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Vacations by Zumper

Siesta Key Vacation Rentals With Pool

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
$1,006/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
Price drop
The Upper Deck
10

Excellent

·
Siesta Key
·
6 br
·
Sleeps 13
·
Pool · Hot Tub · Assigned Parking ·
From
$2,070/night
Check availability
Property
Apartment · 6 Beds · 5 baths
Amenities
Pool
Hot Tub
Assigned Parking
Residents Lounge
Swimming Pool
Wifi
On Site Laundry
Dishwasher
Other spaces
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
$1,004/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
Parrot Beach Cottages Suite #2
9

Excellent

·
Siesta Key
·
1 br
·
Sleeps 2
·
Oven · Kitchen · Wifi ·
From
$226/night
Check availability
Property
Hotel · 1 Bed · 1 bath
Amenities
Oven
Wifi
On Site Laundry
Air Conditioning
Pool
Swimming Pool
Furnished
Other spaces
Kitchen
Price drop
Sunset Gulf
9

Excellent

·
Siesta Key
·
8 br
·
Sleeps 25
·
Air Conditioning · Private Pool · Wifi ·
From
$2,550/night
Check availability
Property
Apartment · 8 Beds · 5 baths
Amenities
Air Conditioning
Private Pool
Wifi
Assigned Parking
Swimming Pool
Ocean
Dishwasher
Waterfront
Other spaces
Workspace, Balcony, Kitchen
Price drop
Avenida Lower
7

Very good

·
Siesta Key
·
2 br
·
Sleeps 8
·
Furnished · Pool · Dishwasher ·
From
$417/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

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.
Mandevilla - U

No rating

·
Siesta Key
·
3 br
·
Sleeps 10
·
Air Conditioning · Dishwasher · Wifi ·
From
$1,081/night
Check availability
Property
Apartment · 3 Beds · 3 baths
Amenities
Air Conditioning
Dishwasher
Wifi
Oven
Assigned Parking
On Site Laundry
Pool
Furnished
Other spaces
Kitchen, Workspace
Mimosa - 5251B

No rating

·
Siesta Key
·
1 br
·
Sleeps 4
·
Wifi · Oven · Outdoor Space ·
From
$384/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Wifi
Oven
On Site Laundry
Swimming Pool
Pool
Furnished
Air Conditioning
Assigned Parking
Other spaces
Kitchen, Workspace
Lantana - 5251A

No rating

·
Siesta Key
·
2 br
·
Sleeps 6
·
Assigned Parking · Swimming Pool · Air Conditioning ·
From
$577/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Assigned Parking
Swimming Pool
Air Conditioning
Oven
Wifi
Furnished
Pool
Dishwasher
Other spaces
Workspace, Kitchen
Honeysuckle - L

No rating

·
Siesta Key
·
3 br
·
Sleeps 10
·
Furnished · On Site Laundry · Outdoor Space ·
From
$1,081/night
Check availability
Property
Apartment · 3 Beds · 3 baths
Amenities
Furnished
On Site Laundry
Pool
Air Conditioning
Oven
Swimming Pool
Wifi
Dishwasher
Other spaces
Workspace, Kitchen
The Hummingbird

No rating

·
Siesta Key
·
6 br
·
Sleeps 20
·
Kitchen · On Site Laundry · Swimming Pool ·
From
$2,195/night
Check availability
Property
Apartment · 6 Beds · 6 baths
Amenities
On Site Laundry
Swimming Pool
Assigned Parking
Private Pool
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen, Balcony, Workspace
Vinca - 5251D

No rating

·
Siesta Key
·
1 br
·
Sleeps 4
·
Outdoor Space · Oven · Kitchen ·
From
$384/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Oven
Air Conditioning
Swimming Pool
Assigned Parking
Furnished
On Site Laundry
Pool
Wifi
Other spaces
Kitchen, Workspace

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
Price drop
Palm Bay Club Bayside Well-Priced Rental Condo on Siesta Key
10

Excellent

·
Siesta Key
·
2 br
·
Sleeps 6
·
Furnished · Oven · Wifi ·
From
$99/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Furnished
Oven
Wifi
Beach
Waterfront
Dishwasher
Package Service
Hot Tub
Other spaces
Balcony, Kitchen
Age restrictedPrice drop
Fall Discount$$$ on 7+nights for Seniors, Active Military-Police-Fire-Healthcare
10

Excellent

·
Siesta Key
·
2 br
·
Sleeps 4
·
In Unit Laundry · Oven · Kitchen ·
From
$103/night
Check availability
Property
Condo · 2 Beds · 1 bath
Amenities
In Unit Laundry
Oven
Swimming Pool
Furnished
Pool
Dishwasher
Air Conditioning
Hot Tub
Other spaces
Kitchen
Price drop
Classic Crescent Beach condo with pool, tennis, pickleball & screened patio

No rating

·
Siesta Key
·
2 br
·
Sleeps 6
·
Wifi · Free Parking · Furnished ·
From
$107/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Wifi
Free Parking
Furnished
In Unit Laundry
Swimming Pool
Pool
Other spaces
Kitchen
Walk to Beaches, Bay Complex, Heated Pool, Wifi, Ground Floor, Renovated, Patio, Parking
10

Excellent

·
Siesta Key
·
2 br
·
Sleeps 6
·
Assigned Parking · Pool · Air Conditioning ·
From
$111/night
Check availability
Property
Condo · 2 Beds · 1 bath
Amenities
Assigned Parking
Pool
Air Conditioning
Ceiling Fan
Beach
Oven
Wifi
In Unit Laundry
Other spaces
Kitchen
Price drop
Walk to Crescent Beach, Wifi, Bay Views From Lanai, Heated Pool, YTube TV, Tennis, On Trolley Line
10

Excellent

·
Siesta Key
·
2 br
·
Sleeps 6
·
Swimming Pool · Pool · In Unit Laundry ·
From
$112/night
Check availability
Property
Condo · 2 Beds · 1 bath
Amenities
Swimming Pool
Pool
In Unit Laundry
Elevator
Wifi
Storage
Dishwasher
Oven
Other spaces
Kitchen

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.
Cozy Siesta Key Vacation Rental

No rating

·
Siesta Key
·
Studio
·
Sleeps 3
·
In Unit Laundry · Dishwasher · Central Heat ·
From
$248/night
Check availability
Property
Apartment · Studio · 1 bath
Amenities
In Unit Laundry
Dishwasher
Central Heat
Oven
Beach
Swimming Pool
Pool
On Site Laundry
Other spaces
Kitchen
Price drop
Siesta Key Condo w/ Balcony - Walk to Beach + Bay!
10

Excellent

·
Siesta Key
·
2 br
·
Sleeps 6
·
Outdoor Space · Wifi · Central Heat ·
From
$113/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Wifi
Central Heat
Swimming Pool
In Unit Laundry
Air Conditioning
Beach
Elevator
Residents Lounge
Other spaces
Balcony, Kitchen
Island House Beach Resort V13
10

Excellent

·
Siesta Key
·
2 br
·
Sleeps 6
·
Wifi · Central Heat · Pool ·
From
$211/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Wifi
Central Heat
Pool
In Unit Laundry
Carpet
Swimming Pool
Air Conditioning
Furnished
Other spaces
Kitchen
Expand your search criteria to see more vacation rentals near Siesta Key.
Home > Florida Vacation Rentals > Siesta Key Vacation Rentals > Siesta Key pool Vacation Rentals
Updated: September 20, 2023