Siesta Key Village (Siesta Key, Florida) Vacation Rentals

(30 rentals)
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Casa Mahalo - Ask About $99 Down!

4 BR | 3 BA | Sleeps 12 | Quick View

2

$669

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pet friendly
  • Private pool

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals 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 ...

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Property Type

Siesta Key House

"Birthday celebration"
Reviewed August 18, 2020

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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Village West VW Unit 102. One Bedroom - Ground Floor Condo - Heated Pool

$128

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly

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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The Hummingbird - Ask About $99 Down!

6 BR | 6 BA | Sleeps 20 | Quick View

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

$878

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pet friendly
  • Private pool

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals 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 ...

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Property Type

Siesta Key House

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Honeysuckle - Ask About $99 Down!

$411

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pet friendly

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals 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 ...

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Property Type

Siesta Key House

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Vinca - Ask About $99 Down!

1 BR | 1 BA | Sleeps 4 | Quick View

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

$138

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals 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 ...

View all property information

Property Type

Siesta Key House

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Lantana - Ask About $99 Down!

2 BR | 2 BA | Sleeps 6 | Quick View

$259

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pet friendly

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals 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 ...

View all property information

Property Type

Siesta Key House

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Mandevilla - Ask About $99 Down!

3 BR | 3 BA | Sleeps 10 | Quick View

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

$400

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals 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 ...

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Property Type

Siesta Key House

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Garden Apartment of Siesta Key Townhouse - Heated Pool -Siesta key Unit 1BR 5239

$127

avg/night

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Key Amenities

  • Full kitchen

About this property

SEASIDE VILLAS: This Siesta Key one bedroom garden apartment vacation rental is located in the heart of Siesta Village – just steps to all the shops and restaurants and only a three minute walk to world famous Siesta Key Crescent Beach! Siesta Village has dozens of shops, fine or casual dining, ...

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Property Type

Siesta Key Apartment

"Sunnyside properties"
Reviewed October 21, 2020

Beautiful week! Apartment was very clean!! We met Tina the cleaning machina! She was very helpful and gave us some beach towels

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Luxury Village Canal Home with Heated Pool & Spa

$500

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Managed by owner
  • Pet friendly
  • Private pool

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"
Reviewed April 25, 2021

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

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Plumbago - Ask About $99 Down!

$234

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals 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 ...

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Property Type

Siesta Key House

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New Pool & Spa! Luxury Canal Home in heart of Siesta Key Village! No car needed

2 BR | 2 BA | Sleeps 7 | Quick View

2

Distance to beach: 0.4 miles to Siesta Key Beach

$375

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Managed by owner
  • Private pool

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"
Reviewed May 2, 2021

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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Mimosa - Ask About $99 Down!

1 BR | 1 BA | Sleeps 4 | Quick View

2

$142

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pet friendly

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals 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 ...

View all property information

Property Type

Siesta Key House

"Vacation"
Reviewed March 1, 2021

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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The Big Kahuna - Ask About $99 Down!

$1381

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pet friendly
  • Private pool

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals 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 ...

View all property information

Property Type

Siesta Key House

"Great experience."
Reviewed January 21, 2021

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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Villa Castile - Ask About $99 Down!

3 BR | 3 BA | Sleeps 10 | Quick View

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

$436

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pet friendly
  • Private pool

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals 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 ...

View all property information

Property Type

Siesta Key House

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Modern Marvel

4 BR | 4 BA | Sleeps 14 | Quick View

$1327

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Private pool

About this property

Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key!This Private Gated Home is located directly on the Gulf of Mexico and in Siesta Key Village. It is hard to find a home with a more ideal location, better views, and more privacy all wrapped into one ...

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Property Type

Siesta Key House

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Great place Siesta key

3 BR | 3 BA | Sleeps 6 | Quick View

1

$314

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Managed by owner
  • Private pool

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

"Close to market"
Reviewed July 19, 2021

Needs some updates but we had a blast! Great handyman Roger! Has everything but towels. Weird smell in master like bad cologne. Great washing machine. Clean pool. Needs new closet rales and new sliding ...

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Bahama Mama

5 BR | 5 BA | Sleeps 14 | Quick View

$1106

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Pet friendly
  • 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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Fern Haven Tropical -Studio Cottage -MONTHLY RENTAL-Pet Friendly-Fully Furnished

1 BR | 1 BA | Sleeps 2 | Quick View

4

Distance to beach: 0.5 miles to Siesta Key Beach

$150

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Managed by owner
  • Pet friendly

About this property

*Calendar month rentals only*May - November (seven-month lease) - $1695 per month plus utilities May - November (three-month lease) - $1995 per month plus utilities December - $2900 per month plus utilities January - $3900 per month plus utilities February and March - $4900 per month plus utilities April ...

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Property Type

Siesta Key Cottage

"Excellent pet-friendly bungalow"
Reviewed March 2, 2020

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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Island Time East

3 BR | 3 BA | Sleeps 13 | Quick View

$493

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Pet friendly
  • 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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Surf View

8 BR | 8 BA | Sleeps 22 | Quick View

$1294

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Pet friendly
  • Private pool

About this property

Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key!This incredible vacation home is an amazing value and one of the best on the Key. It is a bright and sunny 8 bedroom and 8.5 bathroom home, with 7 Master Suites, and it sleeps 22 in beds. It is located ...

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Property Type

Siesta Key House

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Siesta Towers #6F Gulf views and Downtown Sarasota Views. Siesta Key Village

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 800 feet to Siesta Key Beach

$140

avg/night

View Details

Key Amenities

  • Air conditioning
  • Communal pool
  • Full kitchen
  • Kid friendly
  • Managed by owner
  • Oceanfront

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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Canal Place 3/2 Bungalow - WEEKLY/MONTHLY RENTAL -Pet Friendly -Fully Furnished

3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 0.5 miles to Siesta Beach access 7

$177

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Managed by owner
  • Pet friendly

About this property

*Calendar month rentals only*June - November (six-month lease) - $3000 per month plus utilities June - November (three-month lease) - $3900 per month plus utilities December - $5900 per month plus utilities January - $6900 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"
Reviewed August 8, 2018

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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The Pool House

5 BR | 4 BA | Sleeps 16 | Quick View

$1204

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Pet friendly
  • Private pool

About this property

Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key!You HAVE to SEE this Amazing Back Yard! This home is nearly Beachfront, less than 1 minute walk to the beach, and located directly in the Heart of Siesta Key Village. You can walk to EVERYTHING! This ...

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Property Type

Siesta Key House

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Siesta Palooza

8 BR | 8 BA | Sleeps 25 | Quick View

$1380

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Pet friendly
  • 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, it's hard to find a home with a better location! This home is steps to the grocery store, restaurants, shops, nightlife and more, and only a quick walk or bike ride to ...

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Property Type

Siesta Key House

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Sea Spray

8 BR | 6 BA | Sleeps 22 | Quick View

$1502

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Pet friendly
  • 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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Island Time West

3 BR | 3 BA | Sleeps 13 | Quick View

$497

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Pet friendly
  • 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! Your family will love the PRIVATE HEATED ...

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Property Type

Siesta Key House

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On The Rocks

5 BR | 5 BA | Sleeps 15 | Quick View

$1287

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Pet friendly
  • 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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The Oasis

7 BR | 7 BA | Sleeps 18 | Quick View

$1959

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Pet friendly
  • Private pool

About this property

Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key!!Only 3 Houses to the Beach! This home is set up for the Ultimate Vacation! Let's start with the over 3,000 square feet of outdoor covered patios, balconies, pool areas and entertainment space that ...

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Property Type

Siesta Key House

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Point Break

8 BR | 8 BA | Sleeps 24 | Quick View

$1454

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Pet friendly
  • 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, it's hard to find a home with a better location! It is steps to the grocery store, restaurants, shops, nightlife and more, and only a quick walk or bike ride to any one ...

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Property Type

Siesta Key House

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Island House

7 BR | 6 BA | Sleeps 23 | Quick View

$1202

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Pet friendly
  • 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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Siesta Key Village (Siesta Key, Florida) Vacation Rentals