0 941.500.4555 Request a Call

Siesta Key Vacation Rentals

Showing 97–120 of 164 matching vacation rentals, page 5 of 7. Closest capacity matches first.

About Siesta Key
Filters Pet friendly — remove this filter Clear all
Gold Siesta Key Vacation Rental Condo Beach Nearby
Siesta Key

Siesta Key Vacation Rental Condo Beach Nearby

1 Bedroom · 1 Bathroom · Sleeps 2
From $318 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key Condo 897093
Siesta Key

Siesta Key Condo 897093

1 Bedroom · 1 Bathroom · Sleeps 2
From $21,953,450 / week
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 One Bedroom Vacation Condo with Beach Across the Street in Siesta Key
Siesta Key

One Bedroom Vacation Condo with Beach Across the Street in Siesta Key

1 Bedroom · 1 Bathroom · Sleeps 4
From $385 / 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
Call for rates
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 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 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
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Charming 2 Bedroom Cottage Siesta Key Walk to Beach
Siesta Key

Charming 2 Bedroom Cottage Siesta Key Walk to Beach

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $502 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key Walk to Beach 2 Bedroom Vacation Duplex
Siesta Key

Siesta Key Walk to Beach 2 Bedroom Vacation Duplex

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $800 / night
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 Siesta Key Vacation Cottage Two Bedrooms Walk To Beach
Siesta Key

Siesta Key Vacation Cottage Two Bedrooms Walk To Beach

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $581 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold A Rare Gem on Siesta Key 2 Bedroom Vacation Rental
Siesta Key

A Rare Gem on Siesta Key 2 Bedroom Vacation Rental

2 Bedrooms · 2 Bathrooms · Sleeps 6
From $498 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key Vacation Rental Home 4 Bedrooms Sleeps 10
Siesta Key

Siesta Key Vacation Rental Home 4 Bedrooms Sleeps 10

4 Bedrooms · 4 Bathrooms · Sleeps 10
From $852 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key Three Bedroom Luxury Rental Home with Canal View
Siesta Key

Siesta Key Three Bedroom Luxury Rental Home with Canal View

3 Bedrooms · 3 Bathrooms · Sleeps 6
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Three Bedroom Home with Private Pool on Siesta Key
Siesta Key

Three Bedroom Home with Private Pool on Siesta Key

3 Bedrooms · 3 Bathrooms · Sleeps 10
From $6,500 / month
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key Vacation Townhome Private Pool Walk To Beach
Siesta Key

Siesta Key Vacation Townhome Private Pool Walk To Beach

3 Bedrooms · 3 Bathrooms · Sleeps 14
From $1,754 / night
Call to confirm availability941.500.4555 Request a callback & quote
Gold Luxury 3 Bedroom Siesta Key Townhome With Pool
Siesta Key

Luxury 3 Bedroom Siesta Key Townhome With Pool

3 Bedrooms · 3 Bathrooms · Sleeps 14
Call for rates
Call to confirm availability941.500.4555 Request a callback & quote
Gold Siesta Key 3 Bedroom Vacation Home Sleeps Eight Private Pool
Siesta Key

Siesta Key 3 Bedroom Vacation Home Sleeps Eight Private Pool

3 Bedrooms · 2 Bathrooms · Sleeps 8
From $780 / 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.