47 Rentals: Siesta Key 5+ Bedrooms

Get help finding your rental: 941.900.4552

Siesta Key Vacation Home Sleeps Twenty Four Guests

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 24
  • 8 Bedrooms
  • 7 Bathrooms

This Vacation Home Sleeps 22 - Walk to Siesta Key Beaches

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 22
  • 8 Bedrooms
  • 6 Bathrooms

Luxury Siesta Key Six bedroom Pool Home

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  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 22
  • 6 Bedrooms
  • 6 Bathrooms

Large Siesta Key Family Vacation Townhome

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 18
  • 6 Bedrooms
  • 6 Bathrooms

Luxury Siesta Key Vacation Rental Canal Front Close to Beach

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 17
  • 6 Bedrooms
  • 5 Bathrooms

Siesta Key Five Bedroom Vacation Home with Private Pool

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 5 Bedrooms
  • 4 Bathrooms

Siesta Key Luxury Vacation Rental Home Five Bedrooms

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  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 5 Bedrooms
  • 4 Bathrooms

Siesta Key Luxury Pool Vacation Home

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 14
  • 5 Bedrooms
  • 5 Bathrooms

Six Bedroom Luxury Rental Pool Home in Siesta Key

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 18
  • 6 Bedrooms
  • 6 Bathrooms

Siesta Key Luxury Accommodation Sleeps 19 Private Pool

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 6 Bedrooms
  • 5 Bathrooms

Luxury Siesta Key Five Bedroom Vacation Pool Home Sleeps 15

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  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 15
  • 5 Bedrooms
  • 5 Bathrooms

Luxury Siesta Key Five Bedroom Gulf View Vacation Home

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  • Platinum
  • Home/Villa
  • No Pool
  • Max Occupancy: 18
  • 5 Bedrooms
  • 3 Bathrooms

Siesta Key 8 Bedrooms Beachfront Home Sleeps 19 Guests

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 21
  • 8 Bedrooms
  • 7 Bathrooms

Siesta Key Vacation Home with Pool Short Walk To Beach

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 18
  • 6 Bedrooms
  • 6 Bathrooms

The Most Exclusive Beach House in Siesta Key

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  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • Bathrooms

Nearly Beachfront Luxury Home with Pool

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 18
  • 8 Bedrooms
  • 8 Bathrooms

Siesta Key Luxury 5 Bedroom Home Walk to Beach

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 14
  • 5 Bedrooms
  • 5 Bathrooms

Luxury Five Bedroom Townhome with Pool and Spa in Siesta Key

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 14
  • 5 Bedrooms
  • 5 Bathrooms

Walk to Beach Siesta Key Vacation Home 6 Bedroom with Pool

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 18
  • 6 Bedrooms
  • 6 Bathrooms

Luxury Siesta Key Vacation Home with Private Pool & Spa

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 14
  • 6 Bedrooms
  • 6 Bathrooms

Luxurious Vacation Pool Home in Siesta Key Close to Beach

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  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 14
  • 6 Bedrooms
  • 6 Bathrooms

Five Bedroom Town House on Siesta Key with Private Pool

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 15
  • 5 Bedrooms
  • 3 Bathrooms

5 Bedroom Luxury Rental Townhome Just Steps Beach

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 14
  • 5 Bedrooms
  • 3 Bathrooms

Ideally Situated Between the 2 Best Beaches on Siesta

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 10
  • 6 Bedrooms
  • 2 Bathrooms

The Largest Luxury Siesta Key Vacation Rental Sleeps 25

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 25
  • 8 Bedrooms
  • 5 Bathrooms

One of The Largest Siesta Key Rentals 8 Bedrooms Sleeps 25

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 25
  • 8 Bedrooms
  • 5 Bathrooms

Siesta Key Beachfront Vacation Rentals on Sand

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  • Gold
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 5 Bedrooms
  • 4 Bathrooms

Five Bedroom Pool Home Sleeps 15 Siesta Key Luxury

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 15
  • 5 Bedrooms
  • 4 Bathrooms

Waterfront Home with Dock and Gulf Views!

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 22
  • 8 Bedrooms
  • 6 Bathrooms

Largest Vacation Rental Homes on Siesta Key that Sleeps 26 !

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 26
  • 8 Bedrooms
  • 7 Bathrooms

Siesta Key Eight Bedroom Vacation Rental Home Sleep 24

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 22
  • 8 Bedrooms
  • 8 Bathrooms

Luxury Siesta Key Vacation Rental Private Pool Sleeps 23

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 23
  • 7 Bedrooms
  • 6 Bathrooms

Siesta Key Luxury Vacation Rental Pool Home Eight Bedrooms

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 25
  • 8 Bedrooms
  • 8 Bathrooms

Siesta Key Vacation Home Sleeps 12 Short Walk to Beach

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 10
  • 5 Bedrooms
  • 5 Bathrooms

Partial Views Siesta Key Vacation Condo Sleeps 11 Guests

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  • Gold
  • Condo
  • Pool
  • Max Occupancy: 11
  • 5 Bedrooms
  • 5 Bathrooms

Siesta Key Vacation Home 6 Bedrooms Sleeps 22 Guests

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 22
  • 6 Bedrooms
  • 4 Bathrooms

Short Walk to Beach Siesta Key Vacation Condo Six Bedroom

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  • Gold
  • Condo
  • No Pool
  • Max Occupancy: 16
  • 6 Bedrooms
  • 4 Bathrooms

Two Three Bedroom Units Make One Large House

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  • Gold
  • Home/Villa
  • No Pool
  • Max Occupancy: 22
  • 6 Bedrooms
  • 4 Bathrooms

Walk to Beach Siesta Key Vacation Home with Pool Sleeps 16

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 7 Bedrooms
  • 7 Bathrooms

Siesta Key 6 Bedroom Pool Home Close To The Beach Sleeps 16

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  • Gold
  • Home/Villa
  • Pool
  • Max Occupancy: 16
  • 6 Bedrooms
  • 6 Bathrooms

Luxury Vacation Home in Siesta Key with Private Pool and Hot Tub

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  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 14
  • 7 Bedrooms
  • 7 Bathrooms

Siesta Key Vacation Rental Home Short Walk to the Beach

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 20
  • 7 Bedrooms
  • 5 Bathrooms

Siesta Key Vacation Pool Home Sleeps Twenty Four Guests

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 24
  • 8 Bedrooms
  • 6 Bathrooms

Three Bedroom Steps to Beach Siesta Key Vacation Duplex

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 16
  • 6 Bedrooms
  • 6 Bathrooms

Siesta Key Vacation Condo Located At Beach Sleeps 16 Guests

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  • Silver
  • Home/Villa
  • No Pool
  • Max Occupancy: 16
  • 6 Bedrooms
  • 6 Bathrooms

Walk to Beach Siesta Key SIx Bedroom Vacation Rental

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  • Silver
  • Condo
  • Pool
  • Max Occupancy: 21
  • 6 Bedrooms
  • 5 Bathrooms

Siesta Key 10 Large 1 Bedroom Units Private Dock Lagoon View

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  • Silver
  • Home/Villa
  • Pool
  • Max Occupancy: 40
  • 10 Bedrooms
  • 10+ Bathrooms