0 941.500.4555 Request a Call

5 Bedroom Siesta Key Vacation Rentals

Browse 62 professionally managed vacation rentals with at least 5 bedrooms in Siesta Key with Emerald Kite. Showing 1–24 of 62 matching vacation rentals, page 1 of 3. Closest capacity matches first.

About Siesta Key
Filters 5+ bedrooms — remove this filter Clear all
Platinum Luxury Siesta Key Beachfront Home - Private Oasis with Pool & Activities
Siesta Key

Luxury Siesta Key Beachfront Home - Private Oasis with Pool & Activities

5 Bedrooms · 5 Bathrooms · Sleeps 14
From $2,509 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxury Five Bedroom Vacation Rental Steps from Siesta Key Beach
Siesta Key

Luxury Five Bedroom Vacation Rental Steps from Siesta Key Beach

5 Bedrooms · 5 Bathrooms · Sleeps 16
From $1,372 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Siesta Key Vacation Home Five Bedroom Walk to Beach
Siesta Key

Siesta Key Vacation Home Five Bedroom Walk to Beach

5 Bedrooms · 3 Bathrooms · Sleeps 10
From $1,351 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Siesta Key Luxury Vacation Rental - Gulf Coast Family Villa
Siesta Key

Siesta Key Luxury Vacation Rental - Gulf Coast Family Villa

5 Bedrooms · 5 Bathrooms · Sleeps 14
From $1,439 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxury Siesta Key Five Bedroom Gulf View Vacation Home
Siesta Key

Luxury Siesta Key Five Bedroom Gulf View Vacation Home

5 Bedrooms · 3 Bathrooms · Sleeps 19
From $3,766 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxury Siesta Key Five Bedroom Vacation Pool Home Sleeps 15
Siesta Key

Luxury Siesta Key Five Bedroom Vacation Pool Home Sleeps 15

5 Bedrooms · 5 Bathrooms · Sleeps 15
From $3,265 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Siesta Key Luxury Pool Vacation Home
Siesta Key

Siesta Key Luxury Pool Vacation Home

5 Bedrooms · 5 Bathrooms · Sleeps 14
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Siesta Key Luxury Vacation Rental | Gulf-Front 5 Bedroom with Pool
Siesta Key

Siesta Key Luxury Vacation Rental | Gulf-Front 5 Bedroom with Pool

5 Bedrooms · 4 Bathrooms · Sleeps 12
From $3,153 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key Vacation Rental with Private Pool - Luxury Waterfront Home
Siesta Key

Siesta Key Vacation Rental with Private Pool - Luxury Waterfront Home

5 Bedrooms · 3 Bathrooms · Sleeps 16
From $1,265 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key Vacation Home Five Bedroom Walk to Beach
Siesta Key

Siesta Key Vacation Home Five Bedroom Walk to Beach

5 Bedrooms · 3 Bathrooms · Sleeps 14
From $2,135 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key Condo 1024461
Siesta Key

Siesta Key Condo 1024461

5 Bedrooms · 5 Bathrooms · Sleeps 18
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key Vacation Rental 5-Bedroom Beach Home with Private Pool
Siesta Key

Siesta Key Vacation Rental 5-Bedroom Beach Home with Private Pool

5 Bedrooms · 3 Bathrooms · Sleeps 10
From $865 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Partial Views Siesta Key Vacation Condo Sleeps 11 Guests
Siesta Key

Partial Views Siesta Key Vacation Condo Sleeps 11 Guests

5 Bedrooms · 5 Bathrooms · Sleeps 11
Call for rates
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 Beachfront Siesta Key Rental with Stunning Sunset Views
Siesta Key

Beachfront Siesta Key Rental with Stunning Sunset Views

5 Bedrooms · 4 Bathrooms · Sleeps 14
From $2,427 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Five Bedroom Town House on Siesta Key with Private Pool
Siesta Key

Five Bedroom Town House on Siesta Key with Private Pool

5 Bedrooms · 3 Bathrooms · Sleeps 15
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Siesta Key Vacation Home With Gulf Views And Pool
Siesta Key

Siesta Key Vacation Home With Gulf Views And Pool

6 Bedrooms · 6 Bathrooms · Sleeps 16
From $2,003 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Siesta Key Luxury Vacation Rentals - Spacious Beachfront Homes
Siesta Key

Siesta Key Luxury Vacation Rentals - Spacious Beachfront Homes

6 Bedrooms · 6 Bathrooms · Sleeps 18
From $3,152 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum World Class Luxury Walk to Siesta Key Village Vacation Home !
Siesta Key

World Class Luxury Walk to Siesta Key Village Vacation Home !

6 Bedrooms · 6 Bathrooms · Sleeps 16
From $3,446 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Lake View Six Bedroom Vacation Home in Siesta Key
Siesta Key

Lake View Six Bedroom Vacation Home in Siesta Key

6 Bedrooms · 6 Bathrooms · Sleeps 18
From $4,009 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Siesta Key Gulf View Six Bedroom Vacation Rental
Siesta Key

Siesta Key Gulf View Six Bedroom Vacation Rental

6 Bedrooms · 6 Bathrooms · Sleeps 14
From $3,743 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Siesta Key Vacation Home Six Bedroom Walk to Beach 4,000 Sq Ft
Siesta Key

Siesta Key Vacation Home Six Bedroom Walk to Beach 4,000 Sq Ft

6 Bedrooms · 6 Bathrooms · Sleeps 14
From $2,598 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Luxurious Vacation Pool Home in Siesta Key Close to Beach
Siesta Key

Luxurious Vacation Pool Home in Siesta Key Close to Beach

6 Bedrooms · 6 Bathrooms · Sleeps 14
From $4,835 / night
Call to confirm availability941.500.4555 Request a callback & quote
Platinum Siesta Key Luxury Rentals | Beach Home with Pool, Spa & Rooftop
Siesta Key

Siesta Key Luxury Rentals | Beach Home with Pool, Spa & Rooftop

6 Bedrooms · 6 Bathrooms · Sleeps 14
From $4,533 / night
Call to confirm availability941.500.4555 Request a callback & quote

Privacy controls

Choose which cookies we use

Optional cookies are off unless you choose otherwise. You can return to these settings from the footer at any time.

Essential & requested features Required for security and for features you ask us to provide, including saved rentals and remembered search choices. Always active

Cookie PolicyPrivacy Policy

Talk with a Villa Specialist

When should we call you?

Share a few details and an Emerald Kite specialist will call you now or in five minutes.

If you provide a mobile number, you consent to receive messages about your vacation planning. Carrier rates may apply; you can opt out at any time.

Security check loads when this window opens.

Requests after 10 p.m. Eastern Time will be returned the next day.

Having trouble? Use the full Contact page.