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$300

4 BR / 3 BA / Sleeps 9

Casa De Suenos - Siesta Key vacation rentals
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$300

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Casa De Suenos

4 BR / 3 BA / Sleeps 9 | Quick view

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Casa De Suenos Welcome to “Casa De Suenos”, one of the most fabulous vacation homes in Siesta Key. Newly constructed in 2013! The magic begins as you enter the foyer of this beautiful casa and gaze across the expansive living area, and deck area. You know already you made the right choice for your family and …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$400

4 BR / 2 BA / Sleeps 12

La Casa Verde - Siesta Key vacation rentals
1 / 25

$400

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La Casa Verde

4 BR / 2 BA / Sleeps 12 | Quick view

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La Casa Verde The waterfront cottage, 'La Casa Verde' is a very luxurious and large four [4] bedroom canal front heated pool home with two very large bathrooms in approximately 2,800SF of air conditioned living space. As you approach the home you are immediately drawn into it by volumes of lush, lavish tropical …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$450

5 BR / 3 BA / Sleeps 14

Pura Vida Oasis - Siesta Key vacation rentals
1 / 26

$450

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Pura Vida Oasis

5 BR / 3 BA / Sleeps 14 | Quick view

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Pura Vida Oasis This spectacular bright cheerful, canal front cottage with heated pool & spa has 5 bedrooms/3 baths that can sleep up 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 dining area with seating for the entire family…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$400

4 BR / 2 BA / Sleeps 12

Villa Mantequilla - Siesta Key vacation rentals
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$400

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Villa Mantequilla

4 BR / 2 BA / Sleeps 12 | Quick view

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Villa Mantequilla 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 privacy offered…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$250

4 BR / 3 BA / Sleeps 8

1 Reviews

$250

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Well appointed canal front home

4 BR / 3 BA / Sleeps 8 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

This luxury Siesta Key vacation rental was built on the Grand Canal in 2005 and offers 3 bedrooms plus bonus room with 3 full baths. Its great location gives it access to Siesta key beach and Siesta Key village yet secluded enough for you to relax and enjoy the peace and quiet; no thru traffic here. Its well appointed…
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Great House and Location

Left on Jul 25, 2012 for a stay in May 2012

Rent Siesta Key was great to work with. The home was gorgeouse,the location to the beach and village were perfect. The hot tub jets didn't have the thrust I would prefer. We would definitly rent the house again and from Rent Siesta Key.

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$400

5 BR / 5 BA / Sleeps 14

Island Sol - Siesta Key vacation rentals
1 / 24

$400

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Island Sol

5 BR / 5 BA / Sleeps 14 | Quick view

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Island Sol Welcome to Island Sol, our exclusive 5+ bedroom, four and one-half [4.5] bath home with approximately 4,000SF of air conditioned space in Siesta Key. Across the open entry and living room, you look out beyond the exterior lanai into the private courtyard which features an enclosed heated swimming pool …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$197

4 BR / 3 BA / Sleeps 7

1 / 20

$197

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4 bedroom Key West style pool home minutes to village and beach

4 BR / 3 BA / Sleeps 7 | Quick view

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Stay at this large Key West style Siesta Key vacation rental home minutes to Siesta Key village and beaches. The property offers a private backyard with heated pool and Jacuzzi hot tub. Located on a quite street just 1 mile from Siesta Key village puts it at a perfect distance for a easy bicycle ride in the mornings …
  • Hot Tub/Jacuzzi
  • A/C or climate control
  • Deck
  • Fitness Room
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$300

4 BR / 4 BA / Sleeps 12

1 / 33

$300

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Villa Dom Brisa

4 BR / 4 BA / Sleeps 12 | Quick view

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Villa Dom Brisa 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 offering unique sleeping…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$550

4 BR / 3 BA / Sleeps 12

1 / 35

$550

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The Grand Canal Cottage

4 BR / 3 BA / Sleeps 12 | Quick view

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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 blocks of the world’s most …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$450

4 BR / 2 BA / Sleeps 11

1 Reviews

$450

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Overlooking Beach

4 BR / 2 BA / Sleeps 11 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Beautiful location for weddings, receptions, anniversary parties, family reunions and corporate events. Give us a call for more information and package deals. Directly overlooking breathtaking views of private beach on North end of Siesta Key. Just renovated everything brand new. Four bedrooms, 2 baths, sleeps 11, …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(1)

Amazing Vacation!!!

Left on Jun 19, 2013 for a stay in May 2013

My family and I stayed at this amazing vacation home last month and I can't begin to put into words what a wonderful time we had. The beach is literally a few steps from the home! You couldn't get any closer without actually being in the water. The home was immaculate and the owners were so sweet and accommodating to our every need. We especially loved the outdoor common area, that had hammocks, …

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$215

4 BR / 3 BA / Sleeps 10

1 Reviews

$215

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Spacious Siesta Key Canal Front Vacation Rental Home

4 BR / 3 BA / Sleeps 10 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Take a look at this spacious canal front home on Siesta Key with heated pool. This home is great for a large family or even two families with its open floor plan. Enter the home through the double French doors and down the foyer into the heart of the home; the open family room, living room w/ fireplace, and eat-in …
  • Waterfront
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Beautiful place for quite vacation

Left on Mar 03, 2014 for a stay in January 2014

The property was as pictured, most everything is brand new when my family and I had stayed here. There is more than ample room for everyone to convene in the living spaces. We were the first guests to stay at the property since renovation so there were a few kinks to still work out however the management company was prompt in addressing them. The beds were comfortable. The master bath with the …

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$400

4 BR / 4 BA / Sleeps 12

1 / 26

$400

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Villa Cascada

4 BR / 4 BA / Sleeps 12 | Quick view

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Villa Cascada 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 into the Gulf of Mexico. …
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Balcony or terrace
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$400

5 BR / 4 BA / Sleeps 12

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$400

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The Topping Cottage

5 BR / 4 BA / Sleeps 12 | Quick view

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The Topping Cottage The Topping Cottage is a very luxurious and large five [5] bedroom, three and one-half [3.5] bath home with approximately 3,000SF of air conditioned space in Siesta Key. As you enter the foyer, you immediately notice the huge, spacious, bright living room with voluminous, high ceilings dwarfed only…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$300

4 BR / 4 BA / Sleeps 12

1 Reviews

$300

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Villa Margarita

4 BR / 4 BA / Sleeps 12 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

Villa Margarita 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 for larger groups or …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

Details

Reviews

(1)

great villa with pool!

Left on Jul 16, 2014 for a stay in July 2014

We really loved this adorable unit. All furnishings seem new. Great location and the best part was the private pool shared with one other unit.

Only negative is no dishwasher in kitchen.

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$400

4 BR / 4 BA / Sleeps 8

2 Reviews

$400

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Villa Champagne

4 BR / 4 BA / Sleeps 8 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

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 area, then further out across the …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

Details

Reviews

(2)

Great location and spacious place

Left on Oct 21, 2014 for a stay in October 2014

There were 6 adults and 4 children (ages 3-6) that stayed here and we had more than enough room with the great layout of the house. The location was great (Avineda Del Mare is just off Beach Road, just down from the public parking lot) but was "too far" to walk to Siesta for the children, so we drove. However, for adults or teens, it would have been do-able (approx. 3-4 blocks).

The supply…

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$500

4 BR / 4 BA / Sleeps 10

2 Reviews

$500

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Siesta Key Vacation Rental with Dock and Beach Access

4 BR / 4 BA / Sleeps 10 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

***NEW PROPERTY*** This luxury Siesta Key vacation rental gives easy access to both Siesta Key Beach and a day dock for your boating and fishing needs. With four bedrooms, three full bathrooms, and two half baths this property has plenty of room for up to 10 guests. Its private pool area and out door kitchenette is …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Absolutely wonderful home and location

Left on Aug 18, 2014 for a stay in August 2014

This home was breathtaking. We are a very big family with kids and adults. The house was immaculate and cleaned to perfection. We would recommended this home to any & everybody. We were beyond satisfied with the stay here ! My family and I are very picky and we couldn't say one bad thing about the house. It was quiet and the pool was so nice to have. The space in the house was more than adequate …

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$429

4 BR / 3 BA / Sleeps 8

2 Reviews

$429

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Beautiful Siesta Key Home with Pool

4 BR / 3 BA / Sleeps 8 | Quick view
“ Poor ” 2 Reviews

Details

Reviews

(2)

Seasonal Luxury rental on the world famous Siesta Key! Relax in your tropical vacation home or step out to all Siesta Key has to offer! Is an absolutely beautiful and uniquely configured private pool home featuring four bedrooms, three bathrooms [sleeps 8], two living areas. This home is comfortably decorated with …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

Nice location and great master bedroom, but not in good repair.

Left on May 29, 2014 for a stay in May 2014

This home is not for anyone who has trouble with stairs. While main floor is nice, stove and window coverings are in poor shape. Vertical blinds in bedroom are missing lots of panels.

Pool and patio area very nice. Steps steep for little ones and elderly. Home was listed as having 4 bedrooms. The fourth one is in the basement, which can only be gotten to by going downstairs, through the …

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$300

4 BR / 4 BA / Sleeps 12

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$300

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Villa Fiesta

4 BR / 4 BA / Sleeps 12 | Quick view

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Villa Fiesta 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 to larger groups…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$300

4 BR / 4 BA / Sleeps 12

1 / 43

$300

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Villa Brisa Marina

4 BR / 4 BA / Sleeps 12 | Quick view

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Villa Brisa Marina 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 beach [no …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$314

4 BR / 4 BA / Sleeps 12

5 Reviews

$314

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Siesta Key Deluxe Townhouse & Garden Apt (4 BR's)

4 BR / 4 BA / Sleeps 12 | Quick view
“ Excellent ” 5 Reviews

Details

Reviews

(5)

These Siesta Key deluxe townhouse rentals are located in the heart of Siesta Village - just a few steps to all the shops and restaurants and only 1 1/2 blocks (it takes us three minutes to walk) to the world famous Siesta Key Crescent Beach! Relax by your private pool. These Siesta Key townhouses are equipped with …
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(5)

Good time

Left on Apr 10, 2014 for a stay in November 2013

My wife and I stayed in the Garden apartment in November 2013. It was a very good time. It is very clean like all of the Sunnyside Properties. It is a small unit that is just fine for a couple. It is right by the pool. It is very close to the Village and Beach, so all of the fun is very accessible. The grocery store is just a couple blocks away.

I would recommend this place to anyone interested …

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$500

5 BR / 4 BA / Sleeps 10

2 Reviews

$500

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5 Bedroom New Penthouse-2011 Best Beach in USA

5 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Brand New 2009 Beach Villa Penthouse. 5 Bedrooms on 2 floors plus a rooftop patio. Perfect location as 3 minutes walk to beach or 2 minutes to Siesta village - corner of Ocean Blvd and Beach Rd. Gorgeous decor inside this Italian architecture with 6 furnished balconies, semi-private pool with jacuzzi, 12 foot …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(2)

Great Location - Excellent Condo

Left on Aug 20, 2012 for a stay in July 2012

Two families stayed in Late July 2012 for one week. Two sets of husband and wife plus 4 girls ages 9-15.

The condo has two floors on the 3rd and 4th floor (which is the top floor). Above on the roof is a patio with great views and a nice grill reachable with an interior stairway. The pool in the back is reachable with a separate back stairway shared with the other tenants of the building for …

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$442

4 BR / 4 BA / Sleeps 14

11 Reviews

$442

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The Palm Island House- winner at NYJL homes tour!

4 BR / 4 BA / Sleeps 14 | Quick view
“ Excellent ” 11 Reviews

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Reviews

(11)

Prominently featured in the 2013 and 2014 in NYJL House Tour Magazine and winner Spring of 2014 Top Auction Item. This Spanish revival home is located on Palm Island, the heart shaped island within the island of Siesta Key, just steps from the beach and one half mile from the village. Features include- gas fireplace, …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(11)

Wonderful

Left on Jul 04, 2013 for a stay in May 2013

The home is very nice and comfortable. Close to the best beach in the United States.

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$545

6 BR / 2 BA / Sleeps 14

1 / 16

$545

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Siesta Key Beach Estate......Steps from Siesta Key Beach!!!

6 BR / 2 BA / Sleeps 14 | Quick view

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Brand New , Gated Residence steps from Siesta Key Beach . Perfect location between the village and crystal sands of Siesta Beach!! Bar's, Restaurants, Shopping, Sport Rentals……..EVERYTHING is within walking distance…..NO CAR NEEDED!!! This brand new 2700 sq ft private residence is simply spectacular. View of…
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$283

4 BR / 5 BA / Sleeps 10

1 / 23

$283

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Kid friendly Luxury home on Siesta Key

4 BR / 5 BA / Sleeps 10 | Quick view

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SIESTA KEY DREAM HOUSE!!!!!!!!!!!!!!!! Custom designed home. Open flow. Great for entertaining. Custom Kitchen with island. Eat-in area, granite & 2-tone wood cabinetry. Separate living, dining, family/ great rooms plus 4 bedrooms and 4 1/2 baths. 2 master suites. Heated pool with waterfall - screened lanai - Close to…
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$150

5 BR / 1 BA / Sleeps 20

7 Reviews

$150

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Stay on Siesta, Siesta Key Beach Place Cottages

5 BR / 1 BA / Sleeps 20 | Quick view
“ Excellent ” 7 Reviews

Details

Reviews

(7)

Tropical Garden beach cottages located at Siesta Key Beach. The Beach Place is Old Florida charm that's becoming hard to find. Private, quiet and relaxing. Tropical gardens surround our heated pool with tiki cabana bar for guests, poolside and beachfront BBQ. Five fully stocked one bedroom housekeeping cottages, sleep…
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(7)

location, location, location

Left on Dec 10, 2013 for a stay in December 2013

Fine 3 BR accommodation. Small kitchen, BBQ available. Quiet spot, small heated pool. 2 minute walk to the beach and oh the beach! Powder soft white sand! Comfortable beds...plenty of beach chairs, beach towels and even beach sheets. Lanai dining table well-used by our group. Easy walk to Siesta Village. We recommend renting bikes and kayaks from Robin Hood Rentals in the Village. Also …

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$314

4 BR / 4 BA / Sleeps 10

10 Reviews

$314

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4 Bedroom with Gulf View Siesta Key FL Beach Fun

4 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 10 Reviews

Details

Reviews

(10)

Enjoy our 4 bedroom, 3-1/2 bath condo with a Full Gulf view that is 75 steps from the world famous white sand of Siesta Beach. We have remodeled and updated both the kitchen and bathrooms with granite and new cabinetry and vanities. Add our 50-foot pool, sauna, and work out room all on site with tennis, golf, dining…
  • Waterfront
  • Ocean or water views
  • Sauna
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(10)

The condo was located in a wonderful spot and provided privacy f

Left on Mar 13, 2012 for a stay in February 2012

The condo was very well decorated. The location overlooking the water was spectacular. I liked the fact that there were no tall buildings in front of the condo. I could hear and see the water and watch the gorgeous sunrises and sunsets from the lanai. The kitchen was extremely well equipped. I chose not to do very much cooking but the kitchen provided all kinds of pots, pans, dishes, …

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$210

9 BR / 9 BA / Sleeps 24

43 Reviews

$210

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Siesta Sunset Royale

9 BR / 9 BA / Sleeps 24 | Quick view
“ Excellent ” 43 Reviews

Details

Reviews

(43)

Siesta Key's newest beach house located across Beach Rd from access #7 to Siesta Key's Crescent Beach and one-block from the tropical Village of Siesta Key. Property has recently been completely remodeled and amenities include pool and spa, barbecue deck with lanai close to pool, free full property WiFi, free Internet…
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(43)

totally relaxing but within minutes from where the action is

Left on Dec 11, 2010 for a stay in August 2010

minutes from the ocean or minutes from the hip little town of siesta key, it's all here and you're right in the middle in a french riviera -style beach apartment. a small boutique-like atmosphere with extremely helpful,fun(!) owners who can point you in the direction of a funky bar or romantic restaurant. The rooms are clean, very artfully decorated and new appliances. A perfect spot for a …


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