Siesta Key Vacation Rentals

(213 rentals)
Honey Mango Cabana

2 BR | 1 BA | Sleeps 6 | Quick View

$129

per night

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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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Casa Ohana

4 BR | 3 BA | Sleeps 12 | Quick View

2

$288

per night

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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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Sophie’s Cottage

2 BR | 2 BA | Sleeps 8 | Quick View

$330

per night

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Key Amenities

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

About this property

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

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Property Type

Siesta Key House

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Siesta Key Beachfront Condo with Gulf View!

$135

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

You will fall in love with this condo! Everything you would possibly need is provided. Enjoy relaxing on the lanai in the morning with your coffee or a glass of wine in the evening. Nice beach chairs, beach umbrellas, straw mats, small cooler, swim noodles and a beach bag are all in the condo for your ...

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Property Type

Siesta Key Condo

"Beautiful view of a world-class beach!"
Reviewed November 16, 2018

The tidy condo was well located on the 4th floor allowing for a magnificent view of the beach from the lanai. Great place to take our coffee in the morning before our morning walk; or a glass of wine in ...

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B110

2 BR | 2 BA | Sleeps 4 | Quick View

$171

per night

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Key Amenities

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

About this property

From the lanai and your private patio, you are directly on the beach where it is easy to keep an eye on the children playing, or walk down to the Gulf of Mexico for a swim. Located on Turtle Beach, Siesta Key's quiet south end - this lovely Gulf front first floor unit with large washer and dryer and ...

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Property Type

Siesta Key Condo

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Sea the View - One of The Cottages On The Key

$440

per night

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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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"Key West" 378 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

1
Owner special: Fall discount 20% off any one week booking until Dec 28! Please contact us for special rates.

$151

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNTED RATES!2 BEDROOM/2 bath, Large Deluxe unit, King bed, Queen bed and Queen sleeper sofa, 3 TVs, large deck with awning, small screened porch, an upstairs accommodation. Pool Access, WIFI, private W&D, an upstairs accommodation. Local free ...

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Property Type

Siesta Key House

"Best and thoughtful rental company with beautiful beach"
Reviewed June 12, 2019

We have been visiting Siesta Key for the past 10 and renting from the same company. There accommodating attention to their guests has us coming back year after year. We never consider renting with any ...

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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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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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Beachfront Siesta Key, FL.- 3 Bedroom Private Home W/Full Gulf Views!

3 BR | 3 BA | Sleeps 7 | Quick View

3

Distance to beach: 300 feet to Siesta Beach

$395

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Rentals by Owner

About this property

This home has private Siesta Key beach frontage on the prime section of beach, there are no streets to cross or homes between you and the beach. Nearly every room has a full view of the beach and Gulf of Mexico. The entire back of this house opens with stacking glass sliding doors to catch the Gulf breezes ...

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Property Type

Siesta Key House

"Wonderful Location!"
Reviewed March 25, 2019

We had a great stay! We visited for spring break with our two school-age kids and their grandparents. The location was fantastic - right on the beach with your own private path to the beach, and near ...

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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 Stolida

4 BR | 3 BA | Sleeps 8 | Quick View

$257

per night

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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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Siesta Salt Life

6 BR | 4 BA | Sleeps 16 | Quick View

$404

per night

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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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Baybreeze

3 BR | 3 BA | Sleeps 8 | Quick View

$214

per night

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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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Siesta Key Gulf View Palm Bay Club in the Tower

$179

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Rentals by Owner

About this property

Beautiful 2 Bedroom, 2 Full bath condo. Close to everything, right on Crescent Beach, voted #1 beach twice in the last 5 years. King in the master, 2 full size beds in the second.

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Property Type

Siesta Key Condo

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Seaside Cottage

4 BR | 3 BA | Sleeps 10 | Quick View

1

$294

per night

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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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Stroll the Beach....Siesta Palms by the Beach #1D

1 BR | 1 BA | Sleeps 4 | Quick View

1
LAST MINUTE DEAL 8/17 - 9/22: Sweet Summer Deal 15% DISCOUNT FOR WEEKLY RENTALS! $1189 Per Week Plus 12% Tax

Distance to beach: 150 yards to Siesta Key Crescent Beach

$199

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Welcome to our Beach Get-away...where we, The Koch Family, invite you to relax, unwind and enjoy our casual way of life. Resting just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach is our Family owned and operated Tropical Siesta Palms by the Beach. With ...

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Property Type

Siesta Key Condo

"Everything we needed!!"
Reviewed March 12, 2018

Great location! Very clean. Close to the beach. Was really perfect would stay again !

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DEAL
Breathtaking Beachfront "House of the Sun" Rental

2 BR | 2 BA | Sleeps 6 | Quick View

4

Distance to beach: 200 feet to Crescent Beach

$173

per night

View Details

Key Amenities

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

About this property

Unit 402 at the House of the Sun is an attractive condo offering resort living. The unit has just been painted throughout and redecorated. It has two bedrooms and two new full baths. The master has a king size bed, large closets, full bath, a work/makeup station with makeup mirror and large high-def ...

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Property Type

Siesta Key Condo

"The Total Package"
Reviewed April 24, 2019

This beautiful condo is well-appointed and well situated on the quiet end of the key. Everything you need is within walking distance or just a free trolley ride away; restaurants, shopping, groceries and ...

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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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Juicy Mango Cabana

2 BR | 2 BA | Sleeps 6 | Quick View

$129

per night

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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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Turtles Watch – 6925

4 BR | 4 BA | Sleeps 12 | Quick View

Distance to beach: 1 miles to Siesta key Beach

$468

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key House

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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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Sea la Vie – 5321 (R)

3 BR | 2 BA | Sleeps 8 | Quick View

$214

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Sea la Vie! This private 3BR/2BA home is the perfect beach getaway to relax, unwind & take in everything Siesta Key has to offer. 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 la Vie offers a shared heated pool ...

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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

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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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The Hidden Gem – 5290L

2 BR | 1 BA | Sleeps 6 | Quick View

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

$143

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Cottage

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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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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

View Details

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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Sandy Seahorse Cottage

6 BR | 6 BA | Sleeps 16 | Quick View

$284

per night

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Key Amenities

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

About this property

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

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Property Type

Siesta Key House

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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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The Solaster

6 BR | 6 BA | Sleeps 20 | Quick View

$400

per night

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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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Adorable Condo -- On Beach and Bay, 2 Bdr. Ground Floor

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.2 miles to Siesta Key Beach

$136

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Our adorable unit – Casita Siesta - is located at Gulf & Bay Bayside on Siesta Key, on the bay just south of Sarasota and with private beach access to world-famous Siesta Key Beach. The complex is a gated resort community featuring unique “Old Key West style” condominiums only a ...

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Property Type

Siesta Key Condo

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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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"Village Resort" 320 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

2
Owner special: Fall discount 20% off any one week booking until Dec 28! Please contact us for special rates.

$151

per night

View Details

Key Amenities

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

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNT RATES!320 Canal Rd - Village Resort Just steps to #1 voted beach, restaurants, grocery’s, shops, bars & ice cream! (upstairs) - 2 bed/ 2 bath-dishwasher, heated pool, great back yard for BBQ and gatherings. Combine all four units ...

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Property Type

Siesta Key Condo

"Banyon 2019"
Reviewed June 22, 2019

Loved the old Florida feel. Great location. Wonderful courtyard. Since we had 3 units rented, 1 unit was friends of ours, we had a great time in the courtyard. Only drawback was having to enter courtyard ...

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Modernized Direct Waterfront Condo 2BR, 2B,HDTV, WIFI, Washer/Dryer, Gulf Lanai

$164

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Pool
  • Rentals by Owner

About this property

Our Condo is on beautiful Turtle Beach at the southern and most private end of Siesta Key directly on the Gulf of Mexico. When we say directly, we mean directly and not merely a Gulf “View” or a long car ride or a long walk to the Gulf. We call it “Paradise” and you could not ...

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Property Type

Siesta Key Condo

"good"
Reviewed August 19, 2018

we have the time ok but the red tide not let us have good time

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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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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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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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2BR2BA 2nd Floor 800sqft Condo Siesta Key Crescent Beach + WiFi No Road to Cross

2 BR | 2 BA | Sleeps 7 | Quick View

3

Distance to beach: 120 yards to Siesta Key Crescent Beach

$100

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Last Minute Opening (Some with Discounts) Aug 25 - Sep 8; Sep 13-25; Oct 9-19... ... Dr. Beach names Siesta Beach Best Beach in US - just Google 'dr beach names siesta beach best beach in us' and find out why. We have a new 360 degree picture layout of all rooms, similar to Real Estate Salesman version. ...

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Property Type

Siesta Key Condo

"Perfect Beach Stay"
Reviewed June 21, 2019

The condo was great! I couldn't have asked for a better fit for our family vacation. Very clean and quiet! Great proximity to the Private Beach! There are even loungers and chairs at the beach for ...

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The Seascape

8 BR | 9 BA | Sleeps 16 | Quick View

$1100

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

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

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Property Type

Siesta Key Condo

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great area walk to the beach

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.5 miles to Crescent Beach

$71

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

This 1 bedroom is in a great area. Walking distance to the beach, shopping, restaurants and entertainment. Easy on and easy off the island and close to the bridge2 weeks minimum rental or monthly January- April

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Property Type

Siesta Key Condo

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The Islander – 6931

4 BR | 4 BA | Sleeps 12 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$468

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key House

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Luxury Siesta Key 4 bedroom Waterfront Home Only 5 minutes walk to Siesta Beach!

4 BR | 4.5 BA | Sleeps 12 | Quick View

2

Distance to beach: 120 yards to Siesta Beach

$595

per night

View Details

Key Amenities

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

About this property

This Luxury Four Bedroom, Four and a Half Bathroom Home will leave you breathless as you enter. There are not many large rental homes, this close to Siesta Beach, that live like this home. Most Rentals by the beach have their living area 16 feet above the ground level and the pool below, which is not ...

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Property Type

Siesta Key House

"Spring Break 2019"
Reviewed April 1, 2019

The pictures do not do justice what an awesome place to stay. My family loved staying at this home David Butler Owner Agent (first class treatment) very impressed I would give this place a 5-Star x10

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Seahorse Cabana

3 BR | 3 BA | Sleeps 8 | Quick View

$142

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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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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Fishermans Cove A302

2 BR | 2 BA | Sleeps 6 | Quick View

3

$164

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Rentals by Owner

About this property

This colorful custom 3rd floor unit has a commanding view of the Gulf of mexico.This special unit has been decorated by a pro, and shows it! This is an adults only unit, perfect for a mature couple who can take excellent care of things and appreciate the fine nature of this unit.From the modern ...

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Property Type

Siesta Key Condo

"Paradise at Christmas!"
Reviewed January 8, 2019

My family of four traveled to Siesta Key for Christmas week and enjoyed this precious condo on the beach! It was delightful! Fun colorful décor, comfortable, and all amenities included. The Sunset here ...

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Overlooking Beach and one block to Siesta Village - Starfish unit

$250

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Rentals by Owner

About this property

Beautiful, beach front apartments on Siesta Key. One bedroom, one bathroom, all linens, full size modern kitchen, living room with queen size sleeper couch, flat screen tvs in the living room and bedroom with Verizon Fios, and free wi-fi. French doors open onto your own private deck with patio furniture ...

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Property Type

Siesta Key Apartment

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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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Sea Esta – 5319 (L)

3 BR | 2 BA | Sleeps 8 | Quick View

$214

per night

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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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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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Casita Bayou

2 BR | 1 BA | Sleeps 6 | Quick View

$142

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Welcome to Casita Bayou!Casita Bayou is the larger half of this uniquely configured private home called the Coconut Bayou Cottage and it is the perfect escape for you and your guests. This side of the gorgeous home has recently been updated with new furnishings and completely renovated on the interior. ...

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Property Type

Siesta Key House

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Siesta Key Vacation Rentals

Siesta Key Weather

 | 

7122°  5111°
JANUARY
Ocean 6418°
7423°  5412°
FEBRUARY
Ocean 6518°
7725°  5814°
MARCH
Ocean 6719°
8127°  6217°
APRIL
Ocean 7323°
8630°  6820°
MAY
Ocean 7826°
8932°  7323°
JUNE
Ocean 8228°
9133°  7423°
JULY
Ocean 8530°
9133°  7524°
AUGUST
Ocean 8730°
8932°  7323°
SEPTEMBER
Ocean 8529°
8529°  6719°
OCTOBER
Ocean 8228°
7926°  6016°
NOVEMBER
Ocean 7524°
7423°  5412°
DECEMBER
Ocean 6921°

Siesta Key condo rentals in gulf coast Florida's top barrier island

Siesta Key is a barrier island in the Gulf of Mexico, off the coast of Sarasota, Florida. It’s known for its sandy beaches and friendly locals. Fine white sand and gentle gulf breezes keep visitors coming back year after year. An ideal escape for a couple looking for romance, or a family looking to escape the Disney or Panama City crowds.

Siesta Key has amazing beach front with available rentals for you. When staying in one of our Siesta Key vacation rentals instead of hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Use the filters to narrow down your choices and choose the rental that calls to you.

Climate

Prevalent sunshine and gentle coastal breezes should be expected daily. Sounds incredible, right? Well, it is. With well over 300 sunny days per year, you’d be hard pressed to visit Siesta Key at a “bad time”. Low humidity makes the area comfortable, as well as warm. Bring your sunblock to protect against UV rays and don’t forget a few pairs of swim trunks, as the warm gulf waters are perfect for boogie boarding and bodysurfing.

Getting around

From November to September the Siesta Key Trolley will take you from the southernmost part of the island to the north end. The 3 open air trolleys run 7 days a week from 8-Midnight between Turtle Beach to Siesta Village. They will pass by about every 20-30 minutes. So don’t worry too much about getting around this small barrier island. Plus, bike or scooter rentals are everywhere -- so you can exercise while you move from beach to beach.

For those who drive, two bridges link the island to the mainland. The north bridge, Siesta Drive, is within the City of Sarasota and provides convenient access to the city, its business and arts districts, and to the Sarasota/Bradenton International Airport via US Highway 41. The south bridge, Stickney Point Road, provides access to south Sarasota County and a direct route to Interstate 75.

Top activities and attractions

Let’s be serious: you’re visiting Siesta Key for the pristine beaches along the 35 miles of coastline. Here are the names to remember: Siesta Beach, Turtle Beach, and Crescent Beach. Each features soft quartz sand and warm gulf seas. The sand is cool on your feet, so you can take an extended walk by the ocean without fear.

Siesta Beach has relatively shallow waters and it is monitored by lifeguards year-round. Plus, there’s plenty of room to spread out and enjoy a long, relaxing day. Turtle Beach is the most active (think volleyball net and horseshoe pits) while Crescent Beach is known for its seclusion and relaxed atmosphere.

Just off the southern tip of Crescent Beach is Point of Rocks, one of the best places for snorkeling and underwater exploration along the Gulf Coast beaches. It is made up of large chunks of limestone covered with coral and sponges and a range of sea life inhabit these underwater formations.

Bring your clubs here, too. With over 100 golf courses in the area you’ll want to take advantage of the sunny days out on the links. There’s ample opportunity for water sports for those who shun dry land. Visitors can find companies offering kayaking, paddle boarding, deep sea fishing and much more.

Just north of Siesta Beach, Siesta Key Village has many stores ranging from hip and funky to high-end boutiques and, of course, we wouldn't be a beach town without the beach accessory and souvenir shops.

Events 

If you love carefully constructed creations, visit in May for the sand castle competition. Local sand artisans and amateurs try their hand at creating jaw-dropping scenery out of sand.

Every Sunday there’s the Drum Circle featuring a cacophony of sound from various instruments performed by locals and tourists. Enjoy a stroll through the galleries of Palm Avenue on the first Friday of every month. In addition to fine galleries, this area along lower Main Street is known for its unique variety of shops and restaurants.

In April, the aptly named Siesta Fiesta takes place. Stroll along the beach while enjoying fine art and handmade crafts from 200 of the nation’s most talented artists and crafters. Showcasing an extensive collection of work ranging from life-size sculptures, spectacular paintings, one-of-a-kind jewels, photography, ceramics and more, this show truly has something for anyone. Complete with an additional green market, this spectacular show also features plants, body products, and tasty dips.

Siesta Key house rentals on FloridaRentals.com

Booking a condo for rent in Siesta Key on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!