Siesta Key Vacation Rentals

(219 rentals)
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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Siesta Dream House

4 BR | 3.5 BA | Sleeps 12 | Quick View

$254

per night

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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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Gorgeous Views in this Siesta Key Condo

2 BR | 2 BA | Sleeps 6 | Quick View

4

Distance to beach: 0.3 miles to Crescent Beach on Siesta Key

$132

per night

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Key Amenities

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

About this property

Siesta Key Condo - Siesta Key ParadiseLooking for a vacation rental in Siesta Key? Look no further... we have a two bedroom first floor condo located on the spacious, gorgeous landscaped grounds of Midnight Cove ii.Enjoy great views from our lanai watching boats, yachts, and wildlife on the Intracoastal ...

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Property Type

Siesta Key Condo

"Loved it - such an easy experience!"
Reviewed October 18, 2019

The complex was in walking distance to most necessities (would recommend taking the trolley into the village) and a stone's throw to the beach. The owners and the complex were ready to answer any questions ...

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The Nautilus

8 BR | 6 BA | Sleeps 24 | Quick View

2

$514

per night

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Key Amenities

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

About this property

This luxurious 8 bedroom/six bathroom home is a unique combination of two units: “Casa Stolida” and “Casa Tegula” (4000 sq. ft. total). Each unit features a 4 bedroom/3 bathroom configuration, each with their own cabana room, separate living areas, private elevators and your very ...

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Property Type

Siesta Key House

"Beautiful Home"
Reviewed June 19, 2019

The Nautilus was a fantastic home on Siesta Key. Short walk to the beach and we had our own pool. House was well appointed and very comfortable and clean. We will be back and definitely recommend renting ...

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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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Pura Vida Oasis

5 BR | 3 BA | Sleeps 13 | Quick View

$621

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Pura Vida Oasis, a canal front cottage with heated pool & spa features 5 bedrooms/3 baths and can sleep up to 13. Enjoy eclectic wine storage rack, private dock and amazing views. Close to beaches, Siesta Village & trolley stop. This spectacular bright cheerful, canal front cottage ...

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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
Owner special: 10% OFF December & January 7 night stays

Distance to beach: 200 feet to Crescent Beach

$173

per night

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Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

"The Total Package"
Reviewed April 24, 2019

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

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Sandpiper Cottage

5 BR | 5 BA | Sleeps 14 | Quick View

Distance to beach: 0.8 miles to Crescent Beach

$275

per night

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Key Amenities

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

About this property

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

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Property Type

Siesta Key Cottage

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Sea Wave Casita

2 BR | 2 BA | Sleeps 6 | Quick View

2

$143

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool

About this property

The Sea Wave Casita of Villa Brisa Marina is one of two beautiful casitas, uniquely configured, featuring two bedrooms, 2 full bathrooms, a gourmet kitchen and a heated pool. One of 2 homes (along with Sea Shell Casita) that are Villa Brisa Marina.The Sea Wave and Sea Shell are two separate units ...

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Property Type

Siesta Key House

"Beachside single storey"
Reviewed February 10, 2019

Had a great stay at this beautifully decorated and well equipped single storey pad. The beach is so close by as are grocery and other shops offering all you need. It really is quite special and so... ...

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MAGNOLIA 317-319

4 BR | 4 BA | Sleeps 12 | Quick View

6
Owner special: Fall Special! 20% discount off any one week booking until Dec 21.

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 2 BED/ 2 BATH UNIT AND 1 DOWNSTAIRS 2 BED/ 2 BATH 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, RESTAURANTS, ICE CREAM STORE ...

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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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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. 15%

$265

per 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. 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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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 Special! 20% discount off any one week booking until Dec 21.

$163

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

"Excellent choice"
Reviewed July 30, 2019

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

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Caribbean Sol – 6900

5 BR | 5 BA | Sleeps 12 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$523

per night

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Key Amenities

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

About this property

Welcome to Caribbean Sol, 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 5-bedroom/5-bathroom townhome is located near Siesta Key Village and just five minutes from Siesta Key Beach, ...

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Property Type

Siesta Key House

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Coconut Grove

6 BR | 6 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 Coconut Grove! A private home nestled right in the heart of the Siesta Village with the style, elegance and charm of Siesta Key. Enjoy a family home that sleeps 16, a private heated pool, and quite literally in the heart of Siesta Village!Coconut Grove features a unique combination of two ...

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Property Type

Siesta Key House

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

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: Enjoy a Week at beautiful Siesta Key Beach for just $999 + tax. Fabulous Amenities. (1-2 Persons)

$199

per 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, The Koch Family, invite you to relax, unwind and enjoy our casual way of life. Resting just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach is our Family owned and operated Tropical Siesta Key Inn. With no busy streets ...

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Property Type

Siesta Key Condo

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Mermaids Lookout - 6912

4 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$468

per night

View Details

Key Amenities

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

About this property

Welcome to Mermaids Lookout, one of Siesta Key's premier luxury townhomes with private heated pool and spa! Located just five minutes from Siesta Key Beach and Village!This massive and decadent 4-bedroom/3-bathroom townhome is located near Siesta Key Village and just five minutes from Siesta Key Beach, ...

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Property Type

Siesta Key House

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A special SECRET retreat...#26

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 100 yards to Crescent Beach

$128

per night

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Key Amenities

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

About this property

Simply relaxing one bedroom condo with a king bed facing the pool area and just a few steps to the private entrance to" Siesta Key #1 beach" white quartz sand beach . Additionally a Lazyboy queen Air Dream sofa sleeper for separate sleeping area if needed Unit includes a full kitchen for ...

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Property Type

Siesta Key Condo

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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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Sea la Vie – 5321 (R)

3 BR | 2 BA | Sleeps 8 | Quick View

$214

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Sea la Vie! This private 3BR/2BA home is the perfect beach getaway to relax, unwind & take in everything Siesta Key has to offer. The best part? The Salt Life is just 1 minute (seriously!) away from Siesta Key Beach, voted the # 1 beach in the U.S! Sea la Vie offers a shared heated pool ...

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Property Type

Siesta Key House

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The Hidden Gem – 5290L

2 BR | 1 BA | Sleeps 6 | Quick View

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

$143

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Cottage

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Siesta Key Beach direct access from your front door

$144

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Welcome to La Siesta Unit 112! This quiet 2-bedroom 2- full bath end unit is located on the ground floor of the La Siesta Condominiums complex with a direct walk out access to all Siesta Key Beach amenities. We are the closest home to the Sunset Pavilion, children's playground, and snack bar! Easily ...

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Property Type

Siesta Key Apartment

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Private Beach Updated Island Reef Condo

2 BR | 2 BA | Sleeps 4 | Quick View

2

Distance to beach: 500 yards to Island Reef's own

$117

per night

View Details

Key Amenities

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

About this property

Updated 2 Bd -2 Ba condo on Siesta Key! Located on the quiet southern end of Siesta Key, Island Reef condominiums is a beach to bay community. THERE IS A 30 DAY MINIMUM RENTAL, per the condo association rules. The community offers a newly refurbished private beach, 2 heated swimming pools, 2 tennis ...

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Property Type

Siesta Key Condo

"Paradise Found!"
Reviewed March 24, 2019

After spending a glorious month in 303G at Island Reef Resort, let me tell you many of its fantastic assets. First, the condo looks even better than the online photos and welcomes guests with gorgeous, ...

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"Menorca" 378 Canal Rd.

Studio | 1 BA | Sleeps 2 | Quick View

3
Owner special: Fall Special! 20% discount off any one week booking until Dec 21.

$81

per night

View Details

Key Amenities

  • Air Conditioning
  • Private Pool

About this property

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

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Property Type

Siesta Key Studio

"Nice visit"
Reviewed June 13, 2019

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

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Tropical Hideaway Bungalow - MONTHLY RENTAL

2 BR | 1.5 BA | Sleeps 4 | Quick View

2

Distance to beach: 0.3 miles to Siesta Key Beach

$80

per night

View Details

Key Amenities

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

About this property

Situated in the quiet and welcoming neighborhood of Palm Island, the heart of Siesta Key. This beautifully private bungalow sits back from the street and is set in gorgeously secluded tropical gardens. The fabulous surprise of a two story massive flagstone lanai is awaiting behind the zen gate. This home ...

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Property Type

Siesta Key Bungalow

"Tropical Hideaway"
Reviewed April 4, 2019

You can’t go wrong. House is in a quiet and safe neighborhood. The property itself is very zen like. Privacy! Very short walk to the non-crowed section of beautiful Siesta Key beach. The house is very ...

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Peacock Villa

3 BR | 3 BA | Sleeps 9 | Quick View

$214

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

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

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Property Type

Siesta Key House

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

2 BR | 2 BA | Sleeps 6 | Quick View

2

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

$99

per night

View Details

Key Amenities

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

About this property

Resort like stay on Siesta Key! So many amenities - 2 pools, 3 Tennis Courts, Gym, Social Rooms, Kayak & Bike storage. Sweet Siesta Key two bedroom two bathroom condo on Siesta Key! Located in Harbor Towers Yacht & Racquet Club on Siesta Key. Renovated 2 bedroom 2 full bath, in luxury building, ...

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Property Type

Siesta Key Condo

"Great Winter Getaway!"
Reviewed February 25, 2019

Great month in Siesta Key! Sue was easy to work with! Beautiful beach/lovely Marina views. Hope to visit again.

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Mandevilla

3 BR | 3 BA | Sleeps 6 | Quick View

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

$143

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Villa

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Beautiful Siesta Key Beach Condo-GREAT LOCATION! 3 Min WALK to Beach!

$159

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

This 2-bedroom, 2 bath Siesta Key condo can sleep 6 comfortably with a pull-out queen sofa bed and total square feet of 1,773! The beautifully decorated condo, with two updated, tiled bathrooms offers a comfortable, home-away-from-home feel. Sit on your private 20 ft deck and enjoy the view of a lake ...

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Property Type

Siesta Key Condo

"I wish it really were “Our House at the Beach”!"
Reviewed September 24, 2019

Such comfort- I couldn’t ask for much more ! We are currently staying in unit 225 and are loving every minute. We are so comfortable! The unit is quite large and we feel like we have lots of space to ...

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Sun, Sand & *Save 20% to 45% per Week* at Siesta Breakers #603 in Siesta Key, FL

2 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 250 feet to Crescent Beach

$146

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

"Stop clicking around the web, and endless window shopping for your next Siesta Key Vacation Property Rental, and take advantage of the super accommodation cost savings offered in “Every-Day Deals” and “Sell-Off Deals”, with a Direct-with-Owner gulfside Reservation at Siesta ...

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Property Type

Siesta Key Condo

"Perfect Beach Stay"
Reviewed June 23, 2019

Great vacation rental! This condo was super close to the beach (a short walk). The beach was private and had loungers and chairs for our use. The unit itself was very clean and had plenty of room for ...

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Villa Champagne

4 BR | 3 BA | Sleeps 8 | Quick View

1

$294

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This enchanting 4 bedroom/3.5 bathroom cottage is a short walk to the Village and just minutes from world famous Siesta Key Beach! Villa Champagne is the ideal vacation rental for families and groups alike.Villa Champagne can accommodate up to 8 guests with a bedding configuration as follows:• ...

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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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Sandy Cabana

3 BR | 3 BA | Sleeps 8 | Quick View

$142

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to the Sandy Cabana!The Sandy Cabana is one half of the uniquely configured private homes called the Sandy Seahorse Cottage and it is the perfect escape in the tropics of Siesta Key. This property can be rented separately or combined to accommodate a large party! This side of the gorgeous ...

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Property Type

Siesta Key House

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"Village Resort" 320 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

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

$151

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

"Banyon 2019"
Reviewed June 22, 2019

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

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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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"Village Resort" 316 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

3
Owner special: Fall Special! 20% discount off any one week booking until Dec 21.

$151

per night

View Details

Key Amenities

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

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNT RATES!316 Canal Rd - Village Resort Just steps to #1 voted beach, restaurants, grocery’s, shops, bars & ice cream! (downstairs) - 2 bed/ 2 bath-dishwasher, heated pool, great back yard for BBQ and gatherings. Combine all four units ...

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Property Type

Siesta Key Condo

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

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

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Siesta Key Condos - Gulf & Bay Club Bayside Condo

1 BR | 1 BA | Sleeps 2 | Quick View

1
Owner special: 11/6 - 11/23: $100 per night. 11/23 - 12/21: $150 per night. Minimum stay 1 week. Plus taxes.

$111

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

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 equipped with an emphasis on vacation living. ...

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Property Type

Siesta Key Condo

"Fabulous"
Reviewed September 7, 2019

A beautiful complex with a beach house feel ! A very welcoming unit with a generous space. Making the best of the intercostal and gulf !

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Serenity Cottage

3 BR | 3.5 BA | Sleeps 8 | Quick View

$200

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Serenity Cottage!A pristine and elegant home so close to the most beautiful beach in the world most would say, Serenity Cottage offers a delightful and relaxing retreat with maximum comforts in mind, and a spacious abode designed around the needs and comforts of large families traveling ...

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Property Type

Siesta Key House

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

$265

per 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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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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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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Pinacolada

3 BR | 3 BA | Sleeps 8 | Quick View

$214

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

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

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Property Type

Siesta Key Townhome

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Crescent Cottage

4 BR | 3 BA | Sleeps 10 | Quick View

$260

per night

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Key Amenities

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

About this property

Welcome to our beautiful and serene vacation home! A gorgeous beach cottage in a dream destination, Crescent Cottage offers a fun-filled activity-packed vacation plan with all of its great amenities, awesome location so close to the beach, and a spacious abode designed around the needs and comforts of ...

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Property Type

Siesta Key House

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Sand Dollar Cottage

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 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 to the completely remodeled, and newly furnished ...

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Property Type

Siesta Key House

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

$125

per night

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Key Amenities

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

About this property

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

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Property Type

Siesta Key Apartment

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

$295

per night

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Key Amenities

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

About this property

Welcome to our Beach Get-away...where we, The Koch Family, invite you to relax, unwind and enjoy our casual way of life. Resting just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach is our family owned and operated Tropical Siesta Key Inn. With no busy streets ...

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Property Type

Siesta Key Condo

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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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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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Casa Ohana

4 BR | 3 BA | Sleeps 12 | Quick View

2

$288

per night

View Details

Key Amenities

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

About this property

Welcome to Casa Ohana! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 12!!!] can fathom. The location is THE premier location in the heart of Siesta Key Village, just behind Gilligan's and Lelu's Coffee Shop! Inside you’ll enjoy ...

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Property Type

Siesta Key House

"Fantastic Florida Rental"
Reviewed June 22, 2019

Casa Ohana was terrific. Family friendly, close to the beach and main attractions of Siesta Key. Will definitely be returning!

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Tropical Gardens on Secluded Harbor

$200

per night

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Key Amenities

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

About this property

About the PropertyWelcome to TROPICAL GARDENS ON SECLUDED HARBOR, one of Siesta Key's truly secluded and very special locations! Located just five minutes from Siesta Key Beach, voted the # 1 beach in the USA! Siesta Key Village with its excellent restaurants and many eclectic bars, shops and cafes ...

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Property Type

Siesta Key House

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Siesta Key Vacation Rentals

Siesta Key Weather

 | 

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

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

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

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

Climate

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

Getting around

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

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

Top activities and attractions

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

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

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

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

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

Events 

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

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

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

Siesta Key house rentals on FloridaRentals.com

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