The Cottages on the Key

(83 rentals)
The Cottages on the Key
Phone number: +1 (800) 385-1499
17
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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Villa Vista Mare

3 BR | 3 BA | Sleeps 10 | Quick View

1

$334

per night

View Details

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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Enchanting canal-front cottage w/ private heated pool & spa. Minutes to beaches!

$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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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 the completely remodeled, and newly furnished La Contento Casa! This lovely 3 bedroom, 2 bath home comfortably sleeps 6 in beds, with ultra deluxe rollaway beds for an extra 2. Enjoy the peacefulness of a large heated pool with beautiful and breathtaking views of the water via the Intracoastal ...

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Property Type

Siesta Key House

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Casita Sol

2 BR | 1 BA | Sleeps 4 | Quick View

$143

per night

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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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Casa Leone – Breathtaking 5BR/3BA Heated Pool Home with Hot Tub Nestled Away

$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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Casita Coco

1 BR | 1 BA | Sleeps 4 | Quick View

1

$85

per night

View Details

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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Villa Brisa Marina

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

This home features a brand new heated pool and a four minute walk to the Nation’s finest beach [no major streets to cross]. It’s perfect for families or groups up to 12, especially those families who love to travel together or visit the vacationing grandparents. Villa Brisa Marina offers the ...

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Property Type

Sarasota House

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Casa Eulimia

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 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

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 Champagne

4 BR | 3 BA | Sleeps 8 | Quick View

1

$294

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to “Villa Champagne”, one of the most fabulous vacation homes in Siesta Key. It’s also one of the most popular favorites among our many guest families. The magic begins as you enter the foyer of this beautiful villa and gaze across the expansive living area, then further out ...

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Property Type

Siesta Key House

"Indian Rock Beach Vacation"
Reviewed July 2, 2018

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

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Latitude Adjustment

4 BR | 4 BA | Sleeps 10 | Quick View

$294

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Latitude Adjustment! This breathtaking 4 bedroom, 4 bathroom home is perfectly situated between America's #1 beach in the world and Siesta Key's famous North Village! You will not be able to ask for more as you drive up to this tropical oasis, covered with vibrant hot pink bougainvillea flower ...

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Property Type

Siesta Key House

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Siesta Salt Life

6 BR | 4 BA | Sleeps 16 | Quick View

$404

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to The Salt Life! This private 6BR/4BA home is a unique combination of two units: “Sea Esta” & “Sea La Vie” (2328 sq. ft. total). Each unit features a 3BR/2BA configuration, each with their very own common space to include a kitchen, dining area, and private outdoor ...

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Property Type

Siesta Key House

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Casa Ohana

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 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

"Great Family Vacation"
Reviewed March 1, 2018

The condo was great for our three generation family including a 3 year old and an infant. Private pool + easy walk to beach and restaurants met our needs. No parking issues to worry about. The Cottages ...

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Admirals Watch

3 BR | 3 BA | Sleeps 8 | Quick View

$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

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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 Seascape – 8BR/9BA Beachfront, Heated Shared Pool, Private Access to Beach

$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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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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Casita Playa

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

Welcome to Casita Playa of Playa y Blanca. This single level (2 BR/1BA - Master BR/1 Queen & 2nd BR/2 twins -sleeps 4) vacation home features private, gated beach access, a sparkling clean hot tub in a private, lush setting, a communal heated swimming pool with plenty of pool furniture and a bathroom, ...

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Property Type

Siesta Key House

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Casita Morning Star

3 BR | 3 BA | Sleeps 10 | Quick View

$200

per night

View Details

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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The Solaster

6 BR | 6 BA | Sleeps 20 | Quick View

$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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Pinacolada – 3BR/3BA Private Heated Pool in the heart of Siesta Village

$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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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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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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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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The Big Kahuna

8 BR | 6 BA | Sleeps 24 | Quick View

$577

per night

View Details

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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The Nautilus

8 BR | 6 BA | Sleeps 24 | Quick View

1

$514

per night

View Details

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

"Family Birthday Getaway"
Reviewed January 22, 2019

What a great vacation rental, just what we were looking for! Plenty of room for us all and close to restaurants, the beach and all the extras like bicycles, plenty of refrigerators etc. Definitely would ...

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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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Coconut Grove – 6BR/6BA Private Heated Pool in the heart of Siesta Village

$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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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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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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Isla Amor – Stunning 5 BR/3BA Heated Pool Home on The Grand Canal

$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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Sol y Mar

4 BR | 2 BA | Sleeps 8 | Quick View

$287

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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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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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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Sea Wave Casita

2 BR | 2 BA | Sleeps 6 | Quick View

2

$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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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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Luna Flores

6 BR | 4 BA | Sleeps 10 | Quick View

1

$264

per night

View Details

Key Amenities

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

About this property

Luna Flores - a gorgeous 6 bedroom/4 bathroom vacation home comprised of 2 units & heated pools, Villa Las Flores and Luna Nueva. Located just off island with easy access to Siesta Key, ti's within walking distance of an array of restaurants & shops. Luna Flores, a gorgeous 6 bedroom, 4 bathroom ...

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Property Type

Sarasota House

"Amazing vacactions and perfect rental!"
Reviewed January 14, 2019

We are really satisfied with the rental of our house, the location is perfect, the house clean and comfortable. Near the beach can be done by bike easily. Owner easy to join and friendly. Nothing negative ...

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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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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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The Seagull – 2/2 Condo with Heated Shared Pool in Heart of Siesta Key Village

$176

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Welcome to The Seagull, a 2BD/2BA private condo perfectly located only 1/2 mile from Siesta Beach and located in the heart of Siesta Key Village. This spaciously designed open floorplan comfortably sleeps 8! JUST WAIT TO SEE IT! NEWLY UPDATED FURNITURE AND UPDATED PHOTOS TO FOLLOW ON 6/29! The Seagull ...

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Property Type

Siesta Key Condo

"Siesta Key"
Reviewed October 23, 2018

Super place and had easy access to the Village.....would go back for sure!

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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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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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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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Sandy Cabana

3 BR | 3 BA | Sleeps 8 | Quick View

$179

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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Baybreeze – 3BR/3BA Private Heated Pool in the heart of Siesta Village

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Baybreeze! 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!Baybreeze is one-half of the beautiful "Coconut Grove," ...

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Property Type

Siesta Key Townhome

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Crescent Cottage

4 BR | 3 BA | Sleeps 10 | Quick View

$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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Seahorse Cabana

3 BR | 3 BA | Sleeps 8 | Quick View

$179

per night

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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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The Pearl by the Sea

4 BR | 3 BA | Sleeps 12 | Quick View

$550

per night

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Key Amenities

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

About this property

Welcome to The Pearl by the Sea. An absolute one of kind, limited edition home located on prestigous Siesta Key featuring a private heated pool and spa, near America's #1 Beach, on the Grand Canal with intracoastal bay access and a boat dock. You have arrived...If you have ever gone searching for ...

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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

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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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Villa Las Flores - Sarasota home w/ private heated pool. Near Siesta Key Beach!

$132

per night

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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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