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Sarasota Florida Vacation Rentals - Home
1 / 26

Sarasota Home
6 Bedrooms / 5.5 Bathrooms / Sleeps 16
Home / 6 Bedrooms / Sleeps 16

from

$772

/ night

Email Owner
Bedrooms:6
Bathrooms:5.5
Sleeps:16
Type:Home
Per night:$772 - $1,029
Per week:$5,400 - $7,200
Pets allowed:No
Internet:Yes

SOPHIE'S QUARTIER: Welcome to Sophie's Quartier, a waterfront compound consisting of two homes right near Siesta Key Beach! This is a perfect retreat for huge family and friends' get togethers! Enjoy a heated pool, two hot tubs, two docks overlooking The Grand Canal of Siesta...

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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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Sarasota Florida Vacation Rentals - Condo
1 / 16

Sarasota Condo
2 Bedrooms / 1 Bathroom / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

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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Great family vacation

“ Excellent ”
April 13, 2015
Large beautiful home set up with 2 separate master suites for adults, with upstairs BR with queen bed and adjacent room with 4 bunk beds, perfect for 2 family to share. Place has a large well stocked kitchen, 2 LR areas, DR, and huge porch where we had most of our meals overlooking the dock watching the manatee, dolphins, stingray and fishes in the water. Small pool with hot tub, which we never even used, too busy otherwise.Close to the public beach access with garage well stocked with beach accessories, bicycles, and fishing gear. Restaurants, shops and putt putt easily walking distance. Great location, lots of house, all the amenities of a home away from home.
charles chung, NY

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Sarasota Florida Vacation Rentals - Cottage
1 / 10

Sarasota Cottage
4 Bedrooms / 3 Bathrooms / Sleeps 8
Cottage / 4 Bedrooms / Sleeps 8

(1)“ Excellent ”1 Review

from

$186

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Cottage
Per night:$186 - $486
Per week:$1,300 - $3,400
Pets allowed:No
Internet:Yes

THE STARFISH COTTAGE: 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...

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Siesta Key

“ Excellent ”
March 24, 2015
This was our first visit to Siesta Key, and it was a great experience. Our guess at a nice rental was warded with good luck. The condo was i excellent condition, comfortable, quiet, and within easy walk of the restaurants, shopping and beach. And the beach is georgeous! White sand, soft waves, not at all crowded, inspire of peak season.
Doug Baker, Baltimore, MD

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Sarasota Florida Vacation Rentals - Home
1 / 8

Sarasota Home
3 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 3 Bedrooms / 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

VILLA ESPANOLA: 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...

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Siesta Key Florida Vacation Rentals - Home
1 / 30

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

(2)“ Excellent ”2 Reviews

from

$418

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$418 - $643
Per week:$2,925 - $4,500
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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Sarasota Florida Vacation Rentals - Villa
1 / 8

Sarasota Villa
4 Bedrooms / 2 Bathrooms / Sleeps 10
Villa / 4 Bedrooms / 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 - 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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Siesta Key Florida Vacation Rentals - Home
1 / 34

Siesta Key Home
4 Bedrooms / 4 Bathrooms / Sleeps 12
Home / 4 Bedrooms / 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 / 20

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

(1)“ Excellent ”1 Review

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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Sea shell villa

“ Excellent ”
April 28, 2015
The villa was very nice , well equipped, immaculate and very comfortable. We enjoyed the courtyard and pool very much and are stay was very relaxing. The area has everything you would want on vacation along with one of the best beaches. Dave from the management group was very helpful and made the overall rental process a breeze.
Diane Ryan, Chicago, Illinois - USA

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Sarasota Florida Vacation Rentals - Home
1 / 18

Sarasota Home
4 Bedrooms / 1 Bathroom / Sleeps 12
Home / 4 Bedrooms / Sleeps 12

from

$229

/ night

Email Owner
Bedrooms:4
Bathrooms:1
Sleeps:12
Type:Home
Per night:$229 - $458
Per week:$1,600 - $3,200
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
Home / 4 Bedrooms / 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
Home / 2 Bedrooms / 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 / 17

Siesta Key Home
4 Bedrooms / 4 Bathrooms / Sleeps 12
Home / 4 Bedrooms / Sleeps 12

(2)“ Excellent ”2 Reviews

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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Amazing

“ Excellent ”
April 13, 2015
We have recently had the pleasure of renting a home on Peaceable way. The home was amazing very clean, well organized and the decor was exceptional. We rented the house with 2 other families the house was spacious and very accommodating to our needs. If we did encounter of any sort of problem we called Beth and the matter was rectified in a very timely manner. I have been recommending your home rental site to my friends and coworkers. Our family vacation was fabulous my husband and I put in many extra hours of work to provide a vacation to our daughters and we absolutely will be coming back very soon. I want to thank you for the wonderful experience!!!
Cathy Strauss, Buffalo New York

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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 - 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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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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Sarasota Florida Vacation Rentals - Home
1 / 15

Sarasota Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / 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 - 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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Sarasota Florida Vacation Rentals - Villa
1 / 8

Sarasota Villa
4 Bedrooms / 2 Bathrooms / Sleeps 12
Villa / 4 Bedrooms / 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
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 - 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 - 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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The Cottages
The Cottages
From Siesta Key, FL
Member since July, 2013
Languages
English