Siesta Key Vacation Rentals - Siesta Key Condos & Siesta Key Beach Rentals

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                  Siesta Key (37 properties)


Use the filters below to narrow down the 37 Condominiums and rentals we have in Siesta Key

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  • Have A Pool:

  • Are Near Skiing:






Rental Condominium in Siesta Key
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Rental 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     
3 bedroom Holiday Home for rent in Siesta Key
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3 bedroom Holiday Home for rent 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     
Vacation rental Condominium in Siesta Key
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Vacation rental Condominium in Siesta Key

Sunset Royale -Siesta Key-Sarasota,FL

Newly decorated 1 Bedroom Condo with full Gulf of Mexico view. Fifty steps to the white sands of Siesta Beach.

bedrooms  1    bathrooms1
sleeps 2 - 4

$804 - $999
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 Not 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 not Family Friendly Does Not Have Location Map     
Condominium in Siesta Key
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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     
House for 8 people in Siesta Key
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House for 8 people 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     
Condominium for 6 people in Siesta Key
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Condominium for 6 people 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     
Holiday House rental in Siesta Key
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Holiday House rental 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     
Villa in Siesta Key
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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     
House for rent in Siesta Key
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House for rent in Siesta Key

Custom Waterfront Estate

A spectacular waterfront enclave directly on the ‘Grand Canal’ of Siesta Key.

bedrooms  4    bathrooms3
sleeps 10

$1600 - $2200
Per Week
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Not Accepted Not 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 not Family Friendly Does Not Have Location Map     
Holiday Condominium in Siesta Key
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Holiday 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
Add to Shortlist
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     
Siesta Key Condominium
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Siesta Key Condominium

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     
Condominium for rent in Siesta Key
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Condominium for rent 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
Add to Shortlist
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     
2 bedroom Condominium in Siesta Key
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2 bedroom Condominium in Siesta Key

Siesta Key Condo - Affordable

Our two bedroom unit faces Siesta Beach and overlooks the pool. We have many guest who return year after year.

bedrooms  2    bathrooms1
sleeps 4 - 5

$755 - $1110
Per Week
Add to Shortlist
Golf Course Nearby Pets Not Allowed Does Not Have Availability Calender 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 not Family Friendly Does Not Have Location Map     
Holiday Villa rental in Siesta Key, Central Gulf Coast
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Holiday Villa rental in Siesta Key, Central Gulf Coast

2 Bedroom, 2 Bath Villa in Casa Blanca

This free standing villa is located on the Gulf side of Midnight Pass Rd, steps away from Crescent Beach.

bedrooms  2    bathrooms2
sleeps 4 - 6

$690 - $1100
Per Week
Add to Shortlist
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 No Public Transport Nearby Bars or Restaurants Close By Has A Pool Not Near Skiing Is not Family Friendly Does Not Have Location Map     
Holiday Villa rental in Siesta Key, Central Gulf Coast
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Holiday Villa rental in Siesta Key, Central Gulf Coast

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
Add to Shortlist
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     
Holiday House in Siesta Key
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Holiday House in Siesta Key

Siesta Beach Tree House

A serene two story residence overlooking the ‘Tree Canopy’ just one block from the world famous Siesta Beach.

bedrooms  2    bathrooms2
sleeps 6

$1400 - $1900
Per Week
Add to Shortlist
Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Not 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 not Family Friendly Does Not Have Location Map     
Condominium for 2 people in Siesta Key
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Condominium for 2 people in Siesta Key

Sunset Royale

Sunset Royale #104 beautiful sunsets at the beach

bedrooms  1    bathrooms1
sleeps 2

$750 - $1099
Per Week
Add to Shortlist
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     
Holiday Villa rental in Siesta Key, Central Gulf Coast
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Holiday Villa rental in Siesta Key, Central Gulf Coast

Siesta Key Villa

Gulf side villa on Crescent Beach

bedrooms  2    bathrooms2
sleeps 4

$660 - $1100
Per Week
Add to Shortlist
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     
Holiday Condominium rental in Siesta Key
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Holiday Condominium rental in Siesta Key

Sunset Royale #304, Siesta Key

Beautiful Beachfront condo on Crescent Beach. Newly remodeled and very well equipped for your beach vacation.

bedrooms  1    bathrooms1
sleeps 2 - 4

$804 - $1099
Per Week
Add to Shortlist
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 Does Not Have A Pool Not Near Skiing Is not Family Friendly Does Not Have Location Map     
Townhouse for rent in Siesta Key
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Townhouse for rent 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
Add to Shortlist
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     
Condominium in Siesta Key, Central Gulf Coast
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Condominium in Siesta Key, Central Gulf Coast

Sunset Royale #212, Siesta Key

This beautiful, newly renovated, beach condo on Siesta Key offers spectacular views and deluxe accommodations.

bedrooms  2    bathrooms2
sleeps 4 - 6

$915 - $1325
Per Week
Add to Shortlist
Golf Course Nearby Pets Not Allowed Does Not Have Availability Calender 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 Does Not Have A Pool Not Near Skiing Is not Family Friendly Does Not Have Location Map     
Siesta Key Cottage
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Siesta Key Cottage

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     
Rental Condominium in Siesta Key
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Rental Condominium in Siesta Key

Crescent Arms

Gulf front condo located on Siesta key beach

bedrooms  2    bathrooms2
sleeps 4 - 6

$1100 - $1700
Per Week
Add to Shortlist
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 not Family Friendly Does Not Have Location Map     
Rental Villa in Siesta Key
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Rental Villa in Siesta Key

Villa 7- Crystal Sands on Crescent Beach

Beautiful gulfside condominium, comfortable, quiet and bright, a perfect vacation destination

bedrooms  2    bathrooms2
sleeps 6

$900 - $1250
Per Week
Add to Shortlist
Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Not 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 not Family Friendly Does Not Have Location Map     
Holiday Condominium rental in Siesta Key
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Holiday Condominium rental in Siesta Key

Beautiful Condo with Pool - Gulf Beaches

Located within walking distance of Siesta Village, a shopping and restaurant area, and the main Gulf beaches.

bedrooms  2    bathrooms2
sleeps 6 - 7

$600 - $900
Per Week
Add to Shortlist
Not Near A Golf Course Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Not Accepted Not 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 not Family Friendly Does Not Have Location Map     
Siesta Key rental Villa
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Siesta Key rental Villa

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
Add to Shortlist
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     
3 bedroom Cottage for rent in Siesta Key
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3 bedroom Cottage for rent 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     
Holiday Villa rental in Siesta Key
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Holiday Villa rental 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
Add to Shortlist
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     
Holiday Condominium rental in Siesta Key
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Holiday Condominium rental 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
Add to Shortlist
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     
2 bedroom Condominium in Siesta Key
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2 bedroom 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
Add to Shortlist
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     
Siesta Key rental Townhouse
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Siesta Key rental Townhouse

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
Add to Shortlist
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     
Holiday Condominium rental in Siesta Key, Central Gulf Coast
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Holiday Condominium rental in Siesta Key, Central Gulf Coast

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
Add to Shortlist
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     
Holiday Cottage in Siesta Key
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Holiday 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
Add to Shortlist
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     
Vacation Condominium in Siesta Key
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Vacation 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
Add to Shortlist
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     
Condominium in Siesta Key, Central Gulf Coast
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Condominium in Siesta Key, Central Gulf Coast

2 Bedroom, 2 Bath in Midnight Cove I

Across the Street from Crescent Beach. 2 Swimimng Pools, Screened Lania, Tennis Courts, Private Beach Access.

bedrooms  2    bathrooms2
sleeps 4 - 6

$550 - $1200
Per Week
Add to Shortlist
Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Not 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 not Family Friendly Does Not Have Location Map     
Holiday House rental in Siesta Key
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Holiday House rental in Siesta Key

Siesta Key, Siesta By the Sea

Steps to Siesta Key beach, completly redone 2 bed, 2 ba, htd pool, WI-FI, W/D in unit.
Handicapped access.

bedrooms  2    bathrooms2
sleeps 4 - 6

$950 - $1250
Per Week
Add to Shortlist
Golf Course Nearby Pets Not Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Accepted Not Non-Smoking Disabled Access Has Internet Access Near Public Transport Bars or Restaurants Close By Has A Pool Not Near Skiing Is not Family Friendly Does Not Have Location Map     
1 bedroom Villa in Siesta Key
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1 bedroom Villa in Siesta Key

Couples Paradise on Siesta Key, Sarasota

bedrooms  1    bathrooms1
sleeps 2 - 4

$749 - $1159
Per Week
Add to Shortlist
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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