Seaside Rentals in Osceola County

Curated Seaside Rentals and cottages in Osceola County

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

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Home spotlights

The Gulf Sings a Lullaby

The Gulf Sings a Lullaby

  • 6 guests

  • 2 bedrooms

Gulf Shores, Baldwin County

If proximity to the beach is your priority, this breezy condo is sure to hit the spot. You'll find the warm turquoise waters of the Gulf of Mexico just across the street, so you can be splashing in the waves and lounging in the sun in no time.

Singing Sweet Carolina

Singing Sweet Carolina

  • 12 guests

  • 6 bedrooms

Hilton Head Island, Beaufort County

A sweet summer’s day comes easy in this elegant, Georgian-style home. After a rejuvenating sleep in one of the lavish bedrooms, all you’ll want is to get out into the sun.

Orange & Sand

Orange & Sand

  • 6 guests

  • 3 bedrooms

Harbor Beach, Fort Lauderdale

A private dock on the canals of Fort Lauderdale and your own swimming pool by the waterside – this cosy cottage is ideal for boaties and waterbabies. If you’re not exploring the area by kayak, boat or paddleboard, you can rent bikes and go by land.

White Ibis

White Ibis

  • 11 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

This beautiful home has a prime location overlooking the Palmetto Dunes lagoon. Just ten minutes’ walk from Hilton Head’s dazzling sands, it’s an ideal base for a beach holiday.


We selected the top 3% holiday homes in Osceola County Seaside Rentals

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Most popular homes

Call of the Seabird

Call of the Seabird

  • 8 guests

  • 4 bedrooms

Anna Maria, Manatee County

Sunshine Magic

Sunshine Magic

  • 16 guests

  • 8 bedrooms

Coral Ridge, Fort Lauderdale

Sandcastle Retreat

Sandcastle Retreat

  • 2 guests

  • 2 bedrooms

Central Beach, Fort Lauderdale

Oyster & Pearl

Oyster & Pearl

  • 8 guests

  • 3 bedrooms

Hilton Head Island, Beaufort County

Salty Breeze

Salty Breeze

  • 8 guests

  • 3 bedrooms

Hilton Head Island, Beaufort County

Dream of the Open Sea

Dream of the Open Sea

  • 12 guests

  • 6 bedrooms

Harbour Inlet, Fort Lauderdale

Double Trouble

Double Trouble

  • 15 guests

  • 5 bedrooms

Hilton Head Island, Beaufort County

Octopus' Garden

Octopus' Garden

  • 6 guests

  • 3 bedrooms

Orange Beach, Baldwin County

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Frequently asked questions

Explore our collection of Seaside Rentals in Osceola County, Florida, United States. Every property in our curated selection is fully furnished and meticulously equipped, offering the finest amenities for a seamless stay. From well-appointed kitchens to luxurious linens, we ensure every detail is covered. Picture yourself unwinding in the serene coastal atmosphere of one of our luxury homes. Our dedicated team of experts is here to help you find the ideal seaside retreat for your next getaway. Book today and experience the ultimate in coastal living.

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