Siesta Key Vacation Rentals

(222 rentals)
SIESTA KEY #1 voted Beach in America- property right on Siesta Key Beach

2 BR | 2 BA | Sleeps 6 | Quick View

2
Owner special: Fall discount 20% off any one week booking until Dec 21! Please contact us for special rates.

$163

per night

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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 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 LIVING ROOM SET, AND MASTER BEDROOM SET, INCLUDING NEW MATTRESS AND BOX ...

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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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Admirals Watch

3 BR | 3 BA | Sleeps 8 | Quick View

1

$354

per night

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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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Ventana Rosa – 1905

3 BR | 2 BA | Sleeps 10 | Quick View

Distance to beach: 2 miles to Shell Beach

$139

per night

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Key Amenities

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

About this property

Ventana Rosa - One of The Cottages on the KeyWelcome to Ventana Rosa, one of Siesta Key's newest luxury homes with private heated pool! Minutes to world famous Siesta Key Beach and Village!This luxurious and recently renovated (as of 2019) 3-bedroom/2-bathroom home is located in close proximity ...

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Property Type

Siesta Key House

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SIESTA KEY DIRECT GULF FRONT CLEAN/NEAT WKLY RENTALS SECURE WEB

$243

per night

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Key Amenities

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

About this property

If you are looking for a terrific vacation spot tastefully decorated, clean, and comfortable, you just found it. You can be as lazy as the sun and free as the Gulf breeze. We are not underselling ourselves when we say we have the 'Best Location' on 'Crescent Beach.' Experience the Gulf views, breezes, ...

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Property Type

Siesta Key Condo

"Great beachfront"
Reviewed February 4, 2019

Terrific location on Crescent Beach - just as beautiful as Siesta Beach but less busy. Comfortable and clean condo in secure building and complex. Even when evenings were cool or too windy, we enjoyed gorgeous ...

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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

$80

per night

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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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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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Sol y Mar

4 BR | 2 BA | Sleeps 8 | Quick View

$284

per night

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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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Casita Bayou

2 BR | 1 BA | Sleeps 6 | Quick View

$142

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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"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 21! 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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"Menorca" 378 Canal Rd.

Studio | 1 BA | Sleeps 2 | Quick View

3
Owner special: Fall discount 20% off any one week booking until Dec 21! Please contact us for special rates.

$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, 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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Isla Amor

4 BR | 3 BA | Sleeps 8 | Quick View

$604

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Isla Amor. An absolute one of kind, limited edition home located in the "heart of the Siesta Key" on the prestigous Palm Island (the island within the island). Featuring a private heated pool, near America's #1 Beach, on the Grand Canal with intracoastal bay access and a boat dock. ...

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Property Type

Siesta Key House

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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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The Seascape

8 BR | 9 BA | Sleeps 16 | Quick View

$1100

per night

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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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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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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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Latitude Adjustment

4 BR | 4 BA | Sleeps 10 | Quick View

$294

per night

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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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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

$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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MAGNOLIA 317-319

4 BR | 4 BA | Sleeps 12 | Quick View

6
Owner special: Fall discount 20% off any one week booking until Dec 21! Please contact us for special rates.

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

PRICE PER INDIVIDUAL UNIT. DUPLEX: 1 UPSTAIRS UNIT AND 1 DOWNSTAIRS UNIT. SHORT WALK TO VILLAGE, OR BEACH. PRIVATE HEATED POOL, TIKI HUT, GRILL, EACH UNIT HAS OWN WASHER AND DRYER IN UNIT, FULL KITCHENS, WALK TO GROCERY STORE, GIFT SHOPS, RESTURANT'S, ICE CREAM STORE AND BARS.

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Property Type

Siesta Key Apartment

"PERFECT"
Reviewed June 11, 2019

We stayed for two weeks! We had the up & downstairs so our entire family was able to enjoy the privacy of just our family being at the pool! This is absolutely our favorite place to stay, it’s close to ...

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Ocean’s Edge

4 BR | 4 BA | Sleeps 8 | Quick View

$550

per night

View Details

Key Amenities

  • Pool
  • Private Pool

About this property

Welcome to Ocean's Edge! A massive gulf front penthouse located right on Siesta Beach in a newly constructed building. With amazing views, a heated pool, and enough room to sleep up to 8, it is the only way to experience Siesta Key!Ocean's Edge is a luxuriously appointed penthouse in an extremely ...

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Property Type

Siesta Key Condo

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Spend Thanksgiving at the Beach-Autumn in Florida is the BEST!

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 600 yards to Siesta Key Beach

$127

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

There's plenty of room for everyone here at Our House. We have a split-level living area faces a large screen HDTV, so anytime you need a little downtime from all the outdoor fun, settle in with your favorite movie, a bowl of popcorn, and frosty drinks. The kitchen's just a few steps away, and it's got ...

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Property Type

Siesta Key Townhome

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Tropical beach getaway at Sandy's Siesta Key Condo

2 BR | 1.5 BA | Sleeps 4 | Quick View

3

Distance to beach: 200 yards to Crescent Siesta Key Beach

$127

per night

View Details

Key Amenities

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

About this property

Located in beautiful Siesta Key, Fl (consistently ranked #1 beach in the US!!) in Midnight Cove 1, this bayside condo spoils its occupant with all the amenities and luxuries needed for a relaxing, tropical vacation. Nestled amid lush landscaping in this gated community, our unit is newly remodeled and ...

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Property Type

Siesta Key Condo

"Sandy's siesta"
Reviewed October 21, 2018

This condo was perfect! It's absolutely beautiful, top end appliances, beautiful decor and all the comforts of home. The condo is close to the beach and pool. Totally worth it!

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La Contento Casa

3 BR | 2 BA | Sleeps 8 | Quick View

$385

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

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

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Property Type

Siesta Key House

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Casita Playa

2 BR | 1 BA | Sleeps 4 | Quick View

$143

per night

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Key Amenities

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

About this property

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

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Property Type

Siesta Key House

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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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The Grand Canal Cottage

5 BR | 4 BA | Sleeps 12 | Quick View

2

$495

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

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

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Property Type

Siesta Key House

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

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

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5 minutes to Paradise. Walk to the best beach in the nation!

$171

per night

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Key Amenities

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

About this property

Adorable spacious and privately located condo surrounded by tropical palm trees only a five minute walk to Crescent beach at the Point of Rocks. The perfect location for shelling and snorkeling or just basking in the sun on the south end of the public beach. You’ll feel like you’ve found ...

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Property Type

Siesta Key Condo

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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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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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"Everglades" 378 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

4
Owner special: Fall discount 20% off any one week booking until Dec 21! Please contact us for special rates.

$143

per night

View Details

Key Amenities

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

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNTED RATES!2 Bd/2 Bath, King Bed, Two queen beds, Open Deck, ground floor. Pool Access, WIFI, *W&D access, and ground floor.Local free shuttles so no need for a car.Located on the Voted number “#1 Beach in America” popular ...

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Property Type

Siesta Key House

"Perfection in Paradise"
Reviewed June 18, 2019

We stayed in this lovely condo for 10 nights, and enjoyed every minute.The condo was spotless when we arrived, and had all the amenities we needed with ample space.Right outside is the heated pool ...

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Siesta Dream House

4 BR | 3.5 BA | Sleeps 12 | Quick View

$254

per night

View Details

Key Amenities

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

About this property

One of Siesta Key's most alluring homes, with private heated pool & spa! Siesta Dream House is perfect for family get togethers and romantic getaways alike.Welcome to Siesta Dream House! This enchanting 4-bedroom/3.5-bathroom home is located in Siesta’s North Key and is close to Siesta Key ...

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Property Type

Siesta Key House

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Plumbago – 5251C

2 BR | 2 BA | Sleeps 4 | Quick View

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

$96

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Cottage

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Sophie’s Cottage

2 BR | 2 BA | Sleeps 8 | Quick View

$330

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key House

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"Village Resort" 318 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

2
Owner special: Fall discount 20% off any one week booking until Dec 21! 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!318 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

"Spotless property in great location"
Reviewed June 15, 2019

On a quiet street very near to the amenities.Lovely pool and bbq area.Just a short walk to the fab beach. Couldn't fault the property at all, everything was clean and of good standard. My only gripe would ...

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Beautifully Renovated 2 Bedroom 2 Bath Waterview Condo, Pools, Tennis, Gym

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Siesta Key

$171

per night

View Details

Key Amenities

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

About this property

NEWLY REMODELED - LUXURY WATERVIEW CONDO FOR COUPLES or Families GETAWAY - POOLS, GYM, TENNIS - Walk to beach, town, shopping, top restaurants, live music, and entertainment.Walk out of the front door of this fantastic condo, grab your beach gear and take a short walk and you'll hit the beach . ...

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Property Type

Siesta Key Condo

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The Hummingbird

6 BR | 6 BA | Sleeps 12 | Quick View

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

$286

per night

View Details

Key Amenities

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

About this property

Welcome to The Hummingbird, a delightful 6BR/6BA home with private heated pool! Located just steps from world famous Siesta Key Beach and Siesta Key Village This home is perfect for families and small groups.This private six bedroom/six bathroom home is a unique combination of four units: Lantana, ...

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Property Type

Siesta Key House

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Coral Breeze – 4576

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$385

per night

View Details

Key Amenities

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

About this property

This quaint 3-bedroom/2.5-bathroom home is located near Siesta Key Village and just five minutes from Siesta Key Beach, voted the # 1 beach in the USA! This home is ideal for small families and couples alike.Coral Breeze can accommodate up to 6 guests with a bedding configuration as follows:• ...

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Property Type

Siesta Key House

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Vinca – 5251D

1 BR | 1 BA | Sleeps 2 | Quick View

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

$71

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Cottage

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Renovated 4 bedroom directly on No 1 rated beach. Unobstructed views of gulf.

$508

per night

View Details

Key Amenities

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

About this property

December 2017 renovation expands fantastic views of beach, gulf and sunsets New windows, doors, bathrooms, floors, paint and landscaping A front row seat for the famous sands and sunsets of Siesta Key Step barefoot directly on to the award-winning, powdery sand of Crescent Beach Two of four bedrooms ...

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Property Type

Siesta Key House

"Doesn't get much better!"
Reviewed May 25, 2019

This amazing duplex is absolutely perfect for a family getaway! From the cute quiet brick street leading to the house, to the towels embroidered w/colorful fish, you won't be disappointed in the details ...

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Sea Winds 204

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 0.0 miles to Crescent Beach

$114

per night

View Details

Key Amenities

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

About this property

This 2 bedroom second-floor unit has a master bedroom with a king size bed and second bedroom with 2 twin beds. This unit has a pull out sofa sleeper and walk-in shower, heated pool, and coin laundry available. This 2 bedroom 2 bathroom is updated with granite counter tops in kitchen and bathroom. ...

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Property Type

Siesta Key Condo

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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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Tropical Escape 2 Br/2 B Siesta Key Inn #226

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: It's All About the Ambiance...Enjoy a peaceful week at Siesta Key Beach. Add flip flops & food.

$265

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. Resting just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach is our Tropical Siesta Key Inn. With no busy streets to cross, it's a leisurely stroll ...

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Property Type

Siesta Key Condo

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Casa Tegula

4 BR | 3 BA | Sleeps 12 | Quick View

1

$257

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 luxurious premier 4BR/3BA villas that features a private heated pool and cabana room. Casa Tegula is just steps from prestigious Crescent Beach and is centrally located in close proximity to world famous Siesta Key Beach and Village!Once inside the home, you ...

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Property Type

Siesta Key House

"Casa Tegula Review..."
Reviewed July 8, 2019

We LOVED Casa Tegula!!! The house was very clean and stocked with everything we needed. Location was wonderful, only a short walk to the ocean and shops. Sara at The Cottages on the Key was AMAZING and ...

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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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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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25% discount Hour is NOW. #1 USA BEACH SIESTA KEY ISLAND GLASS HOUSE

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 0.5 miles to SIESTA KEY BEACH, EASY ACCESS

$168

per night

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Key Amenities

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

About this property

******PRICE OF A HOTEL OFF THE ISLAND IS 165.00 A NIGHT.******PRICES SUBJECT TO CHANGE WITHOUT NOTICE! ..........BOOK NOW! *PRICE LISTED IS DISCOUNTED PRICE. -------------------------IMPORTANT------------------------------------------------------------ * YOU WILL NOT BE ...

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Property Type

Siesta Key House

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Gran Vista – 6906

6 BR | 4 BA | Sleeps 14 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$633

per night

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Key Amenities

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

About this property

Welcome to 6906 Coronas Park, one of Siesta Key's premier luxury townhomes with private heated pool and spa! Located just five minutes from Siesta Key Beach and Village!This massive and decadent 6-bedroom/4.5-bathroom townhome is located near Siesta Key Village and just five minutes from Siesta Key ...

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Property Type

Siesta Key House

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Deja Blue – 5288R

2 BR | 1 BA | Sleeps 6 | Quick View

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

$143

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

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

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Property Type

Siesta Key Bungalow

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Blue Lagoon Tropical Bungalow (2B/2B) - MONTHLY RENTAL

2 BR | 2 BA | Sleeps 6 | Quick View

2

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

$80

per night

View Details

Key Amenities

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

About this property

Our Blue Lagoon Bungalow - 2bed/2bath -Short walk to Beach & Vllage. Pecky cypress home with gorgeous refinished hardwood floors that shine like a piece of furniture. It has two bedrooms and two bathrooms. The large family room has a wall of sliding glass windows onto a deck with park benches that ...

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Property Type

Siesta Key Bungalow

"Perfect Pet-Friendly Winter Haven"
Reviewed February 26, 2019

We greatly enjoyed our 2 months in the Blue Lagoon cottage. Anyone considering Siesta Key will enjoy staying in any of the cottages offered by Rich and Ali Light. They are well-maintained. Rich and Ali ...

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Couples and Family Friendly. Some pet friendly units are available too.

1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 20 yards to Siesta Key Beach

$171

per night

View Details

Key Amenities

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

About this property

We are full turnkey condos. Our laundry facilities, gas grills around the pool, in unit cleaning supplies and dishwasher detergent are complementary. We are easily within walking distance to the Main Siesta Key beach (100 ft & across beach road to access #10) and the "Village"(most of the ...

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Property Type

Siesta Key Condo

"Awesome Rental"
Reviewed May 27, 2019

We stayed at Sea Spray rentals for a week April 2019. This is the nicest, cleanest rental we have ever stayed at and management was very accommodating.

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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!