is only a short 3-4 minute stroll to the Gulf beach.
  • House in Holmes Beach (Near Anna Maria Island)
  • 6 Bedroom(s), Sleeps 14-16
  • 4.5 Bathroom(s)
Property 108449

Sands of Time

  • Sands of Time is a brand new luxury island tropical home with 6 bedrooms, 4.5 bathrooms and is only a short 2-3 minute stroll to the Gulf beach.
  • House in Holmes Beach (Near Anna Maria Island)
  • 6 Bedroom(s), Sleeps 15
  • 4.5 Bathroom(s)
Property 108458

Pearl Beach

  • Just a short 2-3 minute walk away from the white sand beaches, this gorgeous home offers it all!
  • House in Holmes Beach (Near Anna Maria Island)
  • 6 Bedroom(s)
  • 4.5 Bathroom(s)
Property 108505

Hemingway House

  • This fantastic home offers it all - great location and amenities!
  • House in Holmes Beach (Near Anna Maria Island)
  • 6 Bedroom(s), Sleeps 16
  • 5 Bathroom(s)
Property 108511

Gulfside Oasis

  • Gulfside Oasis is a brand new luxury home that combines comfort, class and convenience.
  • House in Holmes Beach (Near Anna Maria Island)
  • 6 Bedroom(s), Sleeps 16
  • 5 Bathroom(s)
Property 108518

Emerald Seas

  • Come enjoy a large family and friends gathering at this spacious brand new luxury home just a few minutes stroll to the beach.
  • House in Holmes Beach (Near Anna Maria Island)
  • 6 Bedroom(s), Sleeps 16
  • 4.5 Bathroom(s)
Property 108529

Conch House

  • Conch House is a brand new construction, luxury island home with 6 bedrooms and 4.5 bathrooms.
  • House in Holmes Beach (Near Anna Maria Island)
  • 6 Bedroom(s), Sleeps 16
  • 4.5 Bathroom(s)
Property 108550

Blue Water View

  • This new 6 bedroom, 5 full bathroom luxury rental property has large views of the Gulf of Mexico from the roof top deck.
  • House in Holmes Beach (Near Anna Maria Island)
  • 6 Bedroom(s), Sleeps 14-16
  • 5 Bathroom(s)
Property 108554

Beachbreeze

  • Luxury 6 bedroom home West of Gulf Dr and just a short 1-2 minute stroll to the Gulf Beach!
  • House in Holmes Beach (Near Anna Maria Island)
  • 6 Bedroom(s), Sleeps 12-14
  • 3.5 Bathroom(s)
Property 108574

Angel Sea

  • Angel Sea is as versatile as it is gorgeous and instantly welcoming.
  • House in Holmes Beach (Near Anna Maria Island)
  • 6 Bedroom(s), Sleeps 12
  • 3.5 Bathroom(s)
Property 42813

6201 Holmes Boulevard

  • Anna Maria Island Luxury Family Retreat
  • House in Holmes Beach (Near Anna Maria Island)
  • 5 Bedroom(s), Sleeps 10
  • 3 Bathroom(s)
Property 80124

517 Key - 517 Key Royale

  • 517 Key - 517 Key Royale
  • Holmes Beach
  • 5 Bedroom(s), Sleeps 10
  • Weekly Rates from $3,140 - $3,600
  • 532 70TH - 532 70th Street
  • Holmes Beach
  • 5 Bedroom(s), Sleeps 10
  • Weekly Rates from $2,850 - $3,465
  • 541 67TH - 541 67th Street
  • Holmes Beach
  • 5 Bedroom(s), Sleeps 10
  • Weekly Rates from $2,460 - $3,200
Property 88476

Absolutely Perfect

  • HOLMES BEACH ABSOLUTELY PERFECT 5 BEDROOM LUXURY HOME
  • House in Holmes Beach (Near Anna Maria Island)
  • 5 Bedroom(s), Sleeps 10
  • 3.5 Bathroom(s)
  • Weekly Rates from $3,800 - $4,400
Property 96049

Anna Cabana Resort

  • Anna Cabana Resort
  • Anna Maria Island (Near Holmes Beach)
  • 5 Bedroom(s), Sleeps 18
  • 5 Bathroom(s)
  • Weekly Rates from $2,992 - $5,613
Property 106077

Gulf Sound All Units

  • Gulf side, ground level tri-plex with pool that sleeps 10
  • Triplex in Holmes Beach
  • 5 Bedroom(s), Sleeps 10
  • 3 Bathroom(s)
  • Weekly Rates from $2,016 - $2,867


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