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303 vacation rentals
36

NEW Private Siesta Key Vacation Rental Home W/ Heated Pool on Quiet Street

Florida / Siesta Key

Siesta Key condo

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$149

Price per night from

$149

(2) Very Good 

24

Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

Florida / Siesta Key

Siesta Key apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$107

Price per night from

$107

(5) Excellent 

28

Just Minutes from the White Sandy Siesta Beach

Florida / Siesta Key

Siesta Key condo

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Nearest beach 4 mi
  • Swimming pool
  • Child Friendly
“Just Right” Our condo was perfect for us! There was everything we needed inside and stuff for the beach! There was a Publix right across the street and many places to eat. The drive to Siesta Key was right up the road which was a plus as well! When we
…see more

Price per night from

$59

Price per night from

$59

(4) Excellent 

49

Siesta Key 2 BR, 2 1/2 Bath - *Across From Beach - Pool-view* - Newly Renovated

Florida / Siesta Key

Siesta Key apartment

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$149

Responds fast!
avg. 1 hour 48 minutes

Price per night from

$149

(2) Very Good 

38

Grand accomdation on USA #1 Beach - Siesta Key Fl

Florida / Siesta Key

Siesta Key apartment

2 5 14 nights min

  • 2 bedrooms
  • sleeps 5
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

Price per night from

$71

Price per night from

$71

30

Luxury Siesta Key Vacation Rental W/ Pool, Spa, and Walking Distance to Beach

Florida / Siesta Key

Siesta Key condo

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$426

Price per night from

$426

33

Walk to the Beach / Ride to the Village / Pool Home in Siesta Key - Free WiFi

Florida / Siesta Key

Siesta Key condo

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$229

Price per night from

$229

(1) Excellent 

28

1 Block to the Beach on Siesta Key Vacation Rental Home with Swimming Pool

Florida / Siesta Key

Siesta Key house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“Great place, super location” We thoroughly enjoyed our stay at your home. It was very spacious, clean and inviting. We had everything we needed and the location is wonderful. Thanks and we would definitly recommend your home to others
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Price per night from

$294

Price per night from

$294

35

Immaculate Siesta Key Beachside Private Vacation Home w/ Large Heated Pool

Florida / Siesta Key

Siesta Key condo

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$340

Price per night from

$340

24

Siesta Key Village Townhome with Heated Pool and Walking Distance to Beaches

Florida / Siesta Key

Siesta Key condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$224

Price per night from

$224

24

Walk to the Village or the Beach, Everything is in Reach from this SK Rental

Florida / Siesta Key

Siesta Key condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$214

Price per night from

$214

14

Siesta Key Public Beach

Florida / Siesta Key

Siesta Key condo

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child Friendly

Price per night from

$140

Price per night from

$140

17

Fantastic Island House of Siesta w/pool Walk to the beach

Florida / Siesta Key

Siesta Key apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$189

Price per night from

$189

29

Waterfront Siesta Key Vacation Rental Condo with Heated Pool and Water Views

Florida / Siesta Key

Siesta Key condo

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$107

Price per night from

$107

25

Luxury Siesta Key Vacation Rental Home with Heated Pool and Beach Access

Florida / Siesta Key

Siesta Key condo

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$369

Price per night from

$369

24

Spacious vacation rental condo with lagoon views, beach access, and pool

Florida / Siesta Key

Siesta Key condo

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$138

Price per night from

$138

25

Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

Florida / Siesta Key

Siesta Key condo

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$95

Price per night from

$95

36

Piece of Paradise a short Walk to Siesta Key Beach with Heated Pool

Florida / Siesta Key

Siesta Key condo

1 6 min stay varies

  • 1 bedroom
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$266

Price per night from

$266

26

Fully renovated ground floor poolside unit at Bay Oaks with fishing pier-D31

Florida / Siesta Key

Siesta Key apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$149

Price per night from

$149

25

Coastal Siesta Key Vacation Rental Home W/ Heated Pool and Beach Access

Florida / Siesta Key

Siesta Key condo

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$238

Price per night from

$238

8

Sunset Royale - 302

Florida / Siesta Key

Siesta Key apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$126

Responds fast!
avg. 2 hours 38 minutes

Price per night from

$126

25

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Florida / Siesta Key

Siesta Key condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$107

Price per night from

$107

26

Siesta Key Beach Townhouse with Heated Pool and Accommodates up to 8 Guests

Florida / Siesta Key

Siesta Key condo

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$116

Price per night from

$116

10

Sunset Royale 214

Florida / Siesta Key

Siesta Key apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$144

Responds fast!
avg. 2 hours 38 minutes

Price per night from

$144

9

Sunset Royale -106

Florida / Siesta Key

Siesta Key condo

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$144

Responds fast!
avg. 3 hours 9 minutes

Price per night from

$144

11

Sunset Royale - 200

Florida / Siesta Key

Siesta Key apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$144

Responds fast!
avg. 3 hours 25 minutes

Price per night from

$144

26

Affordable Ground Floor Siesta Key Vacation Rental with Heated Pool Access

Florida / Siesta Key

Siesta Key condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$101

Price per night from

$101

24

Excellent Sarasota Vacation Rental Just Minutes to Siesta Key and Downtown

Florida / Siesta Key

Siesta Key condo

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$155

Price per night from

$155

31

Spacious Siesta Key Canal Front Vacation Rental House with Large Heated Pool

Florida / Siesta Key

Siesta Key condo

3 10 14 nights min

  • 3 bedrooms
  • sleeps 10
  • 14 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$229

Price per night from

$229

9

Sunset Royale - 204

Florida / Siesta Key

Siesta Key apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$126

Responds fast!
avg. 3 hours 23 minutes

Price per night from

$126

12

Beachside Bliss !

Florida / Siesta Key

Siesta Key apartment

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$129

Price per night from

$129

15

Sunset Royale - 308

Florida / Siesta Key

Siesta Key condo

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$126

Responds fast!
avg. 2 hours 30 minutes

Price per night from

$126

13

Sunset Royale 104

Florida / Siesta Key

Siesta Key apartment

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$138

Responds fast!
avg. 2 hours 38 minutes

Price per night from

$138

8

Sunset Royale 208

Florida / Siesta Key

Siesta Key apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$126

Responds fast!
avg. 3 hours 23 minutes

Price per night from

$126

24

4 Bedroom Key West Style Home W/ Heated Pool, Close to Village and Beaches

Florida / Siesta Key

Siesta Key condo

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$180

Price per night from

$180

23

Zen Den

Florida / Siesta Key

Siesta Key apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$149

Price per night from

$149

24

Renovated Spacious Three Suite Siesta Key Vacation Rental Home W/ Heated Pool

Florida / Siesta Key

Siesta Key condo

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$218

Price per night from

$218

11

Sunset Royale - 114

Florida / Siesta Key

Siesta Key apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$142

Responds fast!
avg. 2 hours 30 minutes

Price per night from

$142