Siesta Key Village (Siesta Key, Florida) Vacation Rentals

(22 rentals)
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5 BR | 5 BA | Sleeps 15 | Quick View

$2260

avg/night

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Key Amenities

  • Air conditioning
  • Private pool

About this property

Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key!Brand New, Elevated 5 Bedroom Home on Siesta Key with Resort Pool and Waterslide with splash zone! This bright and sunny 5 bedroom and 5 bathroom home, with 4 Master Suites, and 1 Bunk room, sleeps ...

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Property Type

Siesta Key House

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7 BR | 6 BA | Sleeps 23 | Quick View

$2063

avg/night

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Key Amenities

  • Air conditioning
  • Private pool

About this property

Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key!BRAND NEW HOME IN SIESTA KEY VILLAGE!! Your whole party will absolutely love the Private Resort Style Heated Pool that features a Rock Water Slide, Waterfall, Gratto, Swim up bar, Sun Shelf, and Jacuzzi. ...

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Property Type

Siesta Key House

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2 BR | 2 BA | Sleeps 6 | Quick View

$490

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol. We have improved and strengthened ...

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Property Type

Siesta Key House

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3 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 0.2 miles to Siesta Key Beach - Access # 5

$801

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol. We have improved and strengthened ...

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Property Type

Siesta Key House

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3 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 0.4 miles to Siesta Key Beach - Access # 8

$763

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol. We have improved and strengthened our cleaning crews by mandating the highest quality products that are EPA approved to use against COVID-19. Our cleaners also have a longer period of time to complete this ...

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Property Type

Siesta Key House

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8 BR | 6 BA | Sleeps 22 | Quick View

$2952

avg/night

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Key Amenities

  • Air conditioning
  • Private pool

About this property

Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key!Located in Siesta Key Village and the perfect Boater's Dream House with a Private Resort Style Heated Pool for the entire family that features a Rock Water Slide, Waterfall, Gratto, Swim up bar, Sun ...

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Property Type

Siesta Key House

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4 BR | 3 BA | Sleeps 12 | Quick View

2

$1075

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol. We have improved and strengthened ...

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Property Type

Siesta Key House

"Birthday celebration"

Loved staying at the Maharo home. Very spacious and very accommodating. Particularly loved the private pool given the pandemic crisis we are all experiencing.Enjoyed walking through Siesta Key village. ...

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3 BR | 3 BA | Sleeps 10 | Quick View

$862

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol. We have improved and strengthened ...

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Property Type

Siesta Key House

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2 BR | 2 BA | Sleeps 6 | Quick View

$425

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol. We have improved and strengthened ...

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Property Type

Siesta Key House

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6 BR | 6 BA | Sleeps 20 | Quick View

Distance to beach: 0.2 miles to Siesta Key Beach - Access # 5

$1782

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol. We have improved and strengthened ...

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Property Type

Siesta Key House

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5 BR | 5 BA | Sleeps 14 | Quick View

$1962

avg/night

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Key Amenities

  • Air conditioning
  • Private pool

About this property

Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key!Newly Remodeled Siesta Key Home!!You HAVE to SEE this Amazing Back Yard! This Ground Level home, with no stairs or multiple levels, is in the Heart of Siesta Key Village and just steps to Ocean ...

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Property Type

Siesta Key House

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8 BR | 6 BA | Sleeps 24 | Quick View

1

$2899

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol. We have improved and strengthened ...

View all property information

Property Type

Siesta Key House

"Great experience."

Everyone who was on the trip had a great experience at Atlantis! Plenty of room and lots to do in the house and on the island. The information you gave us about the island was very helpful. We had an issue ...

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$171

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

VILLAGE WEST - Deluxe Ground Floor Vacation Condo in Siesta Key Village with Heated PoolLocated right in the Heart of Siesta Village, Sarasota FL - Short Walk to Crescent BeachVILLAGE WEST: This Siesta Key one bedroom ground floor condo vacation rental is located right in the heart of Siesta Village ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 7 | Quick View

2

Distance to beach: 0.4 miles to Siesta Key Beach

$349

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Location, location, location!! New pool and spa just completed! Waterfall edge from spa to pool and deck jets. New landscaping with additional seating areas near pool and canal. Also, lots of green space to enjoy too!Canal home in heart of the Siesta Key Village, no need for a car! Steps away ...

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Property Type

Siesta Key House

"Home Away from Home/Great Location"

We loved the location of this home. Not only because it’s located on a canal and very private, but it’s only a two-minute walk to Siesta Key Village. The beach is also a short walk of only 6-7 minutes. ...

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1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.2 miles to Siesta Key Beach - Access # 5

$280

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol. We have improved and strengthened ...

View all property information

Property Type

Siesta Key House

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1 BR | 1 BA | Sleeps 4 | Quick View

2

$291

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol. We have improved and strengthened ...

View all property information

Property Type

Siesta Key House

"Vacation"

We had a wonderful time and the condo was exactly as presented. Sue was fantastic.This was our first time at Siesta Key as well as first time to stay a month anywhere. Other residents were very friendly ...

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3 BR | 3 BA | Sleeps 13 | Quick View

$1015

avg/night

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Key Amenities

  • Air conditioning
  • Private pool

About this property

Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! Cute and Spacious, and Completely REMODELED!! This 3 bedroom 3.5 bathroom Townhome sleeps 14 people in beds! This Townhome is the perfect beach house for your family getaway! Your family will ...

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Property Type

Siesta Key House

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3 BR | 3 BA | Sleeps 6 | Quick View

2

$314

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Great house on Siesta key with pool and kanal. You can do fishing on the backside or have a jetski, boat there. Sometime you can see seacows on the kanal. 3 bedroom with 3 bath and a nice heated pool tp play in. Nice and quiet place it is, and so close to the Village and beach. Enjoy the place.

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Property Type

Siesta Key House

"Great house with perfect location!"

We stayed over Christmas and had a great time! The house is in a perfect location because it is within walking distance to the downtown and to the beach. You can also use the free trolley or one of the ...

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2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 800 feet to Siesta Key Beach

$140

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Brand New Condo, completely renovated. 2 Bedroom, 2 Bath large condo with granite kitchen and baths. Tile deck flooring. Full water views from our 6th floor location. See all the way to end of Anna Marie on clear day. Ringling bridge, downtown Sarasota, Lido and Bird Key views. King bed in master ...

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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 2 | Quick View

4

Distance to beach: 0.5 miles to Siesta Key Beach

$156

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

*Calendar month rentals only*May - November (seven-month lease) - $2000 per month plus utilities May - November (three-month lease) - $2500 per month plus utilities December - $3500 per month plus utilities January - $4500 per month plus utilities February and March - $5500 per month plus utilities April ...

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Property Type

Siesta Key Cottage

"Excellent pet-friendly bungalow"

This studio was perfect for our 4 week stay in Siesta Key! The neighborhood is beautiful and quiet-and everyone we met was so friendly-to us and to our dog! Every day we walked into the Village-where ...

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3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 0.5 miles to Siesta Beach access 7

$228

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

*Calendar month rentals only*June - November (six-month lease) - $3500 per month plus utilities June - November (three-month lease) - $3900 per month plus utilities December - $6500 per month plus utilities January - $7500 per month plus utilities February & March - $7900 per month plus utilities April ...

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Property Type

Siesta Key Bungalow

"Fabulous location in a comfy pet friendly cottage"

We (2 couples) have stayed at Canal Place in Siesta Key for 5 years. Our hosts, Rich and Ali Light, are gracious hosts and very responsive. Canal Place is in an excellent location, about 10min to the village ...

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$500

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

The home has 3 bedrooms & 2 custom bathrooms. Newly renovated with Terracotta roof tiles for a classic Florida look. The front of the home has an enclosed privacy wall with a landscaped courtyard. A great place for evening gatherings with seating and a grilling area. The interior of the home ...

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Property Type

Siesta Key House

"Perfect house & location"

Our family of 4 had a great vacation at this property. Absolutely everything is as expected and beyond!!

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Siesta Key Village (Siesta Key, Florida) Vacation Rentals