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Siesta Key Florida Vacation Rentals - Home
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Siesta Key Home
4 BR / 2 BA / Sleeps 8 4 8 No min stay
Home / 4 Bedrooms / Sleeps 8
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
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 BR / 2.5 BA / Sleeps 8 3 8 No min stay
Home / 3 Bedrooms / Sleeps 8
Bedrooms:3
Bathrooms:2.5
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
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” ...

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Siesta Key Florida Vacation Rentals - Home
1 / 8

Siesta Key Home
4 BR / 2 BA / Sleeps 8 4 8 No min stay
Home / 4 Bedrooms / Sleeps 8
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
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 / 8

Siesta Key Home
3 BR / 2 BA / Sleeps 10 3 10 No min stay
Home / 3 Bedrooms / Sleeps 10
(1) Excellent 1 Review
Bedrooms:3
Bathrooms:2
Sleeps:10
Type:Home
No rental rates available - please contact the owner
 
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...

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Great accomodations!!

“ Excellent ”
October 29, 2015
Our daughter was married on Siesta Key beach on October 11th. We had 6 adults and 5 children stay here for one week. What a GREAT idea that was. The house is just as pictured. I think if asked everyone would say we spent more time out on the patio than the rest of the house together. It is spacious, has the bar and plenty of seating for everyone whether you want to watch TV or play games or just relax in the sun. It has a partial roof so even if it rains you can still be outside. The cover over the pool is screened so you still can get the sun but no bugs (the little lizards do get in but are fun to watch and harmless). The pool was the BEST. The kids were in the pool the minute they woke up and had a hard time getting them out to do anything (one came home from Disney a day early because she wanted to go back and play in the pool with her cousins!). It was so nice to have an additional full bathroom in the garage (accessed by door directly from the patio). The beach is close by but so nice to have the pool, honestly spent more time there than the beach. The kitchen has everything you would ever need. The beds were extremely comfortable. (Be careful of the feet on the beds, they extend outside the circumference of the bed, not good on the toes). Most importantly it served as a wonderful base for not only our family but the occasional wedding guests that stopped by for well wishes. It is close to everything and plenty of parking, although there are taxis all over the island that will take you anywhere. Never ending supply of things to do. The only thing that would have been better would be to have it sitting right on the beach!! When we left all I heard is "can we come back next year?"
Lauri Cunningham, Toledo, OH

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Siesta Key Florida Vacation Rentals - Townhouse
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Siesta Key Townhouse
3 BR / 3 BA / Sleeps 10 3 10 No min stay
Townhouse / 3 Bedrooms / Sleeps 10
Bedrooms:3
Bathrooms:3
Sleeps:10
Type:Townhouse
No rental rates available - please contact the owner
 
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 - Home
1 / 10

Siesta Key Home
4 BR / 3 BA / Sleeps 10 4 10 No min stay
Home / 4 Bedrooms / Sleeps 10
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
No rental rates available - please contact the owner
 
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 - Home
1 / 17

Siesta Key Home
4 BR / 4 BA / Sleeps 12 4 12 7 night min stay
Home / 4 Bedrooms / Sleeps 12
(2) Excellent 2 Reviews
Bedrooms:4
Bathrooms:4
Sleeps:12
Type:Home
Per night:$215 - $529
Per week:$1,500 - $3,700
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...

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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 - Home
1 / 34

Siesta Key Home
4 BR / 4 BA / Sleeps 12 4 12 7 night min stay
Home / 4 Bedrooms / Sleeps 12
Bedrooms:4
Bathrooms:4
Sleeps:12
Type:Home
Per night:$215 - $529
Per week:$1,500 - $3,700
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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Sarasota Florida Vacation Rentals - Home
1 / 18

Sarasota Home
4 BR / 1 BA / Sleeps 12 4 12 7 night min stay
Home / 4 Bedrooms / Sleeps 12
Bedrooms:4
Bathrooms:1
Sleeps:12
Type:Home
Per night:$215 - $529
Per week:$1,500 - $3,700
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 / 22

Siesta Key Home
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Home / 2 Bedrooms / Sleeps 6
(1) Excellent 1 Review
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$122 - $279
Per week:$850 - $1,950
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 Vacation

“ Excellent ”
January 5, 2016
Had a great time. The condo was clean well furnished and felt like home
Perry Hostetler, Sturgis mi usa

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Sarasota Florida Vacation Rentals - Villa
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Sarasota Villa
4 BR / 2 BA / Sleeps 10 4 10 7 night min stay
Villa / 4 Bedrooms / Sleeps 10
Bedrooms:4
Bathrooms:2
Sleeps:10
Type:Villa
Per night:$186 - $500
Per week:$1,300 - $3,500
Pets allowed:No
Internet:Yes

Welcome to Sol y Mar. This COMPLETELY RENOVATED, single level and uniquely configured (4 BR/2BA - 2 Master BR/1 Queen each & 2 2nd BR/2 twins each- sleeps 8) vacation home [Casita Mar and Casita Sol] has 2 kitchens and 2 living areas, the perfect arrangement for families or groups...

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Siesta Key Florida Vacation Rentals - Home
1 / 34

Siesta Key Home
4 BR / 4 BA / Sleeps 12 4 12 7 night min stay
Home / 4 Bedrooms / Sleeps 12
Bedrooms:4
Bathrooms:4
Sleeps:12
Type:Home
Per night:$215 - $529
Per week:$1,500 - $3,700
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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Sarasota Florida Vacation Rentals - Condo
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Sarasota Condo
2 BR / 1 BA / Sleeps 6 2 6 7 night min stay
Condo / 2 Bedrooms / Sleeps 6
(1) Excellent 1 Review
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Condo
Per night:$58 - $186
Per week:$400 - $1,300
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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Siesta Key Florida Vacation Rentals - Home
1 / 20

Siesta Key Home
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Home / 2 Bedrooms / Sleeps 6
(1) Excellent 1 Review
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$122 - $279
Per week:$850 - $1,950
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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Siesta Key Florida Vacation Rentals - Home
1 / 19

Siesta Key Home
3 BR / 2 BA / Sleeps 8 3 8 7 night min stay
Home / 3 Bedrooms / Sleeps 8
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$172 - $343
Per week:$1,200 - $2,400
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 - Villa
1 / 8

Siesta Key Villa
4 BR / 3 BA / Sleeps 8 4 8 7 night min stay
Villa / 4 Bedrooms / Sleeps 8
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Villa
Per night:$229 - $543
Per week:$1,600 - $3,800
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 ...

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Sarasota Florida Vacation Rentals - Cottage
1 / 10

Sarasota Cottage
5 BR / 4 BA / Sleeps 10 5 10 7 night min stay
Cottage / 5 Bedrooms / Sleeps 10
(1) Excellent 1 Review
Bedrooms:5
Bathrooms:4
Sleeps:10
Type:Cottage
Per night:$229 - $543
Per week:$1,600 - $3,800
Pets allowed:No
Internet:Yes

Starfish Cottage on 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 BR / 2 BA / Sleeps 8 3 8 7 night min stay
Home / 3 Bedrooms / Sleeps 8
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$122 - $250
Per week:$850 - $1,750
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 BR / 3 BA / Sleeps 10 4 10 14 night min stay
Home / 4 Bedrooms / Sleeps 10
(3) Excellent 3 Reviews
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$358 - $586
Per week:$2,500 - $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 ...

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Paradise

“ Excellent ”
October 20, 2015
Beautiful home with so many added features! We are definitely coming back and staying at The Grand Canal!
Sharilyn Wright DeCrastos, Fishers, Indiana

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Sarasota Florida Vacation Rentals - Home
1 / 26

Sarasota Home
6 BR / 5.5 BA / Sleeps 16 6 16 7 night min stay
Home / 6 Bedrooms / Sleeps 16
Bedrooms:6
Bathrooms:5.5
Sleeps:16
Type:Home
Per night:$400 - $886
Per week:$2,800 - $6,200
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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Siesta Key Florida Vacation Rentals - Home
1 / 35

Siesta Key Home
4 BR / 2 BA / Sleeps 8 4 8 7 night min stay
Home / 4 Bedrooms / Sleeps 8
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$175 - $375
Per month:$5,250 - $11,250
Pets allowed:No
Internet:Yes

Casa Antigua is a four (4) bedroom, two (2) bath private home. It is configured for maximum comfort and enjoyment for large families and parties who will find it a well designed retreat and haven to call your own vacation home. Centrally located in the heart of Sarasota, and...

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Siesta Key Florida Vacation Rentals - Home
1 / 35

Siesta Key Home
2 BR / 1 BA / Sleeps 6 2 6 7 night min stay
Home / 2 Bedrooms / Sleeps 6
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Home
Per night:$125 - $225
Per month:$3,750 - $6,750
Pets allowed:No
Internet:Yes

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 in each casita, there are 2 bedrooms / 2 bathrooms and a kitchen with living areas). Suelo y Rio is well located...

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Sarasota Florida Vacation Rentals - Home
1 / 15

Sarasota Home
4 BR / 2 BA / Sleeps 8 4 8 7 night min stay
Home / 4 Bedrooms / Sleeps 8
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
Per night:$186 - $500
Per week:$1,300 - $3,500
Pets allowed:No
Internet:Yes

Welcome to Playa y Blanca. This COMPLETELY RENOVATED, single level and uniquely configured (4 BR/2BA - 2 Master BR/1 Queen each & 2 2nd BR/2 twins each- sleeps 8) vacation home [Casita Blanca and Casita Playa] has 2 kitchens and 2 living areas, the perfect arrangement for families...

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Siesta Key Florida Vacation Rentals - Home
1 / 20

Siesta Key Home
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Home / 2 Bedrooms / Sleeps 6
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$150 - $350
Per month:$4,500 - $10,500
Pets allowed:No
Internet:Yes

The décor is beautifully done and so reminiscent of the seashore with starfish and the reef [found only in the Point of Rocks area] themes. It’s clearly “beachy” but luxurious here. As you might expect Villa Dom Brisa is truly a decorator’s dream offering...

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Siesta Key Florida Vacation Rentals - Townhouse
1 / 27

Siesta Key Townhouse
3 BR / 3.5 BA / Sleeps 10 3 10 7 night min stay
Townhouse / 3 Bedrooms / Sleeps 10
(1) Excellent 1 Review
Bedrooms:3
Bathrooms:3.5
Sleeps:10
Type:Townhouse
Per night:$200 - $458
Per week:$1,400 - $3,200
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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Casa Del Soleil

“ Excellent ”
December 7, 2015
Had a wonderful time condo very clean but a few things didn't work like the coffee pot & the electric was off on the hot tub. However, it was extremely warm & we didn't need it. But for future it needs to be fixed with winter coming on
Mary Eddy, Ohio

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1-25 (of 32)
The Cottages
The Cottages
From Siesta Key, FL
Member since July, 2013
Languages
English