On Our Way Travel Siesta Key
Siesta Key
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Siesta Key

Oct 07 - Oct 08 ·
2 guests

Siesta Key Vacation Rentals

Siesta Key
2 guests

Adults:

2

Children:

0

Child’s age:

Over 1,360 stays assessed to highlight the standout picks

Navigation

1. Beachpoint Cottages

2. Lakeside Hidden Paradise Among Tropical Landscape W/ Heated Pool

3. Bianco Sands By Beachside Management

4. Ten35 Seaside Rentals

Cheap Siesta Key Vacation Rentals

5. Siesta Key Condo - Beach, Pool & Village Fun!

6. Living The Dream By Beachside Management

7. Beautiful Property On Siesta Key

Pet Friendly Vacation Rentals Siesta Key Florida

8. Siesta Key Beach House

9. Gulf Holiday By Beachside Management

10. Siesta Breakers #603, Gulfside In Siesta Key, Fl

Best Siesta Key Vacation Rentals

  • Best-rated
  • Beach access
Hotel Image Hotel Image

Beachpoint Cottages

125 Beach Road
2.1 km (1.3 mi) from city center
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Tennis court
  • Sun loungers
9.1
215 reviews
~ US$369 / night

Beachpoint Cottages

2.1 km (1.3 mi) from city center
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Tennis court
  • Sun loungers

Beachpoint Cottages

9.1
215 reviews
From US$ 369 / night
  • Beach access
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Lakeside Hidden Paradise Among Tropical Landscape W/ Heated Pool

8254 Midnight Pass Road
4.7 km (2.9 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Ironing facilities
  • Heated swimming pool
8.8
148 reviews
~ US$179 / night

Lakeside Hidden Paradise Among Tropical Landscape W/ Heated Pool

4.7 km (2.9 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Ironing facilities
  • Heated swimming pool

Lakeside Hidden Paradise Among Tropical Landscape W/ Heated Pool

8.8
148 reviews
From US$ 179 / night
  • Great deal
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Bianco Sands By Beachside Management

1126 Point Of Rocks Road
2.7 km (1.7 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • Ironing facilities
  • Tea and coffee facilities
  • Heated swimming pool
8.8
78 reviews
~ US$141 / night

Bianco Sands By Beachside Management

2.7 km (1.7 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • Ironing facilities
  • Tea and coffee facilities
  • Heated swimming pool

Bianco Sands By Beachside Management

8.8
78 reviews
From US$ 141 / night

Cheap Siesta Key Vacation Rentals

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Ten35 Seaside Rentals

1035 Seaside Drive
2.2 km (1.4 mi) from city center
  • BBQ facilities
  • Free parking
  • Ironing facilities
  • Tea and coffee facilities
  • Fitness centre
  • Heated swimming pool
10
26 reviews
~ US$347 / night

Ten35 Seaside Rentals

2.2 km (1.4 mi) from city center
  • BBQ facilities
  • Free parking
  • Ironing facilities
  • Tea and coffee facilities
  • Fitness centre
  • Heated swimming pool

Ten35 Seaside Rentals

10
26 reviews
From US$ 347 / night
  • Beach access
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Siesta Key Condo - Beach, Pool & Village Fun!

5132 Calle Minorga
2.1 km (1.3 mi) from city center
71
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Golf course
  • Outdoor swimming pool
9.7
18 reviews
~ US$273 / night

Siesta Key Condo - Beach, Pool & Village Fun!

2.1 km (1.3 mi) from city center
71
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Golf course
  • Outdoor swimming pool

Siesta Key Condo - Beach, Pool & Village Fun!

9.7
18 reviews
From US$ 273 / night
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Living The Dream By Beachside Management

139 Beach Road
2.1 km (1.3 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • Ironing facilities
  • Tea and coffee facilities
9.4
24 reviews
~ US$234 / night

Living The Dream By Beachside Management

2.1 km (1.3 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • Ironing facilities
  • Tea and coffee facilities

Living The Dream By Beachside Management

9.4
24 reviews
From US$ 234 / night

Pet Friendly Vacation Rentals Siesta Key Florida

  • Private beach
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Beautiful Property On Siesta Key

1234 Derby Lane
0.9 km (0.6 mi) from city center
100
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Golf course
  • Heated swimming pool
8.4
63 reviews
~ US$200 / night

Beautiful Property On Siesta Key

0.9 km (0.6 mi) from city center
100
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Golf course
  • Heated swimming pool

Beautiful Property On Siesta Key

8.4
63 reviews
From US$ 200 / night
  • Private beach
Hotel Image Hotel Image

Siesta Key Beach House

1232 Derby Lane
0.9 km (0.6 mi) from city center
131
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Golf course
  • Heated swimming pool
8.5
73 reviews
~ US$237 / night

Siesta Key Beach House

0.9 km (0.6 mi) from city center
131
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Golf course
  • Heated swimming pool

Siesta Key Beach House

8.5
73 reviews
From US$ 237 / night
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Gulf Holiday By Beachside Management

73 Avendia Messina
2.4 km (1.5 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • Ironing facilities
  • Tea and coffee facilities
8.7
25 reviews
~ US$171 / night

Gulf Holiday By Beachside Management

2.4 km (1.5 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • Ironing facilities
  • Tea and coffee facilities

Gulf Holiday By Beachside Management

8.7
25 reviews
From US$ 171 / night

Siesta Key Vacation Rentals Oceanfront

  • Private beach
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Siesta Breakers #603, Gulfside In Siesta Key, Fl

6480 Midnight Pass Road Unit #603
2.0 km (1.3 mi) from city center
118
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Tennis court
  • Pool with view
10
5 reviews
~ US$299 / night

Siesta Breakers #603, Gulfside In Siesta Key, Fl

2.0 km (1.3 mi) from city center
118
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Tennis court
  • Pool with view

Siesta Breakers #603, Gulfside In Siesta Key, Fl

10
5 reviews
From US$ 299 / night
  • Beach access
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Beachfront Getaway In Siesta Key

1129 Seaside Drive 7
2.2 km (1.4 mi) from city center
  • Cookware/ Kitchen utensils
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Garden area
8.8
27 reviews
~ US$224 / night

Beachfront Getaway In Siesta Key

2.2 km (1.4 mi) from city center
  • Cookware/ Kitchen utensils
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Garden area

Beachfront Getaway In Siesta Key

8.8
27 reviews
From US$ 224 / night
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Siesta Key Condo - On The Water !

5955 Midnight Pass Road 14E
0.7 km (0.4 mi) from city center
56
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Golf course
  • Pool with view
9.1
36 reviews
~ US$310 / night

Siesta Key Condo - On The Water !

0.7 km (0.4 mi) from city center
56
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Golf course
  • Pool with view

Siesta Key Condo - On The Water !

9.1
36 reviews
From US$ 310 / night

Siesta Key Vacation Rentals with Private Pool

  • Top location
  • Beach access
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Our House At Turtle Gate

1087 Lake House Cir
0.2 km (0.1 mi) from city center
126
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Golf course
  • Heated swimming pool
10
1 reviews
~ US$175 / night

Our House At Turtle Gate

0.2 km (0.1 mi) from city center
126
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Golf course
  • Heated swimming pool

Our House At Turtle Gate

10
1 reviews
From US$ 175 / night
  • Beach access
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Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

665 Beach Road
0.9 km (0.6 mi) from city center
73
  • Cookware/ Kitchen utensils
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
9.1
22 reviews
~ US$279 / night

Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

0.9 km (0.6 mi) from city center
73
  • Cookware/ Kitchen utensils
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities

Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

9.1
22 reviews
From US$ 279 / night
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Canal 313 - Right In Siesta Key Village!

313 Canal Road
1.9 km (1.2 mi) from city center
93
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Laundry
  • Heated swimming pool
9.8
18 reviews
~ US$386 / night

Canal 313 - Right In Siesta Key Village!

1.9 km (1.2 mi) from city center
93
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Laundry
  • Heated swimming pool

Canal 313 - Right In Siesta Key Village!

9.8
18 reviews
From US$ 386 / night
  • Beach access
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Parrot Beach Cottages Suite #4

60 Avenida Vennecia #4
2.4 km (1.5 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Outdoor swimming pool
9
15 reviews
~ US$189 / night

Parrot Beach Cottages Suite #4

2.4 km (1.5 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Outdoor swimming pool

Parrot Beach Cottages Suite #4

9
15 reviews
From US$ 189 / night
  • Beach access
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Newly Remodeled 8-Steps To Sand Path Of Beach! Unit D

6905 Point Of Rocks Road, Unit #D, Siesta Key, Florida 34242, United States
2.5 km (1.6 mi) from city center
84
  • Cookware/ Kitchen utensils
  • Free parking
  • Tours/Ticket assistance
  • Air conditioning
  • Ironing facilities
  • Fitness centre
9.8
11 reviews
~ US$520 / night

Newly Remodeled 8-Steps To Sand Path Of Beach! Unit D

2.5 km (1.6 mi) from city center
84
  • Cookware/ Kitchen utensils
  • Free parking
  • Tours/Ticket assistance
  • Air conditioning
  • Ironing facilities
  • Fitness centre

Newly Remodeled 8-Steps To Sand Path Of Beach! Unit D

9.8
11 reviews
From US$ 520 / night
  • Beach access
Hotel Image Hotel Image

Siesta Key Village, Heated Pool, Beach Access 4 Min Walk, 1Bdr

5241 Calle Menorca #2, Siesta Key, Fl 34242, Usa
1.8 km (1.1 mi) from city center
56
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Massage
  • Heated swimming pool
9.3
10 reviews
~ US$301 / night

Siesta Key Village, Heated Pool, Beach Access 4 Min Walk, 1Bdr

1.8 km (1.1 mi) from city center
56
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Massage
  • Heated swimming pool

Siesta Key Village, Heated Pool, Beach Access 4 Min Walk, 1Bdr

9.3
10 reviews
From US$ 301 / night
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Key West Villa 3 Min To #1 Beach • Pool • Bbq

378 Canal Road
1.7 km (1.1 mi) from city center
167
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Flat-screen TV
  • Sun terrace
9.1
11 reviews
~ US$271 / night

Key West Villa 3 Min To #1 Beach • Pool • Bbq

1.7 km (1.1 mi) from city center
167
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Flat-screen TV
  • Sun terrace

Key West Villa 3 Min To #1 Beach • Pool • Bbq

9.1
11 reviews
From US$ 271 / night

Are you in a hurry?

Here is a quick list of Vacation Rentals in Siesta Key, selected based on their rating

Name of hotel Accommodation Rating Price, $
Beachpoint Cottages

9.1 / 10

(215 Reviews)

 From 369$
Lakeside Hidden Paradise Among Tropical Landscape W/ Heated Pool

8.8 / 10

(148 Reviews)

 From 179$
Bianco Sands By Beachside Management

8.8 / 10

(78 Reviews)

 From 141$
Ten35 Seaside Rentals

10.0 / 10

(26 Reviews)

 From 347$
Siesta Key Condo - Beach, Pool & Village Fun!

9.7 / 10

(18 Reviews)

 From 273$

Location