50 Best Siesta Key Beach rentals on Holiday Lettings - Vacation rentals

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538 Vacation rentals

(2) Excellent 

26

Vacation villa in Siesta Key

Florida / Siesta Key

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Very spacious, air-conditioned 4 bed detached ranch-type Villa on Siesta Key Bayside. Sleeps 8, 1 King, 1 Queen, 2 Full and 2 twin beds. 1 month minimum Jan-March, 2 week minimum April -Dec. Maximum 3 cars . Large Heated Communal pool, Own Outdoor patio area with  …see more

from $171 / night

$845 - $1292 / week

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from $171 / night

(4) Very Good 

24

Siesta Key Vacation condo rental

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Harbour Towers is perfect for people that like the feeling of a grand hotel. You can play tennis on our Har-Tru tennis courts, swim in the sky blue water of Siesta Beach or relax inside at the heated swimming pools. You can jet ski or snorkel at Point of Rock.Yo  …see more

from $115 / night

$801 - $950 / week

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from $115 / night

(17) Excellent 

23

Siesta Key Vacation condo rental

Florida / Siesta Key

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.01 mi
  • Swimming pool
The condo benefits from its own private pool. The living room, master bedroom, and lanai (balcony) all have stunning ocean views. The lanai, with over $10,000 of new doors and windows, is furnished with a table and chairs to enable you to dine al fresco. There is al  …see more

from $358 / night

$2501 / week

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from $358 / night

(1) Excellent 

24

Home rental in Siesta Key with swimming pool

Florida / Siesta Key

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
Fabulous home on Siesta Key (Sarasota)( two weeks minimum stay ). Just 2 minutes drive to the beach & village. This home features 3 bedrooms and 2 baths with a large kitchen that opens to the family room. Great pool with southern exposure,and enclosed in a screen lana  …see more

from $193 / night

$1351 - $1400 / week

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from $193 / night

(1) Excellent 

18

Vacation condo in Siesta Key

Florida / Siesta Key

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
White Sands Village is located on Siesta Key, just few steps from Siesta Beach and directly on the canal across from Philippee Creek. Highlights of White Sands Unit 303: Free high-speed WiFi Ground floor unit More than 200 channel cable TV DVR to watch your favorite s  …see more

from $108 / night

$750 - $1101 / week

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from $108 / night

(4) Excellent 

29

Florida / Siesta Key

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

 …see more

from $76 / night

$850 - $950 / week

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from $76 / night

18

Florida / Siesta Key

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Air conditioning

 …see more

from $108 / night

$750 - $996 / week

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from $108 / night

31

Florida / Siesta Key

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly

 …see more

from $157 / night

$1300 / week

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from $157 / night

(8) Excellent 

17

Florida / Siesta Key

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning

 …see more

from $185 / night

$1289 / week

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from $185 / night

(16) Excellent 

27

Florida / Siesta Key

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $100 / night

$1050 / week

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from $100 / night

(5) Very Good 

24

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $214 / night

$1491 - $2261 / week

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from $214 / night

(8) Excellent 

16

Florida / Siesta Key

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

 …see more

from $136 / night

$895 - $1606 / week

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from $136 / night

(40) Excellent 

24

Florida / Siesta Key

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

 …see more

from $122 / night

$850 - $1250 / week

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from $122 / night

11

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly

 …see more

from $196 / night

$1150 - $2086 / week

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from $196 / night

30

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children

 …see more

from $151 / night

$850 - $2531 / week

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from $151 / night

(4) Excellent 

17

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $214 / night

$1491 - $2261 / week

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from $214 / night

(7) Excellent 

20

Siesta Key Vacation condo rental

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
This luxurious two bedroom/two bath condo is located on the beach on Siesta Key, an island off the coast of Sarasota. Siesta Key boasts miles of white sugar sand beaches, and a public beach which was rated number one in the U.S. this year and is regularly rated in the  …see more

from $129 / night

$901 / week

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from $129 / night

(1) Excellent 

38

Vacation townhouse in USA East Coast

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
WELCOME TO PARADISE! -- BEST LOCATION on SIESTA KEY! A very clean, cozy 3 level TH with a pool view, a few yards away from the beach, restaurants, bars, bank, grocery&drug store, 7-Eleven, free Wi-Fi, 140 channels on TV, fireplace, washer/dryer in unit, garage, grill,  …see more

from $151 / night

$1001 - $1500 / week

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from $151 / night

(10) Very Good 

27

Florida / Siesta Key

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

 …see more

from $100 / night

$650 - $1001 / week

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from $100 / night

9

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $134 / night

$930 - $1800 / week

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from $134 / night

(1) Excellent 

16

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly

 …see more

from $157 / night

$1099 - $1680 / week

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from $157 / night

(13) Excellent 

17

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $214 / night

$1491 - $2261 / week

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from $214 / night

28

Florida / Siesta Key

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly

 …see more

from $276 / night

$1926 / week

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from $276 / night

(2) Excellent 

19

Florida / Siesta Key

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly

 …see more

from $251 / night

$1700 - $2450 / week

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from $251 / night

(7) Excellent 

19

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $214 / night

$1491 - $2261 / week

Inquire View

from $214 / night

(1) Excellent 

24

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $200 / night

$1396 - $2236 / week

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from $200 / night

(5) Excellent 

25

Florida / Siesta Key

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

 …see more

from $415 / night

$3496 - $3996 / week

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from $415 / night

21

Florida / Siesta Key

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly

 …see more

from $99 / night

$650 - $1201 / week

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from $99 / night

11

Florida / Siesta Key

2 4 14 nights min

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min
  • Child friendly

 …see more

from $143 / night

$1001 / week

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from $143 / night

(1) Excellent 

15

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $157 / night

$1099 - $1680 / week

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from $157 / night

22

Florida / Siesta Key

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $136 / night

$945 - $1635 / week

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from $136 / night

(3) Excellent 

17

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $165 / night

$1156 - $1737 / week

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from $165 / night

(1) Excellent 

7

Florida / Siesta Key

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Ask about pets

 …see more

from $288 / night

$2016 - $2600 / week

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from $288 / night

(1) Excellent 

21

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $214 / night

$1491 - $2261 / week

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from $214 / night

(7) Very Good 

15

Florida / Siesta Key

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly

 …see more

from $194 / night

$1359 - $2030 / week

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from $194 / night

(2) Excellent 

12

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $143 / night

$1001 - $1757 / week

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from $143 / night

(4) Excellent 

17

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $165 / night

$1156 - $1737 / week

Inquire View

from $165 / night

(2) Excellent 

18

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $214 / night

$1491 - $2261 / week

Inquire View

from $214 / night

(1) Excellent 

21

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning

 …see more

from $143 / night

$1001 - $1351 / week

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from $143 / night

31

Vacation condo in Siesta Key

Florida / Siesta Key

2 5 14 nights min

  • 2 bedrooms
  • Sleeps 5
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
This recently renovated, bright and wonderfully furnished residence has panoramic views and opens above the resort's pools and manicured lawns. Wake up to beautiful sunrises and enjoy your morning coffee at the bistro table for two next to the screened lanai area. A 1  …see more

from $115 / night

$801 - $1201 / week

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from $115 / night

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