Holmes Beach Florida Vacation Rentals and Vacation Homes

 303 Rentals in Holmes Beach

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Property 96060

Castnetter Trust Parent

  • Castnetter Trust Parent
  • Anna Maria Island (Near Holmes Beach)
  • 11 Bedroom(s), Sleeps 28
  • 7 Bathroom(s)
  • Weekly Rates from $3,465 - $6,038
  • Each unit has its own private patio and gas grill for an evening of relaxation.
  • Condo in Anna Maria Island (Near Holmes Beach)
  • 9 Bedroom(s), Sleeps 26
  • 5 Bathroom(s)
Property 96069

Garden Villas all units

  • This delightful island locale is situated conveniently across from the Manatee Public Beach and the Gulf of Mexico.
  • Condo in Anna Maria Island (Near Holmes Beach)
  • 8 Bedroom(s), Sleeps 20
  • 4 Bathroom(s)
Property 108404

Tropical Oasis

  • Tropical Oasis is the pinnacle of Anna Maria Island luxury vacationing.
  • House in Holmes Beach (Near Anna Maria Island)
  • 8 Bedroom(s), Sleeps 16
  • 5 Bathroom(s)
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)
  • The Islands West Resort, located at 3605 Gulf Drive in Holmes Beach, is a ground level resort with a large heated pool.
  • Resort in Anna Maria Island (Near Holmes Beach)
  • 7 Bedroom(s), Sleeps 24
  • 5 Bathroom(s)
Property 96049

Anna Cabana Resort

  • The Anna Cabana Resort, consists of five units, all located less than one block to the beach.
  • Resort in Anna Maria Island (Near Holmes Beach)
  • 7 Bedroom(s), Sleeps 24
  • 5 Bathroom(s)
  • Weekly Rates from $3,591
Property 108401

View of the Gulf

  • Located in a secluded spot in Holmes Beach, this 7 bedroom, 4 full and 2 half bathroom island home takes vacation rentals to the next level.
  • House in Holmes Beach (Near Anna Maria Island)
  • 7 Bedroom(s), Sleeps 14
  • 5 Bathroom(s)
  • New large family pool home on canal 6 bedrooms- 5 bathrooms .
  • House in Holmes Beach
  • 6 Bedroom(s), Sleeps 12
  • 5 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 80124

517 Key - 517 Key Royale

  • 517 Key Royale - Beautiful View of Tampa Bay from upstairs Deck.
  • House in Holmes Beach (Near Anna Maria Island)
  • 5 Bedroom(s), Sleeps 10
  • 541 67th. Street----5 bedroom 4 bath canal front home.
  • House in Holmes Beach (Near Anna Maria Island)
  • 5 Bedroom(s), Sleeps 10
  • 4 Bathroom(s)
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 $2,028
Property 108393

Villa Portofino

  • This upscale 5 bedroom, 3.5 bathroom Mediterranean Villa is only a short 3 minute walk from the beautiful white sand beaches.
  • Villa in Holmes Beach (Near Anna Maria Island)
  • 5 Bedroom(s), Sleeps 12
  • 3.5 Bathroom(s)
Property 108421

Sunset Landing

  • Sunset Landing is a brand new 5 bedroom+ bonus room, 4.5 bathroom vacation home sitting West of Gulf Dr. and an easy 2 minute walk to the beach.
  • House in Holmes Beach (Near Anna Maria Island)
  • 5 Bedroom(s), Sleeps 12
  • 4.5 Bathroom(s)


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