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Islamorada Estate Homes for Rent

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View all 107 Islamorada Vacation Home Rentals or all 284 Upper Florida Keys Vacation Home Rentals

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Islamorada Luxury Florida Keys Estate

  • 3 BR/3 BA Estate (sleeps 8)
    $12,600/month
    per property, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Islamorada Incredible Luxury Home 5/5 with 400’ Waterfront !! Paradise !!

  • 5 BR/5 BA, 1 half bath Estate (sleeps 13) Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

Islamorada Peaceful Bay front with pool, jacuzzi and outdoor sports. Relax by the pool!

  • 3 BR/3 BA Estate (sleeps 8) pets considered, Hot Tub, Beach, Downtown, Jacuzzi, Lawn / Garden, Balcony, Air Conditioning, Internet
SPECIAL OFFER! we are open May May 1 - May 31

Islamorada Oceanfront Estate the Keys Largest and Most Prestigious Home

  • 8 BR/5 BA, 1 half bath Estate (sleeps 20)
    $500 - $715/nt
    $3,500 - $5,000/wk
    $14,000 - $20,000/month
    per property, wheelchair accessible, Beach, Village, Waterfront, Private Pool, terrace, Balcony, Air Conditioning, Internet, Satellite / Cable
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