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Siesta Key Florida Vacation Rentals - Home
1 / 34

Siesta Key Home
4 Bedrooms / 4 Bathrooms / Sleeps 12

from

$229

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:12
Type:Home
Per night:$229 - $486
Per week:$1,600 - $3,400
Pets allowed:No
Internet:Yes

Villa Margarita located at 1109- 1111 Crescent Street is a vibrant, festive newly decorated four bedroom/four bathroom/two kitchen home now available for vacation rentals with The Cottages. It’s the latest standout in our boutique collection of fine vacation homes now available...

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Siesta Key Florida Vacation Rentals - Home
1 / 22

Siesta Key Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$129

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$129 - $258
Per week:$900 - $1,800
Pets allowed:No
Internet:Yes

Welcome to Casita Salado of Villa Margarita! Enjoy an master bedroom featuring a colorful king size bed (sleeps 2) and en suite master bathroom, and a second bedroom with two twin beds (sleeps 2) and a separate living room with a very comfy, queen size sofa sleeper (sleeps 2) all...

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Siesta Key Florida Vacation Rentals - Home
1 / 20

Siesta Key Home
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$129

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$129 - $258
Per week:$900 - $1,800
Pets allowed:No
Internet:Yes

The Sea Shell and Sea Wave Casitas are two separate units which can be uniquely configured to create Villa Brisa Marina, an absolutely beautiful and stunning private pool home. (Please note: These units can be rented separately. If one unit is not available, please inquire about...

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Siesta Key Florida Vacation Rentals - Home
1 / 18

Siesta Key Home
4 Bedrooms / 1 Bathroom / Sleeps 12

from

$229

/ night

Email Owner
Bedrooms:4
Bathrooms:1
Sleeps:12
Type:Home
Per night:$229 - $486
Per week:$1,600 - $3,400
Pets allowed:No
Internet:Yes

Villa Dom Brisa or "Sun Breeze" at 1123- 1125 Crescent Street is another beautifully decorated, exciting new 4BR/4BA/2Kit home recently added to our boutique collection of fine vacation homes at The Cottages. This home is part of the Las Brisa complex of two beautiful 4- BR homes...

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Siesta Key Florida Vacation Rentals - Home
1 / 34

Siesta Key Home
4 Bedrooms / 4 Bathrooms / Sleeps 12

from

$229

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:12
Type:Home
Per night:$229 - $486
Per week:$1,600 - $3,400
Pets allowed:No
Internet:Yes

Villa Fiesta at 1115 Crescent Street is another beautifully decorated, exciting new 4BR/4BA/2Kit home recently added to The Cottages collection of fine vacation homes. Villa Fiesta and its sister home, Villa Margarita are two beautiful 4- BR pool homes offering unique sleeping combinations...

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Siesta Key Florida Vacation Rentals - Home
1 / 30

Siesta Key Home
4 Bedrooms / 3 Bathrooms / Sleeps 12

“ Excellent ”2 Reviews

from

$415

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:12
Type:Home
Per night:$415 - $586
Per week:$2,900 - $4,100
Pets allowed:No
Internet:Yes

THE GRAND CANAL COTTAGE: The Grand Canal Cottage, perhaps one of Siesta Key’s favorite luxury vacation homes, is a highly landscaped canal- front private luxury home featuring a heated pool with sun shelf and a separate 8- person spa. It is situated on Siesta Key within two walking...

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One Family Vacation to Remember

“ Excellent ”
January 9, 2015
A 5 star vacation in very possible way. 1) Great owner. 2) Fruendly neighborhood 3) Beautiful weather 4) Nice pool and patio. 5) Shopping nearby. We are going back . Redd Family
JAMES REDD, Cadiz, Ky .

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Siesta Key Florida Vacation Rentals - Home
1 / 17

Siesta Key Home
4 Bedrooms / 4 Bathrooms / Sleeps 12

“ Excellent ”1 Review

from

$229

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:12
Type:Home
Per night:$229 - $486
Per week:$1,600 - $3,400
Pets allowed:No
Internet:Yes

Villa Brisa Marina or "Sea Breeze" at 1119- 1121 Crescent Street is an exciting new 4BR/4BA/2Kit home just added to our boutique collection of fine vacation homes and it's sure to be a standout. This home features a brand new heated pool and a three minute walk to the Nation’s finest...

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great family get away

“ Excellent ”
September 1, 2014
Wonderful place to stay with young children. Warm shallow pool, steps from incredible beach with calm waters. Great customer service from Eric and Heather. Will come again :)
Tina Brienza, Toronto, Canada

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Sarasota Florida Vacation Rentals - Villa
1 / 8

Sarasota Villa
4 Bedrooms / 2 Bathrooms / Sleeps 10

from

$200

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:10
Type:Villa
Per night:$200 - $486
Per week:$1,400 - $3,400
Pets allowed:No
Internet:Yes

Point of Rocks, located just south of the Stickney Point Bridge, the most notable location on Siesta Key, is blessed with the soft, white quartz sand found on Siesta Key beach, but geologically unique and named for the formation of limestone rock that extends from the beach out...

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Siesta Key Florida Vacation Rentals - Home
1 / 19

Siesta Key Home
3 Bedrooms / 2 Bathrooms / 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

NEW! HEATED POOL! READY FOR OCTOBER 2014! Sophie’s Cottage ( 2 week minimum Rental ) is a smart, sophisticated upscale waterfront retreat with an oversized hot tub, boat dock, and a short walk to Siesta Key Beach. Ideally, it accommodates 6 but can easily sleep up to 8 with...

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Siesta Key Florida Vacation Rentals - Villa
1 / 8

Siesta Key Villa
4 Bedrooms / 3 Bathrooms / Sleeps 10

from

$258

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Villa
Per night:$258 - $486
Per week:$1,800 - $3,400
Pets allowed:No
Internet:Yes

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 area, then further...

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Sarasota Florida Vacation Rentals - Home
1 / 8

Sarasota Home
3 Bedrooms / 2 Bathrooms / Sleeps 8

from

$136

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$136 - $236
Per week:$950 - $1,650
Pets allowed:No
Internet:Yes

Centrally located in the heart of Sarasota, and only minutes away from our world famous Siesta Key Beach, Villa Espanola offers a bright and cheerful retreat with a heated swimming pool and a privately fenced backyard. Perfect for larger families that enjoy the peaceful serenity...

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Sarasota Florida Vacation Rentals - Home
1 / 26

Sarasota Home
7 Bedrooms / 5.5 Bathrooms / Sleeps 16

from

$772

/ night

Email Owner
Bedrooms:7
Bathrooms:5.5
Sleeps:16
Type:Home
Per night:$772 - $1,029
Per week:$5,400 - $7,200
Pets allowed:No
Internet:Yes

Welcome to Sophie's Quartier! This is a perfect retreat for huge family and friends' get togethers! Enjoy two heated pools, one hot tub, and two docks overlooking The Grand Canal of Siesta Key. And only just a few minutes walk from the world famous Siesta Key Beach and Siesta ...

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Sarasota Florida Vacation Rentals - Cottage
1 / 10

Sarasota Cottage
4 Bedrooms / 3 Bathrooms / Sleeps 10

from

$186

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Cottage
Per night:$186 - $486
Per week:$1,300 - $3,400
Pets allowed:No
Internet:Yes

Siesta Key is a small magical Island lying just off the coast of the City of Sarasota that can boast having the Number One beach in the entire United States as well as placing in the top twenty beaches in the entire world. And is it so popular with vacationing families…! Just after...

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Sarasota Florida Vacation Rentals - Condo
1 / 16

Sarasota Condo
2 Bedrooms / 1 Bathroom / Sleeps 6

from

$115

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Condo
Per night:$115 - $200
Per week:$800 - $1,400
Pets allowed:No
Internet:Yes

Centrally located in the heart of downtown Sarasota, and only minutes away from our Siesta Key and Lido Key Beach, 1670 Laurel Park offers a bright and cheerful affordable luxury retreat within walking distance to the vibrant Main Street of Sarasota and Bayfront Park. Perfect for...

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Siesta Key Florida Vacation Rentals - Home
1 / 8

Siesta Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$400

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$400
Per week:$2,800
Pets allowed:No
Internet:Yes

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 Florida with...

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Sarasota Florida Vacation Rentals - Villa
1 / 8

Sarasota Villa
4 Bedrooms / 2 Bathrooms / Sleeps 12

from

$243

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:12
Type:Villa
Per night:$243
Per week:$1,700
Pets allowed:No
Internet:Yes

Welcome to Suelo y Rio! This uniquely configured private home featuring a heated pool, a screened in lanai overlooking the beautiful Phillippi Creek, and 4 bedrooms, 2 bathrooms that sleeps 12, with 2 living areas and 2 kitchens. Suelo y Rio is well located just five minutes ...

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Siesta Key Florida Vacation Rentals - Home
1 / 8

Siesta Key Home
3 Bedrooms / 2.5 Bathrooms / 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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Siesta Key Florida Vacation Rentals - Townhouse
1 / 8

Siesta Key Townhouse
3 Bedrooms / 3 Bathrooms / Sleeps 10

from

$200

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:10
Type:Townhouse
Per night:$200
Per week:$1,400
Pets allowed:No
Internet:Yes

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, you are invited...

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Sarasota Florida Vacation Rentals - Home
1 / 8

Sarasota Home
4 Bedrooms / 3 Bathrooms / Sleeps 10

from

$186

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$186
Per week:$1,300
Pets allowed:No
Internet:Yes

Welcome to Casa Benevento! This bright, and exquisitely decorated private home boasts gorgeous open spaces that have been recently redesigned and redecorated! Enjoy the private heated pool in a completely screened in enclosure that overlooks a nature preserve, and walls of privacy...

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Siesta Key Florida Vacation Rentals - Home
1 / 8

Siesta Key Home
4 Bedrooms / 2 Bathrooms / Sleeps 8

from

$372

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$372
Per week:$2,600
Pets allowed:No
Internet:Yes

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. This home has been completely renovated and features...

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Sarasota Florida Vacation Rentals - Home
1 / 15

Sarasota Home
4 Bedrooms / 2 Bathrooms / Sleeps 8

from

$186

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$186 - $415
Per week:$1,300 - $2,900
Pets allowed:No
Internet:Yes

Point of Rocks, located just south of the Stickney Point Bridge, the most notable location on Siesta Key, is blessed with the soft, white quartz sand found on Siesta Key beach, but geologically unique and named for the formation of limestone rock that extends from the beach out...

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Siesta Key Florida Vacation Rentals - Townhouse
1 / 26

Siesta Key Townhouse
3 Bedrooms / 3.5 Bathrooms / Sleeps 10

from

$200

/ night

Email Owner
Bedrooms:3
Bathrooms:3.5
Sleeps:10
Type:Townhouse
Per night:$200
Per month:$6,000
Pets allowed:No
Internet:Yes

This luxury Townhouse features all of the high end amenities typical to a Cottages Home. A fabulous open floor- plan, with 3 bedrooms and 3. 5 baths, over 2, 688 square feet of pure luxury just 1 block from the beach and the north Village! This luxury Townhouse features all...

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Siesta Key Florida Vacation Rentals - Home
1 / 8

Siesta Key Home
4 Bedrooms / 2 Bathrooms / Sleeps 8

from

$372

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$372
Per week:$2,600
Pets allowed:No
Internet:Yes

Welcome to Villa Mantequilla, a lovely butter colored 4 bedroom, 2 bath 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 love the sense of complete...

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The Cottages
The Cottages
From Siesta Key, FL
Member since July, 2013
Languages
English