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Siesta Key Vacation Rental Accommodations - Page 1 of 6

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SPECIAL OFFER! Up to 7 wks,12/7-1/25 for the price of 4 December 7 - January 25

Siesta Key 5 Star 'True' Direct Beach-Front ! (The Absolute Best of the Best !)

  • 2 BR/1 BA, 1 half bath Condo (sleeps 5)
    $4,995 - $6,995/month
    per property, Beach, Resort, Village, Waterfront, Communal Pool, Sauna, Tennis Court, terrace, Balcony, Fitness Room / Equipment, Air Conditioning
SPECIAL OFFER! discounted beachhouse on Siesta Key!! May 26 - August 31

Siesta Key Charming Gulf front 1916 Siesta Key Beach House with Gazebo

  • 2 BR/2 BA House (sleeps 6) Beach, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, barbecue, Fireplace

Siesta Key 20% off stays July-Oct. Wi-Fi, HDTV, Boat Docking Available!

  • 2 BR/1 BA, 1 half bath Condo (sleeps 4)
    $568 - $1,070/wk
    per property, accept credit card, Beach, Waterfront, Communal Pool, Tennis Court, terrace, Balcony, Air Conditioning, Internet

Siesta Key Siesta Key Luxury Condo Across the Street from the Beaches

  • 2 BR/1 BA Condo (sleeps 6)
    $150/nt
    $875/wk
    $3,000/month
    per property, accept credit card, Beach, Near The Ocean, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Siesta Key Siesta Bayside: Living on the Water in Siesta Key

  • 2 BR/1 BA, 1 half bath Apartment (sleeps 5)
    $574 - $1,000/wk
    $1,600 - $3,340/month
    per property, accept credit card, Beach, Waterfront, Communal Pool, Internet, Satellite / Cable, Television, DVD Player

Siesta Key Luxury Siesta Key Home

  • 3 BR/3 BA House (sleeps 6)
    $3,700 - $7,000/month
    per property, Private Pool

Siesta Key Private Beachfront and Pool, Tennis Court ,Siesta Key Condo w/ all Amenities

  • 2 BR/2 BA Condo (sleeps 6)
    $1,150 - $1,250/wk
    per property, accept credit card, wheelchair accessible, Beach, Resort, Tennis Court, Balcony, Air Conditioning, Internet, Satellite / Cable

Siesta Key 2,150 Square Foot Gulfside Beachfront Townhouse.

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6) Beach, Resort, Tennis Court, terrace, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Siesta Key 2-Bedroom - Beachfront Condo - Luxury - Directly on Crescent Beach

  • 2 BR/2 BA Condo (sleeps 6)
    $1,425/wk
    per property, accept credit card, Beach, Waterfront, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Siesta Key The Hummingbird Beach House!Short Walk to Beach & Village

  • 6 BR/6 BA House (sleeps 20) wheelchair accessible, Beach, Village, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Siesta Key Siesta Key Beach #1 in USA steps to Banyan Tree Beach Resort 'Key West' unit

  • 2 BR/2 BA House (sleeps 6) Beach, Village, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Siesta Key *LAST MINUTE MAY 2013* Fantastic Bay View - Private Beach-FREE WIFI

  • 2 BR/1 BA, 1 half bath Apartment (sleeps 4)
    $730 - $910/wk
    per property, Beach, Near The Ocean, Waterfront, Communal Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Siesta Key Crescent Beach - 2-Bedroom - Beachfront Condo Complex

  • 2 BR/2 BA Condo (sleeps 6)
    $1,225/wk
    per property, accept credit card, Beach, Village, Sauna, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Siesta Key Siesta Key - Sundance Rental - Affordable - Key West Style - Private Pool

  • 2 BR/2 BA Apartment (sleeps 6)
    $885/wk
    per property, accept credit card, Beach, Village, terrace, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable

Siesta Key Deluxe Town home - Garden Apartment, Private Pool

  • 1 BR/1 BA Condo (sleeps 4)
    $625/wk
    per property, accept credit card, Beach, Village, Private Pool, Jacuzzi, Balcony, Air Conditioning, Internet, Satellite / Cable

Siesta Key !Morgan - Crystal Sands #607 - Completely Renovated 2 Bedroom / 2 Bath

  • 2 BR/2 BA Condo (sleeps 6)
    $1,800 - $2,000/wk
    $7,714 - $8,571/month
    per property, Beach, Waterfront, Air Conditioning, Internet, Satellite / Cable, DVD Player

Siesta Key !Morgan - Palm Bay Club #84 Tower - Completely Renovated 1 Bedroom / 1 Bath

  • 1 BR/1 BA Condo (sleeps 4)
    $196 - $229/nt
    $1,375 - $1,600/wk
    $5,893 - $6,857/month
    per property, Air Conditioning, Internet, Satellite / Cable, DVD Player

Siesta Key !Morgan - Crystal Sands #311 - Completely Renovated 2 Bedroom / 2 Bath

  • 2 BR/2 BA Condo (sleeps 6)
    $286/nt
    $1,800 - $2,000/wk
    $7,714 - $8,571/month
    per property, Beach, Waterfront, Air Conditioning, Internet, Satellite / Cable, DVD Player

Siesta Key !Morgan - Crystal Sands #V22 - Completely Renovated 2 Bed / 2 Bath w/ Garage

  • 2 BR/2 BA Villa (sleeps 6)
    $214/nt
    $1,200 - $1,500/wk
    $5,143 - $6,429/month
    per property, Beach, Near The Ocean, Air Conditioning, Internet, Satellite / Cable, DVD Player

Siesta Key !Morgan - Crystal Sands #910 - Completely Renovated 2 Bedroom / 2 Bath

  • 2 BR/2 BA Condo (sleeps 6)
    $286/nt
    $1,800 - $2,000/wk
    $7,714 - $8,571/month
    per property, Beach, Waterfront, Air Conditioning, Internet, Satellite / Cable, DVD Player

Siesta Key !Morgan - Crystal Sands #V12A - Completely Renovated 3 Bed / 2 Bath w/Garage

  • 3 BR/2 BA Villa (sleeps 6)
    $257/nt
    $1,600 - $1,800/wk
    $6,857 - $7,714/month
    per property, Beach, Near The Ocean, Waterfront, Air Conditioning, Internet, Satellite / Cable, DVD Player

Siesta Key !Morgan - Crystal Sands #V4 - Updated 2 Bedroom / 2 Bath with Garage

  • 2 BR/2 BA Villa (sleeps 6)
    $214/nt
    $1,200 - $1,500/wk
    $5,143 - $6,429/month
    per property, Beach, Near The Ocean, Waterfront, Air Conditioning, Internet, Satellite / Cable, DVD Player

Siesta Key !Morgan - Crystal Sands #803 - Completely Renovated 2 Bedroom / 2 Bath

  • 2 BR/2 BA Condo (sleeps 6)
    $286/nt
    $1,800 - $2,000/wk
    $7,714 - $8,571/month
    per property, Beach, Waterfront, Air Conditioning, Internet, Satellite / Cable, DVD Player

Siesta Key Beautiful Beach Cottage in high-rise condominium with water views

  • 2 BR/2 BA Condo (sleeps 4)
    $179 - $210/nt
    $1,255 - $1,473/wk
    per property, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Siesta Key Spacious vacation rental condo with lagoon views, beach access, and pool

  • 3 BR/2 BA, 1 half bath Condo (sleeps 6)
    $129 - $185/nt
    $800 - $1,295/wk
    $2,800 - $5,120/month
    per property, Beach, Waterfront, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

Siesta Key Tropical landscape, easy access, affordable rates.

  • 2 BR/2 BA Condo (sleeps 6)
    $93 - $143/nt
    $650 - $1,000/wk
    $1,800 - $4,045/month
    per property, Beach, Resort, Communal Pool, Sauna, Air Conditioning, Internet, Satellite / Cable, DVD Player

Siesta Key Delightful Apartment - Walk to Beach, shops, bars & restaurants

  • 1 BR/1 BA Apartment (sleeps 2)
    $80 - $90/nt
    $429 - $699/wk
    per property, Beach, Village, Air Conditioning, Satellite / Cable, Television, DVD Player, Parking

Siesta Key A Brief Walk to Siesta Key Village and the Beach

  • 2 BR/2 BA Condo (sleeps 6)
    $165 - $250/nt
    $1,300/wk
    $4,750/month
    per property, accept credit card, Beach, Near The Ocean, Town, Village, Waterfront, Private Pool, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Siesta Key #1 minute to Siesta Key beach

  • 3 BR/3 BA Townhome (sleeps 8)
    $2,900 - $3,100/wk
    per property, accept credit card, wheelchair accessible, Beach, Village, Private Pool, terrace, Balcony, pets considered, Air Conditioning

Siesta Key Beautiful 2 Bed/2 Bath Beachfront Condo on Siesta Key Beach

  • 2 BR/2 BA Condo (sleeps 4)
    $3,000/month
    per property, accept credit card, Beach, Near The Ocean, Communal Pool, Tennis Court, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

Siesta Key #1 minute Siesta Key Beach and 5 blocks to Village

  • 3 BR/3 BA Townhome (sleeps 6)
    $2,700 - $2,900/wk
    per property, accept credit card, wheelchair accessible, Beach, Village, terrace, Balcony, Air Conditioning, Internet, Satellite / Cable

Siesta Key Siesta Key Ocean Front Luxury Condo - The Best Location on Siesta Key

  • 2 BR/2 BA Condo (sleeps 4) accept credit card, wheelchair accessible, Beach, Waterfront, Private Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Internet

Siesta Key Luxury Siesta Key Canal Front Home with Pool & Spa / Walk to Beach !!

  • 4 BR/2 BA, 1 half bath House (sleeps 12) accept credit card, Beach, Near The Ocean, Waterfront, Private Pool, Communal Pool, Jacuzzi, Balcony, pets considered, Air Conditioning

Siesta Key Bay Tree Club Condo 308A

  • 2 BR/2 BA Condo (sleeps 6)
    $1,000 - $1,500/wk
    $4,000 - $6,000/month
    per property, Communal Pool, Balcony, Television

Siesta Key Island Home in Paradise

  • 3 BR/2 BA House (sleeps 8) accept credit card, wheelchair accessible, Near The Ocean, Waterfront, Private Pool, pets considered, Air Conditioning, Internet, Satellite / Cable

Siesta Key Resort across from Crescent Beach! All NEW!

  • 2 BR/2 BA Townhome (sleeps 6)
    $985/wk
    per property, accept credit card, Beach, Resort, Waterfront, Communal Pool, Sauna, Tennis Court, Balcony, Fitness Room / Equipment, Air Conditioning

Siesta Key Siesta Jewel Villa, Walk to the Beach & Village...or hang by the pool

  • 1 BR/1 BA Villa (sleeps 4)
    $95/nt
    $595 - $975/wk
    $2,500 - $3,400/month
    per property, accept credit card, Beach, Village, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Siesta Key Siesta Dunes - Week of June 1st still available 20% Discount

  • 2 BR/2 BA Condo (sleeps 6)
    $900 - $1,400/wk
    per property, Beach, Communal Pool, Tennis Court, Air Conditioning, Internet, Television, DVD Player

Siesta Key Upscale - Beachfront One Bedroom Condo at Fisherman's Cove

  • 1 BR/1 BA Condo (sleeps 4)
    $890/wk
    per property, accept credit card, Beach, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Siesta Key Siesta Jewel beach house- A Great place for the Whole Family!

  • 3 BR/2 BA House (sleeps 8)
    $1,295 - $1,795/wk
    per property, Beach, Village, Private Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Siesta Key My Perfect Siesta Key beach House, Yours Too ! (not a duplex or condo)

  • 3 BR/3 BA House (sleeps 6)
    $1,295/wk
    per property, Beach, Village, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Siesta Key Gulf & Bay Bayside 3 BR w/ Bay Views

  • 3 BR/2 BA Townhome (sleeps 6)
    $1,255/wk
    per property, accept credit card, Beach, Resort, Communal Pool, Sauna, Tennis Court, Balcony, Fitness Room / Equipment, Air Conditioning

Siesta Key !Morgan - Crystal Sands #608 - Completely Renovated 2 Bed / 2 Bath

  • 2 BR/2 BA Condo (sleeps 6)
    $1,800 - $2,000/wk
    $7,714 - $8,571/month
    per property, Beach, Waterfront, Air Conditioning, Internet, Satellite / Cable, DVD Player

Siesta Key !Morgan - Crystal Sands #208 - Updated 2 Bedroom/2 Bath, all new furnishings

  • 2 BR/2 BA Condo (sleeps 6)
    $257/nt
    $1,600 - $1,800/wk
    $6,857 - $7,714/month
    per property, Air Conditioning, Internet, Satellite / Cable, DVD Player

Siesta Key !Morgan - Crystal Sands #702 - Completely Renovated 2 Bedroom / 2 Bath

  • 2 BR/2 BA Condo (sleeps 6)
    $286/nt
    $1,800 - $2,000/wk
    $7,714 - $8,571/month
    per property, Beach, Waterfront, Air Conditioning, Internet, Satellite / Cable, DVD Player

Siesta Key !Morgan - Crystal Sands #206 - Completely Renovated 2 Bedroom / 2 Bath

  • 2 BR/2 BA Condo (sleeps 6)
    $286/nt
    $1,800 - $2,000/wk
    $7,714 - $8,571/month
    per property, Beach, Waterfront, Air Conditioning, Internet, Satellite / Cable, DVD Player

Siesta Key !Morgan - Crystal Sands #504 - Completely Renovated 2 Bedroom / 2 Bath

  • 2 BR/2 BA Condo (sleeps 6)
    $286/nt
    $1,800 - $2,000/wk
    $7,714 - $8,571/month
    per property, Beach, Waterfront, Air Conditioning, Internet, Satellite / Cable, DVD Player

Siesta Key Luxury Private Siesta Key Condo on Award-Winning Crescent Beach

  • 2 BR/2 BA Condo (sleeps 6) accept credit card, Beach, Near The Ocean, Village, Communal Pool, Tennis Court, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable

Siesta Key Ebb Tide Villa #2 w Private Patio; Heated Pool; Beach 3 min walk!

  • 1 BR/1 BA Villa (sleeps 4)
    $700 - $1,150/wk
    $2,400 - $4,200/month
    per property, accept credit card, Beach, Village, Communal Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

Siesta Key Siesta Key Poolside Villa

  • 2 BR/1 BA, 1 half bath Villa (sleeps 4)
    $800/wk
    $3,200/month
    per property, wheelchair accessible, Beach, Near The Ocean, Village, Waterfront, Communal Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television
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