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Air conditioning
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Beach or lakeside relaxation
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Golf course on site or within 15 min walk
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255 condos

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Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$437

☆ King in Master • 1st Floor • Heated Pool • ¼ mile walk to Siesta Key ☆

Sarasota condo

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$193

Orchid at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$490

Coconut at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Rental types, Boat available

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Price per night from

$490

Split Leaf at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Rental types, Boat available

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Price per night from

$489

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Rental types, Boat available

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Price per night from

$345

Bird of Paradise at The Wildflower

Siesta Key apartment

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$490

Close to Siesta key with hot tub, fire pit and butterfly garden

Gulf Gate Estates guest house

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$193

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 5

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Price per night from

$206

Sandy Toes Town Home

Siesta Key townhouse

3 bedrooms
3 bathrooms

sleeps 6

“Time in Paradise” We recently had the luck to spend two months in paradise. This condo was comfortably appointed, well stock to meet all our needs, and most importantly in the perfect location. The beach was a short walk to the left and stores and restaurants were just a short walk to the right. We had a great time and enjoyed everything Sarasota, Siesta Key, and this Sandy Toes Condo had to offer. Thanks Mark!

1 of 2 match: Rental types, Boat available

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Price per night from

$273

Siesta Key private beach access

Siesta Key villa

3 bedrooms
3 bathrooms

sleeps 8

“Siesta Key Townhouse” This was a wonderful place to stay! The house was very clean and spacious and had everything we needed for a week at the beach.

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Price per night from

$510

Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!

Siesta Key apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 1 hour 1 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$267

2 bedroom Condo Bay Oaks Siesta Key

Sarasota condo

2 bedrooms
1 bathroom

sleeps 3

1 of 2 match: Boat available, Rental types

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Price per night from

$574

Beautiful Crescent Beach on Siesta Key One of the

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$301

Amazing Beachfront Condo, Siesta Key,

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Boat available, Rental types

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Price per night from

$345

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN CONDO!

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Boat available, Rental types

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Price per night from

$272

Monthly Rental, 2 bed, 2 bath, Ocean view.

Sarasota condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Boat available, Rental types

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Price per night from

$115

Beachfront Condo Siesta Key

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!

1 of 2 match: Boat available, Rental types

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Price per night from

$454

Newly discounted rates! Gorgeous one bedroom across from beach, near village!

Siesta Key condo

1 bedroom
1 bathroom

sleeps 3

“Anniversary Trip” Had a wonderful time at LA Siesta Condominiums for our anniversary vacation. Beautifully furnished and do close to the best beach in the USA

1 of 2 match: Boat available, Rental types

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Price per night from

$246

Charming Siesta Key Village Unbeatable Location

Siesta Key condo

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$190

Midnight Cove #532 in Siesta Key, FL- Sun, Sand & Save 7.5% to 22.5% per Week

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 4

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

1 of 2 match: Boat available, Rental types

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Price per night from

$144

Piece of Paradise

Sarasota condo

2 bedrooms
3 bathrooms

sleeps 6

Responds fast! avg. 3 minutes

1 of 2 match: Boat available, Rental types

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Price per night from

$96

Beautiful, Affordable Close to famous Siesta Beach

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 4

“It was wonderful!” Everything about the trip and condo was great! Mike met us to give us the keys and we called him for suggestions about restaurants, etc. and he was very helpful. The condo was very clean and had everything we needed. It was also great that we were able to use the beach chairs and umbrella. I am already trying to figure out when we can go again.

1 of 2 match: Boat available, Rental types

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Price per night from

$163

Ideal Retreat next to USA's #1 Beach—Siesta Key

Sarasota condo

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Boat available, Rental types

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Price per night from

$161

Jamaica Royale #104! Completely renovated, Gulf side, beautiful 2b/2b Condo!

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Boat available, Rental types

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Price per night from

$338

Siesta Key, Heated pool, Gulf and Bay, Cute Siesta Key Condo, Gated - Siesta Sky

Siesta Key condo

1 bedroom
1 bathroom

sleeps 2

1 of 2 match: Boat available, Rental types

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Price per night from

$333

Siesta Key - 2bdrm on the beach - amazing views!!

Siesta Key condo

2 bedrooms
2 bathrooms

sleeps 5

“Escape from reality” We had an amazing vacation. Accommodations were great and very comfortable. Breakfast on the lanai and sunset fishing on the beach were 2 of our families favorite things to do. You also have the bay right behind you where you can kayak or paddle board. The community was quiet which was prefect for our getaway. We will definitely be staying here again.

1 of 2 match: Boat available, Rental types

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Price per night from

$603

Lovely Siesta Key 3BR 2.5BA Condo, Island Paradise

Siesta Key condo

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Boat available, Rental types

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Price per night from

$493

#1 Beach - "Super Clean" - 2 Level Townhouse - 1400sf 2Br/2.5 Bth- 5 Star Rating

Siesta Key condo

2 bedrooms
3 bathrooms

sleeps 6

“Great stay in Sarasota” My husband and our two daughters spent a wonderful four days in Sarasota. The townhome we stayed in was beautiful and had all the amenities we needed. We spent every day at the beach and relaxed at the townhome in the evenings. We would definitely stay here again and have recommended this place to our family and friends. Thanks Louie!

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Boat available, Rental types

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Price per night from

$435

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

1 bedroom
1 bathroom

sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

1 of 2 match: Boat available, Rental types

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Price per night from

$115