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51-100 of 195 Siesta Key Rentals

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Pool & Patio
1 / 35

Siesta Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 7
Home / 3 Bedrooms / Sleeps 7

(28)“ Excellent ”28 Reviews

from

$134

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$134 - $167
Per week:$934 - $1,167
Pets allowed:No
Internet:Yes

Please see CALENDAR below for availabilty: Also the VIRTUAL TOUR is at the bottom of the page. Description: Surrounded by a tropical garden our secluded Villa is situated in a quiet cul de sac edged on two sides by Lake Nancy. The Lounge, kitchen and bedrooms one and ...

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Siesta vacation

“ Excellent ”
November 17, 2014
Fantastic location and Siesta Key is a wonderful location. Instantly felt at home here and the heated pool was an added bonus. Although the bikes weren't included in the rental, we were able to use them and cycled into the village and/or beach most days from the house. Had great fun meeting and greeting the wildlife that frequented the garden. A truly peaceful and relaxing place to stay. Thoroughly recommended!
Jo Davis, Brighton, England

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Siesta Key Florida Vacation Rentals - Condo
1 / 30

Siesta Key Condo
2 Bedrooms / 3 Bathrooms / Sleeps 5
Condo / 2 Bedrooms / Sleeps 5

from

$190

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:5
Type:Condo
Per night:$190 - $224
Per week:$1,330 - $1,564
Pets allowed:No
Internet:Yes

If you are looking for a place to unwind and decompress, this is the ideal place for you. Experience Siesta paradise with incredible sunsets and balmy breezes directly on the Gulf of Mexico with its beautiful white sand beaches stretching for miles. And not to brag, but the number...

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Siesta Key Florida Vacation Rentals - Villa
1 / 10

Siesta Key Villa
2 Bedrooms / 1.5 Bathrooms / Sleeps 6
Villa / 2 Bedrooms / Sleeps 6

(2)“ Excellent ”2 Reviews

from

$139

/ night

Email Owner
Bedrooms:2
Bathrooms:1.5
Sleeps:6
Type:Villa
Per night:$139 - $193
Per week:$968 - $1,351
Pets allowed:No
Internet:Yes

Our vacation home is just steps away from the #1 rated beach in the USA - Siesta Key beach. It is in a complex located on the GULFSIDE (or Beach side) of the island. It is a comfortable villa with a master bedroom, guest bedroom, living room, kitchen with dining area, and...

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absolutely beautiful

“ Excellent ”
January 5, 2013
This property was beautiful. Clean, spacious, close to the gulf and the pool. The beach was amazing! I definitely see why it was voted #1 beach in USA. We rented bikes - what a great deal ... the rental was located just before entrance to Siesta key. Great guys there! Siesta village was a comfortable ride, which we did on the beach. The gelato place in is worth going to! Owners Monica and Fabio, wonderful people and fantastic gelatinous!
Jo-Anna Mitrano, San Diego, CA

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Siesta Key Florida Vacation Rentals - Condo
1 / 7

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

(3)“ Excellent ”3 Reviews

from

$125

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$125 - $198
Per week:$875 - $1,384
Pets allowed:No
Internet:Yes

Wonderful 2 bedroom 2 bath, upstairs condo with a nice heated pool which is only shared by our two other condos. Pool area has a large deck with lounge chairs, picnic table with umbrella, and gas grill. This is on the BEACH side of Midnight Pass Road, 200 feet down a private lane...

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Traverse City Girls

“ Excellent ”
April 4, 2012
We had a wonderful stay at Siesta by the Sea - 1138 Windsong Ln. The pool was clean and very nice and just a short walk to the beautiful beach. The owner Don made sure we had everything we needed. The condo had all the dishes, washer and dryer, and linens we could use. I would recommend this unit and management to anyone looking for a wonderful stay on Siesta Key.
Mary Peterson, Traverse City, MI USA

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Siesta Key Florida Vacation Rentals - Condo
1 / 21

Siesta Key Condo
1 Bedroom / 1 Bathroom / Sleeps 3
Condo / 1 Bedroom / Sleeps 3

from

$186

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:3
Type:Condo
Per night:$186 - $228
Per week:$1,302 - $1,595
Pets allowed:No
Internet:Yes

THIS UNIT IS ALREADY BOOKED THROUGH April 20, 2015. Taking reservations for 2016 already. Newly Upgraded 1BR/1 BA condo with full sleeper sofa and twin sleeper chair in LR. New Top of the Line King Size Bed will give you a great night sleep after a wonderful day at the beach and ...

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Siesta Key Florida Vacation Rentals - Townhouse
1 / 19

Siesta Key Townhouse
4 Bedrooms / 3.5 Bathrooms / Sleeps 12
Townhouse / 4 Bedrooms / Sleeps 12

(10)“ Excellent ”10 Reviews

from

$90

/ night

Email Owner
Bedrooms:4
Bathrooms:3.5
Sleeps:12
Type:Townhouse
Per night:$90 - $293
Per week:$625 - $2,045
Pets allowed:No
Internet:No

1 to 8 bedrooms units; sleep occupancy 24 Free Wi- Fi INTERNET + HEATED PRIVATE POOL+ GREAT LOCATION! ! ! Our Deluxe Town homes are in the heart of great Siesta village- Just steps to many restaurants, shops and 1 and ½ block only 3 minutes to great Crescent Beach world ...

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Everything you Need

“ Excellent ”
January 12, 2015
We stayed in the one-bedroom garden unit on the left side. It was perfect for us. Plenty of room to spread out and relax. The kitchen was well equipped and the bed was comfortable. Having a swimming pool, laundry, and an outside grill was a big plus. We practically had the pool to ourselves for most of our stay. The location was ideal. A local market, the beach, and the village within a 5 minute walk. We enjoyed the little beach wagon which we used to transport our stuff for a day on the beach. Quiet neighborhood. Would definitely stay here again.
Sabine Hedberg, Rockport, MA USA

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1 / 10

Siesta Key Townhouse
4 Bedrooms / 4 Bathrooms / Sleeps 10
Townhouse / 4 Bedrooms / Sleeps 10

from

$425

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:10
Type:Townhouse
Per night:$425 - $675
Per week:$3,200 - $4,400
Pets allowed:Yes
Internet:Yes

This is one of the nicest rental properties that you will find on Siesta Key! It has views that are to die for of the bay looking east, south and north to Downtown skyline plus it has some Gulf of Mexico views looking west. All rooms in the house have something special to admire...

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Gumbo Limbo Vacation Resort
1 / 26

Siesta Key Apartment
3 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 3 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$220

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$220 - $295
Per month:$6,600 - $8,850
Pets allowed:Yes
Internet:Yes

Beautiful high quality duplexes with award winning tropical landscape design. A sensational heated black bottom pool with rocky mountain quartzite deck, and a rock waterfall. The property sits across the street from the world famous Siesta Key Public Beach within 1/2 mile of ...

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650D Beachwalk

“ Excellent ”
January 3, 2015
If you want to vacation but still want to be at home then this is the place to come! This 3 bedroom townhouse is decorated nicely and is a stone's throw from the beach. It is kid friendly and a perfect place to relax. Dealing with Virginia was a pleasure, she made things so easy. Her assistant Susan is also on the ball and any queries are answered promptly.Siesta Key Beach feels as if you are on a Caribbean Island with its white velvet sand and blue water!The restaurants are fabulous. For supper try The Lobster Pot in Siesta Key Village. A nice lunch can be had at Sweet Tomatoes on Tamiani and a must is ice cream from Olaf's in the village.We will be back!
Kris Koken, Toronto, Ontaro Canada

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Sunrise from the lanai
1 / 19

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

(4)“ Excellent ”4 Reviews

from

$118

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$118 - $186
Per week:$820 - $1,300
Pets allowed:No
Internet:Yes

Siesta Key Condo - Siesta Key Paradise Looking 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,...

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Siesta paradise

“ Excellent ”
February 16, 2015
Gorgeous views along the Intercoastal! Perfect size for the two of us. It is comfortable, lovely amenities fully equipped with gulf beach nearby. Thoughtful owners .....a great winter get away! Close proximity to super restaurants, shopping, the cultural activities of Sarasota!!!!
MaryJo Melberger, Philadelphia area, PA

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Spacious living room
1 / 9

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

(3)“ Excellent ”3 Reviews

from

$128

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$128 - $216
Per week:$890 - $1,510
Pets allowed:No
Internet:Yes

A warm welcome to our Gulf view condominium at wonderful Siesta Key! We have the best location - - across from the Siesta Public Beach, and walking distance to Siesta Village that offers great gourmet dining, shopping, and entertainment. The condo has beach décor with cheerful...

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Fantastic Location

“ Excellent ”
April 13, 2015
We enjoyed our stay so much! The condo is in a wonderful location. At first we thought it was a little too far to the village, but we changed our minds and came to enjoy the walk. The proximity to the beach was amazing! Being able to walk back to the condo for a quick lunch and to reapply sunscreen was a Godsend. Also, being able to watch the gorgeous sunset and then just stroll "home" made for perfect evenings. The condo itself was clean and comfortable. We absolutely loved the shower in the Master bathroom! I don't remember seeing that in the photos, so it was a bonus. If I had to make any improvements, I would say it would be nice to have a King bed in the Master, but I knew it was a Queen going in. The covered parking space was very close to the condo itself, so that was very much appreciated. We would stay here again in a heartbeat!
Nancy Szeromski- Gorham, Canton, MI

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Siesta Key Florida Vacation Rentals - Townhouse
1 / 12

Siesta Key Townhouse
3 Bedrooms / 3 Bathrooms / Sleeps 10
Townhouse / 3 Bedrooms / Sleeps 10

from

$143

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:10
Type:Townhouse
Per night:$143 - $400
Per week:$1,000 - $2,800
Pets allowed:No
Internet:Yes

VILLA CASTILE: Welcome to Villa Castile! A beautifully decorated Spanish Mediterrean 3 bedroom, 3 bathroom townhome with a hot tub in the heart of Siesta Key Village! Once you pass The Village, you'll turn to enter the quaint neighborhood on Avenida De Cortez. At the driveway,...

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Siesta Key Florida Vacation Rentals - Condo
1 / 24

Siesta Key Condo
2 Bedrooms / 1.5 Bathrooms / Sleeps 4
Condo / 2 Bedrooms / Sleeps 4

(4)“ Excellent ”4 Reviews

from

$97

/ night

Email Owner
Bedrooms:2
Bathrooms:1.5
Sleeps:4
Type:Condo
Per night:$97 - $204
Per week:$675 - $1,428
Pets allowed:No
Internet:No

Sun, Sand & SAVE 20% to 35% per Week at Midnight Cove #714, Direct- with- Owner "All- In Price" DISCOUNTED RENTAL RATES from $655 to $1, 385 /Wk & SAVINGS from $239 to $601 /Wk depending on the Season. Contact owner if you wish to make an on- line reservation, and you will...

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Convienent location

“ Excellent ”
July 11, 2014
This rental was awesome! Location, location, location! The nice shaded area off of the back porch was a welcoming place for morning coffee. Easy rental through owner. Midnight Cove providing beach chairs and umbrellas is a big PLUS! easy access to the beach. Condo had everything you need. Nice and clean gas grills near condo were perfect! We would definitely stay here again!
Jennifer Legendre, Louisiana

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Siesta Key Florida Vacation Rentals - Home
1 / 19

Siesta Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$229

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$229 - $358
Per week:$1,600 - $2,500
Pets allowed:No
Internet:Yes

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

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Siesta Key Florida Vacation Rentals - Condo
1 / 6

Siesta Key Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

from

$295

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Condo
Per night:$295 - $445
Per month:$8,850 - $13,350
Pets allowed:Yes
Internet:Yes

The Master Bedroom has a King size bed and Glamorous Bath. Second Bedroom has a Queen size bed and a second private bath. The Den has a Queen size Sleeper Sofa. Fully equipped Cottage Style Kitchen with Corian countertops. Washer and Dryer, WIFI, Tropical patio / Pool, plus lounge...

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Siesta Key Florida Vacation Rentals - Condo
1 / 8

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4
Condo / 2 Bedrooms / Sleeps 4

(1)“ Excellent ”1 Review

from

$200

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
Per night:$200 - $217
Per week:$1,400 - $1,517
Pets allowed:No
Internet:No

Casarina is the most prestigious building on Siesta Key. With only 88 units Casarina is upscale, quiet and friendly. It sits on a private beach on the world famous Crescent Beach (rated one of the top 10 beaches by The Travel Channel). Our spacious 1, 500 sq. ft. condo, is on...

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Couldn't be more perfect!

“ Excellent ”
August 22, 2014
We've just returned from taking our son down to college in Sarasota and we stayed at this most perfect 2 bdrm condo right on the fabulous Crescent Beach with a beautiful swimming pool and wonderful views of the gulf. We plan to book this condo whenever we go to Sarasota!
Sherry Mandel, Hudson Valley, NY, USA

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Siesta Key Florida Vacation Rentals - Home
1 / 8

Siesta Key Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$429

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$429 - $529
Per week:$3,000 - $3,700
Pets allowed:No
Internet:Yes

VILLA MANTEQUILLA: Welcome to Villa Mantequilla, a lovely butter colored 4 bedroom, 2 bath heated pool cottage just 1 block from the Village and 3 blocks to the beach. This remarkable 4 bedroom home features a beautiful pool that overlooks the canal & a private fishing dock. You’ll...

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Siesta Key Florida Vacation Rentals - Townhouse
1 / 27

Siesta Key Townhouse
3 Bedrooms / 3.5 Bathrooms / Sleeps 10
Townhouse / 3 Bedrooms / Sleeps 10

from

$186

/ night

Email Owner
Bedrooms:3
Bathrooms:3.5
Sleeps:10
Type:Townhouse
Per night:$186 - $400
Per week:$1,300 - $2,800
Pets allowed:No
Internet:Yes

CASA DEL SOLEIL: Welcome to Casa Del Soleil, a luxury Townhouse featuring a swim spa, fabulous open floor- plan, with 3 bedrooms and 3. 5 baths. This townhouse is over 2, 688 square feet of pure luxury just 1 block from the beach and the north Village. Furnishings are upscale ...

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Siesta Key Florida Vacation Rentals - Villa
1 / 8

Siesta Key Villa
4 Bedrooms / 3 Bathrooms / Sleeps 8
Villa / 4 Bedrooms / Sleeps 8

from

$258

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Villa
Per night:$258 - $486
Per week:$1,800 - $3,400
Pets allowed:No
Internet:Yes

VILLA CHAMPAGNE: Welcome to “Villa Champagne”, one of the most fabulous vacation homes in Siesta Key. It’s also one of the most popular favorites among our many guest families. The magic begins as you enter the foyer of this beautiful villa and gaze across the expansive living...

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Gulf View of Condo (corner unit; 2nd floor)
1 / 15

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$178

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$178 - $246
Per week:$1,246 - $1,718
Pets allowed:No
Internet:Yes

AAA 2 DIAMOND RATED & TRIP ADVISOR RECOMMENDED! Locaed at Crescent Royale Condominiums - one of the finest gated communities on Siesta Key, this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - VOTED #1 BEST BEACH...

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condo 6D

“ Excellent ”
July 26, 2013
EXCELLENT EXPERIENCE.bEAUTIFULLY DECORATED WITH ALL THE EXTRAS.kITCHEN WELL EQUIPTED WITH ALL THE NECESSARY THINGS I NEEDED.i LOVE TO COOK ON OUR VACATIONS AND ENJOYED THE WONDERFUL AMINITIES.Best extra for the beach were the chairs and terrific umbrella.We get sunburned easily so we used it every day! We plan to return again!
Kathy and David Faircloth, North Augusta,SC

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Siesta Key Florida Vacation Rentals - Condo
1 / 14

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

from

$160

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$160 - $250
Per week:$1,120 - $1,745
Pets allowed:No
Internet:Yes

Welcome to a bit of heaven! Newly udpdated throughout including large flat panel HDTV with PREMIUM CABLE including HBO, DVR and WIRELESS INTERNET FREE! A gorgeous gulf- front vacation awaits you as you come and enjoy this enchanting condo! Located directly on newly replenished...

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Siesta Key Florida Vacation Rentals - Apartment
1 / 4

Siesta Key Apartment
1 Bedroom / 1 Bathroom / Sleeps 4
Apartment / 1 Bedroom / Sleeps 4

from

$295

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$295 - $360
Per month:$8,850 - $10,800
Pets allowed:Yes
Internet:Yes

This 1 bedroom Beach Suite is totally newly remodeled with a tiled Kitchen and Bath with new furnishings throughout. This property is right on the sandy beach, The Sandbox has the best of it all. It is like small town USA combined with one of the top beaches in the world. The...

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1 / 15

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4
Condo / 2 Bedrooms / Sleeps 4

from

$171

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
Per night:$171 - $285
Per week:$1,195 - $1,995
Pets allowed:No
Internet:Yes

WE WE HAVE THE ABSOLUTE BEST SPOT ON THE ABSOLUTE BEST BEACH! (Reuters, May 27, 2011) 7 day Sat to Sat minimum stay. CHECK OUT OUR AWARD- WINNING This unit is booked solid through May 9, 2015 but early booking discounts are being offered for later dates. You will not find ...

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1 / 24

Siesta Key Condo
2 Bedrooms / 1.5 Bathrooms / Sleeps 4
Condo / 2 Bedrooms / Sleeps 4

(43)“ Excellent ”43 Reviews

from

$97

/ night

Email Owner
Bedrooms:2
Bathrooms:1.5
Sleeps:4
Type:Condo
Per night:$97 - $204
Per week:$675 - $1,428
Pets allowed:No
Internet:No

Sun, Sand & SAVE 20% to 35% per Week at Midnight Cove #532, Direct- with- Owner "All- In Price" DISCOUNTED RENTAL RATES from $655 to $1, 385 /Wk & SAVINGS from $239 to $601 /Wk depending on the Season. Contact owner if you wish to make an on- line reservation, and you will...

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Vacation close to the beach

“ Excellent ”
January 2, 2013
Excellent property with lot of parking, laundy on site and warm water in the pool, which was really appreciated on the cooler dates, speacially by the kids. Close walk to a white sandy beach was on asset. Condo was very spacious and full equipped. We have enjoed the stay.Will use the property for sure again. Love teh area.
Krystyna Bebee, Mississauga, Ontario, Canada

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Siesta Key Florida Vacation Rentals - Condo
1 / 22

Siesta Key Condo
1 Bedroom / 1 Bathroom / Sleeps 4
Condo / 1 Bedroom / Sleeps 4

from

$150

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Condo
Per night:$150 - $255
Per month:$4,500 - $7,650
Pets allowed:No
Internet:Yes

Village West # 101 is the perfect place for your Siesta Key Vacation. With rentals by the day, by the week, or longer this location is sure to please. Our newly Remodeled Siesta Key Ground Floor Apartment is in the heart of the Village of Siesta Key. This apartment is well appointed...

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Siesta Key Florida Vacation Rentals - Condo
1 / 7

Siesta Key Condo
2 Bedrooms / 3 Bathrooms / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

from

$295

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Condo
Per night:$295 - $445
Per month:$8,850 - $13,350
Pets allowed:Yes
Internet:Yes

Privacy, Luxury, 99 steps to the Beach. The Master Bedroom has a King size Bed and Glamorous Bath. Second Bedroom has a Queen Bed and Private Bath. The Den has a Pullout Sleeper Sofa plus a (newly installed) First Quality Murphy Bed. Fully equipped GOURMET style kitchen with...

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Siesta Key Florida Vacation Rentals - Condo
1 / 24

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

(32)“ Excellent ”32 Reviews

from

$139

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$139 - $255
Per week:$973 - $1,781
Pets allowed:No
Internet:No

Sun, Sand & SAVE 20% to 35% per Week at Siesta Breakers #603, Direct- with- Owner "All- In Price" DISCOUNTED RENTAL RATES from $944 to $1, 728 /Wk & SAVINGS from $374 to $698 /Wk depending on the Season. Contact owner if you wish to make an on- line reservation, and you will...

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Beautiful Beach

“ Excellent ”
July 14, 2014
This was our first trip to Siesta Key, but not our last! We are already booking another stay at Siesta Breakers for next year. It is a great location on the Beach and great access to the mainland.
Helen Hussey, Vidalia, GA

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Sunset on Siesta Key
1 / 11

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

(4)“ Excellent ”4 Reviews

from

$107

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$107 - $114
Per week:$747 - $794
Pets allowed:No
Internet:Yes

Location, Location, Location! Siesta Key #1 Beach in USA Our condo is only a 3 minute walk to Crescent Beach on beautiful Siesta Key FL. Siesta Key Beach rated #1 beach in the USA. We rent by the month or for the season. Our two bedroom, two bath has a screened in lanai, large...

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Really Nice Condo!!

“ Excellent ”
August 30, 2013
We recently stayed at this condo for a few weeks. The condo is in very good shape and is charming. The management staff is amazing and always easy to reach. Very close to the beach and the pool. Overall, we had a pleasant experience.
tanya yudin, Washington

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Perfect Place to Watch the Sunset
1 / 11

Siesta Key Home
4 Bedrooms / 2 Bathrooms / Sleeps 9
Home / 4 Bedrooms / Sleeps 9

(2)“ Excellent ”2 Reviews

from

$158

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:9
Type:Home
Per night:$158 - $258
Per week:$1,100 - $1,800
Pets allowed:Yes
Internet:Yes

Your home away from home- - our beautiful four bedroom house is located in a quiet, upscale neighborhood only two blocks to Siesta Beach, the largest and most beautiful beach on the key. We are also an easy walk to the Village for restaurants, shopping and entertainment. Our...

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Dream place!

“ Excellent ”
August 28, 2014
Perfect place to spend vacations with the family. Perfectly clean, with a great kitchen equipment, very good matresses, and a lot of outdoor activities equipment. Great clean pool in a garden with privacy. Calm, sunny and close (10mn walking distance) to beautiful Siesta key!
Anne Closuit, New-York, USA

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Siesta Key Florida Vacation Rentals - Home
1 / 10

Siesta Key Home
4 Bedrooms / 3 Bathrooms / Sleeps 10
Home / 4 Bedrooms / Sleeps 10

from

$429

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$429 - $572
Per week:$3,000 - $4,000
Pets allowed:No
Internet:Yes

PURA VIDA OASIS: This spectacular bright cheerful, canal front cottage with a heated pool & spa has 5 bedrooms and 3 baths and it can sleep a total of 13. As you enter Pura Vida Oasis, you will notice an eclectic wine storage rack and desk area awaiting on your right and a lovely...

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Siesta Key Florida Vacation Rentals - Condo
1 / 11

Siesta Key Condo
2 Bedrooms / 3 Bathrooms / Sleeps 5
Condo / 2 Bedrooms / Sleeps 5

from

$300

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:5
Type:Condo
Per night:$300
Per week:$2,100
Pets allowed:No
Internet:No

Well maintained and fully equiped with all big amenties and needful things for your perfect vacation. This is perfect place for you if you looking for active and beautiful vacation here you will get many. Public tennis courts, walk to the beach and vollyball sand courts. Segways ...

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Siesta Key Florida Vacation Rentals - Home
1 / 9

Siesta Key Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

from

$458

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$458 - $529
Per week:$3,200 - $3,700
Pets allowed:No
Internet:Yes

VILLA DE PARADISIO: Welcome to the beautiful Villa De Paradisio! This gorgeous waterfront cottage is a very luxurious and large four [4] bedroom canal front heated pool home with two bathrooms in approximately 1, 800SF of air conditioned living space with a heated pool overlooking...

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Siesta Key Florida Vacation Rentals - Home
1 / 8

Siesta Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 10
Home / 3 Bedrooms / Sleeps 10

from

$386

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:10
Type:Home
Per night:$386 - $458
Per week:$2,700 - $3,200
Pets allowed:No
Internet:Yes

VILLA LAGO: Villa Lago is a fantastic waterfront villa with a heated pool located only ½ mile to the Village. It is unquestionably one of our most colorful homes and is now considered by many to be the perfect Florida vacation getaway. It’s an amazing, luxurious home that exudes...

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From the beach
1 / 8

Siesta Key Home
3 Bedrooms / 3.5 Bathrooms / Sleeps 7
Home / 3 Bedrooms / Sleeps 7

(1)“ Excellent ”1 Review

from

$229

/ night

Email Owner
Bedrooms:3
Bathrooms:3.5
Sleeps:7
Type:Home
Per night:$229 - $286
Per week:$1,600 - $2,000
Pets allowed:Yes
Internet:Yes

Tiffany Sands is a group of 9 townhouses directly on Crescent Beach. Our beach house is a stand alone unit(unattached). We have full gulf views with 2 decks facing the Gulf of Mexico. It is a spacious 1, 800 sq. ft. and newly decorated with a fully appointed kitchen, plus 3 1/2 ...

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Absolutely Amazing

“ Excellent ”
November 20, 2014
When we pulled into Tiffany Sands, we knew it was going to be something special! We had a week of pure bliss. The amenities were unbelievable. Every morning we were greeted by warm sun and the sound of rolling waves. One of the many benefits of this rental was that you had your own beach that was off of the beaten path. The main beach is withinn walking distance but you would never know that you were even close. We leisurely walked outside and down the path to what we called "our spot" on the beach. We even made friends as we were the only ones in our small section of beach everyday. The property leaves no stone unturned in how nice it is. The master bedroom is amazing and the view from the balcony makes it even better! We travelled with 3 couples and had an amazing time. If I would have had a family and kids, this would be a prime location for all family vacations. Do not overlook this property as you will be absolutely amazed!
Scott Schenker, Orlando, FL

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Siesta Key Florida Vacation Rentals - Home
1 / 21

Siesta Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 7
Home / 3 Bedrooms / Sleeps 7

(5)“ Excellent ”5 Reviews

from

$350

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$350 - $500
Per week:$2,400 - $3,400
Pets allowed:Yes
Internet:Yes

BEACH FRONT :Wander out 100 yards to the gorgeous white sand beaches of the Gulf of Mexico and only one block to SIESTA KEY VILLAGE! Our gorgeous three bedroom two bath beach- house is a one- of- a- kind private home with amazing water views from the private patio, (grilling on ...

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Wonderful Vacation

“ Excellent ”
December 11, 2014
Light, airy, attractive condo perfectly situated next to the beach and Siesta Key Village. Our days were filled with the beach, lunch (sometimes back at the condo, sometimes on the beach), beach, a coctail and "apps" in the village and back to the beach to look at the sunset. This was followed by dinner and bed. Wake up and do all over again. A wonderful time and we can't wait to do it again at Barb and Jay's!
Wendy Sinclair, Boston, MA

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Siesta Key Florida Vacation Rentals - Apartment
1 / 3

Siesta Key Apartment
Studio / 1 Bathroom / Sleeps 2
Apartment / Studio / Sleeps 2

from

$185

/ night

Email Owner
Bedrooms:Studio
Bathrooms:1
Sleeps:2
Type:Apartment
Per night:$185
Per month:$5,550
Pets allowed:Yes
Internet:Yes

Beachfront charming Studio directly on Gulf of Mexico. Queen size comfortable Murphy bed plus a Futon. Galley kitchen with full size refrigerator. Propane BBQ plus umbrella table, four chairs. Beach chairs. WIFI, Cable TV, Air conditioned, of course. Ground floor. Walk to Siesta...

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Siesta Key Florida Vacation Rentals - Home
1 / 24

Siesta Key Home
7 Bedrooms / 5 Bathrooms / Sleeps 16
Home / 7 Bedrooms / Sleeps 16

from

$999

/ night

Email Owner
Bedrooms:7
Bathrooms:5
Sleeps:16
Type:Home
Per night:$999 - $1,500
Per month:$29,970 - $45,000
Pets allowed:No
Internet:Yes

This stunning home features 10 foot ceilings, top of the line VIKING appliances including a wall mounted double oven, stove, and side by side refrigerator. The kitchen has a massive center island with lots of room for multiple chefs or families and friends to sit and chat after...

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Siesta Key Florida Vacation Rentals - Home
1 / 8

Siesta Key Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

from

$393

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:8
Type:Home
Per night:$393 - $500
Per week:$2,750 - $3,500
Pets allowed:No
Internet:Yes

Perhaps the most fantastic view in all Siesta Key, this beach front penthouse, Hermosa Vista (Beautiful View) can only be described as remarkable, rare and truly endearing. Many condominiums can be found along the landscape of Siesta Key all seemingly “cookie- cut” from the...

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Block to the beach
1 / 10

Siesta Key Apartment
1 Bedroom / 1 Bathroom / Sleeps 3
Apartment / 1 Bedroom / Sleeps 3

from

$200

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:3
Type:Apartment
Per night:$200 - $250
Per week:$1,300
Pets allowed:Yes
Internet:Yes

Siesta Village in the heart of it all! Brand new construction; second story fully furnished adorable "flat" type apartment, all appliances, washer dryer, beachy cool amenities and a great deck over- looking all of the action in the iconic village! Enjoy coffee in the morning...

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Siesta Key Florida Vacation Rentals - Condo
1 / 6

Siesta Key Condo
3 Bedrooms / 2 Bathrooms / Sleeps 8
Condo / 3 Bedrooms / Sleeps 8

(6)“ Excellent ”6 Reviews

from

$485

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Condo
Per night:$485 - $570
Per month:$14,550 - $17,100
Pets allowed:Yes
Internet:Yes

This 3 bedroom 2 Bath Beach Suite is totally newly remodeled with a tiled Kitchen and Bath with new furnishings throughout. This property is right on the sandy beach, The Sandbox has the best of it all. It is like small town USA combined with one of the top beaches in the world....

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Fabulous beachfront property

“ Excellent ”
January 22, 2014
We had a family gathering here (4 days) & it was wonderful in every way! None of us had ever been to Siesta Key & felt so fortunate to find such nice accommodations --& liked the location, as the north end of the island is much less crowded than the middle & southern end--yet only couple of blocks from the Village shops & restaurants. The condo was, as described, newly renovated & well furnished. There is a large patio facing the beach---perfect for eating outside & enjoying the sunsets. They even had a generous supply of beach chairs which we could take to the beach. The condo was also very clean. Nice touches like coffee, sugar, creamer, salt, pepper, kleenex , soap, shampoo, etc. The whole staff was very nice & helpful. Frank, the manager & Roger, the owner, gave us wonderful recommendations for restaurants. It was an added pleasure to have our dogs there with us---very dog friendly place. We plan to come back & stay longer!
Grace Gokturk, Naples, FL & Fairfield Bay, AR

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Siesta Key Florida Vacation Rentals - Apartment
1 / 16

Siesta Key Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

(2)“ Excellent ”2 Reviews

from

$211

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$211 - $320
Per month:$6,330 - $9,600
Pets allowed:No
Internet:Yes

Island House Beach Resort! Newly remodeled! ! Crescent Beach, Siesta Key Florida! This attractive complex is located on the widest part of one of the best beaches in central florida. This condo is 1300 sq. ft and is located on the 4th floor. It is 2 bedrooms, 2 baths, King, ...

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Siesta Key Florida Vacation Rentals - Villa
1 / 16

Siesta Key Villa
2 Bedrooms / 2 Bathrooms / Sleeps 6
Villa / 2 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$163

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Villa
Per night:$163 - $246
Per month:$4,890 - $7,380
Pets allowed:No
Internet:Yes

Island House Beach Resort, Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 2 bath unit is approx. 1000 sq. ft. It has a large living area, dining area, fully equipped kitchen, all appliances, screened lanai, covered parking, central ac/heat, 3 tvs, free wi-...

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Siesta Key Florida Vacation Rentals - Apartment
1 / 17

Siesta Key Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$211

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$211 - $320
Per month:$6,330 - $9,600
Pets allowed:No
Internet:Yes

Island House Beach Resort - Siesta Key, Crescent Beach, Ground Floor unit! This unit is located at Island House Beach Resort on sunny Siesta Key. It is 2 bedrooms, 2 baths, 1300 squart feet. King, full, futon. It has a large living room, fully equipped kitchen, all appliances,...

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Siesta Key Florida Vacation Rentals - Apartment
1 / 17

Siesta Key Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

(5)“ Excellent ”5 Reviews

from

$211

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$211 - $320
Per month:$6,330 - $9,600
Pets allowed:No
Internet:Yes

Island House Beach Resort! Siesta Key Florida, Crescent Beach. This beautifully maintained complex is located on one of the best beaches in Florida. The condo offers view of palm trees, white sand and the turquoise waters of the Gulf of Mexico. The view is picturesque and the sunsets...

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Siesta Key Florida Vacation Rentals - Apartment
1 / 17

Siesta Key Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

(3)“ Excellent ”3 Reviews

from

$211

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$211 - $320
Per month:$6,330 - $9,600
Pets allowed:No
Internet:Yes

Island House Beach Resort! Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on one of the best beaches in central Florida. This 3rd floor, 2 bedroom, 2 bath condo offers views of palm trees, white sand and the turquoise waters of the Gulf of ...

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Siesta Key Florida Vacation Rentals - Apartment
1 / 25

Siesta Key Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$211

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$211 - $320
Per month:$6,330 - $9,600
Pets allowed:No
Internet:No

Island House Beach Resort - Siesta Key Florida - Crescent Beach. This beautifully maintained complex is located on the widest part of one of the best beaches in Central Florida. This 2nd floor condo offers views of palm trees, white sand and the turquoise waters of the Gulf of ...

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Siesta Key Florida Vacation Rentals - Apartment
1 / 24

Siesta Key Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

(7)“ Excellent ”7 Reviews

from

$211

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$211 - $320
Per month:$6,330 - $9,600
Pets allowed:No
Internet:Yes

DIRECT GULF FRONT! ! 2 Bedrooms, 2 bathrooms at Island House Beach Resort. 4th Floor unit. The unit is 1300 sq. ft. King, 2 twins, sleeper. This beautifully maintained complex is lococated on Siesta Key on Crescent Beach. The luxury apartment offers direct gulf view of the turquoise...

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Siesta Key Florida Vacation Rentals - Apartment
1 / 15

Siesta Key Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

(7)“ Excellent ”7 Reviews

from

$211

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$211 - $320
Per month:$6,330 - $9,600
Pets allowed:No
Internet:Yes

Island House Beach Resort, Crescent Beach, Siesta Key Florida! Direct Gulf Front - Panoramic Views! This beautifully maintained complex is located on the widest part of one of the best beaches in central florida. The condo is 1300 sq. ft. and is located on the 2nd floor. KIng,...

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Siesta Key Florida Vacation Rentals - Apartment
1 / 16

Siesta Key Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

(4)“ Excellent ”4 Reviews

from

$211

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$211 - $320
Per month:$6,330 - $9,600
Pets allowed:No
Internet:Yes

Island House Beach Resort - Crescent Beach, Siesta Key Florida. 2nd Floor unit, 2 bedrooms, 2 baths. This beautifully maintained complex is located on one of the best beaches in Florida. This condo offers a view of palm trees, white sand and the turquoise waters of the Gulf of...

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Siesta Key Florida Vacation Rentals - Villa
1 / 15

Siesta Key Villa
2 Bedrooms / 2 Bathrooms / Sleeps 6
Villa / 2 Bedrooms / Sleeps 6

from

$152

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Villa
Per night:$152 - $232
Per month:$4,560 - $6,960
Pets allowed:No
Internet:Yes

Island House Beach Resort - Siesta Key Florida, Crescent Beach. This 2 bedroom, 2 bath duplex is located on the ground floor and is 1000 sq. ft. It has a full kitchen, living room, dining area, lanai. There is a king, 2 twins, sleeper sofa. The unit is located close to the...

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Siesta Key Florida Vacation Rentals - Villa
1 / 15

Siesta Key Villa
2 Bedrooms / 1 Bathroom / Sleeps 6
Villa / 2 Bedrooms / Sleeps 6

(2)“ Excellent ”2 Reviews

from

$137

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Villa
Per night:$137 - $212
Per month:$4,110 - $6,360
Pets allowed:No
Internet:Yes

Island House Beach Resort - Siesta Key Florida - Crescent Beach. This 2 bedroom, 1 bath villa duplex is 1000 sq. ft. living room, dining area, full kitchen ( all appliances), lanai. Central heat/ac. The unit has a king, 2 twins, sleeper. 3 tvs. It is located across from our...

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About Siesta Key

If you're planning a vacation to this island paradise, you may want to consider Siesta Key vacation rentals. This beautiful barrier island spans eight miles just off the coast of Sarasota in the Gulf of Mexico. Many resorts and hotels can be found here, but popular accommodations also include Siesta Key condo rentals that provide privacy and access to the island's world-renowned white sand beaches.

Resorts can be overcrowded and overpriced, but Siesta Key vacation home rentals are always private and generally quite affordable. This destination is known as a great romantic getaway, and there are plenty of cozy little cottages for two that will set the perfect mood for your honeymoon or other romantic rendezvous. Regardless of your lifestyle and budget, there is something here to meet your needs.

We couldn't call it an "island paradise" if it didn't offer warm breezes, cool water, swaying palm trees, and some of the world's finest beaches, including Turtle Beach and Palmer Point Beach. Relaxing on the pure quartz beaches with family and friends is certainly a favorite pastime here, and visitors enjoy the charming beach hideaways and ample bird-watching opportunities. You might also spot some friendly dolphins and manatees dotting the surrounding gulf and bay waters.

If you visit the island during the beginning of May, the beach literally comes alive with figures made of sand during the island's unique sand sculpture contest that draws in world-class artists. Of course, anyone can try their hand at a sandcastle or sand sculpture any time of year.

If staying on dry land sounds like a bore, you'll find almost 50 miles of waterways and canals inside the island, not to mention the surrounding Gulf of Mexico and Sarasota and Roberts Bays. Many Siesta Key, FL vacation rentals by owner provide boat docks, and boat rentals are available for you to get out and explore the waters. Other water sports are popular here as well, including fishing, snorkeling, parasailing, and sailboarding.

If you'd rather not captain your own ship, plenty of local charter companies offer guided tours. Many of the local restaurants also offer temporary docking, so that you can go to dinner straight from your afternoon on the water. What better way to work up an appetite for some fresh seafood than a day spent in the sand, sun, and surf?

Of course, the beaches are just the beginning of all there is to see and do in Siesta Key. This tropical island also offers plenty of events and attractions, ...

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