The Cottages on the Key

(17 rentals)
The Cottages on the Key
24
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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

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

"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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Key Amenities

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

About this property

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

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Property Type

Siesta Key House

"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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Key Amenities

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

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

"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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4 BR | 3 BA | Sleeps 12 | Quick View

4.9 rating on other travel sites

$300

avg/night

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Key Amenities

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

About this property

Welcome to Casa Tegula, your luxurious tropical oasis on the Southern end of Siesta Key. This stunning beach house offers an unparalleled experience for large groups seeking both privacy and space. With 4 bedrooms and 3 full baths, it is the perfect choice for family reunions, group getaways, or special ...

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Property Type

Siesta Key House

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4 BR | 3 BA | Sleeps 12 | Quick View

2

Distance to beach: 1 miles to Siesta Key Beach

$309

avg/night

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Key Amenities

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

About this property

Welcome to Casa Stolida, your luxurious tropical oasis on the Southern end of Siesta Key. This stunning beach house offers an unparalleled experience for large groups seeking both privacy and space. With 4 bedrooms and 3 full baths, it is the perfect choice for family reunions, group getaways, or special ...

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Property Type

Siesta Key House

"Bliss"

Home was fantastic! Maintenance was speedy on my TV problem and fixed it while I was out at the beach. I stayed with three couples. Beds were comfortable for all. Unit had everything we needed. Steps from ...

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Key Amenities

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

About this property

Welcome to Casa Leone, a luxurious home nestled on the northern end of Siesta Key. This exquisite property offers an array of amenities and comforts to ensure a memorable and relaxing stay.As you ascend up the stairs to the main level of the home, you will be greeted by a spacious and elegantly decorated ...

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Property Type

Siesta Key House

"Casa Tegula Review..."

We LOVED Casa Tegula!!! The house was very clean and stocked with everything we needed. Location was wonderful, only a short walk to the ocean and shops. Sara at The Cottages on the Key was AMAZING and ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Welcome to Endless Views, a luxurious 3 bedroom 3 bathroom vacation rental 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 can find ...

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Property Type

Siesta Key House

"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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3 BR | 2 BA | Sleeps 8 | Quick View

5.0 rating on other travel sites

$626

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

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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Key Amenities

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

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

"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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Key Amenities

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

About this property

Welcome to Bay Isle Bliss, a luxurious 3 bedroom, 2 bathroom vacation home that offers a serene retreat from the hustle and bustle of everyday life. Located just 0.3 miles from Shell Beach and 1.7 miles from Siesta Key Village, this exquisite property provides the perfect vacation getaway for families, ...

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Property Type

Siesta Key House

"Perfect pet-friendly property"

Great location close to the beach and Sarasota downtown. The property is completely fenced, and located in a very quiet neighborhood. My kids enjoyed the pool and the hot tub...We will visit again.

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Key Amenities

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

About this property

Welcome to Casa Ohana, a stunning vacation home 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 walk ...

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Property Type

Siesta Key House

"Great place!"

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

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1 BR | 1 BA | Sleeps 4 | Quick View

4.8 rating on other travel sites

$228

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Welcome to Sea Angel, the perfect destination for small families or couples looking for an intimate yet unforgettable vacation experience. Located within the heart of Siesta Key Village and less than 400 feet to the world-renowned Siesta Key Beach, this property offers the ultimate combination of convenience ...

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Property Type

Siesta Key House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Welcome to Sandy Cabana, a beautiful home 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 or opt ...

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Property Type

Siesta Key House

"Quiet and close to the beach"

Our family had a wonderful spring break staying at Sandy Cabana. Quick walk to the beach and close enough you can walk to local market, shops and restaurants. Condo was clean and well stocked. The neighborhood ...

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3 BR | 3 BA | Sleeps 10 | Quick View

4.7 rating on other travel sites

$285

avg/night

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Key Amenities

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

About this property

Escape to Casita Morning Star, a magnificent 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 location just a short ...

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Property Type

Siesta Key House

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3 BR | 3 BA | Sleeps 8 | Quick View

5.0 rating on other travel sites

$346

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Welcome to Peacock Villa, an exquisite Siesta Key retreat that offers a unique opportunity for a customizable vacation experience. This magnificent property can be rented separately or as a whole - Casa De Mariposa. Whether you're traveling with a large group or looking for a more intimate stay, ...

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Property Type

Siesta Key House

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4 BR | 3 BA | Sleeps 12 | Quick View

2

Distance to beach: 5 miles to Siesta Key Beach

$496

avg/night

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Key Amenities

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

About this property

Welcome to Casa Mahalo, a stunning vacation home 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 walk ...

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Property Type

Siesta Key House

"Very comfortable and Clean"

Lily Casita is truly a Cozy Sarasota Home . We were greeted to the home with lights on and music playing the home was very clean and equipped with anything you may need. This was our first time in the ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Welcome to Hemingway House, a charming retreat located on the northern end of Siesta Key. This delightful home offers a perfect blend of comfort and convenience, ensuring an unforgettable vacation experience. Just a short 5-minute walk will lead you to the serene shores of Shell Beach, where you can soak ...

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Property Type

Siesta Key House

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