0 941.500.4555 Request a Call

Siesta Key Vacation Rentals

Showing 25–48 of 164 matching vacation rentals, page 2 of 7. Closest capacity matches first.

About Siesta Key
Filters Pet friendly — remove this filter Clear all
Platinum Luxury Siesta Key Vacation Rental with Private Pool & Rooftop Deck
Siesta Key

Luxury Siesta Key Vacation Rental with Private Pool & Rooftop Deck

8 Bedrooms · 7 Bathrooms
From $2,832 / 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 Luxury Pool Vacation Home
Siesta Key

Siesta Key Luxury Pool Vacation Home

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $14,376 / month
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key Luxury Vacation Rental - Four-Bedroom Private Pool Home
Siesta Key

Siesta Key Luxury Vacation Rental - Four-Bedroom Private Pool Home

4 Bedrooms · 3 Bathrooms · Sleeps 10
From $827 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key Four Bedroom Walk to Beach Vacation Rental
Siesta Key

Siesta Key Four Bedroom Walk to Beach Vacation Rental

4 Bedrooms · 3 Bathrooms · Sleeps 13
From $3,453 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Stunning Vacation Home 3 Bedroom Canalfront
Siesta Key

Stunning Vacation Home 3 Bedroom Canalfront

3 Bedrooms · 3 Bathrooms · Sleeps 8
From $1,179 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Tropical Oasis with 4 Bedrooms in Siesta Key
Siesta Key

Tropical Oasis with 4 Bedrooms in Siesta Key

4 Bedrooms · 4 Bathrooms · Sleeps 8
From $20,800 / month
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key Vacation Rental with 8 Bedrooms Total
Siesta Key

Siesta Key Vacation Rental with 8 Bedrooms Total

8 Bedrooms · 6 Bathrooms · Sleeps 22
From $5,388 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Lovely Siesta Key Vacation Rental with Private Pool
Siesta Key

Lovely Siesta Key Vacation Rental with Private Pool

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $1,072 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Beachside Getaway Four Bedroom Vacation Rental in Siesta Key
Siesta Key

Beachside Getaway Four Bedroom Vacation Rental in Siesta Key

4 Bedrooms · 5 Bathrooms · Sleeps 12
From $1,093 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Exquisite 3 Bedroom Coastal Rental in Siesta Key
Siesta Key

Exquisite 3 Bedroom Coastal Rental in Siesta Key

3 Bedrooms · 2 Bathrooms · Sleeps 6
From $1,166 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Sarasota Magnificent Home with 3 Bedrooms
Siesta Key

Sarasota Magnificent Home with 3 Bedrooms

3 Bedrooms · 3 Bathrooms · Sleeps 6
From $387 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key Home with 3 Bedroom and private Pool
Siesta Key

Siesta Key Home with 3 Bedroom and private Pool

3 Bedrooms · 3 Bathrooms · Sleeps 8
From $18,000 / month
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 Vacation Home Three Bedroom
Siesta Key

Siesta Key Vacation Home Three Bedroom

3 Bedrooms · 2 Bathrooms · Sleeps 9
From $18,255 / month
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key Vacation Home 200 Steps to Beach
Siesta Key

Siesta Key Vacation Home 200 Steps to Beach

3 Bedrooms · 4 Bathrooms · Sleeps 8
From $1,047 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key Vacation Condo Two Bedroom Walk to Beach
Siesta Key

Siesta Key Vacation Condo Two Bedroom Walk to Beach

2 Bedrooms · 2 Bathrooms · Sleeps 4
From $453 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Charming Waterfront Two Bedroom Cottage Close to Everything
Siesta Key

Charming Waterfront Two Bedroom Cottage Close to Everything

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $765 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Chaming Siesta Key Vacation Condo - Two Bedroom, Walk to Beach
Siesta Key

Chaming Siesta Key Vacation Condo - Two Bedroom, Walk to Beach

2 Bedrooms · 2 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Located on two Canals by the Village
Siesta Key

Located on two Canals by the Village

3 Bedrooms · 3 Bathrooms · Sleeps 8
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Charming One Bedroom Vacation Duplex in Siesta Key with Pool
Siesta Key

Charming One Bedroom Vacation Duplex in Siesta Key with Pool

1 Bedroom · 1 Bathroom · Sleeps 2
From $576 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold SIESTA KEY 2 BEDROOM BEACH VACATION RENTAL
Siesta Key

SIESTA KEY 2 BEDROOM BEACH VACATION RENTAL

2 Bedrooms · 1 Bathroom · Sleeps 4
Call for rates
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.