Siesta Key Vacation House Rentals

32 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.
🏝Tropical Siesta Key Home with Incredible Pool & HotTub Patio
10

Excellent

·
Siesta
·
5 br
·
Sleeps 10
·
Workspace · Air Conditioning · Private Pool ·
From
$866/night
Check availability
Property
House · 5 Beds · 4 baths
Amenities
Air Conditioning
Private Pool
Furnished
Beach
Garage Parking
Oven
Lake
Hot Tub
Other spaces
Workspace, Outdoor Space, Kitchen
Your Personal Resort-7BR, Pool, Bocce Ball, Boating & so much more!
10

Excellent

·
Siesta
·
7 br
·
Sleeps 15
·
In Unit Laundry · Pool · Fitness Center ·
From
$1,133/night
Check availability
Property
House · 7 Beds · 5 baths
Amenities
In Unit Laundry
Pool
Fitness Center
Fireplace
Air Conditioning
Swimming Pool
Residents Lounge
Oven
Other spaces
Workspace, Balcony, Kitchen
Large Siesta Key Home On Water With Pool/Spa
10

Excellent

·
Siesta Beach
·
5 br
·
Sleeps 14
·
In Unit Laundry · Dishwasher · Wifi ·
From
$807/night
Check availability
Property
House · 5 Beds · 5 baths
Amenities
In Unit Laundry
Dishwasher
Wifi
Pool
Private Pool
Garage Parking
Ocean
Waterfront
Other spaces
Balcony, Kitchen, Workspace
Palm Paradise | Pet Friendly Home on Siesta Key w/ Large Heated Private Pool & Outdoor Area!
10

Excellent

·
Siesta
·
5 br
·
Sleeps 10
·
Residents Lounge · Outdoor Space · Beach ·
From
$375/night
Check availability
Property
House · 5 Beds · 3 baths
Amenities
Residents Lounge
Beach
Wifi
Pool
Dishwasher
In Unit Laundry
Furnished
Garage Parking
Other spaces
Kitchen, Balcony
Beachside Private Vacation Home w/ Large Heated Pool
10

Excellent

·
Siesta
·
3 br
·
Sleeps 6
·
Beach · Private Pool · Kitchen ·
From
$337/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Beach
Private Pool
Furnished
Oven
In Unit Laundry
Air Conditioning
Pool
Swimming Pool
Other spaces
Kitchen, Outdoor Space
Hemingway House | Beautiful Traditional Home w/ Spacious Outdoor Dining Area & Lush Landscaping
10

Excellent

·
Siesta
·
3 br
·
Sleeps 8
·
In Unit Laundry · On Site Laundry · Wifi ·
From
$299/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
In Unit Laundry
On Site Laundry
Wifi
Dishwasher
Residents Lounge
Furnished
Beach
Pool
Other spaces
Kitchen, Balcony

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.
$7,800 - 2 Bedroom 2 Bathroom Cottage In Siesta Key With Great Amenities

No rating

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Siesta Key
·
2 br
·
Swimming Pool · Air Conditioning · Wheelchair Accessible ·
From
$260/night
Min stay: 30 nights
Property
House · 2 Beds · 2 baths
Amenities
Swimming Pool
Air Conditioning
Wheelchair Accessible
Dishwasher
In Unit Laundry
Ceiling Fan
Furnished
Assigned Parking
Other spaces
Deck
Luxurious Paradise with Tiki Bar and Heated Pool, Just Remodeled!

No rating

·
Siesta
·
5 br
·
Sleeps 10
·
Dishwasher · Outdoor Space · Furnished ·
From
$762/night
Check availability
Property
House · 5 Beds · 3 baths
Amenities
Dishwasher
Furnished
Pool
Swimming Pool
In Unit Laundry
Fitness Center
Air Conditioning
Private Pool
Other spaces
Workspace, Kitchen, Balcony
New Listing | Pet Friendly Home on Siesta Key w/ Outdoor Patio & Private Screened-In Heated Pool!

No rating

·
Siesta Beach
·
3 br
·
Sleeps 8
·
On Site Laundry · Kitchen · Garage Parking ·
From
$669/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
On Site Laundry
Garage Parking
Pool
Beach
Air Conditioning
In Unit Laundry
Residents Lounge
Wifi
Other spaces
Kitchen, Outdoor Space

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 $155. Use the price filter at the top of the page to search for more specific prices.
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, Outdoor Space
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
Outdoor Space, Kitchen
Single family home

No rating

·
Siesta
·
3 br
·
Dishwasher · Swimming Pool · Outdoor Space ·
From
$217/night
Min stay: 30 nights
Property
House · 3 Beds · 2 baths
Amenities
Dishwasher
Swimming Pool
Furnished
In Unit Laundry
Garage Parking
Other spaces
Outdoor Space, Walk In Closets
Canal-front home near Shell Beach with access to bay, private hot tub, & deck

No rating

·
Siesta
·
2 br
·
Sleeps 6
·
Free Parking · Waterfront · Dishwasher ·
From
$219/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Free Parking
Waterfront
Dishwasher
In Unit Laundry
Oven
Furnished
Air Conditioning
Hot Tub
Other spaces
Kitchen, Balcony
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Updated: February 25, 2024