Siesta Key Vacation Rentals

(350 rentals)
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203 Gulf Front Apartment

1 BR | 1 BA | Sleeps 4 | Quick View

$231

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This 1 bedroom Apartment is centered on the second floor it has a king bed in the master bedroom a sleeper sofa in the living room, enjoy lunch on the screened in Lanai over looking the Gulf of Mexico. The kitchen has recently been updated this unit features Flat screen TV's and private wireless for ...

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Property Type

Siesta Key Apartment

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Siesta Key Beach Private Pool Home

3 BR | 3 BA | Sleeps 6 | Quick View

1

Distance to beach: 200 feet to Siesta Key Public Beach

$289

avg/night

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Key Amenities

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

About this property

Single family home with private heated caged pool. Large open floor plan in living area to kitchen and enclosed pool and deck. 3 bedrooms, 2 of which are master suites with ensuite full baths, flat screen TV's, king beds, and sliding glass doors to either caged pool deck or open air sundeck. 3rd bedroom ...

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Property Type

Siesta Key House

"Siesta Key"
Reviewed July 4, 2020

We are a family of 6 spending time together in this beautiful house. Very clean and confortable home, walking distance to the beach. We are in love with everything in this area. Thanks to Cindy and ...

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

2 BR | 2 BA | Sleeps 6 | Quick View

20

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

$249

avg/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

"Lovely"
Reviewed March 7, 2021

Fresh clean updated condo with beach amenities. Walking, biking, kayaking added up to a lovely week.

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Mermaids Lookout - Ask About $99 Down!

4 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$468

avg/night

View Details

Key Amenities

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

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Sweet Tranquility! Siesta Key Inn Royal Palm #1B

2 BR | 2 BA | Sleeps 5 | Quick View

Owner special: Time to book your next Siesta Key Beach vacation! Comfy condo, Sunshine, blue skies, beach and pool.

$316

avg/night

View Details

Key Amenities

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

About this property

Welcome to the Siesta Key Inn! 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 to cross, ...

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Property Type

Siesta Key Condo

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Home away from home

2 BR | 2 BA | Sleeps 6 | Quick View

$243

avg/night

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Key Amenities

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

About this property

This two bedroom(master King bed), second bedroom double bed/ single bed (with pull out trundle) full kitchen, dining, living room and lanai open into living space. Out back you sit on the bay and across the street is number 1 beach in the U.S. Pool heated year round 80 degrees, grill areas and laundry ...

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Property Type

Siesta Key Condo

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Deluxe 2-BR Siesta Key Townhouse - Heated Pool - Siesta Key Village 2BR 5239

$243

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

SEASIDE VILLAS: This Siesta Key deluxe 2-Bedroom townhouse rental is located in the heart of Siesta Village – just steps to all the shops and restaurants and only a three minute walk to world famous Siesta Key Crescent Beach! Siesta Village has dozens of shops, fine or casual dining, pubs and clubs, ...

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Property Type

Siesta Key Townhome

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Casa Blanca D08 Villa

1 BR | 1 BA | Sleeps 4 | Quick View

$162

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to your home away from home! Casa Blanca unit D08 was entirely renovated at the end of 2015. Everything inside is brand new and beautifully updated. Features include a king size bed, walk-in shower, new furniture, new appliances, and brand new tile throughout. Casa Blanca is within walking distance ...

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Property Type

Siesta Key Villa

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Breathtaking Beachfront "House of the Sun" Rental

2 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to beach: 200 feet to Crescent Beach

$191

avg/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

"Paradise"
Reviewed February 9, 2020

I stayed in a dream come true condo. It was right on the ocean with a view to know your socks off. Be able to leave the sliding doors open( because the lanai was screened in) was heavenly , being able to ...

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Casa Blanca B06 Villa

2 BR | 2 BA | Sleeps 6 | Quick View

$210

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

2 Bedroom/ 2 Bath Large Private Villa, Close to Pool, Clubhouse, and Laundry. A few Steps to our Private Beach.Additional person fees may apply.

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Property Type

Siesta Key Villa

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Mandevilla - Ask About $99 Down!

3 BR | 3 BA | Sleeps 10 | Quick View

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

$272

avg/night

View Details

Key Amenities

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

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key Villa

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Vacation Paradise to Stroll the Beach....Siesta Key Inn Pineapple Palm#1D

1 BR | 1 BA | Sleeps 4 | Quick View

2
Owner special: Wishing you were at Siesta Key Beach with sand between your toes? We have a deal for you.

Distance to beach: 150 yards to Siesta Key Crescent Beach

$222

avg/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 Key Inn. With no busy streets ...

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Property Type

Siesta Key Condo

"House of sun"
Reviewed February 1, 2020

House of sun is everything you need for a perfect vacation . If your not in the mood for a beach day relax on the roof deck wich has an awesome view and Is very peaceful . Shops and restraints across the ...

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Beach, Beach, Beach! 1 BR Siesta Key Inn Pineapple Palm #2D

1 BR | 1 BA | Sleeps 4 | Quick View

2
Owner special: Book a Beach Get-Away Now in this spacious Siesta Key fully equipped condo with a concierge touch.

Distance to beach: 150 yards to Siesta Key Crescent Beach

$231

avg/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 Siesta Palms 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 ...

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Property Type

Siesta Key Condo

"Paradise by the beach!"
Reviewed November 20, 2020

We loved staying at this beautiful condo! Communication from the beginning was great- from the detailed initial response to the check-in and check-out process. We can't say enough about how this family ...

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Fishermans Cove A302

2 BR | 2 BA | Sleeps 6 | Quick View

4

$198

avg/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

"AMAZING view!"
Reviewed July 6, 2020

This condo has it all! This is the first condo I have ever stayed at that had ALL the kitchen utinsels you could ever need (minus and Instant Pot, but it does have a crockpot)! The view makes it seem ...

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Beach Time! - 2Br/2B Siesta Palms Sea Escape#225

2 BR | 2 BA | Sleeps 5 | Quick View

1
Owner special: Longing for that feeling of powdery white Siesta Key sand between your toes? We have a deal for you.

$304

avg/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 Palms by the Beach 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 ...

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Property Type

Siesta Key Condo

"Wonderful"
Reviewed December 1, 2020

We absolutely loved it here. Everything was so nice. The room was so clean and decorated nice. All the furniture was so comfortable. We slept so good every night. The pool and hot tub was really nice and ...

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Casa Blanca A 06 Villa

2 BR | 2 BA | Sleeps 6 | Quick View

$210

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Enjoy a perfect vacation in this spacious 2 bedroom, 2 bath large villa. With 2 Queen and 2 Twin beds, this is the perfect villa even for a large family up to 6. From this villa, you are just steps to Crescent Beach - world renowned whitest sand. Enjoy Wi-Fi community internet access, a 32" flat ...

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Property Type

Siesta Key Villa

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Beachy Keen – 302L

3 BR | 3 BA | Sleeps 8 | Quick View

$354

avg/night

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Key Amenities

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

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key House

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Only on Siesta! Siesta Key Inn Majesty Palm #2C

2 BR | 1 BA | Sleeps 4 | Quick View

Owner special: Soak up the Florida Sunshine on Siesta Key! Filling up fast - email for availability.

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

$269

avg/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 Key Inn, it's a leisurely ...

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Property Type

Siesta Key Condo

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Sweet Island Beauty Just Steps to Beach! Siesta Palms Sea Gem #124

1 BR | 1 BA | Sleeps 4 | Quick View

1
Owner special: Relax and Unwind - take a Beach Vacation to Siesta Key Inn our fully equipped condo!

$212

avg/night

View Details

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 Palms by the Beach 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 ...

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Property Type

Siesta Key Condo

"Beautiful Condo, minutes from beach!"
Reviewed February 5, 2020

We loved the Siesta Key Inn. Kind people to deal with, very nice accommodations, so many perks with condo rental, soap, paper towel, sunscreen, coffee, tissue paper, supplies, and so much more. We will ...

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Midnight Cove 2 Bed With Den & Water Views; Private Beach!

$190

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Water, water everywhere! Spacious, spectacular and nicely decorated third floor 2 bedroom/2 bath with den; corner unit, light and bright overlooking the intra-coastal waterway. Watch the boats glide by! Only a brief walk across road to a private piece of world famous Crescent Beach with beach chair ...

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Property Type

Siesta Key Condo

"Wonderful!"
Reviewed April 29, 2021

The apartment is amazing! Very spacious, very quiet and super clean. It is on the third floor of the unit so you feel safe and secure. There is a huge screened terrace facing north to the bay (very good ...

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Villa Champagne - Ask About $99 Down!

$354

avg/night

View Details

Key Amenities

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

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivalsThis includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key House

"Indian Rock Beach Vacation"
Reviewed July 2, 2018

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

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Gorgeous Beachfront Condo directly on #1 Beach in USA - #111

1 BR | 1 BA | Sleeps 3 | Quick View

4

Distance to beach: 150 yards to Crescent Beach

$220

avg/night

View Details

Key Amenities

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

About this property

1 Week Minimum Stay Required. Newly Upgraded 1BR/1 BA condo with full sleeper sofa and twin sleeper chair in LR. Kitchen fully remodeled in June 2017 with new top of the line appliances. New Top of the Line King Size Bed will give you a great night sleep after a wonderful day at the beach and a great ...

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Property Type

Siesta Key Condo

"Perfect in every way!"
Reviewed May 5, 2021

The condo had absolutely everything you would need, I was very happy with the amenities. The owner was very prompt with communication and I especially enjoyed the updates to the unit. The condo is situated ...

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Crescent Royale 4B Gulf and Siesta Key Beach View

2 BR | 2 BA | Sleeps 4 | Quick View

4

Distance to beach: 200 feet to across street

$181

avg/night

View Details

Key Amenities

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

About this property

2 bedroom gorgeous condo overlooking Siesta Key Beach and Gulf of Mexico. Complex with large community pool, sauna, covered parking, secure gated area. Gas grills, party room, beautiful property. 2 full bathrooms with granite walk in showers and basin, etc. King bed in master with ensuite full bath, ...

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Property Type

Siesta Key Condo

"Great vacation!!!!!"
Reviewed April 5, 2021

Great condo! Beautiful location! The beach is across the street. Gorgeous views, great pool, clean facilities.

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

$662

avg/night

View Details

Key Amenities

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

About this property

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 have gulf views Ideal for families or small groups of up to 8 people Enjoy access to an Olympic-sized pool Fully equipped kitchen Screened ...

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Property Type

Siesta Key House

"Amazing!"
Reviewed December 2, 2020

Beautiful, gorgeous, breathtaking! If you are looking for a bungalow on the beach, look no further. Our family of five with 3 teenagers fit beautifully here. Wonderful accommodations with a stocked kitchen ...

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Casa Blanca D06 Villa

2 BR | 2 BA | Sleeps 5 | Quick View

$210

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Casa Blanca is within walking distance of Crescent Beach Village restaurants and shops, with Siesta Key Village just a short drive north on the key. Our villas are located between the pool area and famous Crescent Beach. Each villa is individually decorated, fully equipped and professionally landscaped. ...

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Property Type

Siesta Key Villa

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Upscale 3-BR Siesta Key Townhouse - Heated Pool - Siesta Key Village 3BR 5241

$253

avg/night

View Details

Key Amenities

  • Air Conditioning

About this property

SEASIDE VILLAS: This Siesta Key deluxe 3-Bedroom townhouse rental is located in the heart of Siesta Village – just steps to all the shops and restaurants and only a three minute walk to world famous Siesta Key Crescent Beach! Siesta Village has dozens of shops, fine or casual dining, pubs and clubs, ...

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Property Type

Siesta Key Townhome

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Casa Blanca D12 Villa

2 BR | 2 BA | Sleeps 6 | Quick View

$205

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This unit features a King bed in the master with a brand new bathroom, the guest bedroom offers a queen bed where there is a washer and Dryer in the unit for your convenience. The Second bathroom was added in late 2013. There is a new kitchen that will delight the chef in each of you. The living room ...

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Property Type

Siesta Key Villa

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The Water is Great! Siesta Palms Sea Breeze #125

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: Tired of Work? Enjoy a week at beautiful Siesta Key Beach - where your troubles will fade away!

$212

avg/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 Palms by the Beach 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 ...

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Property Type

Siesta Key House

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Best location! Luxury Canal Home in Siesta Key Village! Pool/Spa Done July 2021

2 BR | 2 BA | Sleeps 8 | Quick View

2

Distance to beach: 0.4 miles to Siesta Key Beach

$249

avg/night

View Details

Key Amenities

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

About this property

Location, location, location!!Canal home in heart of the Siesta Key Village, no need for a car! Steps away from great restaurants, shops, and even the local supermarket! Plus, only an 6 minute walk to the #1 ranked Siesta Key beach.Your needs are complete for a day at the beach with a beach ...

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Property Type

Siesta Key House

"Home Away from Home/Great Location"
Reviewed May 2, 2021

We loved the location of this home. Not only because it’s located on a canal and very private, but it’s only a two-minute walk to Siesta Key Village. The beach is also a short walk of only 6-7 minutes. ...

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Siesta Key Luxury Condo 2/2, Pools, Tennis, Gym, walk to beach.

2 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to beach: 0.4 miles to Siesta Key Main Beach, #1 in America!

$192

avg/night

View Details

Key Amenities

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

About this property

We are following strict CDC Guidelines for cleaning and sanitizing our condo before and after each Guest Stay. WE HAVE KEYLESS ENTRY ON BUILDING AND CONDO SO NO HUMAN CONTACT REQUIRED AT CHECK-IN OR DURING STAY.Resort like stay on Siesta Key in this spacious and bright 2 bedroom 2 bath condo. The ...

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Property Type

Siesta Key Condo

"COVID 19 TRIP TO SIESTA KEY"
Reviewed June 19, 2020

Sue is incredibly host. Easy to deal with and she is always there for you .Highly recommended! We would love to stay there again.

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Sol y Mar - Ask About $99 down!

$282

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key House

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Midnight Cove townhouse! Private Beach with lounge chairs on beach!

2 BR | 2.5 BA | Sleeps 6 | Quick View

2
Owner special: Special monthly rate for August and September! $3600 a month!

$168

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

This spacious, beautifully decorated and updated 2 BR/2.5 bath townhome overlooks the canal and boat basins and is located directly across the street from the gorgeous Siesta Beach. The kitchen and all baths have been renovated and the newly furnished living room features a sofa bed and 55” smart ...

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Property Type

Siesta Key Townhome

"Midnight Cove"
Reviewed April 16, 2021

We stayed at Midnight Cove for spring break. Our condo was very nice! It overlooked the pool and the bay. The whole complex is beautiful and it was actually very quiet at night considering it was spring ...

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Midnight Cove II Bayside #734 Beautiful top floor condo overlooks bay

2 BR | 1.5 BA | Sleeps 5 | Quick View

Distance to beach: 250 feet to Siesta Key

$171

avg/night

View Details

Key Amenities

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

About this property

On Siesta Key - Quick walk to Siesta Key's world famous beach. Beautiful and private, this updated condo with granite kitchen and tile floors overlooks the bay inlet and boat basin. Across street from world famous beach. Fully amenitied condo in amentied condo complex. Large community pool, tennis ...

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Property Type

Siesta Key Condo

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Luxury Village Canal Home with Heated Pool & Spa

$450

avg/night

View Details

Key Amenities

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

About this property

The home has 3 bedrooms & 2 custom bathrooms. Newly renovated with Terracotta roof tiles for a classic Florida look. The front of the home has an enclosed privacy wall with a landscaped courtyard. A great place for evening gatherings with seating and a grilling area. The interior of the home ...

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Property Type

Siesta Key House

"Perfect house & location"
Reviewed April 25, 2021

Our family of 4 had a great vacation at this property. Absolutely everything is as expected and beyond!!

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Fishermans Cove A102 - On Turtle Beach on Siesta Key

$198

avg/night

View Details

Key Amenities

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

About this property

My ground floor rental is directly on the beach on the Gulf of Mexico, with incredible views and sunsets!The lanai has a back door directly out to the Beach. The front of my unit faces the Lagoon where we have a FREE DOCK for your boat or other water craft. (So you have water views in both directions)! ...

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Property Type

Siesta Key Condo

"Peaceful"
Reviewed April 18, 2021

Really enjoyed staying at this quieter end of the island. It was a much needed break. Carrie is very sweet and easy to deal with. Will definitely be returning again.

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Isla Amor - Ask About $99 down!

$594

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

View all property information

Property Type

Siesta Key House

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Casa Blanca D15 Villa

2 BR | 2 BA | Sleeps 4 | Quick View

$210

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to D15 here you will truly find all the comforts of home, the owners have decorated this unit to give their guest the best with relaxation on everyone's mind you will find it here. The living room has all new furniture, including a 60" TV for your viewing pleasure. The Master bedroom features ...

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Property Type

Siesta Key Villa

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Located Directly on the Beach in Siesta Key-Beautiful First Floor-Walk Out

$206

avg/night

View Details

Key Amenities

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

About this property

Our condo is directly on the beach and is direct oceanfront (Gulf-front).When we travel over 1,000 miles to enjoy a beach vacation we're not interested in being steps from the beach, across from the beach, or having what is often euphemistically advertised as, “a view of the beach.” ...

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Property Type

Siesta Key Condo

"So Close to the Beach!"
Reviewed February 23, 2021

We have stayed in A107 at Fisherman’s Cove for the last five years. We return each year because Russ and Dina have provided everything we need in this condo that allows us to step onto sand right outside ...

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The Islander – Ask About $99 down!

4 BR | 4 BA | Sleeps 12 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$468

avg/night

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Key Amenities

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

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Ground Floor 104B

$205

avg/night

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Key Amenities

  • Air Conditioning

About this property

Fisherman’s Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos to the Gulf on all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront condo! Located at Turtle Beach on ...

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Property Type

Siesta Key Condo

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Beautifully updated 2BR condo with great gulf view

$150

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

The completely updated 6th floor unit in Casarina has a magnificent gulf view, exceptional pool, hot-tub and BBQ area, and a prime in-garage parking space, steps from the elevator.

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Property Type

Siesta Key Condo

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Amazing Ocean View Beach Front Property Directly on the #1 Beach in the USA-#608

3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 20 yards to Crescent Beach, Siesta Key

$294

avg/night

View Details

Key Amenities

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

About this property

Unit 608 is a large 3 bedroom, 2 bath high-rise unit in Horizons West, Siesta Key, Florida. The unit has recently undergone a complete makeover by a Chicago designer. The interior was fully demolished and rebuilt. No detail or expense was spared in completing the perfect beach condo: large panoramic ocean ...

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Property Type

Siesta Key Condo

"Stunning Condo"
Reviewed January 22, 2021

My family stayed in this stunning condo and absolutely loved it. Beautiful views, fabulous modern furniture, high tech TVs and sound system, awesome high end kitchen and baths.

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

3 BR | 3 BA | Sleeps 7 | Quick View

6

Distance to beach: 300 feet to Siesta Beach

$526

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key House

"Beautiful home"
Reviewed December 27, 2020

Just as pictured. Clean and comfortable. Beds were great. Nice patio and easy access to beach.owner easy to work with.

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Casa Blanca C09 Villa

2 BR | 1 BA | Sleeps 4 | Quick View

$194

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to our little oasis on Siesta Key. We have just completed a full remodel, so be one of the first to enjoy this home. Tastefully decorated in a beach theme, the unit is fully tiled, has granite countertops and, a walk-in shower. We also added a new half bath in the master bedroom. And for your ...

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Property Type

Siesta Key Villa

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BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS -RENOVATED 310B

$253

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront

About this property

op beachfront unit at Fisherman's Cove!! Fisherman’s Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos to the Gulf on all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront ...

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Property Type

Siesta Key Condo

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Sea Esta - Ask About $99 Down!

3 BR | 2 BA | Sleeps 8 | Quick View

1

$253

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key House

"Perfect Location & Gorgeous Home!!!"
Reviewed January 16, 2021

Cleanest rental I have ever stayed in!! Very modern and well-manicured property! Within walking distance to tons of restaurants and shops but lots of privacy in the backyard!! Pool and hot tub were wonderful!

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Casa Stolida - Ask About $99 Down!

$422

avg/night

View Details

Key Amenities

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

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key House

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Enchanting and Carefree! Siesta Palms Sea Breeze #126

1 BR | 1 BA | Sleeps 4 | Quick View

2
Owner special: It's all about the ambiance...are you ready for that Florida Escape. Book Now.

$212

avg/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 Palms by the Beach 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 ...

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Property Type

Siesta Key Condo

"Paradise in Siesta Key"
Reviewed January 15, 2021

Linda and Mary Ann were so helpful and wonderful. The condo had everything we needed and more! Great location. Easy walk to the beach. They provide everything from beach chairs to pool towels!! They ...

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

$116

avg/night

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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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Casa Blanca A 09 Villa

2 BR | 2 BA | Sleeps 6 | Quick View

$205

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to Villa A09. You will love this newly remodeled Villa. It is located on the beautiful white-sand shores of Siesta Key, rated the #1 beach in the USA. This is a non-smoking 2 bedroom, 2 bathroom private Villa, centerally located just steps from the beach and large heated pool. The master ...

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Property Type

Siesta Key Villa

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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!