The Cottages on the Key

(9 rentals)
The Cottages on the Key
18 reviews
Here at The Cottages on the Key, we understand what makes a luxury vacation home right for you. We make it our business to find a vacation rental that meets all of your needs and goes above and beyond your expectations. What better place in the world to visit than right here on Siesta Key in Sarasota, Florida. Ranked #1 Beach in the United States! By providing the finest ...
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Here at The Cottages on the Key, we understand what makes a luxury vacation home right for you. We make it our business to find a vacation rental that meets all of your needs and goes above and beyond your expectations. What better place in the world to visit than right here on Siesta Key in Sarasota, Florida. Ranked #1 Beach in the United States! By providing the finest in vacation rentals in Siesta Key, we can ensure that your vacation is a success no matter which home is right for you.
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Siesta Key House
3 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Villa Castile, a luxurious retreat located just outside the vibrant Siesta Key Village. This stunning vacation rental duplex offers the perfect blend of sophistication and comfort, providing an unforgettable experience for your stay. Whether you're seeking relaxation by the private heated ...

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Property Type

Siesta Key House

Featured review

"Excellent Property"

Super close to Siesta Village’s shops and restaurants, plus an easy walk to the beach. Very comfortable home, well equipped with everything you need for a great stay.

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Siesta Key House
4 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 4 bedrooms, 3 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Casa Ohana, a stunning vacation rental duplex that promises to exceed all your expectations. Nestled in the heart of Siesta Key Village, this extraordinary retreat offers an abundance of luxurious amenities and unparalleled convenience for an unforgettable getaway.Located just a two-minute ...

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Property Type

Siesta Key House

Featured review

"Great place!"

Nice pool! Beautiful area and nice area. We will Be visiting soon and bringing the family. Smooth time.

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Siesta Key House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Endless Views, a luxurious 3 bedroom 3 bathroom vacation rental duplex located in the heart of Siesta Key, Florida. This stunning property is just a 3 minute walk away from the world-famous Siesta Key Beach, and is conveniently located within walking distance to Siesta Key Village, where you ...

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Property Type

Siesta Key House

Featured review

"Siesta Key Family Vacation"

Awesome condo. Owners go above and beyond to make sure your stay is pleasant. Will rent this condo again. Close to beach and siesta key village. We walked to everything. Thanks for allowing my family to ...

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Siesta Key House
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Welcome to Sandy Cabana, a beautiful duplex property nestled between the quiet streets of south Siesta Key. This charming duplex offers the perfect retreat for your vacation, featuring a spacious outdoor lanai and a shared heated swimming pool. Whether you choose to rent Sandy Cabana as a standalone retreat ...

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Property Type

Siesta Key House

Featured review

"Lovely cottage"

This place is even nicer than I thought it would be! The cottage was clean and well stocked. The surrounding area was very quiet. At night, we couldn’t hear any outside noise. The walk to the beach ...

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Sarasota House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Ocean Sky, a luxurious retreat that offers the perfect combination of comfort, convenience, and style. From the moment you step inside, you'll be greeted by a meticulously designed interior that caters to your every need.Ocean Sky features three spacious bedrooms and two full baths, ...

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Property Type

Sarasota House

Featured review

"Wonderful house"

A beautiful home with everything that you can possibly need. The pool was outstanding since the temps were 90 degrees plus! The communication with the office was fantastic. Everything was provided for ...

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Sarasota House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
3 reviews

$457

avg/night

$457
avg per night
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Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Casamigos, a rare upscale jewel in a sea of vacation rentals. This beautiful, newly furnished 4 Bedroom (all King Beds) /3BA home offers an exceptional vacation experience for your family and friends.It begins with lavish tropical landscaping (Malaysian and Areca Palms, Bougainvillea) and ...

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Property Type

Sarasota House

Featured review

"Highly recommend this host"

Beautiful home. It was spotless when we arrived. All the beds and pillows were extremely comfortable. The Host was very accommodating to all our needs all week. Outside pool and Tiki Bar were a big hit ...

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Siesta Key House
4 BR | 2.5 BA | Sleeps 12 | Quick View
Sleeps 12, 4 bedrooms, 2.5 bathrooms
2 reviews

$647

avg/night

$647
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Island Escape, a breathtaking haven located within the heart of Siesta Key! This gorgeous 4-bedroom, 2.5-bathroom home has just undergone a stunning renovation, ensuring that every moment of your stay is filled with comfort and luxury.Step inside and be greeted by a beautifully designed ...

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Property Type

Siesta Key House

Featured review

"Great Vacation Home"

Very nice house with many amenities. Short walk to the beach. Great place for a family vacation!Carla

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Siesta Key House
3 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 3 bathrooms
4.7 rating on other travel sites

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Escape to Casita Morning Star, a magnificent vacation rental duplex retreat that offers nothing but luxury and relaxation. This coastal villa can be rented separately or as a whole as The Solaster, providing you with the flexibility to choose the perfect accommodation for your vacation. With its prime ...

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Property Type

Siesta Key House

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Siesta Key House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
5.0 rating on other travel sites

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to Bali Hai House, a stunning waterfront home located on the tropical island of Siesta Key. This exceptional property offers a truly blissful retreat with an array of exciting amenities and convenient proximity to Siesta Key Village and Siesta Key Public Beach Access.Situated less than 1 mile ...

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Property Type

Siesta Key House

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