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Siesta Key Vacation Homes & Villas

Browse 216 professionally managed vacation homes and villas in Siesta Key with Emerald Kite. Showing 121–144 of 216 matching vacation rentals, page 6 of 9. Closest capacity matches first.

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Gold Siesta Key Two Bedroom Luxury
Siesta Key

Siesta Key Two Bedroom Luxury

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $5,700 / night
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Gold Siesta Key Four Bedroom Vacation Home Sleeps 8 Guests
Siesta Key

Siesta Key Four Bedroom Vacation Home Sleeps 8 Guests

4 Bedrooms · 3 Bathrooms · Sleeps 8
From $672,011,000 / month
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key Two Bedroom Duplex Close To Beach
Siesta Key

Siesta Key Two Bedroom Duplex Close To Beach

2 Bedrooms · 1 Bathroom · Sleeps 6
From $422 / night
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Gold Siesta Key Vacation Rental with Gulf Views - Contemporary Luxury Townhome Near Siesta Beach
Siesta Key

Siesta Key Vacation Rental with Gulf Views - Contemporary Luxury Townhome Near Siesta Beach

3 Bedrooms · 3 Bathrooms · Sleeps 8
From $936 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key, Florida Vacation Rental
Siesta Key

Siesta Key, Florida Vacation Rental

3 Bedrooms · 2 Bathrooms · Sleeps 10
From $1,495 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Newly Renovated-Lovely 2 Bed 2 Bath Private Home with Pool
Siesta Key

Newly Renovated-Lovely 2 Bed 2 Bath Private Home with Pool

2 Bedrooms · 2 Bathrooms · Sleeps 8
From $35,007,500 / month
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Gold Two Bedroom Rentals Sleeps 6 with Pool in Siesta Key
Siesta Key

Two Bedroom Rentals Sleeps 6 with Pool in Siesta Key

2 Bedrooms · 2 Bathrooms · Sleeps 6
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Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Siesta Key Vacation Rental Private Pool
Siesta Key

Luxury Siesta Key Vacation Rental Private Pool

7 Bedrooms · 6 Bathrooms · Sleeps 19
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Fantastic Siesta Key Three Bedroom Vacation Home Great Pool
Siesta Key

Fantastic Siesta Key Three Bedroom Vacation Home Great Pool

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,013 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key - Eight Bedroom Luxury Residence Sleeps 24 Guests
Siesta Key

Siesta Key - Eight Bedroom Luxury Residence Sleeps 24 Guests

8 Bedrooms · 6 Bathrooms · Sleeps 24
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Call to confirm availability941.500.4555 Request a callback & quote
Gold Largest Vacation Rental Homes on Siesta Key that Sleeps 23!
Siesta Key

Largest Vacation Rental Homes on Siesta Key that Sleeps 23!

8 Bedrooms · 7 Bathrooms · Sleeps 23
From $2,616 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Waterfront Home with Dock and Gulf Views!
Siesta Key

Waterfront Home with Dock and Gulf Views!

8 Bedrooms · 6 Bathrooms · Sleeps 22
From $5,395 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key Vacation Rental with Pool Luxury 5-Bed Beach House
Siesta Key

Siesta Key Vacation Rental with Pool Luxury 5-Bed Beach House

5 Bedrooms · 4 Bathrooms · Sleeps 15
From $2,249 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Beautiful 3 Bedroom Siesta Key Home Steps to Beach
Siesta Key

Beautiful 3 Bedroom Siesta Key Home Steps to Beach

3 Bedrooms · 2 Bathrooms · Sleeps 10
From $481 / night
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Gold Siesta Key 2 Bedroom Home With Private Pool Sleeps 8
Siesta Key

Siesta Key 2 Bedroom Home With Private Pool Sleeps 8

2 Bedrooms · 2 Bathrooms · Sleeps 8
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key Value Priced Four Bedroom Vacation Home
Siesta Key

Siesta Key Value Priced Four Bedroom Vacation Home

4 Bedrooms · 2 Bathrooms · Sleeps 8
From $8,795 / month
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Vacation Cottage Sleeps Ten Guests
Siesta Key

Siesta Vacation Cottage Sleeps Ten Guests

3 Bedrooms · 2 Bathrooms · Sleeps 10
From $10,000 / month
Call to confirm availability941.500.4555 Request a callback & quote
Gold One of the Top High End Siesta Key Vacation Pool Homes
Siesta Key

One of the Top High End Siesta Key Vacation Pool Homes

4 Bedrooms · 3 Bathrooms · Sleeps 8
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Call to confirm availability941.500.4555 Request a callback & quote
Gold One of The Largest Siesta Key Rentals 8 Bedrooms Sleeps 25
Siesta Key

One of The Largest Siesta Key Rentals 8 Bedrooms Sleeps 25

8 Bedrooms · 5 Bathrooms · Sleeps 25
From $2,798 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold The Largest Luxury Siesta Key Vacation Rental Sleeps 25
Siesta Key

The Largest Luxury Siesta Key Vacation Rental Sleeps 25

8 Bedrooms · 5 Bathrooms · Sleeps 25
From $4,021 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Four Bedroom- Luxury Siesta Key Home with Pool on the Water
Siesta Key

Four Bedroom- Luxury Siesta Key Home with Pool on the Water

4 Bedrooms · 3 Bathrooms · Sleeps 10
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Vacation Rental Home 3 Bedrooms Stroll to Beach Villa Style
Siesta Key

Vacation Rental Home 3 Bedrooms Stroll to Beach Villa Style

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $43,958,695 / month
Call to confirm availability941.500.4555 Request a callback & quote
Gold One of Siesta Keys Best Rental Homes with Private Pool
Siesta Key

One of Siesta Keys Best Rental Homes with Private Pool

4 Bedrooms · 3 Bathrooms · Sleeps 11
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury Two Bedroom Upscale Home Private Pool Village Nearby
Siesta Key

Luxury Two Bedroom Upscale Home Private Pool Village Nearby

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $750 / night
Call to confirm availability941.500.4555 Request a callback & quote

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