Skip to navigationSkip to main contentSkip to footer
Vacations by Zumper

Vacation Rentals in Siesta Key, FL

PRICE PER NIGHT

ACCOMMODATION TYPES

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
·
Private Pool · Wifi · Hot Tub ·
From
$978/night
Check availability
Property
Apartment · 3 Beds · 3 baths
Amenities
Private Pool
Wifi
Hot Tub
Dishwasher
Pool
Furnished
On Site Laundry
Air Conditioning
Other spaces
Kitchen, Workspace
Direct Access to Splendid White Sands at Siesta Beach, Rated Best Beach in USA
10

Excellent

·
Siesta Key
·
2 br
·
Sleeps 6
·
Beach · Swimming Pool · Dishwasher ·
From
$243/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Beach
Swimming Pool
Dishwasher
Fitness Center
Wifi
Pool
Furnished
Elevator
Other spaces
Kitchen, Balcony
Price drop
2-Story Siesta Key Family Home with Private Pool. 3 Bedrooms + Bonus Room. Small Dogs Considered
10

Excellent

·
Siesta
·
3 br
·
Sleeps 8
·
On Site Laundry · Oven · Swimming Pool ·
From
$264/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
On Site Laundry
Oven
Swimming Pool
High Ceilings
Hot Tub
Residents Lounge
Air Conditioning
Walk In Closets
Other spaces
Kitchen, Balcony
Enjoy the Beach & the Bay! Sensational Condo & Fantastic Amenities at Palm Bay Club 335
10

Excellent

·
Siesta Key
·
2 br
·
Sleeps 6
·
On Site Laundry · Beach · Pool ·
From
$283/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
On Site Laundry
Beach
Pool
Fitness Center
Hot Tub
Furnished
Elevator
Air Conditioning
Other spaces
Kitchen, Balcony
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
$977/night
Check availability
Property
Apartment · 3 Beds · 3 baths
Amenities
Hot Tub
Oven
Swimming Pool
On Site Laundry
Wifi
Furnished
Beach
Private Pool
Other spaces
Workspace, Kitchen
Price drop
Canal 313 - Right in Siesta Key Village!
8.3

Very good

·
Siesta Key
·
2 br
·
Sleeps 7
·
Private Pool · Kitchen · Swimming Pool ·
From
$418/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Private Pool
Swimming Pool
Pool
Residents Lounge
Air Conditioning
Assigned Parking
Wifi
Oven
Other spaces
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.
Price drop
Avenida Lower
7

Very good

·
Siesta Key
·
2 br
·
Sleeps 8
·
Furnished · Pool · Dishwasher ·
From
$404/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Furnished
Pool
Dishwasher
Air Conditioning
On Site Laundry
Swimming Pool
Wifi
Hot Tub
Other spaces
Workspace, Kitchen
Price drop
Avenida Upper
6

Good

·
Siesta Key
·
2 br
·
Sleeps 8
·
Beach · Air Conditioning · Workspace ·
From
$439/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Beach
Air Conditioning
Furnished
Swimming Pool
Hot Tub
On Site Laundry
Private Pool
Pool
Other spaces
Workspace, Kitchen, Balcony
Price drop
Siesta-Retreats - Key West Unit

No rating

·
Siesta Key
·
2 br
·
Sleeps 6
·
Outdoor Space · Swimming Pool · Residents Lounge ·
From
$581/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Swimming Pool
Residents Lounge
On Site Laundry
Air Conditioning
Pool
Smoking Allowed
Assigned Parking
Beach
Other spaces
Kitchen, Balcony
Price drop
Top Gulf

No rating

·
Siesta Key
·
6 br
·
Sleeps 14
·
Assigned Parking · Beach · Dishwasher ·
From
$2,453/night
Check availability
Property
Apartment · 6 Beds · 6 baths
Amenities
Assigned Parking
Beach
Dishwasher
Swimming Pool
Hot Tub
Pool
Furnished
On Site Laundry
Other spaces
Kitchen, Balcony

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 $86. Use the price filter at the top of the page to search for more specific prices.
Price drop
SUPER SPECIAL RATES at Harbor Towers Aug 5 - Aug 19
10

Excellent

·
Siesta Key
·
2 br
·
Sleeps 6
·
Ocean · Outdoor Space · Waterfront ·
From
$86/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Ocean
Waterfront
Furnished
Oven
Residents Lounge
Air Conditioning
Assigned Parking
In Unit Laundry
Other spaces
Kitchen, Balcony
Siesta Key Beach - Bari 665 #2
7.5

Very good

·
Siesta Key
·
1 br
·
Sleeps 3
·
Kitchen · Workspace · Air Conditioning ·
From
$95/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Furnished
In Unit Laundry
Beach
Other spaces
Kitchen, Workspace
Age restrictedPrice drop
Fall Discount$$$ on 7+nights for Seniors, Active Military-Police-Fire-Healthcare
10

Excellent

·
Siesta Key
·
2 br
·
Sleeps 4
·
Oven · Outdoor Space · Kitchen ·
From
$99/night
Check availability
Property
Condo · 2 Beds · 1 bath
Amenities
Oven
Swimming Pool
Furnished
Pool
Dishwasher
Air Conditioning
Hot Tub
On Site Laundry
Other spaces
Kitchen
Cozy Siesta Key studio 5 minute walk to Village
10

Excellent

·
Siesta Key
·
Studio
·
Sleeps 2
·
Oven · Wifi · Air Conditioning ·
From
$107/night
Check availability
Property
Condo · Studio · 1 bath
Amenities
Oven
Wifi
Air Conditioning
Furnished
On Site Laundry
Other spaces
Kitchen
Garden Terrace Studio Cottage - Walk To Siesta Beach & Village - Pets Welcome!
10

Excellent

·
Siesta Key
·
1 br
·
Sleeps 2
·
On Site Laundry · Beach · Residents Lounge ·
From
$109/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
On Site Laundry
Beach
Residents Lounge
Oven
Air Conditioning
Fitness Center
Wifi
Furnished
Other spaces
Kitchen
Age restricted
Siesta Harbor Beach Access Only a 6 Min Walk, Canal Views, WiFi, Pool/Hot Tub, Corner Unit
10

Excellent

·
Siesta Key
·
2 br
·
Sleeps 4
·
Fitness Center · Kitchen · Outdoor Space ·
From
$112/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Fitness Center
Pool
Swimming Pool
On Site Laundry
Elevator
Oven
Air Conditioning
Furnished
Other spaces
Kitchen, Workspace

Vacation Rentals With AC and/or Heat in Siesta Key, FL

Whether you need air conditioning or central heating, these vacation rentals are for you.
Price drop
Cozy Siesta Key Vacation Rental

No rating

·
Siesta Key
·
Studio
·
Sleeps 3
·
Swimming Pool · Oven · Central Heat ·
From
$241/night
Check availability
Property
Apartment · Studio · 1 bath
Amenities
Swimming Pool
Oven
Central Heat
Dishwasher
Beach
Pool
On Site Laundry
Wifi
Other spaces
Kitchen
Price drop
Siesta Key Condo w/ Balcony - Walk to Beach + Bay!
10

Excellent

·
Siesta Key
·
2 br
·
Sleeps 6
·
Outdoor Space · Furnished · Fitness Center ·
From
$116/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Furnished
Fitness Center
Central Heat
Swimming Pool
Air Conditioning
Wifi
Residents Lounge
Pool
Other spaces
Balcony, Kitchen
Island House Beach Resort V13
10

Excellent

·
Siesta Key
·
2 br
·
Sleeps 6
·
Wifi · Furnished · On Site Laundry ·
From
$237/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Wifi
Furnished
On Site Laundry
Central Heat
Beach
Swimming Pool
Air Conditioning
Carpet
Other spaces
Kitchen

Family-Friendly Vacation Rentals in Siesta Key, FL

Heading to Siesta Key for your next family vacation? Check out these family-friendly vacation rentals, which have more bedrooms and more space for you and your loved ones. Use the filters at the top of the page to narrow your search and find what you need.
Price drop
Walk to the beach - Island Villa

No rating

·
Siesta Key
·
1 br
·
Sleeps 4
·
Beach · Swimming Pool · Hardwood Floor ·
From
$400/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Beach
Swimming Pool
Hardwood Floor
Fireplace
Wifi
Assigned Parking
On Site Laundry
Pool
Other spaces
Kitchen, Workspace, Balcony
LuLu’s Green in the Heart of Siesta Key Village, 4 Minute Walk to Beach, Pool, Washer/dryer
10

Excellent

·
Siesta Key
·
1 br
·
Sleeps 4
·
Pool · Air Conditioning · On Site Laundry ·
From
$274/night
Check availability
Property
Condo · 1 Bed · 1 bath
Amenities
Pool
Air Conditioning
On Site Laundry
Swimming Pool
Furnished
Assigned Parking
Residents Lounge
Dishwasher
Other spaces
Workspace, Kitchen
Siesta Keys - Rated #1 Beach in USA
10

Excellent

·
Siesta Key
·
1 br
·
Sleeps 4
·
Balcony · Waterfront · Wifi ·
From
$183/night
Check availability
Property
Condo · 1 Bed · 1 bath
Amenities
Waterfront
Wifi
On Site Laundry
Swimming Pool
Elevator
Wheelchair Accessible
Air Conditioning
Fitness Center
Other spaces
Balcony, Kitchen
Expand your search criteria to see more vacation rentals near Siesta Key.
Home > Florida Vacation Rentals > Siesta Key Vacation Rentals
Updated: September 23, 2023