Siesta Key Vacation Rentals

(207 rentals)
Playa y Blanca

Playa y Blanca

4 BR | 2 BA | Sleeps 10 | Quick View

$266

per night

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Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Communal Pool
  • Free WiFi

About this property

Welcome to Playa y Blanca! A combo of Casita Blanca & Casita Playa, the 4 bed/2 bath home sleeps up to 8, or you can book the 2 units separately. Surrounded by lush gardens with a private spa & beach access, there's also a shared heated pool. Welcome ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Beautiful Beach front condo

Beautiful Beach front condo

2 BR | 1 BA | Sleeps 1 | Quick View

$333

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Beachfront
  • Oceanfront
  • Communal Pool
  • Kid Friendly

About this property

Located on the beautiful white sand beach of Siesta Key. We are a short 5 minute walk to The Village of Siesta Key where you can find a wide selection of restaurants, and fun shopping. This is the perfect place to relax on the beach take a swim in the ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Ocean’s Edge- 4BR/4.5BA Beachfront Condo, Heated Pool, With Private Beach Access

$550

per night

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Key Amenities

  • Private Pool
  • Communal Pool
  • Free WiFi

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Siesta Salt Life

Siesta Salt Life

6 BR | 4 BA | Sleeps 16 | Quick View

$396

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Free WiFi

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Casa De Mariposa

Casa De Mariposa

6 BR | 6 BA | Sleeps 16 | Quick View

$396

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Beachfront
  • Communal Pool
  • Free WiFi

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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SIESTA KEY HEAVEN

SIESTA KEY HEAVEN

2 BR | 2 BA | Sleeps 4 | Quick View

$171

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront

About this property

WE WE HAVE THE ABSOLUTE BEST SPOT ON THE ABSOLUTE BEST BEACH! (Reuters, May 27, 2011) 7 day Sat to Sat minimum stay.You will not find a more-convenient location or a better view anywhere else on the key! To take a couple short tours, see more photos, and ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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West Shore - 4BR/4.5BA Beach Front Condo, Heated Pool, With Private Beach Access

$550

per night

View Details

Key Amenities

  • Private Pool
  • Communal Pool
  • Free WiFi

About this property

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

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Gulf Front with amazing sunsets and Free Boat Dock

$164

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Beachfront
  • Oceanfront
  • Communal Pool
  • Kid Friendly

About this property

A millionaire's retreat!  This completely remodeled first floor unit with view of the Gulf of Mexico and amazing sunsets awaits you on Siesta Key.  Walk out the lanai door directly to the beach where children can play within view, or walk over ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

"Right on the ocean"
Reviewed June 8, 2018

This condo was very nice and gave our family plenty of room to relax and have fun. Everything we needed was right there! Much better than being in a hotel. You could walk out the back door and be right ...

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"SITTING ON THE DOCK OF THE BAY" "Coastal Courtyard" 6151 Midnight Pass Rd.

"SITTING ON THE DOCK OF THE BAY" "Coastal Courtyard" 6151 Midnight Pass Rd.

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT! PLEASE CONTACT US FOR RATES.

$77

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Waterfront
  • Non-Smoking
  • No Pets Allowed
  • Managed by Property Manager
  • Free WiFi

About this property

1 Bedroom - 1 Bath, upstairs, king bed, queen sleeper sofa, loveseat, kitchenette. Open deck, combines with Peaceful Waters to make 2 Bedroom/2 Baths. WIFI, Pool Access

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Sophie’s Cottage

Sophie’s Cottage

2 BR | 2 BA | Sleeps 8 | Quick View

$196

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Pet Friendly
  • Free WiFi

About this property

Sophie’s Cottage is a smart, sophisticated upscale waterfront retreat with a private heated pool with sunshelf, boat dock, and a short walk to Siesta Key Beach. Ideally, it accommodates 6, but can easily sleep up to 8 with 2 private bedrooms, and ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Casita Blanca

Casita Blanca

2 BR | 1 BA | Sleeps 4 | Quick View

$146

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Communal Pool
  • Free WiFi

About this property

Welcome to Casita Playa of Playa y Blanca. This COMPLETELY RENOVATED, single level (2 BR/1BA - Master BR/1 Queen & 2nd BR/2 twins -sleeps 4) vacation home features private, gated beach access, a sparkling clean hot tub in a private, lush setting, a ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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The Grand Canal Cottage - One of The Cottages on the Key

$500

per night

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Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Free WiFi

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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

$164

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Non-Smoking
  • No Pets Allowed
  • Managed by Owner
  • Free WiFi

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 million dollar view. The intercoastal waterway, with its parade ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Seaside Cottage

Seaside Cottage

4 BR | 3 BA | Sleeps 10 | Quick View

1

$286

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Free WiFi

About this property

Welcome to Seaside Cottage! A 4 bedroom, 3 bathroom vacation home with a heated pool is across the street from the No. 1 beach in the world! Hop on the trolley or a bike for easy access to Siesta Village. Enjoy the best of island living! Welcome to Seaside ...

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Location Information

Siesta Key, Florida, 34242

Property Type

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

$485

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Beachfront
  • Communal Pool
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed

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, ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Admirals Watch

Admirals Watch

3 BR | 3 BA | Sleeps 8 | Quick View

$346

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Beachfront
  • Oceanfront
  • Communal Pool
  • Kid Friendly

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Sandy Seahorse Cottage

Sandy Seahorse Cottage

6 BR | 6 BA | Sleeps 16 | Quick View

$336

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Communal Pool
  • Free WiFi

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! ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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*All New Villa* #1 Beach USA~ Gulfside Condo - Siesta Key

$149

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Beachfront
  • Oceanfront
  • Communal Pool
  • Kid Friendly

About this property

Our villa is a tastefully furnished and fully equipped with state of the art kitchen on the widest part of Crescent (Siesta Key) Beach. The villa is located GULFSIDE just steps to the beach, no streets to cross, It is just two villas away and a short 20 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Villa

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Stunning Siesta Key Condo - Heated pool, Gulf/Bay

Inquire for rates

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed
  • Managed by Owner

About this property

Sea Club II, featured on HGTV's Beachfront Bargain Hunt! 5 minute walk to the beach. Gated complex. Our condo has just been remodeled with granite counter tops, stainless steel appliances, dishwasher, cabinets, new tile, new bathroom, and new furniture. ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Latitude Adjustment

Latitude Adjustment

4 BR | 4 BA | Sleeps 10 | Quick View

$286

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Free WiFi

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, ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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"Fiji" 378 Canal Rd.

"Fiji" 378 Canal Rd.

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT! PLEASE CONTACT US FOR RATES.

$97

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Private Pool
  • Communal Pool
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed
  • Managed by Property Manager

About this property

1 Bedroom King Bed, queen sleeper, screened porch. Pool Access, WIFI *W&D access, and ground floor.

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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The Pearl by the Sea

The Pearl by the Sea

4 BR | 3 BA | Sleeps 12 | Quick View

$232

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Pet Friendly
  • Free WiFi

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Siesta Key Condos - Gulf & Bay Club Bayside Condo

$111

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed
  • Managed by Property Manager
  • Free WiFi

About this property

The Siesta Key vacation condo rental is a one bedroom / one bathroom individually owned condominium at the Gulf and Bay Club Bayside and is furnished with the basic household items necessary for normal living. This unique Old Key West style condo is fully ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Villa Vista Mare

Villa Vista Mare

3 BR | 3 BA | Sleeps 10 | Quick View

1

$326

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Beachfront
  • Oceanfront
  • Communal Pool
  • No Pets Allowed
  • Free WiFi

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Town Home

"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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Juicy Mango Cabana

Juicy Mango Cabana

2 BR | 2 BA | Sleeps 6 | Quick View

$146

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Pet Friendly
  • Communal Pool
  • Free WiFi

About this property

Welcome to the Juicy Mango Cabana! This beautiful and vibrant 2 bedroom, 2 bathroom vacation home accommodates up to 6 people. Part of Mango Manor, Juicy Mango Cabana can be reserved alone or along with Honey Mango Cabana for big families or groups. Welcome ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Sand Dollar Cottage

Sand Dollar Cottage

3 BR | 2 BA | Sleeps 8 | Quick View

$179

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Free WiFi

About this property

Welcome to Sand Dollar Cottage! This lovely 3 bedroom, 2 bath north Siesta Key vacaiton home comfortably sleeps 6 in beds, with a soft ultra plush sofa sleeper in the living room for an extra 2. Enjoy heated pool and waterview of Intracoastal canal. Welcome ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Casita Playa

Casita Playa

2 BR | 1 BA | Sleeps 4 | Quick View

$146

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Communal Pool
  • Free WiFi

About this property

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

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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"Village Resort" 316 Canal Rd.

"Village Resort" 316 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT! PLEASE CONTACT US FOR RATES.

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Kid Friendly
  • Non-Smoking
  • Managed by Property Manager

About this property

(downstairs) - 2 bed/ 2 bath- 1 king, 1 queen, queen sleeper, private laundry room, full kitchen including DW, heated pool, great back yard for BBQ and gathering.

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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La Casa Verde

La Casa Verde

4 BR | 2 BA | Sleeps 10 | Quick View

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Free WiFi

About this property

The waterfront cottage, ‘La Casa Verde’ is a very luxurious and large four [4] bedroom canal front heated pool home with two very large bathrooms in approximately 2,800 square feet of air conditioned living space. As you approach the home you ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Just steps to #1 voted beach, restaurants, grocery’s, shops, bars & ice cream!

Just steps to #1 voted beach, restaurants, grocery’s, shops, bars & ice cream!

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT! PLEASE CONTACT US FOR RATES.

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Communal Pool
  • Kid Friendly
  • Non-Smoking

About this property

322 Canal Rd - Village resort (upstairs) - 2 bed/ 2 bath- 1 king, 1 queen, queen sleeper, private laundry room, full kitchen including DW, heated pool, great back yard for BBQ and gatherings. Combine all four units at this location for Family reunions.

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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12% OFF NOV & DEC - Beautiful Condo, walk to Siesta Key Beach! 2 weeks minimum

12% OFF NOV & DEC - Beautiful Condo, walk to Siesta Key Beach! 2 weeks minimum

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 0.5 miles to Siesta Key Beach

$90

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Non-Smoking
  • No Pets Allowed
  • Managed by Owner
  • Free WiFi

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 double beds in second bedroom. New porcelain wood-look floors, new kitchen ...

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Location Information

Siesta Key, Florida, USA

Property Type

Condo

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Serenity Cottage

Serenity Cottage

3 BR | 3.5 BA | Sleeps 8 | Quick View

$206

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Free WiFi

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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

$243

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Beachfront
  • Oceanfront
  • Communal Pool
  • Kid Friendly

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Breathtaking Beachfront "House of the Sun" Rental

Breathtaking Beachfront "House of the Sun" Rental

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 200 feet to Crescent Beach

$171

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Wheelchair Accessible
  • Full Kitchen
  • Beachfront
  • Communal Pool
  • Kid Friendly
  • Non-Smoking

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Siesta Key Beachfront Condo with Gulf View!

$135

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Beachfront
  • Communal Pool
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

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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"Key West" 378 Canal Rd.

"Key West" 378 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT! PLEASE CONTACT US FOR RATES.

$151

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed
  • Managed by Property Manager
  • Free WiFi

About this property

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 shuttles so no need ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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The Solaster

The Solaster

6 BR | 6 BA | Sleeps 20 | Quick View

$396

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Free WiFi

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Elegant Privately Owned Siesta Key Gulf-Front Condo

$125

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Wheelchair Accessible
  • Full Kitchen
  • Private Pool
  • Communal Pool
  • Kid Friendly
  • No Pets Allowed

About this property

AAA 2-DIAMOND RATED & TRIP ADVISOR RECOMMENDEDLocated at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta ...

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Location Information

Siesta Key, Florida, USA

Property Type

Condo

"Siesta Key Trip with Friends"
Reviewed September 10, 2018

The condo was very comfortable and very clean. Location was great. We walked across the street and had our morning walk on the beach every day. The pool was beautiful. Overall, a very nice place to stay. ...

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Large 1300sqft 2BR2BA 4th Floor Siesta Key Crescent Beach WiFi No Road to Cross

Large 1300sqft 2BR2BA 4th Floor Siesta Key Crescent Beach WiFi No Road to Cross

2 BR | 2 BA | Sleeps 5 | Quick View

10

Distance to beach: 100 yards to Siesta Key Crescent Beach

$161

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Beachfront
  • Oceanfront

About this property

***This Condo is for sale, if interested call Peg Davant, Premier Sotheby's Realty Sarasota Downtown and ask for info on Excelsior 406 or email me for phone number*** See Below for Availability from Now until Apr 2019... Ask for Last Minute Discounts ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

"Beautiful siesta key vacation!"
Reviewed August 15, 2018

Condo at Excelsior was equiped with everything you needed for a wonderful beach vacation! It felt like home away from home. The 4th floor unit which was on the gulf side was very spacious and clean. ...

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"Menorca" 378 Canal Rd.

"Menorca" 378 Canal Rd.

Studio | 1 BA | Sleeps 2 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT! PLEASE CONTACT US FOR RATES.

$81

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Private Pool
  • Non-Smoking
  • No Pets Allowed
  • Managed by Property Manager
  • Free WiFi

About this property

Studio/Efficiency, Queen Bed, Next to pool. Pool Access, WIFI *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, Florida, the perfect ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Studio

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"Everglades" 378 Canal Rd.

"Everglades" 378 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT! PLEASE CONTACT US FOR RATES.

$143

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed
  • Managed by Property Manager

About this property

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 Siesta Key in Sarasota, ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Honey Mango Cabana

Honey Mango Cabana

2 BR | 1 BA | Sleeps 6 | Quick View

$136

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen

About this property

Welcome to the Honey Mango Cabana! This beautiful and vibrant 2 bedroom, 1 bathroom vacation home accommodates up to 6 people. Part of Mango Manor, Honey Mango Cabana can be reserved alone or along with Juicy Mango Cabana for big families or groups. Welcome ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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"Village Resort" 318 Canal Rd.

"Village Resort" 318 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT! PLEASE CONTACT US FOR RATES.

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Communal Pool
  • Kid Friendly
  • Non-Smoking

About this property

(upstairs) - 2 bed/ 2 bath- 1 king, 1 queen, queen sleeper, private laundry room, full kitchen including DW, heated pool, great back yard for BBQ and gathering.

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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"Tropical Tree House" 6151 Midnight Pass Rd.

"Tropical Tree House" 6151 Midnight Pass Rd.

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT! PLEASE CONTACT US FOR RATES.

$81

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Non-Smoking
  • No Pets Allowed
  • Managed by Property Manager
  • Free WiFi

About this property

1 Bedroom - 1 Bath, upstairs (over carport) full kitchen. King bed, Queen sleeper sofa, living room opens to screened porch. WIFI, heated Pool .

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Fishermans Cove A302

Fishermans Cove A302

2 BR | 2 BA | Sleeps 6 | Quick View

2

$164

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Beachfront
  • Oceanfront
  • Communal Pool
  • Kid Friendly

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

"Amazing!"
Reviewed July 2, 2018

This Condo was everything and more! The owner was so helpful and such a sweet lady! Will most definitely be renting from her again! We loved how close you are to the beach and water! It's so peaceful and ...

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Mango Manor

Mango Manor

4 BR | 3 BA | Sleeps 12 | Quick View

$266

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Kid Friendly
  • Free WiFi

About this property

Welcome to the Mango Manor! A beautiful and vibrant 4 bedroom, 3 bathroom vacation home with a heated pool accommodates up to 12 people. The attractive property, a combination of Honey Mango Cabana & Juicy Mango Cabana, is perfect for large families. Welcome ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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"Village Resort" 320 Canal Rd.

"Village Resort" 320 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT! PLEASE CONTACT US FOR RATES.

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Communal Pool
  • Kid Friendly
  • Non-Smoking

About this property

(downstairs) - 2 bed/ 2 bath- 1 king, 1 queen, queen sleeper, private laundry room, full kitchen including DW, heated pool, great back yard for BBQ and gathering.

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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

$206

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • 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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Town Home

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Sea the View

Sea the View

4 BR | 3 BA | Sleeps 10 | Quick View

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Free WiFi

About this property

Welcome to Sea the View! This luxurious and exquisite home features 4 bedrooms and 3 full baths, a heated pool and spa, overlooking gorgeous water views of the grand canal, with easy access to Bay and Gulf by boat, and so very close to Siesta Key Beach! ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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

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

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT! PLEASE CONTACT US FOR RATES.

$163

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Beachfront
  • Communal Pool
  • Kid Friendly
  • Non-Smoking

About this property

This is a 2 Bedroom / 2 Bath unit on the Beach and within walking distance to the south Village This unit has its own washer and dryer, a full kitchen, sleeper sofa in the living room and a Balcony to watch the sunsets. This unit has Cable TV & WI-FI. ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Siesta Key Vacation Rentals

Local 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!