The Cottages on the Key

(51 rentals)
The Cottages on the Key
32
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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3 BR | 2 BA | Sleeps 10 | Quick View

4.8 rating on other travel sites

$306

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Ventana Rosa, the essence of luxury and relaxation in Sarasota, Florida. This stunning vacation rental offers 3 bedrooms and 2 bathrooms, perfect for a family or group of friends seeking the ultimate getaway.Upon arrival, you will be in awe of the lush greenery surrounding the entire property. ...

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Property Type

Sarasota House

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Key Amenities

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

About this property

This inviting 3-bedroom/two-bath vacation rental home has everything for your most memorable Siesta Key vacation! Luna Nueva is centrally located near downtown Sarasota and just a short drive to world famous Siesta Key Beach, voted the #1 beach in the USA! Along with its sister property Villa Las Flores, ...

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Property Type

Sarasota House

"Love the Pool and walking distance to stores and restaurants!"

This house was in perfect location for us. We come to Sarasota couple times a year. My brother lives in Sarasota few minutes away and the beach is the same distance so it was perfect for us. Having Walgreens ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Welcome to Siesta Sunset! This stunning modern home offers all the amenities you need for your most memorable Siesta Key vacation, offering amazing ocean views and an unbeatable location just steps away from world famous Siesta Key Beach, voted the # 1 beach in the USA! This home is ideal for family get ...

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Property Type

Siesta Key House

"Peaceful family getaway"

We loved the house. It was perfect for my husband and I and our two young kids. The pool was the perfect temp and having the back of the house covered in windows was great b/c we could keep and eye on ...

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Key Amenities

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

About this property

This inviting 3 bedroom/2 bathroom home features a private heated pool and is centrally located near downtown Sarasota. With just a short drive to world famous Siesta Key Beach, you will truly be living the Florida Life! Villa Las Flores is the ideal home for small families and couples looking for a tropical ...

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Property Type

Sarasota House

"Awsome time at Villa Las Flores"

My family and I had a wonderful time at the Villa Las Flores! The house was clean, accommodations were comfortable, and the self-checking-in was simple and easy. Restaurants, beaches, and shopping areas ...

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3 BR | 2 BA | Sleeps 7 | Quick View

4.8 rating on other travel sites

$653

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Coconut Cottage! Sit back, relax, and escape into the tropical island of Lido Key, Florida. This coastal 3 bedroom 2 bathroom home features a serene backyard oasis, allowing you to live like a true local. Not only does this backyard paradise include a resort style private heated pool & ...

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Property Type

Lido Key House

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4 BR | 4 BA | Sleeps 10 | Quick View

5.0 rating on other travel sites

$807

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Manatee Cove is a luxurious 4 bedroom, 4 bathroom waterfront vacation rental located in the stunning Lido Key, Florida. With its prime location, this vacation home is just a 30 second walk away from the world-renowned St. Armand's Circle.But that's not all - this vacation rental is also just a 5-minute ...

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Property Type

Lido Key House

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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

"Great location"

Only a couple blocks to the beach and super close to the main, commercial street, yet away from the noise and crowds. The apt was very basic, though clean with up to date furnishings. Smaller than I ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Paradise Palms! This luxurious 4-bedroom/2.5-bathroom home is the paradise retreat you've been waiting for. It offers all of the amenities you could imagine for your most perfect Siesta Key vacation. Paradise Palms is just a short drive to Siesta Key Village and world famous Siesta Key Beach, ...

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Property Type

Sarasota House

"Indian Rock Beach Vacation"

GREAT Views / Great house on beach / Quiet Our family of 9 had a ball

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4 BR | 3 BA | Sleeps 14 | Quick View

4.8 rating on other travel sites

Distance to beach: 2 miles to Shell Beach

$460

avg/night

View Details

Key Amenities

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

About this property

Welcome to Casa Coquina! This luxurious and spacious 4 bedroom/3 bathroom home is located just steps from Crescent Village & minutes from Siesta Key Beach, voted the # 1 beach in the USA! When reserved with its sister property Casa Antilles, both units make up The Conch.Cross the drawbridge from ...

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Property Type

Siesta Key House

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3 BR | 3 BA | Sleeps 8 | Quick View

4.7 rating on other travel sites

$360

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Welcome to Monarch Villa! This colorful, vibrant 3 bedroom 3 bathroom vacation rental home on Siesta Key features gorgeous panoramic views of the Gulf of Mexico, offering an unbeatable location. Located just minutes away from Siesta Key Village and a short 1 minute walk to Siesta Key Beach, this villa ...

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Property Type

Siesta Key House

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3 BR | 3 BA | Sleeps 10 | Quick View

4.8 rating on other travel sites

Distance to beach: 0.1 miles to Siesta Key Beach - Access # 13

$310

avg/night

View Details

Key Amenities

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

About this property

Welcome to Casita Sun Star! This luxurious and newly renovated home offers all of the amenities you need for your most memorable Siesta Key getaway at an unbeatable location! Casita Sun Star is just a short walk to Point of Rocks Beach and minutes from Crescent Village.Casita Sun Star is one-half ...

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Property Type

Siesta Key House

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3 BR | 2 BA | Sleeps 8 | Quick View

4.8 rating on other travel sites

$232

avg/night

View Details

Key Amenities

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

About this property

Introducing Casa Tortuga! This quaint 3 bedroom 2 bathroom vacation home has everything you need to relax on your most memorable Siesta Key vacation! This home is centrally located near downtown Sarasota, being just a short drive to local restaurants, entertainment, and the crystal clear waters of Siesta ...

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Property Type

Sarasota House

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Key Amenities

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

About this property

Welcome to Crescent Cottage! This charming Siesta Key Vacation home offers all of the amenities you can fathom and at absolutely unbeatable location in the heart of Point of Rocks and close to world famous Siesta Key Beach, voted the # 1 beach in the USA! Crescent Cottage has recently been completely ...

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Property Type

Siesta Key House

"Vacation 2020"

I visited siesta key and loved my stay. Stayed in the village Evey thing was In walking distance.beach was walking distance

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Welcome to Sea la Vie! This private 3BR/2BA home is the perfect beach getaway to relax, unwind & take in everything Siesta Key has to offer. Sea la Vie is just 1 minute (seriously!) away from Siesta Key Beach, voted the # 1 beach in the U.S! Sea la Vie offers a semi-private heated pool with its sister ...

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Property Type

Siesta Key House

"Great location"

Excellent location. Walk across the street to the beach or around the corner to Siesta Village. The place was very clean and most everything was supplied for us. The company made the process so easy. I ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Crystal Sands, your cozy yet luxuriously modern home away from home! This colorful and vibrant 3 bedroom 2.5 bathroom vacation home features gorgeous panoramic views of Siesta Key Beach and spectacular ocean views from the rooftop, where you are able watch the sun fade into the night. Crystal ...

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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

$949

avg/night

View Details

Key Amenities

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

About this property

Welcome to Casa Mahalo! This luxurious and recently constructed 4 bedroom/3 bathroom home offers all of the amenities for your vacation, including a private heated pool and outdoor cabana room! This vacation home is centrally located in the heart of Siesta Key Village and just a short walk to world famous ...

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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
  • Private pool

About this property

Welcome to Gulf Birdie! This exciting yet serene 3 bedroom 2 bathroom waterfront vacation home is perfect for your family getaway to the tropical island of Siesta Key. Not only does it include a spacious heated luxury pool and hot tub, but it also sits directly on the canal with gorgeous water views. ...

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Property Type

Siesta Key House

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7 BR | 6.5 BA | Sleeps 16 | Quick View

5.0 rating on other travel sites

$1390

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Tropical Oasis. This private family home is perfect for large families, with the ability to accommodate up to 16 guests, with 7 bedrooms and 6.5 bathrooms.The backyard is a twinkling mirage, secluded by rows of palms that will have you feeling like you're thousands of miles away in a tropical ...

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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 Florita's Key! This coastal 5-bedroom/3-bathroom home features all the amenities you can think of for your beach vacation and offers an unbeatable location. Located just minutes from Shell Beach and close to world famous Siesta Key Beach, voted the # 1 beach in the USA, this home is ideal for ...

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Property Type

Siesta Key House

"Fabulous Place"

Excellent Location close to the Crescent Beach and Restaurants. I would stay there again the next time I visit Siesta Key.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Welcome to Seahorse Cabana! This wonderful beach cottage has been recently updated with brand new furnishings throughout. When reserved with its sister property Sandy Cabana, both units make up Sandy Seahorse Cottage.The welcoming entryway of Seahorse Cabana opens up with a roomy, screened-in lanai ...

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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 Ocean Sky! This luxurious and recently renovated 3-bedroom/2-bathroom home is located in the heart of Sarasota with close proximity to downtown Sarasota, Siesta Key Village, and Siesta Key Beach, voted the #1 beach in the USA! With so much to do in the area and a private pool, you will truly ...

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Property Type

Sarasota House

"Very nice and very clean! However..."

Very clean and nicely decorated. The kitchen was very well stocked with nice cookware and utensils which in our experience is hit or miss. Close to Siesta Key, Bradenton or Longboat Key. The pool ...

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Key Amenities

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

About this property

Enjoy the relaxed atmosphere and top-notch amenities of Casa Leone with a tropical garden view. This property has 4 Bedrooms & 3 full baths and can accommodate up to 10 Guests. Casa Leone is located less than a 5 minute drive to Siesta Key Village and Siesta Key Beach, voted #1 Beach in the USA. Practice ...

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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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4 BR | 3 BA | Sleeps 8 | Quick View

4.9 rating on other travel sites

$454

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Siesta Soul! This tranquil vacation rental in Siesta Key offers all of the amenities needed for your most relaxing beach vacation at an absolutely unbeatable location! This home is equipped with a private heated pool and outdoor shower (runs hot water), perfect for rinsing off after a relaxing ...

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Property Type

Siesta Key House

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4 BR | 4 BA | Sleeps 10 | Quick View

5.0 rating on other travel sites

$664

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Latitude Adjustment! This stellar 4 bedroom/4 bathroom canal home is centrally located close to Siesta Key Village and just a 3 minute walk to world famous Siesta Key Beach, voted the # 1 beach in the USA! This home offers all of the amenities you could imagine at an absolutely unbeatable location, ...

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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

Bay Isle Bliss is a unique single-family 3 bedroom 2 bathroom vacation rental home on Siesta Key's north end. Escaping to the immaculate outdoors is easy thanks to the many access points throughout the home and the spacious outdoor patio area. Equipped with a private heated pool, spa, gas grill, fire ...

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Property Type

Siesta Key House

"FANTASTIC FUN FAMILY FRIENDLY BEACH CONDO"

FROM THE MOMENT I BOOKED THE CONDO UNTIL THE MOMENT I LEFT THE CONDO NOTHING BUT PROFESSIONALISM, CARE, CONCERN AND A UNIQUE TWIST ON MAKING US FEEL SO WELCOME. OUR NAME ON THE WALL OUR NAME ON THE CUPCAKES ...

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Key Amenities

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

About this property

Welcome to Island Escape, where you're able to escape from reality into the tropical island of Siesta Key! This beautiful 4 bedroom / 2.5 bathroom home features a newly renovated kitchen & master bathroom, private heated saltwater pool, gourmet outdoor kitchen, cabana room, and several other exciting ...

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Property Type

Siesta Key House

"Our vacation was wonderful!!"

Island escape was a great place to stay, 100 percent satisfaction when we needed something, called in the morning and maintenance guy was there by noon and fixed the bathroom door. Lots of space for our ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Spend your vacation soaking up the sun at Silver Shore! This colorful and vibrant 3 bedroom 2.5 bathroom vacation home features gorgeous panoramic views of Siesta Key Beach and spectacular ocean views from the rooftop, where you are able watch the sun fade into the night. Silver Shore is equipped to anticipate ...

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Property Type

Siesta Key House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to Sun Sea Terrace! This luxurious 4 bedroom/3.5 bathroom penthouse is one block from Siesta Key Village and 2 blocks from Siesta Key Beach, voted the #1 beach in the USA! Sun Sea Terrace features two living rooms, 6 balconies on multiple levels, and a private roof top space with views of the ...

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Property Type

Siesta Key House

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3 BR | 2 BA | Sleeps 8 | Quick View

4.8 rating on other travel sites

$290

avg/night

View Details

Key Amenities

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

About this property

Welcome to Baydream Bungalow! This quaint 3 bedroom 2 bathroom vacation rental home located on Siesta Key's north end is perfect the ultimate Florida vacation. Here, you're able to catch up on your latest reads by the private heated screened-in pool, catch some rays at the beach, or grill out with the ...

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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

$315

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Welcome to Peacock Villa! This colorful and vibrant Siesta Key home features all of the amenities you could dream of for your beach vacation and an unbeatable location! Peacock Villa is located minutes away from Siesta Key Village and just a 1 minute walk to world famous Siesta Key Beach, voted the # ...

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Property Type

Siesta Key House

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3 BR | 3 BA | Sleeps 10 | Quick View

4.8 rating on other travel sites

$390

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to Fiesta Playa, where your vacation is nothing less than a luxurious getaway to paradise! This fully equipped 3 bedroom 3 bathroom Siesta Key vacation home is located just a short two minute walk to the crystal clear waters on Crescent Beach. Also being less than a half a mile to the South Village, ...

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Property Type

Siesta Key House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Let your worries fade away when escaping to The Key Canal, located on the gorgeous island of Siesta Key. Load up your luggage on the private elevator and head upstairs to your gorgeous home away from home! This coastal 3 bedroom 3 bathroom vacation rental offers spectacular rooftop and balcony views of ...

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Property Type

Siesta Key House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Welcome to Sea Esta! This private 3BR/2BA home is the perfect beach getaway to relax, unwind & take in everything Siesta Key has to offer. The best part? Siesta Salt Life is just 1 minute (seriously!) away from Siesta Key Beach, voted the # 1 beach in the U.S! Sea Esta offers a semi-private heated ...

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Property Type

Siesta Key House

"Ultimate getaway"

The moment you walk in your in vacation mode. Pure relaxation plus a outdoor space that puts it over the top. There’s nothing to want for The lazy river pool is fabulous

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Key Amenities

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

About this property

Welcome to Casa Eulimia! This newly constructed 4 bedroom 3 bathroom luxury home features a spacious kitchen and living area, a spacious outdoor patio & private heated outdoor pool with cabana room and HDTV. With modern and coastal decor throughout, you will feel comfortable and cozy in your "home ...

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Property Type

Siesta Key House

"Miramar"

Stay was nice there was a lot of ants in the house love the master room jacuzzi and shower love the night with the pool led lights the scenic view was beautiful

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to Casa Bella Vita! This luxurious 3 bedroom/3 bathroom Siesta Key vacation home has everything you could fathom for your most memorable vacation yet at an absolutely UNBEATABLE location, just a two minute walk to Crescent Beach and close to world famous Siesta Key beach (voted the #1 beach in ...

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Property Type

Siesta Key House

"The unit was absolutely beautiful and very clean and we would definitely stay there again"

The unit was absolutely beautiful and very clean and we would definitely stay there again we love the pool in the privacy of the unit was wonderful it was our fourth girls trip to Sarasota there were seven ...

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Key Amenities

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

About this property

Welcome to Casa Ohana! This stunning and recently constructed 4 bedroom/3 bathroom home offers all of the amenities for your beach vacation, including a private heated pool and outdoor cabana room! This vacation home offers luxurious accommodations in an unbeatable location in the heart of Siesta Key ...

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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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3 BR | 3 BA | Sleeps 10 | Quick View

4.6 rating on other travel sites

$393

avg/night

View Details

Key Amenities

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

About this property

Welcome to Villa Castile! This captivating 3-bedroom/3-bathroom townhome features all the amenities you can think of for your beach vacation and offers an unbeatable location. With beach decor throughout, you will truly be living the "Beach Life." Villa Castile is centrally located in the heart ...

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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! This wonderful beach cottage has been recently updated with brand new furnishings throughout. When reserved with its sister property Seahorse Cabana, both units make up Sandy Seahorse Cottage. This home is ideal for small families and beachcombers alike!The welcoming entryway ...

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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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4 BR | 3 BA | Sleeps 12 | Quick View

1

Distance to beach: 1 miles to Siesta Key Beach

$632

avg/night

View Details

Key Amenities

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

About this property

Welcome to Casa Stolida! This gorgeous vacation home is the definition of Siesta Key living. With coastal décor and brand-new furnishings throughout; you will truly feel like a Siesta Key local! Casa Stolida is ideal for large families and groups.Cross the drawbridge from Sarasota to enter ...

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Property Type

Siesta Key House

"Family Christmas vacation"

We loved the house and close to the beach and trolley stops. The 8 of us enjoyed our time while we were there. The only complaint was the shower pressure in the Jack and Jill bathroom, was not as good ...

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4 BR | 3 BA | Sleeps 12 | Quick View

4.8 rating on other travel sites

$485

avg/night

View Details

Key Amenities

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

About this property

Welcome to Casa Tegula, one of Siesta Key's premier 4BR/3BA homes. This vacation home is the definition of Siesta Key living. With coastal décor and brand-new furnishings throughout, you will truly feel like a Siesta Key local! Casa Tegula is ideal for large families and groups.Cross the drawbridge ...

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Property Type

Siesta Key House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Welcome to Hemingway House, your new home away from home! Only a short 5 minute walk to Shell Beach on Siesta Key, this quaint 3 bedroom 2.5 bathroom vacation home is equipped to anticipate your needs for a luxurious stay. This property features a spacious outdoor oasis that include a large dining area, ...

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Property Type

Siesta Key House

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3 BR | 3 BA | Sleeps 8 | Quick View

4.9 rating on other travel sites

$682

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Villa Vista Mare is a beautiful Florida style 3 bedroom 3 bathroom home, perfect for your much needed tropical getaway! Not only is this home located just steps away from Siesta Key Beach Access #11, but is also located less than a mile from, delicious restaurants, entertainment, and nightlife in the ...

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Property Type

Siesta Key House

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3 BR | 2 BA | Sleeps 8 | Quick View

5.0 rating on other travel sites

$422

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Everything you're looking for in a comfortable and convenient vacation is waiting for you at Bali Hai House! This gorgeous waterfront home is fully equipped with a spacious outdoor patio, fire pit, and private screened in heated pool. Hang out on the hammock and watch boats drift by or take a short walk ...

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Property Type

Siesta Key House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Welcome to Admirals Watch, also known as a little slice of paradise! Load up your luggage on the private elevator, head upstairs to your gorgeous vacation rental on Siesta Key, and enjoy the panoramic views of the # 1 Beach in America! This home is located directly across the street from Beach Access ...

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Property Type

Siesta Key House

"Wonderful Stay"

Admirals Watch, Siesta Key was a great place to stay with an amazing view! Everything is just like the picture. The rental company "The Cottages on the Key" checked in with us a couple of times to make ...

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3 BR | 3.5 BA | Sleeps 8 | Quick View

5.0 rating on other travel sites

$322

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to Serenity Cottage! This tranquil oasis has everything need for your most perfect beach getaway at an absolutely UNBEATABLE location in Crescent Village and just minutes away from world famous Siesta Beach, voted the #1 beach in the USA! Serenity Cottage is the ideal vacation home for family ...

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Property Type

Siesta Key House

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4 BR | 3 BA | Sleeps 12 | Quick View

4.9 rating on other travel sites

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

$632

avg/night

View Details

Key Amenities

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

About this property

Welcome to Casa Antilles! This luxurious and coastal 4 bedroom/3 bathroom home is located just steps from Crescent Village & minutes from Siesta Key Beach, voted the # 1 beach in the USA! When reserved with its sister property Casa Coquina, both units make up The Conch.Cross the drawbridge from ...

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Property Type

Siesta Key House

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4 BR | 3.5 BA | Sleeps 8 | Quick View

4.9 rating on other travel sites

Distance to beach: 5 miles to Siesta Key Beach

$593

avg/night

View Details

Key Amenities

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

About this property

Welcome to Villa Champagne! This enchanting 4 bedroom/3.5 bathroom cottage is a short walk to Siesta Key Village and just minutes from Siesta Key Beach, voted the # 1 beach in the USA!Walk up the stairs of Villa Champagne, front, porch and step into the multi-story foyer and cozy sitting room. The ...

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Property Type

Siesta Key House

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4 BR | 4 BA | Sleeps 10 | Quick View

5.0 rating on other travel sites

$830

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Welcome to The Pearl on the Bay! This astonishing 4 bedroom /4 bathroom home offers everything you will need for the most memorable Siesta Key beach vacation at an unbeatable location. Enjoy a spacious and exquisitely decorated interior or relax in your very own backyard oasis with a private heated pool ...

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Property Type

Sarasota House

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3 BR | 3 BA | Sleeps 10 | Quick View

4.7 rating on other travel sites

$382

avg/night

View Details

Key Amenities

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

About this property

Welcome to Casita Morning Star! This newly renovated home has all the amenities for your perfect Siesta Key getaway at an unbeatable location! Casita Morning Star is a short walk to Point of Rocks Beach and centrally located in the heart of Crescent Village.Casita Morning Star is one-half of a single-floor ...

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Property Type

Siesta Key House

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$255

avg/night

View Details

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

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