The Cottages on the Key

(107 rentals)
The Cottages on the Key
Phone number: +1 (800) 385-1499
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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Deja Blue – 5288R

2 BR | 1 BA | Sleeps 6 | Quick View

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

$143

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

Welcome to Deja Blue, 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 Bungalow

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Casita Morning Star

3 BR | 3 BA | Sleeps 10 | Quick View

$200

per night

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Key Amenities

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

About this property

Welcome to Casita Morning Star! Our newly renovated luxury cottage (completion date of June 2017) has all the amenities your family [up to 10] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout gorgeous and decadent bathrooms, new appliances, new washers/dryers, ...

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Property Type

Sarasota House

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Sunset Fiesta

4 BR | 2 BA | Sleeps 12 | Quick View

$286

per night

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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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Crescent Cottage

4 BR | 3 BA | Sleeps 10 | Quick View

$260

per night

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Key Amenities

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

About this property

Welcome to our beautiful and serene vacation home! A gorgeous beach cottage in a dream destination, Crescent Cottage offers a fun-filled activity-packed vacation plan with all of its great amenities, awesome location so close to the beach, and a spacious abode designed around the needs and comforts of ...

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Property Type

Siesta Key House

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Casa Junonia

4 BR | 3 BA | Sleeps 12 | Quick View

$257

per night

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Key Amenities

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

About this property

This upscale four-bedroom/three-bathroom luxury condo features a spacious kitchen and living area, outdoor patios & private heated outdoor pool with cabana room. With modern and coastal decor throughout, you will truly be living “the beach life.” This home is ideal for large families & ...

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Property Type

Sarasota House

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Villa Cascada

4 BR | 4 BA | Sleeps 12 | Quick View

$287

per night

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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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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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Gran Vista – 6906

6 BR | 4 BA | Sleeps 14 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$633

per night

View Details

Key Amenities

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

About this property

Welcome to 6906 Coronas Park, 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 6-bedroom/4.5-bathroom townhome is located near Siesta Key Village and just five minutes from Siesta Key ...

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Property Type

Siesta Key House

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The Nautilus

8 BR | 6 BA | Sleeps 24 | Quick View

2

$514

per night

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Key Amenities

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

About this property

This luxurious 8 bedroom/six bathroom home is a unique combination of two units: “Casa Stolida” and “Casa Tegula” (4000 sq. ft. total). Each unit features a 4 bedroom/3 bathroom configuration, each with their own cabana room, separate living areas, private elevators and your very ...

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Property Type

Siesta Key House

"Beautiful Home"
Reviewed June 19, 2019

The Nautilus was a fantastic home on Siesta Key. Short walk to the beach and we had our own pool. House was well appointed and very comfortable and clean. We will be back and definitely recommend renting ...

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Pura Vida Oasis

5 BR | 3 BA | Sleeps 13 | Quick View

$621

per night

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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 Blue Laguna – 2053

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 5 miles to Siesta Key Beach

$64

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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CocoBayou Cottage

3 BR | 2 BA | Sleeps 10 | Quick View

$229

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Welcome to CocoBayou Cottage, a 3 bedroom/3bathroom home with a heated pool. Featuring two units (Casita Bayou & Casita Coco), CocoBayou Cottage sleeps up to 10 and is near the beach, Crescent Village & the Intercoastal. Great for a big group! Welcome to CocoBayou Cottage!This uniquely configured ...

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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

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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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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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Topsail Cottage

4 BR | 4 BA | Sleeps 12 | Quick View

$260

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Welcome to Topsail! Our newly constructed luxury cottage has all the amenities your group [up to 12] can fathom. Inside you’ll enjoy travertine flooring throughout the entire three-story building, garden soaking tub in the master, new appliances, oversized washer/dryer, granite countertops, and ...

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Property Type

Sarasota House

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Admirals Watch

3 BR | 3 BA | Sleeps 8 | Quick View

1

$354

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Welcome to Admirals Watch! This beautiful, luxurious and modern 3 bedroom, 3 bathroom, heated pool, townhome boasts the best views of the world famous No. 1 Siesta Key Beach Access! With absolutely unobstructed views, this home is part of only a handful of private residences that can claim such gorgeous ...

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Property Type

Siesta Key Condo

"Wonderful Stay"
Reviewed July 1, 2019

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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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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La Contento Casa

3 BR | 2 BA | Sleeps 8 | Quick View

$385

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to La Contento Casa, one of Siesta Key’s most alluring 3BR/2BA canal-front cottages, with private heated pool and breathtaking views of Siesta Key’s intracoastal waterway!This exquisite 3BR/2BA cottage is centrally located close to the Village and Siesta Key Beach, continually ...

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Property Type

Siesta Key House

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Isla Amor

4 BR | 3 BA | Sleeps 8 | Quick View

$604

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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Pinacolada

3 BR | 3 BA | Sleeps 8 | Quick View

$214

per night

View Details

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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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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Jasmine Casita – 2052

2 BR | 2 BA | Sleeps 6 | Quick View

$84

per night

View Details

Key Amenities

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

About this property

This charming two-bedroom/two-bathroom cottage is located in close proximity to downtown Sarasota and Siesta Key Beach, voted the #1 beach in the USA! With plantation shutters and beachy décor throughout, you’ll truly be living “The Florida Life.” This home is perfect for small ...

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Property Type

Sarasota Cottage

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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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Casita Sun Star

3 BR | 3 BA | Sleeps 8 | Quick View

$200

per night

View Details

Key Amenities

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

About this property

Welcome to Casita Sun Star! Our newly renovated luxury cottage (completion date of June 2017) has all the amenities your family [up to 8] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout gorgeous and decadent bathrooms, new appliances, new washers/dryers, quartz ...

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Property Type

Sarasota House

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Coral Reef Casita

2 BR | 2 BA | Sleeps 6 | Quick View

$143

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool

About this property

The Coral Reef and Star Fish Casitas are two separate units which can be uniquely configured to create Villa Dom Bisa, features its own brand new, private heated pool with “sun shelf” and a three minute walk to the Nation’s finest beach [no major streets to cross].The décor ...

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Property Type

Sarasota House

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Villa Trinidad

4 BR | 2 BA | Sleeps 10 | Quick View

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Centrally located in the heart of Sarasota, and only minutes away from our world famous Siesta Key Beach, the completely renovated Villa Trinidad offers a cool and soothing retreat with a heated swimming pool and a spectacular waterfront view! Centrally located in the heart of Sarasota, and only minutes ...

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Property Type

Sarasota House

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La Casa Verde

4 BR | 2 BA | Sleeps 10 | Quick View

$440

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

The waterfront cottage, ‘La Casa Verde’ is a very luxurious and large four [4] bedroom canal front heated pool home with two very large bathrooms in approximately 2,800 square feet of air conditioned living space. As you approach the home you are immediately drawn into it by volumes of lush, ...

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Property Type

Siesta Key House

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The Conch

8 BR | 6 BA | Sleeps 24 | Quick View

$514

per night

View Details

Key Amenities

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

About this property

Welcome to The Conch! Our newest luxury cottage has all the amenities your large group [up to 24!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing from the ground floor, gorgeous and decadent ...

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Property Type

Sarasota House

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Mango Manor

4 BR | 3 BA | Sleeps 12 | Quick View

$257

per night

View Details

Key Amenities

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

About this property

Welcome to Mango Manor, a unique combination of two units: “Juicy Mango Cabana” and “Honey Mango Cabana.” When booked together, Mango Manor offers a private heated pool and is just a short walk to prestigious Crescent Beach!This tropical 4 bedroom/3 bathroom beach villa is ...

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Property Type

Siesta Key House

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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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Casita Sol

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 Sol 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 Mar for large groups.Welcome to Casita Sol of Sol y Mar. This COMPLETELY RENOVATED, ...

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Property Type

Sarasota House

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Seahorse Cabana

3 BR | 3 BA | Sleeps 8 | Quick View

$142

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to the Seahorse Cabana!The Seahorse 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

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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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Baydream Bungalow

3 BR | 2 BA | Sleeps 6 | Quick View

$204

per night

View Details

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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Sophie’s Cottage

2 BR | 2 BA | Sleeps 8 | Quick View

$330

per night

View Details

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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Sea Esta – 5319 (L)

3 BR | 2 BA | Sleeps 8 | Quick View

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

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? The Salt Life is just 1 minute (seriously!) away from Siesta Key Beach, voted the # 1 beach in the U.S! Sea Esta offers a shared heated pool with ...

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Property Type

Siesta Key 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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Casa Antilles

4 BR | 3 BA | Sleeps 12 | Quick View

$257

per night

View Details

Key Amenities

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

About this property

Welcome to Casa Antilles! Our newest south Siesta Key luxury cottage has all the amenities your large group - up to 12. Enjoy a private heated pool & nearby beach access. When reserved with Casa Coquina to become The Conch, you can sleep up to 24. Welcome to Casa Antilles! Our newly constructed luxury ...

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Property Type

Sarasota House

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Star Fish Casita

2 BR | 2 BA | Sleeps 6 | Quick View

$143

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool

About this property

The Star Fish and Coral Reef casitas are two separate units which can be uniquely configured to create Villa Dom Brisa, features its own brand new, private heated pool with “sun shelf” and a three minute walk to the Nation’s finest beach [no major streets to cross].The décor ...

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Property Type

Sarasota House

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Vinca – 5251D

1 BR | 1 BA | Sleeps 2 | Quick View

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 Vinca, 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 Cottage

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Coconut Grove

6 BR | 6 BA | Sleeps 16 | Quick View

$404

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Coconut Grove! 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 16, a private heated pool, and quite literally in the heart of Siesta Village!Coconut Grove features a unique combination of two ...

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Property Type

Siesta Key House

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Seaside Cottage

4 BR | 3 BA | Sleeps 10 | Quick View

1

$294

per night

View Details

Key Amenities

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

About this property

Welcome to Seaside Cottage, one of Siesta Key's most dazzling 4BR/3BA homes, with private heated pool. Steps from world famous Siesta Key beach and just minutes so Siesta Key Village!! This remarkable 4 bedroom/3 bathroom home features a private heated pool. With its location less than a mile from Siesta ...

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Property Type

Siesta Key Cottage

"Wonderful"
Reviewed May 3, 2018

Great place, very comfortable beds, all the items you need - kitchen equipped with great tools. Very clean.

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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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Casa Stolida

4 BR | 3 BA | Sleeps 8 | Quick View

$257

per night

View Details

Key Amenities

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

About this property

Luxurious 4BR/3BA villa features a private heated pool and cabana room. Casa Stolida is just steps from prestigious Crescent Beach and is centrally located in close proximity to Siesta Key Beach, voted the #1 beach in the USA!Once inside the home, you will see that Casa Stolida is the definition ...

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Property Type

Siesta Key House

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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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Casa De Mariposa

6 BR | 6 BA | Sleeps 16 | Quick View

$404

per night

View Details

Key Amenities

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

About this property

Welcome to Casa de Mariposa! This gorgeous property is comprised of two units, Monarch and Peacock Villa which are both mirror images of one another. Each unite features a 3 bedroom, 3 bathroom configuration with their very own common space to include a kitchen, dining area, private balconies, and private ...

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Property Type

Siesta Key House

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Casa Leone

4 BR | 3 BA | Sleeps 8 | Quick View

$254

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Private Pool

About this property

Welcome to Casa Leone. An absolute one of kind, limited edition home located on prestigous Siesta Key featuring an extremely private and lushly landscaped heated pool and hot tub area, near America's #1 Beach, minutes away from Siesta Key Village!It's time for that vacation! And there is no better ...

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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

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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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Lantana – 5251A

2 BR | 2 BA | Sleeps 4 | Quick View

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

$96

per night

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Key Amenities

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

About this property

Welcome to Lantana, 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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Monarch Villa

3 BR | 3 BA | Sleeps 9 | Quick View

$214

per night

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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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