The Cottages on the Key

(86 rentals)
The Cottages on the Key
Phone number: +1 (800) 385-1499
20
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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Sophie’s Quartier

6 BR | 5 BA | Sleeps 16 | Quick View

$594

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Sophie’s Quartier, a waterfront compound consisting of two homes right near Siesta Key Beach! This is a perfect retreat for huge family and friends’ get togethers! Enjoy a heated pool, one hot tub, two docks overlooking The Grand Canal of Siesta Key. Minutes walk from the world ...

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Property Type

Siesta Key House

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The Grand Canal Cottage

5 BR | 4 BA | Sleeps 12 | Quick View

2

$495

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to The Grand Canal Cottage, one of Siesta Key's most enchanting canal-front cottages, with private heated pool & spa. This idyllic 5 bedroom/4 bathroom home is just a short walk to Siesta Key Village and 2 blocks from Siesta Key Beach, voted the # 1 beach in the USA! The Grand Canal Cottage ...

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Property Type

Siesta Key House

"Salt Life TWO THUMBS UP!"
Reviewed May 2, 2019

Location is literally right across a beach entrance a short 5min walk to the village. We rented both units and combined the common pool area for my whole extended family. It was fantastic!

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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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Villa Dom Brisa

4 BR | 4 BA | Sleeps 12 | Quick View

$287

per night

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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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Casita Coco

1 BR | 1 BA | Sleeps 4 | Quick View

1

$85

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Welcome to Casita Coco, a 1 bedroom/1 bathroom Siesta Key vacation home with a shared heated pool. When reserved with Casita Bayou to become CocoBayou Cottage, you can sleep up to 10! Near beach, Crescent Village & the Intercoastal.Welcome to Casita Coco!Casita Coco is one part of the uniquely ...

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Property Type

Siesta Key House

"Cute cottage."
Reviewed September 14, 2018

My daughter, my new grandson and I enjoyed the cottage immensely. The cupcake welcome was delicious. Everything was clean and we couldn't have asked for a better location. Loved the nearby restaurants. ...

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La Contento Casa

3 BR | 2 BA | Sleeps 8 | Quick View

$385

per night

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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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Baydream Bungalow

3 BR | 2 BA | Sleeps 6 | Quick View

$204

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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Crescent Cottage

4 BR | 3 BA | Sleeps 10 | Quick View

Owner special: 20% Off Summer Rates! (Until August 10th, Call to Inquire about this Deal).

$260

per night

View Details

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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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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Casita Playa

2 BR | 1 BA | Sleeps 4 | Quick View

$143

per night

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Key Amenities

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

About this property

Explore Casita Playa, a quaint 2BR/1BA bungalow located within walking distance from Crescent Beach/Village. This home is the perfect beach escape for small families and couples alike!This lovely 2BR/1BA beach bungalow is just a short walk to prestigious Crescent Beach and close to world famous Siesta ...

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Property Type

Siesta Key House

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Sea Shell Casita

2 BR | 2 BA | Sleeps 6 | Quick View

1
Owner special: 15% Off Summer Rates! (Until August 10th, Call to Inquire about this Deal).

$143

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool

About this property

The Sea Shell and Sea Wave are two separate units which can be uniquely configured to create Villa Brisa Marina, an absolutely beautiful and stunning private pool home.Each of the two Casitas [Sea Shell and Sea Wave] in Villa Brisa Marina which are connected by a common entry lanai, combine to offer ...

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Property Type

Sarasota House

"Relaxing"
Reviewed March 9, 2018

The property was everything we expected and we had a great & relaxing experience

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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 Solaster

6 BR | 6 BA | Sleeps 20 | Quick View

Owner special: 20% Off Summer Rates! (Until August 10th, Call to Inquire about this Deal).

$400

per night

View Details

Key Amenities

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

About this property

The Solaster is a combination of two units (Casita Morning Star and Casita Sun Star) within walking distance of Point of Rocks Beach. Each unit has 3 bedrooms, 3 bathrooms, their own heated pool & a private screened in lanai. Ideal for large groups! Welcome to The Solaster! Our newly renovated luxury ...

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Property Type

Siesta Key House

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Sea Grape Cottage

5 BR | 3.5 BA | Sleeps 12 | Quick View

2

$271

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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Coconut Grove

6 BR | 6 BA | Sleeps 16 | Quick View

Owner special: 20% Off Summer Rates! (Until August 10th, Call to Inquire about this Deal).

$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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Casa Junonia

4 BR | 3 BA | Sleeps 12 | Quick View

Owner special: 15% Off Summer Rates! (Until August 10th, Call to Inquire about this Deal).

$257

per night

View Details

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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Casa Ohana

4 BR | 3 BA | Sleeps 12 | Quick View

2
Owner special: 15% Off Summer Rates! (Until August 10th, Call to Inquire about this Deal).

$288

per night

View Details

Key Amenities

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

About this property

Welcome to Casa Ohana! 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

"Fantastic Florida Rental"
Reviewed June 22, 2019

Casa Ohana was terrific. Family friendly, close to the beach and main attractions of Siesta Key. Will definitely be returning!

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Casita Blanca

2 BR | 1 BA | Sleeps 4 | Quick View

$143

per night

View Details

Key Amenities

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

About this property

Explore Casita Blanca, a cozy 2BR/1BA bungalow located minutes from prestigious Crescent Beach. This home is the perfect beach retreat for small families and couples alike!This inviting beach bungalow is just a short walk to prestigious Crescent Beach and close to world famous Siesta Key Beach, continually ...

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Property Type

Siesta Key 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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Casa Coquina

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 Coquina! Our newest luxury cottage has all the amenities your large group [up to 12!!!] 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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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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West Shore

4 BR | 4 BA | Sleeps 8 | Quick View

$550

per night

View Details

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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The Palms Cottage

4 BR | 2 BA | Sleeps 10 | Quick View

$385

per night

View Details

Key Amenities

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

About this property

This charming recently updated four-bedroom, 2-bathroom home is just a short walk to Siesta Key Village and minutes from Siesta Key Beach, voted the # 1 beach in the USA! This home is ideal for families and couples looking for their perfect tropical getaway.The Palms Cottage can accommodate up to ...

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Property Type

Siesta Key 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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Casa Mahalo

4 BR | 3 BA | Sleeps 12 | Quick View

$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

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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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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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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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Juicy Mango Cabana

2 BR | 2 BA | Sleeps 6 | Quick View

$129

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool

About this property

Welcome to Juicy Mango Cabana, an adorable Siesta Key beach bungalow with heated pool. When combined with its sister property Honey Mango Cabana, both units make up Mango Manor.This tropical 2 bedroom/2 bathroom cottage is just a five minute walk to Crescent Beach and a short drive to The Village ...

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Property Type

Siesta Key House

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Peacock Villa

3 BR | 3 BA | Sleeps 9 | Quick View

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

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

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Property Type

Siesta Key House

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The Canopy Cottage

4 BR | 3 BA | Sleeps 9 | Quick View

$330

per night

View Details

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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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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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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Sol y Mar

4 BR | 2 BA | Sleeps 8 | Quick View

Owner special: 15% Off Summer Rates! (Until August 10th, Call to Inquire about this Deal).

$284

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Sol y Mar! A uniquely configured South Siesta Key private home with 4 bedrooms, 2 bathrooms that sleeps 8. May also be used as 2 separate units surrounded by lush gardens with a private beach access, a heated swimming pool and hot tub. Welcome to Sol y Mar. This COMPLETELY RENOVATED, single ...

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Property Type

Siesta Key House

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Sunset Fiesta

4 BR | 2 BA | Sleeps 12 | Quick View

Owner special: 20% Off Summer Rates! (Until August 10th, Call to Inquire about this Deal).

$287

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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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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Sea the View - One of The Cottages On The Key

$440

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Sea the View - one of Siesta Key's most tranquil canal-front homes, with private heated pool and spa! This home is ideal for large families.This picturesque 4 bedroom/3 bathroom home features a brand new outdoor tiki bar and is located within walking distance to Siesta Key Village and ...

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Property Type

Siesta Key House

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Casa Eulimia

4 BR | 3 BA | Sleeps 12 | Quick View

Owner special: 15% Off Summer Rates! (Until August 10th, Call to Inquire about this Deal).

$257

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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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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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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CocoBayou Cottage

3 BR | 2 BA | Sleeps 10 | Quick View

$229

per night

View Details

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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Sandy 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 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

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Sea Wave Casita

2 BR | 2 BA | Sleeps 6 | Quick View

2
Owner special: 15% Off Summer Rates! (Until August 10th, Call to Inquire about this Deal).

$143

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool

About this property

The Sea Wave Casita of Villa Brisa Marina is one of two beautiful casitas, uniquely configured, featuring two bedrooms, 2 full bathrooms, a gourmet kitchen and a heated pool. One of 2 homes (along with Sea Shell Casita) that are Villa Brisa Marina.The Sea Wave and Sea Shell are two separate units ...

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Property Type

Siesta Key House

"Beachside single storey"
Reviewed February 10, 2019

Had a great stay at this beautifully decorated and well equipped single storey pad. The beach is so close by as are grocery and other shops offering all you need. It really is quite special and so... ...

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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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The Abalone

8 BR | 6 BA | Sleeps 24 | Quick View

Owner special: 15% Off Summer Rates! (Until August 10th, Call to Inquire about this Deal).

$514

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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Coral Reef Casita

2 BR | 2 BA | Sleeps 6 | Quick View

$143

per night

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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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The Big Kahuna

8 BR | 6 BA | Sleeps 24 | Quick View

$577

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to The Big Kahuna! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 24!!!] can fathom. It also boasts the very BEST location, in the heart of Siesta Key Village, just behind Gilligan's and Lelu's Coffee Shop! Inside you’ll ...

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Property Type

Siesta Key House

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Pinacolada

3 BR | 3 BA | Sleeps 8 | Quick View

Owner special: 20% Off Summer Rates! (Until August 10th, Call to Inquire about this Deal).

$214

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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Isla Amor

4 BR | 3 BA | Sleeps 8 | Quick View

$604

per night

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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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Villa Vista Mare

3 BR | 3 BA | Sleeps 10 | Quick View

1

$334

per night

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Key Amenities

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

About this property

Welcome to Villa Vista Mare! This beautiful and luxurious 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 and ...

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Property Type

Siesta Key Townhome

"Best ever..."
Reviewed May 27, 2018

This was the first time we have ever rent without see the property or at least know the owner. I was very nervous about the whole situation, as you can imagine. We were in Siesta Key for our daughters ...

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