The Cottages on the Key

(115 rentals)
The Cottages on the Key
Phone number: +1 (800) 385-1499
30
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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Serenity Cottage

3 BR | 3.5 BA | Sleeps 8 | Quick View

$200

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Serenity Cottage!A pristine and elegant home so close to the most beautiful beach in the world most would say, Serenity Cottage offers a delightful and relaxing retreat with maximum comforts in mind, and a spacious abode designed around the needs and comforts of large families traveling ...

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Property Type

Siesta Key House

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Playa y Blanca

4 BR | 2 BA | Sleeps 10 | Quick View

1

$287

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool
  • Private Pool

About this property

Explore Playa y Blanca, a charming 4BR/2BA beach bungalow located steps from Crescent Beach. This home is the perfect beach escape for small families and couples alike!Welcome to Playa y Blanca! This uniquely configured 4BR/2BA villa is a combination of two units: “Casita Blanca” and “Casita ...

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Property Type

Siesta Key House

"Great stay in Siesta Key!"
Reviewed February 9, 2020

Sarasota Surf and Racquet Club. We rented two condos at this property. They were clean and well appointed, with everything we needed. The location on the beach was perfect and the service was great! Would ...

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Ventana Rosa – 1905

3 BR | 2 BA | Sleeps 10 | Quick View

Distance to beach: 2 miles to Shell Beach

$139

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Ventana Rosa - One of The Cottages on the KeyWelcome to Ventana Rosa, one of Siesta Key's newest luxury homes with private heated pool! Minutes to world famous Siesta Key Beach and Village!This luxurious and recently renovated (as of 2019) 3-bedroom/2-bathroom home is located in close proximity ...

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Property Type

Siesta Key House

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The Blue Serenity

6 BR | 10 BA | Sleeps 22 | Quick View

Distance to beach: 0.2 miles to Siesta Key Public Beach - Access # 2

$700

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This massive and decadent 6-bedroom/10-bathroom home is a unique combination of two units: Heron House and Sailors Looking. Each unit features a 3-bedroom/5-bathroom configuration, each with their own common space that include a kitchen, dining area, game room and living room. Relax in the sparkling outdoor ...

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Property Type

Siesta Key House

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The Hummingbird

6 BR | 6 BA | Sleeps 12 | Quick View

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

$286

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Welcome to The Hummingbird, a delightful 6BR/6BA home with private heated pool! Located just steps from world famous Siesta Key Beach and Siesta Key Village This home is perfect for families and small groups.This private six bedroom/six bathroom home is a unique combination of four units: Lantana, ...

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Property Type

Siesta Key House

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Casita Coconut – 305U

2 BR | 2 BA | Sleeps 6 | Quick View

$125

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This adorable two bedroom/two bathroom home features a shared heated salt water pool (when booking Lime in a Coconut, pool is private). Casita Coconut offers all of the amenities for the ultimate beach getaway at an unbeatable location in the heart of Siesta Key Village and just two blocks from world ...

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Property Type

Siesta Key House

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Casa Eulimia

4 BR | 3 BA | Sleeps 12 | Quick View

$264

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

Welcome to Casa Eulimia, a Siesta Key luxury villa that features a private heated pool and cabana room and is located near Crescent Village and close to beaches and Siesta Key Village!This stunning four-bedroom/three-bathroom luxury villa features a spacious kitchen and living area, outdoor patios ...

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Property Type

Sarasota House

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The Canopy Cottage

4 BR | 3 BA | Sleeps 9 | Quick View

$330

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This tranquil 4 bedroom/3 bathroom home features a private heated pool & spa, and is located within close proximity to Siesta Key Village and world famous Siesta Key Beach, voted the #1 beach in the USA! The Canopy Cottage is the ideal vacation home for couples and families alike.The Canopy Cottage ...

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Property Type

Siesta Key House

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Baydream Bungalow

3 BR | 2 BA | Sleeps 6 | Quick View

$179

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Private Pool

About this property

Situated on the northern part of Siesta Key within walking distance to Nora Patterson’s Park, this original Sarasota home is tucked within the Bay Island! With just a short drive to main beach access parking and even closer to the shops both on the Key and off, this location is the perfect setting ...

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Property Type

Sarasota Bungalow

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Sandy Seahorse Cottage

6 BR | 6 BA | Sleeps 16 | Quick View

$284

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool
  • Private Pool

About this property

Welcome to the Sandy Seahorse Cottage!This uniquely configured private home [Sandy Cabana and Seahorse Cabana] is the perfect escape for you and your family and friends. This gorgeous beachy getaway comfortably sleeps 12 with a little room for more! The property has recently been updated with new ...

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Property Type

Siesta Key House

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Isla Amor

4 BR | 3 BA | Sleeps 8 | Quick View

$578

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Isla Amor. An absolute one of kind, limited edition home located in the "heart of the Siesta Key" on the prestigous Palm Island (the island within the island). Featuring a private heated pool, near America's #1 Beach, on the Grand Canal with intracoastal bay access and a boat dock. ...

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Property Type

Siesta Key House

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Coral Breeze – 4576

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$385

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This quaint 3-bedroom/2.5-bathroom home is located near Siesta Key Village and just five minutes from Siesta Key Beach, voted the # 1 beach in the USA! This home is ideal for small families and couples alike.Coral Breeze can accommodate up to 6 guests with a bedding configuration as follows:• ...

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Property Type

Siesta Key House

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The Tropical Gardens

6 BR | 5 BA | Sleeps 16 | Quick View

Distance to beach: 5 miles to Siesta Key Beach

$233

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool

About this property

This tropical island retreat is a combination of three units, each with their own kitchen and living spaces. With a heated pool and coastal décor throughout, you’ll be living “The Florida Life” at The Tropical Gardens! This home is ideal for families and groups.The Tropical ...

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Property Type

Sarasota House

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Ocean’s Edge

4 BR | 4 BA | Sleeps 8 | Quick View

$550

per night

View Details

Key Amenities

  • Pool
  • Private Pool

About this property

Welcome to Ocean's Edge! A massive gulf front penthouse located right on Siesta Beach in a newly constructed building. With amazing views, a heated pool, and enough room to sleep up to 8, it is the only way to experience Siesta Key!Ocean's Edge is a luxuriously appointed penthouse in an extremely ...

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Property Type

Siesta Key Condo

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Sophie’s Cottage

2 BR | 2 BA | Sleeps 8 | Quick View

$330

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

Welcome to one of Siesta Key’s most charming canal-front cottage, with private heated pool and boat dock! Sophie's Cottage is located close to shops/restaurants and is just a 5 minute walk to world famous Siesta Key Beach!This Picturesque 2 bedroom/2 bathroom water-front cottage features a ...

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Property Type

Siesta Key House

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Villa Las Flores - One of the Cottages on the Key

$132

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

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Monarch Villa

3 BR | 3 BA | Sleeps 9 | Quick View

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Welcome to Monarch Villa, a beautiful 3 bedroom, 3 bathroom townhome just steps from the beach. Along with its sister property Peacock Villa, reserve Casa de Mariposa for the ultimate corporate retreat, family reunion or destination wedding setting! Welcome to Monarch Villa! The luxurious three (3) bedroom, ...

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Property Type

Siesta Key House

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Sunset Fiesta

4 BR | 2 BA | Sleeps 12 | Quick View

$257

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Sunset Fiesta, a unique combination of two units: “The Hidden Gem” and “Deja Blue.” This cozy beach villa features a private heated pool and is located in the heart of Siesta Key Village!This charming 4BR/2BA beach villa is centrally located in the heart of Siesta ...

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Property Type

Siesta Key House

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Luna Nueva

3 BR | 2 BA | Sleeps 6 | Quick View

$125

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Luna Nueva, a 3 bedroom/2 bathroom home with a heated pool is located just off island with easy access to Siesta Key. When reserved with Villa Las Flores to become Luna Flores, the vacation home will be a great setting for large groups. Luna Nueva, a gorgeous 3 bedroom 2 bathroom villa, is one of two ...

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Property Type

Sarasota House

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Sandpiper Cottage

5 BR | 5 BA | Sleeps 14 | Quick View

Distance to beach: 0.8 miles to Crescent Beach

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This captivating and completely upgraded (as of 2019) luxury villa is centrally located just 10 minutes from Siesta Key Beach, continually ranked as one of the top 10 beaches in the USA! With brand new furniture and beach décor throughout, you will truly be living the beach life! Sandpiper Cottage ...

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Property Type

Siesta Key Cottage

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Pinacolada

3 BR | 3 BA | Sleeps 8 | Quick View

$186

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Pinacolada! A private home nestled right in the heart of the Siesta Village with the style, elegance and charm of Siesta Key. Enjoy a family home that sleeps 8, a shared heated pool, and quite literally in the heart of Siesta Village!Pinacolada is one-half of the exquisite "Coconut ...

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Property Type

Siesta Key Townhome

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Villa Magnolia

4 BR | 4 BA | Sleeps 12 | Quick View

Distance to beach: 5 miles to Siesta Key Beach

$169

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool

About this property

This impeccably decorated coastal cottage is a unique combination of two units: Jasmine Casita & Lily Casita and offers a shared heated salt water pool and beach décor throughout. With a location minutes from downtown Sarasota and just a short drive to world famous Siesta Key Beach, you’ll ...

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Property Type

Sarasota Villa

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The Hidden Gem – 5290L

2 BR | 1 BA | Sleeps 6 | Quick View

Distance to beach: 0.3 miles to Siesta Key Beach (Access # 2)

$129

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

Welcome to The Hidden Gem, one of Siesta Key’s newest and coziest 2BR/1BA beach bungalows with heated pool and located in the heart of Siesta Key Village!This charming 2BR/1BA cottage is located in the heart of Siesta Key Village and is just minutes from world famous Siesta Key Beach, continually ...

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Property Type

Siesta Key Cottage

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Orchid Villa

2 BR | 2 BA | Sleeps 6 | Quick View

1

$143

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool

About this property

The Orchid and Hibiscus Villas are two separate units which can be uniquely configured to create Villa Cascada, an absolutely beautiful and stunning private pool home.When rented separately, each unit features two bedrooms and a sleeping den that sleeps up to 6, with 2 full bathrooms, a gourmet kitchen, ...

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Property Type

Sarasota House

"Restful vacation"
Reviewed February 12, 2019

Great place to stay. Pool in back was heated to a comfortable temperature. Amenities were great. Short walk down the road to the beach access. They even had cupcakes in the fridge to welcome us upon arrival!

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Siesta Dream House

4 BR | 3.5 BA | Sleeps 12 | Quick View

$254

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

One of Siesta Key's most alluring homes, with private heated pool & spa! Siesta Dream House is perfect for family get togethers and romantic getaways alike.Welcome to Siesta Dream House! This enchanting 4-bedroom/3.5-bathroom home is located in Siesta’s North Key and is close to Siesta Key ...

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Property Type

Siesta Key House

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Honey Mango Cabana

2 BR | 1 BA | Sleeps 6 | Quick View

$129

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to Honey Mango Cabana, one of Siesta Key’s most tropical beach bungalows with heated pool. When combined with its sister property Juicy Mango Cabana, both units make up Mango Manor.This tropical 2 bedroom/1 bathroom cottage is just a five minute walk to Crescent Beach and a short drive ...

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Property Type

Siesta Key House

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Blu Sky Cottage – 5037

3 BR | 2 BA | Sleeps 10 | Quick View

$385

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This stunning 3BR/2BA home is centrally located close to the Village and Siesta Key Beach, continually ranked as one of the top ten beaches in the USA! This home is ideal for small families and groups.Blu Sky Cottage can accommodate up to 10 guests with a bedding configuration as follows:• ...

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Property Type

Siesta Key Cottage

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Mermaids Lookout - 6912

4 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$468

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Welcome to Mermaids Lookout, one of Siesta Key's premier luxury townhomes with private heated pool and spa! Located just five minutes from Siesta Key Beach and Village!This massive and decadent 4-bedroom/3-bathroom townhome is located near Siesta Key Village and just five minutes from Siesta Key Beach, ...

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Property Type

Siesta Key House

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Sandy Cabana

3 BR | 3 BA | Sleeps 8 | Quick View

1

$142

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to the Sandy Cabana!The Sandy Cabana is one half of the uniquely configured private homes called the Sandy Seahorse Cottage and it is the perfect escape in the tropics of Siesta Key. This property can be rented separately or combined to accommodate a large party! This side of the gorgeous ...

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Property Type

Siesta Key House

"Fabulous Place"
Reviewed February 19, 2020

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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The Seascape

8 BR | 9 BA | Sleeps 16 | Quick View

$1100

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Welcome to The Seascape! The Seascape is the combination of two massive gulf front penthouses located right on Siesta Beach in a newly constructed building. With amazing views, a heated pool, and enough room to sleep up to 16, it is the only way to experience Siesta Key.The Seascape is the unique ...

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Property Type

Siesta Key Condo

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The Sun Dial

4 BR | 4 BA | Sleeps 12 | Quick View

$550

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to The Sun Dial! An absolute one of kind, limited edition home located in a beautifully secluded private neighborhood only minutes from Siesta Key's main beach access. Featuring a private heated pool, near America's #1 Beach, on the canal with intracoastal bay access and a boat dock. You have ...

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Property Type

Siesta Key Apartment

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Casa Mahalo

4 BR | 3 BA | Sleeps 12 | Quick View

1

$288

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

Welcome to Casa Mahalo! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 12!!!] can fathom. The location is THE premier location in the heart of Siesta Key Village, just behind Gilligan's and Lelu's Coffee Shop! Inside you’ll enjoy ...

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Property Type

Siesta Key House

"Campbell’s review"
Reviewed March 18, 2020

We had a wonderful holiday. The house was perfect for the 7 of us. Decor was charming with a fully equipped kitchen meeting all our needs. We had a problem with the hot tub/pool and TV upon arrival and ...

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Sea Grape Cottage

5 BR | 3.5 BA | Sleeps 12 | Quick View

2

$286

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to Sea Grape Cottage! The luxurious tri-level Siesta Key home features gourmet kitchen, heated pool with a sloped beach entry, hot tub, covered lanai with outdoor kitchen & 2-car garage. Perfect for a dream beach vacation for up to 12! Built in June 2017, this tri-level home completely captures ...

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Property Type

Siesta Key House

"Family vacation"
Reviewed July 14, 2018

Sea grape cottage is stunningly beautiful and fit our family of 13 with room to spare. The pool was a hit with everyone. The home is furnished with everything you need for a wonderful group vacation,

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Lily Casita – 2051

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 5 miles to Siesta Key Beach

$84

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool

About this property

Welcome to Lily Casita! This tropical two-bedroom/two-bathroom cottage is located in close proximity downtown Sarasota and just minutes from world famous Siesta Key Beach! With plantation shutters and coastal décor throughout, you’ll truly be living “The Beach Life.” This home ...

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Property Type

Sarasota Cottage

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Villa Dom Brisa

4 BR | 4 BA | Sleeps 12 | Quick View

$287

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

Villa Dom Brisa is a beautifully decorated 4 bedroom, 4 bathroom, 2 kitchem home located on Crescent Street in South Siesta Key. This home is part of the Las Brisa complex of two beautiful 4-BR homes offering unique sleeping combinations to larger groups or families traveling together.Combine Villa ...

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Property Type

Sarasota House

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Hibiscus Villa

2 BR | 2 BA | Sleeps 6 | Quick View

1

$143

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool

About this property

The Hibiscus and Orchid Villas are two separate units which can be uniquely configured to create Villa Cascada, an absolutely beautiful and stunning private pool home.When rented separately, each unit features two bedrooms and a sleeping den that sleeps up to 6, with 2 full bathrooms, a gourmet kitchen, ...

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Property Type

Sarasota House

"Beautiful condo!"
Reviewed April 1, 2019

Beautiful 2 bedroom condo! Great location! Right across the street from beach and a few minute walk to public beach access. Restaurants within walking distance also. The condo was tastefully decorated and ...

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Plumbago – 5251C

2 BR | 2 BA | Sleeps 4 | Quick View

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

$96

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Welcome to Plumbago, a charming 2BR/2BA home with heated pool located in the heart of Siesta Key Village and just steps from world famous Siesta Key Beach! This home is perfect for small families and groups.This adorable 2 bedroom/2 bathroom home is a unique combination of 4 units that can be rented ...

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Property Type

Siesta Key Cottage

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Honeysuckle

3 BR | 3 BA | Sleeps 6 | Quick View

$143

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Welcome to Honeysuckle, one of Siesta Key's most inviting homes with heated pool! This home is a unique combination of two units: Lantana and Mimosa. This home is ideal for families and small groups.This inviting 3 bedroom/3 bathroom home is located right in the heart of Siesta Key Village and just ...

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Property Type

Siesta Key House

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Villa Cascada

4 BR | 4 BA | Sleeps 12 | Quick View

$250

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Villa Cascada is a uniquely configured private home featuring a heated pool/waterfall, 4 bedrooms, 4 bathrooms that sleeps 12, with 2 living areas and 2 kitchens and an almost unbelievable pool courtyard surrounded by lush gardens and a tall privacy wall enclosing the entire property.Each of the two ...

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Property Type

Sarasota House

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The Blue Laguna – 2053

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 5 miles to Siesta Key Beach

$84

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool

About this property

Welcome to The Blue Laguna! This inviting 2-bedroom/1-bathroom coastal cottage is located in close proximity to downtown Sarasota and just minutes from Siesta Key Beach, continually ranked as one of the top ten beaches in the USA! This home is ideal for small families and couples alike!The Blue ...

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Property Type

Sarasota Cottage

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Buccaneer’s Hideaway

4 BR | 2 BA | Sleeps 12 | Quick View

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Buccaneer's Hideaway is a stunning 4 bedroom, 2.5 bath home that boasts a very private backyard with a heated pool, screened in lanai, a dock and canal that leads straight to your heart's home... the Gulf of Mexico via the Intracoastal Waterway. Bring your boat, your fishing tackle, and even your finest ...

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Property Type

Sarasota House

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Mimosa – 5251B

1 BR | 1 BA | Sleeps 2 | Quick View

1

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

$71

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Welcome to Mimosa, a charming 1BR/1BA home with heated pool located in the heart of Siesta Key Village and just steps from world famous Siesta Key Beach! This home is perfect for small families and groups.This adorable 1 bedroom/1 bathroom home is a unique combination of 4 units that can be rented ...

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Property Type

Siesta Key House

"Fantastic location, Clean and Comfortable"
Reviewed October 21, 2019

We thoroughly enjoyed our stay here... the location is awesome, less than 5 minutes to the beach. The condo was spacious, clean and very comfortable. The beds were good.. all amenities up to date. We ...

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Casita Mar

2 BR | 1 BA | Sleeps 4 | Quick View

$142

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Casita Mar of Sol y Mar is one of two uniquely configured beach casitas featuring 2 beds/1 bath, gourmet kitchen, beautiful landscaping with an outdoor courtyard, a shared hot tub and a heated pool. Book along with Casita Sol for large groups.Welcome to Casita Mar of Sol y Mar. This single level (2 ...

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Property Type

Sarasota House

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Pura Vida Oasis

5 BR | 3 BA | Sleeps 13 | Quick View

$621

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Pura Vida Oasis, a canal front cottage with heated pool & spa features 5 bedrooms/3 baths and can sleep up to 13. Enjoy eclectic wine storage rack, private dock and amazing views. Close to beaches, Siesta Village & trolley stop. This spectacular bright cheerful, canal front cottage ...

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Property Type

Siesta Key House

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The Abalone

8 BR | 6 BA | Sleeps 24 | Quick View

$529

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

Welcome to The Abalone! This newly constructed 8 bedroom/6 bathroom luxury condo is a combination of two units: Casa Eulimia & Casa Junonia. Each unit features a 4 bedroom/3 bathroom configuration, each with their own common space, kitchen, outdoor patios & private heated outdoor pool. With modern ...

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Property Type

Sarasota House

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West Shore

4 BR | 4 BA | Sleeps 8 | Quick View

$550

per night

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Key Amenities

  • Pool
  • Private Pool

About this property

Welcome to West Shore! A massive gulf front penthouse located right on Siesta Beach in a newly constructed building. With amazing views, a heated pool, and enough room to sleep up to 8, it is the only way to experience Siesta Key!West Shore is a luxuriously appointed penthouse in an extremely private ...

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Property Type

Siesta Key Condo

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Caribbean Sol – 6900

5 BR | 5 BA | Sleeps 12 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$523

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Welcome to Caribbean Sol, one of Siesta Key's premier luxury townhomes with private heated pool and spa! Located just five minutes from Siesta Key Beach and Village!This massive and decadent 5-bedroom/5-bathroom townhome is located near Siesta Key Village and just five minutes from Siesta Key Beach, ...

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Property Type

Siesta Key House

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Villa De Paradisio

4 BR | 2 BA | Sleeps 12 | Quick View

$385

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to the beautiful Villa De Paradisio! This gorgeous waterfront cottage is a very luxurious and large four [4] bedroom canal front heated pool home with two bathrooms in approximately 1,800SF of air conditioned living space with a heated pool overlooking the dock and canal. This home has been completely ...

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Property Type

Siesta Key House

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Lime in the Coconut

4 BR | 4 BA | Sleeps 12 | Quick View

$250

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Pet Friendly
  • Private Pool

About this property

This private 4 bedroom/4 bathroom home is a unique combination of two units: "Casita Lime" and "Casita Coconut" (1920 sq. ft. total). Each unit features a 2 bedroom/2 bathroom configuration, each with their own living space, kitchen and outdoor patio. When booked together, Lime in ...

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Property Type

Siesta Key House

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The Islander – 6931

4 BR | 4 BA | Sleeps 12 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$468

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Welcome to The Islander, one of Siesta Key's premier luxury townhomes with private heated pool and spa! Located just five minutes from Siesta Key Beach and Village!This massive and decadent 4-bedroom/4.5-bathroom townhome is located near Siesta Key Village and just five minutes from Siesta Key Beach, ...

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Property Type

Siesta Key House

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