Siesta Key Vacation House Rentals

Top-Rated Vacation Rentals in Siesta Key, FL

Book a vacation rental in Siesta Key that has the highest visitor rating. Here are 6 of the best vacation rentals in Siesta Key.
Price drop
Canal Upper-Gorgeous 3 bed 3 bath near SK Village
10

Excellent

·
Siesta Key
·
3 br
·
Sleeps 10
·
Beach · Wifi · Hot Tub ·
From
$914/night
Check availability
Property
Apartment · 3 Beds · 3 baths
Amenities
Beach
Wifi
Hot Tub
Private Pool
Dishwasher
In Unit Laundry
Pool
Air Conditioning
Other spaces
Kitchen, Workspace
The Upper Deck
10

Excellent

·
Siesta Key
·
6 br
·
Sleeps 13
·
Pool · Wifi · Dishwasher ·
From
$2,070/night
Check availability
Property
Apartment · 6 Beds · 5 baths
Amenities
Pool
Wifi
Dishwasher
Residents Lounge
Free Parking
Swimming Pool
On Site Laundry
Beach
Other spaces
Kitchen
The Plaza
9.7

Excellent

·
Siesta Key
·
Studio
·
Sleeps 19
·
Air Conditioning · Balcony · Dishwasher ·
From
$2,300/night
Check availability
Property
Apartment · Studio · 7 baths
Amenities
Air Conditioning
Dishwasher
Private Pool
Oven
Swimming Pool
Assigned Parking
Beach
Free Parking
Other spaces
Balcony, Kitchen
Price drop
Canal Lower-Gorgeous 3 bed 3 bath near SK Village
9.3

Excellent

·
Siesta Key
·
3 br
·
Sleeps 10
·
Workspace · Hot Tub · Oven ·
From
$912/night
Check availability
Property
Apartment · 3 Beds · 3 baths
Amenities
Hot Tub
Oven
Swimming Pool
Pool
Wifi
In Unit Laundry
Furnished
Beach
Other spaces
Workspace, Kitchen
Price drop
Canal 313 - Right in Siesta Key Village!
8.3

Very good

·
Siesta Key
·
2 br
·
Sleeps 7
·
Pool · Swimming Pool · Wifi ·
From
$402/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Pool
Swimming Pool
Wifi
Oven
Assigned Parking
Residents Lounge
Furnished
Air Conditioning
Other spaces
Kitchen
Price drop
Canal 309 - Right in Siesta Key Village!
8.2

Very good

·
Siesta Key
·
2 br
·
Sleeps 5
·
Furnished · Swimming Pool · Beach ·
From
$402/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Furnished
Swimming Pool
Beach
Residents Lounge
Free Parking
Dishwasher
Air Conditioning
Private Pool
Other spaces
Workspace, Kitchen

Our Recommended Vacation Rentals in Siesta Key, FL

We analyzed vacation rentals in Siesta Key from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Siesta Key to help you find a deal for your next trip.
Commonwealth Casas
4

Good

·
Siesta Beach
·
1 br
·
Sleeps 4
·
Furnished · Outdoor Space · Swimming Pool ·
From
$178/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
Swimming Pool
Air Conditioning
Wifi
On Site Laundry
Oven
Other spaces
Kitchen
CJs on Siesta - 104

No rating

·
Siesta Key
·
6 br
·
Sleeps 24
·
Dishwasher · Outdoor Space · Air Conditioning ·
From
$2,790/night
Check availability
Property
Apartment · 6 Beds · 6 baths
Amenities
Dishwasher
Air Conditioning
Free Parking
Assigned Parking
On Site Laundry
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen, Workspace
Vinca - 5251D

No rating

·
Siesta Key
·
1 br
·
Sleeps 4
·
Air Conditioning · Kitchen · Assigned Parking ·
From
$361/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Assigned Parking
Free Parking
Furnished
Oven
Swimming Pool
In Unit Laundry
On Site Laundry
Other spaces
Kitchen, Workspace
Plumbago - 5251C

No rating

·
Siesta Key
·
2 br
·
Sleeps 6
·
Swimming Pool · Kitchen · Oven ·
From
$541/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Swimming Pool
Oven
Furnished
Air Conditioning
Wifi
Free Parking
On Site Laundry
Assigned Parking
Other spaces
Kitchen, Workspace
Sea Foam - 173

No rating

·
Siesta Key
·
1 br
·
Sleeps 4
·
Oven · In Unit Laundry · Furnished ·
From
$438/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Oven
In Unit Laundry
Furnished
Free Parking
On Site Laundry
Assigned Parking
Wifi
Air Conditioning
Other spaces
Workspace, Kitchen
Sea Escape - 172

No rating

·
Siesta Key
·
1 br
·
Sleeps 4
·
Wifi · Assigned Parking · Air Conditioning ·
From
$438/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Wifi
Assigned Parking
Air Conditioning
In Unit Laundry
Free Parking
On Site Laundry
Oven
Furnished
Other spaces
Workspace, Kitchen

Budget-Friendly Vacation Rentals in Siesta Key, FL

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Siesta Key starting at $119. Use the price filter at the top of the page to search for more specific prices.
Siesta Key Beach - Tropea 665 #3
8.3

Very good

·
Siesta Key
·
1 br
·
Sleeps 4
·
Kitchen · Assigned Parking · Beach ·
From
$119/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Assigned Parking
Beach
Air Conditioning
Wifi
Oven
Furnished
Free Parking
Other spaces
Kitchen
1.3 miles to the number one beach in the USA
10

Excellent

·
Siesta Beach
·
1 br
·
Sleeps 2
·
Air Conditioning · Dishwasher · Furnished ·
From
$125/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Air Conditioning
Dishwasher
Furnished
Oven
In Unit Laundry
Wifi
Other spaces
Kitchen
Siesta Key Beach 665 #1
7.5

Very good

·
Siesta Key
·
2 br
·
Sleeps 6
·
Furnished · Kitchen · Wifi ·
From
$144/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Furnished
Wifi
Beach
Oven
Air Conditioning
Free Parking
Assigned Parking
Other spaces
Kitchen
Siesta Key bungalow walking distance to beach ! name: Siesta Side (A)
10

Excellent

·
Siesta
·
1 br
·
Sleeps 3
·
Kitchen · Air Conditioning · Furnished ·
From
$155/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Tropical Island Home
10

Excellent

·
Siesta Beach
·
2 br
·
Sleeps 4
·
In Unit Laundry · Furnished · Private Pool ·
From
$160/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
In Unit Laundry
Furnished
Private Pool
Pool
Fitness Center
Air Conditioning
Swimming Pool
Wifi
Other spaces
Kitchen
Price drop
Sky Spacious Bungalow walking distance from beach!Name Sky Side A

No rating

·
Siesta
·
1 br
·
Sleeps 2
·
On Site Laundry · Furnished · Air Conditioning ·
From
$166/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
On Site Laundry
Furnished
Air Conditioning
Wifi
Other spaces
Kitchen

Pet-Friendly Vacation Rentals in Siesta Key, FL

Pets are part of the family, so instead of leaving them at home, book one of these pet-friendly vacation rentals in Siesta Key. Read the details of each rental more closely for specific pet policies.
Price drop
Top Gulf

No rating

·
Siesta Key
·
6 br
·
Sleeps 14
·
Dishwasher · Furnished · Assigned Parking ·
From
$2,070/night
Check availability
Property
Apartment · 6 Beds · 6 baths
Amenities
Dishwasher
Furnished
Assigned Parking
Free Parking
Swimming Pool
Wifi
Pool
Private Pool
Other spaces
Balcony, Kitchen
Price drop
The 19th Hole

No rating

·
Siesta Key
·
6 br
·
Sleeps 14
·
Outdoor Space · Furnished · Residents Lounge ·
From
$2,070/night
Check availability
Property
Apartment · 6 Beds · 6 baths
Amenities
Furnished
Residents Lounge
Dishwasher
Air Conditioning
On Site Laundry
Swimming Pool
Free Parking
Beach
Other spaces
Balcony, Kitchen
Price drop
Bahama Mama

No rating

·
Siesta Key
·
5 br
·
Sleeps 14
·
In Unit Laundry · Swimming Pool · Wifi ·
From
$1,935/night
Check availability
Property
Apartment · 5 Beds · 5 baths
Amenities
In Unit Laundry
Swimming Pool
Wifi
Furnished
Assigned Parking
Dishwasher
Air Conditioning
Free Parking
Other spaces
Workspace, Balcony, Kitchen
Expand your search criteria to see more vacation rentals near Siesta Key.
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Updated: September 6, 2023