Siesta Key Vacation Rentals

(221 rentals)
Carefree Sunny Fun! 1 Br Siesta Palms by the Beach #2A

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 150 yards to Siesta Key, Crescent Beach

$214

per night

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Key Amenities

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

About this property

Welcome to the Siesta Palms by the Beach! Owned and operated on site by the Koch Family since 1979 (we are not an investor owned property). This Tropical Beach Get-away offers condos just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach. With no busy streets ...

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Property Type

Siesta Key Condo

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Beach Time! - 2Br/2B Siesta Key Inn #225

$265

per night

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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 invite you to relax, unwind and enjoy our casual Siesta Key way of life. The Siesta Key Inn is just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach at Point of Rocks. With no streets to cross, it's 75 steps to the Gulf ...

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Property Type

Siesta Key Condo

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The Canopy Cottage

4 BR | 3 BA | Sleeps 9 | Quick View

$330

per night

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Key Amenities

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

About this property

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

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Property Type

Siesta Key House

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Vacation Paradise to Stroll the Beach....Siesta Palms by the Beach #1D

1 BR | 1 BA | Sleeps 4 | Quick View

1

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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Siesta Key Inn 3Br/2B Sea Dream #223

3 BR | 2 BA | Sleeps 6 | Quick View

Owner special: Book your get away Now in this spacious Siesta Key fully equipped condo with a concierge touch.

$295

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • 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 Key Inn. With no busy streets ...

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Property Type

Siesta Key Condo

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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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Casita Coco

1 BR | 1 BA | Sleeps 4 | Quick View

1

$71

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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Sunset Fiesta

4 BR | 2 BA | Sleeps 12 | Quick View

$257

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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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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Breathtaking Beachfront "House of the Sun" Rental

2 BR | 2 BA | Sleeps 6 | Quick View

4

Distance to beach: 200 feet to Crescent Beach

$179

per night

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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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BEAUTY AT THE BEACH--Full front Gulf view!! Crescent Arms 601S

$225

per night

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Key Amenities

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

About this property

THE BEACH IS CALLING AND I MUST GO!! *We invite you to come stay with us in the Crescent Arms South Tower--Condo 601S--directly on the #1 famous Crescent Beach with a FULL view of the Gulf on a private 32 foot lanai.*Decorated in a "beachy motif" with granite counter tips in the kitchen ...

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Property Type

Siesta Key Condo

"safe, secure, phenomenal ocean viewing from your lanai,"
Reviewed January 13, 2020

wonderful set up for a friendly get away. the lanai with the full open front to the ocean was wonderful. having your own bathroom attached to your bedroom, full kitchen with a good sized living room was ...

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Playa y Blanca

4 BR | 2 BA | Sleeps 10 | Quick View

$287

per night

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Key Amenities

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

About this property

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

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Property Type

Siesta Key House

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“SANDPIPER” Siesta Key Beach -Vote #1 beach in America with crystal quartz sand

1 BR | 1 BA | Sleeps 4 | Quick View

9
Owner special: END OF SEASON DISCOUNT: 10% OFF FROM 4/11-4/18

$115

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Pool

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNTS RATES!VOTED #1 BEACH IN AMERICA! JUST MINUTES TO YOUR DOOR WAY. THREE POOLS, SHUFFLE BOARD, GRILLS, PRIVATE BEACH AREA, LAUNDRY FACILITIES, PATIO FOR COOKING AND EATING OUTDOORS. SHORT WALK TO SOUTH VILLAGE WITH RESTAURANTS, GROCERY STORE, NIGHT ...

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Property Type

Siesta Key Condo

"Sandpiper #23"
Reviewed January 8, 2020

The property was generally in good shape, clean and made for a pleasant stay. We also felt safe and the property was fairly priced.

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Casita Blanca

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 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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The Lily Patch Bungalow - MONTHLY RENTAL

2 BR | 2 BA | Sleeps 4 | Quick View

2

Distance to beach: 0.4 miles to Beach access 10 of Siesta Beach

$214

per night

View Details

Key Amenities

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

About this property

Situated in the quiet and secluded neighborhood of Palm Island, the Lily Patch is a cozy pecky cypress bungalow with two bedrooms and two bathrooms. Hardwood floors throughout add to its charm. Double sets of double French doors lead from the living and dining rooms onto the large private Mexican tiled ...

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Property Type

Siesta Key Bungalow

"The Lily Pad...a piece of paradise to cherish"
Reviewed February 26, 2019

The location offers you incredible privacy and easy access to the Siesta Key village and Sarasota proper.This is a great family-friendly bungalow that allows you to bring the family dog with added room ...

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Mimosa – 5251B

1 BR | 1 BA | Sleeps 2 | Quick View

1

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

$71

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key House

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

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

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"Menorca" 378 Canal Rd.

Studio | 1 BA | Sleeps 2 | Quick View

3
Owner special: END OF PRIME SEASON SPECIAL: 4/11-4/18 10% OFF!

$81

per night

View Details

Key Amenities

  • Air Conditioning
  • Private Pool

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNTED RATES!Studio/Efficiency with Queen Bed, Next to pool. Pool Access, WIFI *FREE W&D* access, ground floor. Local free shuttles so no need for a car.Located on the Voted number “#1 Beach in America” popular Siesta Key in Sarasota, ...

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Property Type

Siesta Key Studio

"Nice visit"
Reviewed June 13, 2019

We love the location of the rental and the friendly staff. During the last two times we stayed with the Banyan Tree on Canal ,the pool temperature could have been warmer and consistently warmer morning ...

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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

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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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Casita Bayou

2 BR | 1 BA | Sleeps 6 | Quick View

$129

per night

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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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Pinacolada

3 BR | 3 BA | Sleeps 8 | Quick View

$186

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

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

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Property Type

Siesta Key Townhome

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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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Monarch Villa

3 BR | 3 BA | Sleeps 9 | Quick View

$214

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

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

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Property Type

Siesta Key House

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Only on Siesta! Siesta Palms by the Beach #2C

2 BR | 2 BA | Sleeps 4 | Quick View

Owner special: Relax & Unwind - Take a beach vacation to Siesta Key in our spacious fully equipped condo!

Distance to beach: 150 yards to Siesta Key, Crescent Beach

$243

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

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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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Avail in March *Fantastic Bay View Condo* Siesta Key #1 Beach of the US

2 BR | 1.5 BA | Sleeps 4 | Quick View

Owner special: BOOK NOW! Availability from March 21 through April 30 - Escape the cold - Enjoy our sunny beaches

$125

per night

View Details

Key Amenities

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

About this property

Vacation rental with private beach on the # 1 beach in the USA - Siesta Key on the Gulf of Mexico (Sarasota)Siesta Key, awarded for its pristine, powdery white beaches and its azur blue waters is the perfect escape from everyday life.Whether you are looking for a perfect destination for your vacation, ...

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Property Type

Siesta Key Apartment

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Siesta Key Beachfront Condo with Gulf View!

$135

per night

View Details

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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Sandpiper Cottage

5 BR | 5 BA | Sleeps 14 | Quick View

Distance to beach: 0.8 miles to Crescent Beach

$275

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Cottage

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Siesta Salt Life

6 BR | 4 BA | Sleeps 16 | Quick View

1

$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

"Wow !!! Best place to stay."
Reviewed October 28, 2019

Your villa was just amazing. The villas were very clean and very spacious. I felt like it was home. Everything you need to go on vacation, it was there for you from linens to beach towels and chairs ,bikes. ...

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Fishermans Cove A302

2 BR | 2 BA | Sleeps 6 | Quick View

3

$164

per night

View Details

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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SIESTA KEY #1 voted Beach in America- property right on Siesta Key Beach

2 BR | 2 BA | Sleeps 6 | Quick View

2
LAST MINUTE DEAL 1/25 - 2/1: LAST MINUTE DISCOUNT: 25% off Jan 25- Feb 1.

$163

per night

View Details

Key Amenities

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

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNTED RATES! This rental has a 2 week minimum stay during the prime winter season.This is a 2 Bedroom / 2 Bath unit on the Beach and within walking distance to the south Village. Just steps away from the beach! JUNE 2019- WE JUST INSTALLED A NEW ...

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Property Type

Siesta Key Condo

"Excellent choice"
Reviewed July 30, 2019

We stayed 1 week and everything was perfect. Great location, great accommodation and anything you need is within minutes away. It is definitely my home away from home. Looking forward to booking next year.

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DEAL
Tropical Resort-Like Oasis! 1 Br Siesta Key Inn #123

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: Need Sunshine? Plan your Great Escape to Siesta Key - we have your beach chair ready....

$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 invite you to relax, unwind and enjoy our casual Siesta Key way of life. The Siesta Key Inn is just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach at Point of Rocks. With no streets to cross, it's 75 steps to the Gulf ...

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Property Type

Siesta Key Condo

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MAGNOLIA 317-319

4 BR | 4 BA | Sleeps 12 | Quick View

7
LAST MINUTE DEAL 1/25 - 2/1: CANCELED BOOKING DISCOUNT: 25% OFF JANUARY 25th TO FEBRUARY 1st.

Distance to beach: 0.3 miles to SIESTA KEY BEACH

$167

per night

View Details

Key Amenities

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

About this property

ONE UNIT STILL AVAILABLE FOR JANUARY, 2020! PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNTS RATES! PRICE PER INDIVIDUAL UNIT. THE SECOND FLOOR UNIT IS NOW AVAILABLE FOR JANUARY 2020! DUPLEX: 1 FIRST FLOOR 2 BED/ 2 BATH UNIT AND 1 SECOND FLOOR 2 BED/ 2 BATH UNIT. SHORT WALK TO VILLAGE ...

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Property Type

Siesta Key Apartment

"Excellent location, great pool!"
Reviewed January 7, 2020

Magnolia House is superbly located yards from Siesta Key Village and only 200 yards from the beach. It is split into two apartments which is great for two families. The pool is warm and a good size and ...

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DEAL
Direct Beachfront Gulf Condo

2 BR | 2 BA | Sleeps 6 | Quick View

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Pool

About this property

Direct Beachfront Condo on the Gulf of Mexico located on Siesta Key. 2 bed, 2 bath condo loaded with amenities. Just remodeled, completely new, finished with tile flooring, granite counters, stainless appliances, washer and dryer and all new furniture. Both Bedrooms have king beds and separate baths. ...

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Property Type

Siesta Key Condo

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The Nautilus

8 BR | 6 BA | Sleeps 24 | Quick View

2

$529

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

"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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Best Of Both Worlds- Direct View Of Intercoastal Waterway and Walk to Beach

$179

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

You have access to a private deeded walkway from your condo to the white sand and turquoise waters of Siesta Beach/Crescent Beach while living directly on the intercoastal waterway with a great view. The intercoastal waterway, with its parade of all types of boats and dolphins swimming by, is visible ...

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Property Type

Siesta Key Condo

"Wonderful accommodations! The intercostal location and views are spectacular!!"
Reviewed January 15, 2020

Great place to stay for a couple and day visits with family and friends. Close to Siesta Key, beach, restaurants and things to do.

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Closest Condo to the Gulf of Mexico on Siesta Key - Direct Oceanfront

2 BR | 2 BA | Sleeps 6 | Quick View

18

Distance to beach: 0.0 feet to We are directly on the beach and direct oceanfront

$171

per night

View Details

Key Amenities

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

About this property

Our condo is directly on the beach and is direct oceanfront (Gulf-front). Unfortunately, there are properties on this site that falsely claim to be beachfront / oceanfront. We encourage travelers to ask property owners to verify those claims.When we travel over 1,000 miles to enjoy a beach vacation ...

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Property Type

Siesta Key Condo

"Absolutely stunning, perfect vacation rental"
Reviewed September 14, 2019

First of all, I want to say that dealing with Paul, the owner, was the best experience I have ever had interacting with a vacation renter. He goes far above and beyond to answer questions, provide information ...

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"Village Resort" 316 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

3
Owner special: OFF SEASON SPECIAL: 10% DISCOUNT FOR 5/16-5/23

$151

per night

View Details

Key Amenities

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

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNT RATES!316 Canal Rd - Village Resort Just steps to #1 voted beach, restaurants, grocery’s, shops, bars & ice cream! (downstairs) - 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

"Location and quiet environment with clean conditions"
Reviewed June 10, 2019

We have stayed at the Banyan Tree Resort Properties for about 20 years. The management and properties have all been very efficient and comfortable. We enjoy the Village and the location of the properties.

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Coconut Grove

6 BR | 6 BA | Sleeps 16 | Quick View

$371

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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Quiet Luxury Siesta Key Village

$214

per night

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Key Amenities

  • Air Conditioning
  • Private Pool
  • Rentals by Owner

About this property

Enjoy all the comforts in this cozy 2 Bedroom 1 bath Luxury Siesta Key Village location private villa. Brand new top notch furnishings and decor with king size select comfort bed and washer dryer in unit. Beautiful private heated pool and grill for use. Includes off street parking, internet and premium ...

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Property Type

Siesta Key Villa

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"Village Resort" 322 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

2
LAST MINUTE DEAL 1/25 - 2/1: LAST MINUTE DISCOUNT! 25% OFF FROM JANUARY 25TH TO FEBRUARY 1ST.

$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!322 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

"Great location for a relaxing stay!"
Reviewed June 6, 2019

Rental was very clean and well stocked with towels, kitchen items, and even beach towels and folding beach chairs. Location is great for a relaxing and walking to the beach and village. Enjoy seeing ...

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DEAL
Sea Wave Casita

2 BR | 2 BA | Sleeps 6 | Quick View

2

$125

per night

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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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Honeysuckle

3 BR | 3 BA | Sleeps 6 | Quick View

$143

per night

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Key Amenities

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

About this property

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

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Property Type

Siesta Key House

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Vinca – 5251D

1 BR | 1 BA | Sleeps 2 | Quick View

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

$71

per night

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Key Amenities

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

About this property

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

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Property Type

Siesta Key Cottage

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Sweet Island Beauty Just Steps to Beach! Siesta Key Inn #124

1 BR | 1 BA | Sleeps 4 | Quick View

LAST MINUTE DEAL 1/19 - 3/1: Book your Tropical Escape now to the white sand beaches on Siesta Key! Filling up fast.

$199

per night

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Key Amenities

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

About this property

Welcome to our Beach Get-away...where we invite you to relax, unwind and enjoy our casual Siesta Key way of life. The Siesta Key Inn is just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach at Point of Rocks. With no streets to cross, it's 75 steps to the Gulf ...

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Property Type

Siesta Key Condo

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DEAL
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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Sea Grape Cottage

5 BR | 3.5 BA | Sleeps 12 | Quick View

2

$286

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 Islander – 6931

4 BR | 4 BA | Sleeps 12 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$468

per night

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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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Beautifully renovated condo, walk to Siesta Key Beach!

2 BR | 2 BA | Sleeps 4 | Quick View

2

Distance to beach: 0.5 miles to Siesta Key Beach

$100

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

Newly Renovated Vacation Rental on Siesta Key. Fully furnished, 2 bedroom/2 bathrooms in the prestigious Harbor Towers Yacht & Racket Club. Condo sleeps 4. King Bed in Master, 2 twin beds in second bedroom. New porcelain wood-look floors, new kitchen appliances, beautifully furnished, cable TV and ...

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Property Type

Siesta Key Condo

"Nice Condo"
Reviewed June 7, 2019

Nice clean condo, nice location (2 minutes drive from the free beach parking), nice gated complex with harbor view, pool, tennis courts.

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Charming! Siesta Palms by the Beach #1A

1 BR | 1 BA | Sleeps 4 | Quick View

LAST MINUTE DEAL 1/19 - 3/1: Soak up the Florida Sunshine on Siesta Key! Email for last minute January weekly rates.

$214

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 no ...

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Property Type

Siesta Key Condo

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DEAL
Plumbago – 5251C

2 BR | 2 BA | Sleeps 4 | Quick View

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

$96

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Cottage

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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!