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                  Siesta Key (42 properties)

Family Friendly holidays in Siesta Key

Select a location below to drill down, or click on a property image to see the family friendly properties in Siesta Keythat we have to offer.

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Family friendly Villa in Siesta Key
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Family friendly Villa in Siesta Key

Waterfront Siesta Home Steps 2 the Beach

This is a fantastic 5 bd/3 bath family friendly waterfront enclave just steps from siesta key beach!!

bedrooms  5    bathrooms3
sleeps 10 - 14

$900 - $1100
Per Week
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Golf Course Nearby Pets Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Disabled Access Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly House in Siesta Key
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Family friendly House in Siesta Key

Exclusive Waterfront Siesta Residence

Exclusive Waterfront Siesta Residence close to village and Siesta key beach

bedrooms  3    bathrooms2
sleeps 6 - 10

$1600 - $2000
Per Week
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Golf Course Nearby Pets Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Disabled Access Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Condominium in Siesta Key
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Family friendly Condominium in Siesta Key

Ebb Tide Beach Club

Cottage Condo has great floor plan and enclosed rear patio and a short stroll to pool and Crescent Beach.....

bedrooms  1    bathrooms1
sleeps 2

$490 - $840
Per Week
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Townhouse in Siesta Key
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Family friendly Townhouse in Siesta Key

All NEW! Beautiful and Luxurious!

Completely Renovated TownHome in BAYSIDE Resort. Across from private access to Crescent Beach. FREE Internet

bedrooms  2    bathrooms2
sleeps 4 - 6

$895 - $1231
Per Week
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Villa in Siesta Key
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Family friendly Villa in Siesta Key

Casa Blanca (#D-07) GOLF/GULF&Sunsets!!

ON THE COOL, WHITE 'QUARTZ' SANDS OF CRESCENT BEACH.

bedrooms  2    bathrooms2
sleeps 4

$940 - $1320
Per Week
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Golf Course Nearby Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Condominium in Siesta Key
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Family friendly Condominium in Siesta Key

Siesta Breakers #603, Siesta Key, FL

*Sun, Sand & SAVE 25% to 50%* at Siesta Breakers #603, an Updated, Gulf Side, Beach Condo.

bedrooms  2    bathrooms2
sleeps 6

$833 - $1543
Per Week
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Disabled Access Does Not Have Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Condominium in Siesta Key
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Family friendly Condominium in Siesta Key

Midnight Cove II Condo on Siesta Key

Peaceful Haven with Crescent Beach Access

bedrooms  2    bathrooms2
sleeps 4 - 6

$700 - $1000
Per Week
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Villa in Siesta Key
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Family friendly Villa in Siesta Key

Siesta Key Villa - Voted #2 Best Beach

Gorgeous white sand & fantastic sunsets when you rent my Casa Blanca Villa C-16 for your Siesta Key vacation

bedrooms  2    bathrooms1
sleeps 6

$820 - $1070
Per Week
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Golf Course Nearby Pets Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly House in Siesta Key
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Family friendly House in Siesta Key

Heron Lagoon Private Beach Sarasota

Located on a private road with views of Heron Lagoon & the beach just steps away.

bedrooms  3    bathrooms2
sleeps 8

$2500 - $5500
Per Month
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Golf Course Nearby Pets Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Condominium in Siesta Key
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Family friendly Condominium in Siesta Key

Midnight Cove #532, Siesta Fey, FL

*Sun, Sand & SAVE 25% to 50%* at Midnight Cove #532, an Updated, Bayside Condo with Beach Amenities Access

bedrooms  2    bathrooms2
sleeps 4 - 6

$545 - $1075
Per Week
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Villa in Siesta Key
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Family friendly Villa in Siesta Key

Beautiful 3bd/2bth Siesta Villa

3bd/2bth Siesta Villa Just 1 mile to Siesta Beach and Village and Very Affordable!!

bedrooms  3    bathrooms2
sleeps 6 - 8

$900 - $1100
Per Week
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Golf Course Nearby Pets Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Disabled Access Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Condominium in Siesta Key
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Family friendly Condominium in Siesta Key

The Southern Cross @ Siesta Key, Florida

Welcome to our Beachfront Paradise !!!

bedrooms  2    bathrooms2
sleeps 4 - 6

$3500 - $4500
Per Month
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Disabled Access Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Villa in Siesta Key
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Family friendly Villa in Siesta Key

Siesta Key Getaways

Siesta Key Getaways - Welcome to our Cresent Beach Vacation Villas on the Florida Suncoast.

bedrooms  2    bathrooms1
sleeps 4

$665 - $1100
Per Week
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Not Near A Golf Course Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Not Disabled Friendly Does Not Have Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Villa in Siesta Key
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Family friendly Villa in Siesta Key

Siesta Key Villa

Gulf side villa on Crescent Beach

bedrooms  2    bathrooms2
sleeps 4

$660 - $1100
Per Week
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Golf Course Nearby Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Condominium in Siesta Key
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Family friendly Condominium in Siesta Key

Crystal Sands & Sunsets on Siesta Key FL

Luxury 2BR 2BA Penthouse condo on 12th (top) floor with year round sunsets located directly on Gulf of Mexico

bedrooms  2    bathrooms2
sleeps 4 - 6

$1350 - $1850
Per Week
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Not Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Villa in Siesta Key
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Family friendly Villa in Siesta Key

Beachfront Siesta Key Penthouse

One-bedroom 1,000 square foot condo with large open balcony and unobstructed panoramic view of beach and Gulf

bedrooms  1    bathrooms1
sleeps 2 - 4

$990 - $1290
Per Week
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Does Not Have A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Holiday Home in Siesta Key
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Family friendly Holiday Home in Siesta Key

Sarasota Pool Home

Walk to the beach.......Enjoy your private pool.......Watch our beautiful sunsets..... .

bedrooms  3    bathrooms2
sleeps 6

$1100 - $1800
Per Week
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Condominium in Siesta Key
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Family friendly Condominium in Siesta Key

Fisherman's Cove, Siesta Key

Ocean Front / Beach Front condo with Intercoastal Bock Docks. Surrounded by water and beach. Panoramic views.

bedrooms  2    bathrooms2
sleeps 4 - 6

$895 - $1495
Per Week
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Golf Course Nearby Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Disabled Access Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Condominium in Siesta Key
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Family friendly Condominium in Siesta Key

Sunset Royale

Sunset Royale #104 beautiful sunsets at the beach

bedrooms  1    bathrooms1
sleeps 2

$750 - $1099
Per Week
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Does Not Have A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly House in Siesta Key
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Family friendly House in Siesta Key

SiestaSandcastle stps to village & beach

Large duplex w/pool and Jacuzzi. Conveniently located in village steps to beach. Very clean, very beautiful.

bedrooms  3    bathrooms3
sleeps 6 - 8

$1395 - $2195
Per Week
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Golf Course Nearby Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Condominium in Siesta Key
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Family friendly Condominium in Siesta Key

La Dolce Vita @Sandy Cove, Siesta Key

To see La Dolce Vita and Siesta Key is to fall in love... http://vt.realbiz360.com/MLS-65969.html#

bedrooms  1    bathrooms1
sleeps 2 - 4

$1850 - $2950
Per Month
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Golf Course Nearby Pets Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Disabled Access Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Condominium in Siesta Key
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Family friendly Condominium in Siesta Key

Anchorage

Penthouse - Gulf and Bay Views!

bedrooms  2    bathrooms2
sleeps 6

$828 - $1185
Per Week
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Not Disabled Friendly Does Not Have Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Cottage in Siesta Key
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Family friendly Cottage in Siesta Key

Beachaven 54

Great Small Senior Association Gulfside on Siesta Key
1 bed. with Loft, sleeps 4, on the Beach!

bedrooms  1    bathrooms1
sleeps 2 - 4

€2200 - €3350
Per Month
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Condominium in Siesta Key
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Family friendly Condominium in Siesta Key

Crescent Arms Condo on Siesta Key

Beach-Front Luxurious Condo on the Gulf of Mexico

bedrooms  2    bathrooms2
sleeps 4 - 6

$1200 - $1725
Per Week
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Townhouse in Siesta Key
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Family friendly Townhouse in Siesta Key

Gorgeous Bay Views - Beautifully Updated

BAYSIDE Resort Town Home with views of Little Sarasota Bay. Across from Crescent Beach.

bedrooms  3    bathrooms2
sleeps 6

$1142 - $1495
Per Week
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Condominium in Siesta Key
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Family friendly Condominium in Siesta Key

Bella Vista on Siesta Key

Panoramic views of the Gulf of Mexico from this spacious, elegant 2-bed, 2-bath, beachfront condo.

bedrooms  2    bathrooms2
sleeps 4

$2900 - $5600
Per Month
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Cottage in Siesta Key
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Family friendly Cottage in Siesta Key

Midnight Pass

What views of the lagoon from home & private pool

bedrooms  3    bathrooms2
sleeps 6

$2500 - $5000
Per Month
Add to Shortlist
Golf Course Nearby Pets Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Cottage in Siesta Key
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Family friendly Cottage in Siesta Key

Beach Palms Sarasota

Beach view Suites and Cottages

bedrooms  2    bathrooms1
sleeps 2 - 4

$225 - $325
Per Day
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Not Near A Golf Course Pets Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Does Not Have A Pool Not Near Skiing Is Family Friendly Has Location Map     
Family friendly Villa in Siesta Key
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Family friendly Villa in Siesta Key

Couples Paradise on Siesta Key, Sarasota

bedrooms  1    bathrooms1
sleeps 2 - 4

$749 - $1159
Per Week
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is Family Friendly Has Location Map     

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