- Harbor Towers Yacht & Racquet Club
- Harbour Towne Yacht Club
- Horizons West
- House of the Sun
- Inlets
- Island House
- Island Reef
- Jamaica Royale
- La Siesta
- Midnight Cove
- Midnight Cove Bayside
- Midnight Cove II
- Midnight Sea
- Moorings
- Our House at The Beach
- Palm Bay Club
- Peppertree Bay
- Peppertree Gulfside
- Polynesian Gardens
- Private Homes
- Private Homes, Siesta Isles
- Private Homes, Siesta Key Village
- Private Homes: Palm Island
- Private Homes: Siesta Village
- Provincial Gardens
- Sandbox on the Beach
- Sandy Cove
- Sara Sea
- Sarasota By The Sea
- Sarasota Surf & Racquet Club
- Sea Club II
- Sea Crest
- Sea Shell
- Sea Winds
- Shells On Siesta Key
- Siesta Beach House
- Siesta Breakers
- Siesta Dunes
- Siesta Palms by the Beach
- Siesta Sands
- Siesta Shores
- Summer Cove on Siesta
- Sun & Sea Island Hideaway
- Sunrise Cove
- Sunset Point
- Sunset Royale
- Tortuga
- Twin Banyan
- Twin Palms
- Vista Hermosa
- Whispering Sands
- White Sands Village
- Aloha Kai
- Anchorage
- At The Beach Apartments
- Banana Bay Club Beachside
- Banana Bay Club Waterside
- Banyan Tree Beach Resort
- Bay Oaks
- Bay Tree Club
- Beach Villas
- Beachaven
- Boca Siesta
- Calle Minorga
- Casa Blanca
- Casa Mar
- Casa Siesta
- Casarina
- Castaway Cove
- Cozy Cove
- Crescent Arms
- Crescent Royale
- Crescent Siesta Key
- Crescent Towers
- Crystal Sands
- Ebb Tide
- El Presidente
- Excelsior Beach
- Fisherman's Cove
- Fisherman's Haven
- Gulf & Bay Club
- Gulf & Bay Club Bayside
- Gulf Haven
- Gulf Holiday
- Gumbo Limbo
- Other Siesta Key Properties
- Siesta Key
This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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Siesta Key Vacation Rentals Show this location only Back to top
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Siesta Key Village Apartment - Sleeps 4 - One Block to Beach
1BR+/1BA
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Sleeps 2-4
– Private Homes, Siesta Key Village #399800
$125.00 - $175.00
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Peppertree Gulfside on the Beach 8/15-9/30 $890
2BR/2BA
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Sleeps 4
– Peppertree Gulfside #460360
$889 - $1365 per week 7 night min stay
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Luxurious Siesta Key Bayfront Townhouse - 3 BR/2.5 BA
3BR/2.5BA
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Sleeps 6
– Other Siesta Key Properties #10981
$3500- $6000/mo
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Siesta Key Beach Apartment
1BR/1BA
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Sleeps 2-4
– Siesta Beach House #171030
$200 per night 2 night min stay
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Castaway Cove 3b, on Lagoon Near Beach, Pet Friendly, Siesta Key
2BR/1BA
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Sleeps 5
– Other Siesta Key Properties #397326
$100 - $200 per night 2-4 night min stay
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Fun in the Sun on Siesta Key
2BR/2BA
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Sleeps 4-5
– Harbor Towers Yacht & Racquet Club #150381
$650-$950/wk - $1600-$3800/mo
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Outstanding Top Floor View! Summer Specials!
1BR+/1BA
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Sleeps 2-4
– Sunrise Cove #369197
$1475/ $3650 mo
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Lovely Tropical Villa, Patio,Heated Pool,Great Value!
1BR+/1BA
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Sleeps 2-4
– Ebb Tide #379835
$80nt or $560/ $975 wk
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Beautiful Villa with Crescent Beach and Intracoastal Access
2BR+/2BA
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Sleeps 4-6
– Provincial Gardens #62791
$525- $800/wk
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2BR/2BA Newly Renovated Condo, Sleeps 6
2BR/2BA
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Sleeps 6
– Harbor Towers Yacht & Racquet Club #197907
$575- $895/wk
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Wonderful Waterfront Apartment with Siesta Key Beach Access
1BR/1BA
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Sleeps 2
– Provincial Gardens #12455
$420- $700/wk
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Adorable Key West Style Cottage on Siesta Key, Steps to White
1BR+/2BA
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Sleeps 4-5
– Twin Palms #381251
From $700- $910/wk
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Siesta Key - Hey ! Look No Further, Fantastic Location
2BR/1.75BA
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Sleeps 4
– Midnight Cove II #51101
$800- $1100/wk
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Paradise in Seista Key - Minimum Rental Period 30-Days
3BR/2BA
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Sleeps 6-8
– Other Siesta Key Properties #3552541ha
$7500 - $10950 per month 30 night min stay
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Best View of Gulf in Bay Oaks!
2BR+/2BA
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Sleeps 4-6
– Bay Oaks #278289
From $650/wk - $2000/mo
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Palm Bay Club Gulfside 2BR/2BA Largest, Closest Club to Beach!
2BR/2BA
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Sleeps 6
– Palm Bay Club #337521
Flexible & Last Minute from $100/nt!
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Delightful Villa W Private Patio! 3 Min Walk to the Beach!
1BR+/1BA
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Sleeps 2-4
– Ebb Tide #378881
$169 nightly or $700-$1150 wk
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Incredible Gulf Front Beach Home
3BR+/3BA
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Sleeps 6-8
– Private Homes #409708
$2100 - $3850 per week 7 night min stay
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Private Pool Home, Turtle Beach on Siesta Key!
3BR/3BA
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Sleeps 6
– Private Homes #336473
$1,150 - $1,800/wk
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Desirable First Floor 2BR/2BA in Midnight Cove I
2BR+/2BA
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Sleeps 4-6
– Midnight Cove #33973
$735- $1250/wk
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Just Remodeled, Private Beach W/ Lounges and Umbrellas
2BR/1.5BA
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Sleeps 4-6
– Midnight Cove Bayside #424387
$700.00 to $ $1120.00/week
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Sun, Sand & Save 25% to 55% Per Week at Siesta Breakers #603
2BR/2BA
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Sleeps 6
– Siesta Breakers #208534
$853-$1586/wk - $2986-$5708/mo US Dollars (USD)
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House of the Sun - Directly on Gulf! Discounts for Summer and Fall!
2BR+/2BA
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Sleeps 4-6
– House of the Sun #358370
From $1255/wk
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Jamaica Royale 91 Rental, Heated Pool, Beach Access,Wifi
2BR/2BA
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Sleeps 6
– Jamaica Royale #397456
$200 - $350 per night 2-4 night min stay
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Our House at the Beach 504, 5th Floor, Gulf Views, with Heated Pool
2BR/2BA
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Sleeps 6
– Other Siesta Key Properties #397355
$114 - $166 per night 2-4 night min stay
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Modern Condo on Siesta Key Beach - Fabulous Look and Location!
Studio/1BA
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Sleeps 2-3
– Casa Mar #400209
$137 per night 3 night min stay
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Townhouse with Garage - Across from Siesta Key Beach!
2BR+/2BA
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Sleeps 4-6
– Our House at The Beach #210898
$875 to $1302
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Stunning Ocean Views * Magnificent Sunsets * Beachfront Condo
2BR+/2BA
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Sleeps 4-5
– Sunset Royale #287621
$749 - $1,325/wk
- Welcome to Sugarland, Your Dream Home Directly on the Beach! 2BR/2BA – Sleeps 6 – Gulf & Bay Club #216498
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Beautiful View from Sarasota Surf and Racquet Club-Siesta Key
2BR/2BA
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Sleeps 6-7
– Sarasota Surf & Racquet Club #155347
$1275- $2450/wk
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Step Onto the Gulf Sands - Your Own Siesta Key "Beach House"
1BR+/1BA
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Sleeps 2-4
– Fisherman's Cove #170883
$935- $1545/wk
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Gulf-Front Condo - Siesta Key, Florida
2BR+/2BA
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Sleeps 6
– Midnight Cove #41562
$1416-$1879/wk - $5098-$6767/mo
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Beautiful Condo with Pool on Siesta Key in Sarasota!
1BR+/1BA
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Sleeps 2
– Bay Oaks #379627
$82 - $118 per night 2-7 night min stay
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Great Unit--1 Bedroom 1 Bath-Walk to Beach & Shops
1BR+/1BA
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Sleeps 4
– Private Homes, Siesta Key Village #432803
$115+/ per night - $650+/ per week
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Sun, Sand & Save 25% to 55% Per Week at Midnight Cove #714
2BR/1BA
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Sleeps 4
– Midnight Cove #364077
$587-$1,148/Wk & $1,988-$4,049/Mo
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Gulf-Front Beach Cottage
3BR+/2BA
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Sleeps 7
– Private Homes #42167
$1950- $2350/wk
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Gulf Side Community on #1 Rated Beach in USA
1BR/1BA
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Sleeps 2-4
– Beachaven #449421
$75 - $110 per night 14-30 night min stay
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Siesta Key Garden Studio Just 150 Yards to Beach!
Studio/1BA
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Sleeps 2
– Ebb Tide #445348
$125 per night 3 night min stay
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Beach Front Condo on Siesta Key #1 Beach in the USA, with Gulf Views
2BR/2BA
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Sleeps 6
– El Presidente #452583
$1,350 - $2,050 Weekly
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Exquisite, Luxury 5BR 3.5BA Home W/Pool, Short Walk to Beac
5BR+/3.75BA
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Sleeps 10
– Private Homes #378874
$3,000- 3,300 PER WEEK
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Lovely Apartment - Walk to Beach, Restaurants, Shops
1BR/1BA
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Sleeps 2
– Private Homes #424645
From $429 per week
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Awesome Siesta Key Village Villa in Siesta Key
2BR+/2BA
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Sleeps 4-5
– Private Homes #408573
$840 - $1148 per week 7 night min stay
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Affordable Condo on Siesta Key!
1BR/1BA
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Sleeps 2-4
– Bay Oaks #452677
$500 - $775 wkly / $1300 - $3000 mthly
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4 Bedroom Right on Top Rated Beach, Siesta Key, Florida
4BR/2BA
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Sleeps 8
– Aloha Kai #294661
$2,095 - $3,795/wk US or Canadian Dollars
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Walk to Beach and Shops-Pool, Onsite Free Laundry
2BR/2BA
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Sleeps 4-6
– Private Homes, Siesta Key Village #433031
$150+/per night- $950+/per week
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Private Beach & on Water/Heron Lagoon
3BR/2BA
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Sleeps 8
– Private Homes #78477
$2500- $5700/mo
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Siesta Key Gulf Front Condo with Great View of the #1 Beach in America
2BR/2BA
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Sleeps 5-6
– Other Siesta Key Properties #439947
$1010 - $1598 per week 7 night min stay
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Waterfront Canal~Walk to Beach & Siesta Village/Pool/Jacuzzi
3BR/2BA
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Sleeps 6
– Private Homes #219135
$1500wk- $6700mo
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Siesta Key - on the Water
2BR+/1BA
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Sleeps 5-6
– Sea Club II #257847
$110 - $120 per night 5 night min stay
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Tropical Waterfront 4 BR Luxury Pool Home on Canal W/ Boat Dock
4BR/2BA
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Sleeps 9-11
– Private Homes #981741ha
$1927 - $3250 per week
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Siesta Key, Midnight Cove II, Available Jan 4-19, Apr 10
2BR/1BA
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Sleeps 4
– Midnight Cove II #329638
$750- $1110/wk
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Lovely, Updated Condo - Gulf Side - Siesta Key
1BR/1BA
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Sleeps 2-4
– Jamaica Royale #451442
$700 - $1050 per week 7 night min stay
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Siesta Key with Boat Dock
2BR+/2BA
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Sleeps 5
– Cozy Cove #260667
$125 - $157 per night 2-7 night min stay
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Beautiful Siesta Key Condo on the Gulf
1BR+/1.5BA
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Sleeps 4
– Palm Bay Club #85217
From $150/nt USA
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Gulf and Bay 207f, Siesta Key Beach Front, 3 Pools, Spa, Wifi
2BR/2BA
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Sleeps 6
– Gulf & Bay Club #397322
From $2495/mo
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Vacation in Style - Family Friendly
2BR+/2BA
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Sleeps 4-6
– Excelsior Beach #260183
$900-$1370/week + $100 +12% FL Tax
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Excelsior 107, 1st Flr, 2 Heated Pool, Spa, Wifi, Beach Access
2BR/2BA
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Sleeps 6
– Excelsior Beach #397318
From $1,995/ 2 weeks $2,995/month
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Walk to Beautiful Crescent Beach on Siesta Key in Sarasota.
1BR+/1BA
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Sleeps 4
– Casa Siesta #354559
$57 - $80 per night 6-14 night min stay
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Siesta Key Condo French Connection
2BR/2BA
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Sleeps 4
– Siesta Key #453053
$105 - $150 per night 21-30 night min stay
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Ground Level Bayfront W/ Water View W/ Deeded Beach Access
2BR+/1BA
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Sleeps 4-6
– Midnight Cove II #313846
$900- $1750/week US or Canadian Dollars
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Luxury Siesta Key Beach Front Home
2BR+/3BA
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Sleeps 5-6
– Private Homes: Siesta Village #201270
$150- $3000/wk
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Just Steps to the Sugar-Sand Beach Ranked #1 in U.S.
2BR+/2BA
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Sleeps 5
– Crescent Royale #275884
$1200- $1673/wk
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Sweet Florida Cottage in Great Location Across from Beach!
3BR/3BA
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Sleeps 6
– Siesta Shores #439392
$840 - $1925 per week 7-30 night min stay
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The Closest Beachfront Condo to the Gulf of Mexico on Siesta Key!
2BR/2BA
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Sleeps 6
– Fisherman's Cove #448079
$1120 - $1745 per week 7 night min stay
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Contemporary Condo on Siesta Beach in Florida
2BR+/2BA
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Sleeps 4-6
– Peppertree Gulfside #278905
$980 per week 7 night min stay
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On the Beach- Large 2 Bedroom / 2 Bath Condo. Terrific Views.
2BR+/2BA
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Sleeps 6-7
– Island House #306126
$1442- $2200/wk
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Siesta 2 BR Gulf View on the Beach (30 Day Min)
2BR/2BA
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Sleeps 4-6
– Tortuga #458538
$3500 - $4800/Month ( One month minimum)
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Sarasota's Best Waterfront Spacious Home with a Pool
4BR/3BA
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Sleeps 6
– Other Siesta Key Properties #815084ha
$228 - $242 per night
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Siesta Key Large 3 BR/2 BA, Beautiful Water Views and Beach
3BR+/2BA
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Sleeps 6
– Sunrise Cove #321258
$2010 per month 30 night min stay
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Beautiful Beaches on Siesta Key - Great Spring and Summer Specials
1BR+/1BA
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Sleeps 2-4
– Harbor Towers Yacht & Racquet Club #363149
$525- $835
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Annette's Seaside Villas
2BR/0BA
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Sleeps 4
– Sarasota By The Sea #445252
$650 - $1050 per week 7 night min stay
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Bay Tree Club - Heaven on the Bay!
2BR+/2BA
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Sleeps 6
– Bay Tree Club #222640
$900-$1200/wk - $3200-$4000/mo
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Siesta Key Beach Pool Home - Why Stay in a Condo ???
2BR+/2BA
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Sleeps 4-6
– Private Homes #395332
$3000 - $5000 per month 30 night min stay
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Walk to Your Pool, Private Beach and Bustling Siesta Village
3BR+/2BA
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Sleeps 5-6
– Whispering Sands #412346
2 MONTH MINIMUM
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Villa Cascada - Luxury 4BR/4BA/2kit- Short 4 Min Walk to Beach
4BR+/4BA
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Sleeps 14
– Private Homes #430568
$3,000- $3,500 per week
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Groundfloor - Poolside - Waterfront! Siesta Serenity & Luxury!
1BR/1BA
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Sleeps 2
– Inlets #356506
$1250 or $2500/month
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Best of Both Worlds- Beach Access and Spectacular View of the Bay
2BR/2BA
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Sleeps 4
– Midnight Cove II #415095
$875- $1300/wk
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Beachside 2 Bedroom Condo - Gulf and Bay (Gulf Side)
2BR/2BA
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Sleeps 6
– Gulf & Bay Club #304493
1,660/wk - summer
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Quiet, 2 Bed, 2 Bath, Spectacular Beach View
2BR/2BA
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Sleeps 6
– Crystal Sands #418235
$1360 - $1980/week
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1 Beach Home on #1 USA Siesta Key Beach!
3BR/3BA
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Sleeps 8-10
– Sunset Point #468287
$300 - $400 per night 1 night min stay
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Paradise Awaits You! Enjoy the 'Sugar' Sands of Siesta Key
2BR/2BA
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Sleeps 4-6
– Polynesian Gardens #477556
$700 - $1300 per week 7-31 night min stay
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Private Beach Paradise
1BR/1BA
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Sleeps 2
– Sandy Cove #99452
$1600- $2400/mo
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Affordable 5-Star Condo Steps from Beach! Views! Amenities!
2BR+/2BA
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Sleeps 6
– Our House at The Beach #104833
$1,008- $1,372/wk
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Island Getaway: 1 Block to Beach, 1 Block to Shops, Restaurant
2BR/2BA
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Sleeps 4
– Private Homes: Siesta Village #219714
$890- $1300/wk
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Fabulous Spacious Condo!
2BR+/2BA
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Sleeps 4-6
– Excelsior Beach #319861
$840- $1280/wk
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Waterfront Pool House Steps from Siesta Village
2BR+/2BA
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Sleeps 4-6
– Private Homes: Siesta Village #182314
$1295-$1600/wk - $4800-$5400/mo
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Siesta Key Bayfront Beach with Marina
2BR+/1BA
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Sleeps 4-6
– Midnight Cove II #152189
$675- $1050/wk
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5 BR Luxury Waterfront W/Pool & Spa - 'Oasis' Near Village & Beach!
5BR/3BA
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Sleeps 13-15
– Other Siesta Key Properties #3002420ha
$289 - $500 per night
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Remodeled Condo - Resort is on #1 Beach in the USA
1BR+/1BA
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Sleeps 2-4
– Casa Mar #389037
$651 - $1,043/wk
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Siesta Key Beach Front Unit Facing Gulf - Aug & Fall Dates Still Available
2BR/2BA
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Sleeps 4-6
– Crescent Royale #432606
7 night minimum $963 - $1,385 per week
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3BR/3bath, Pool/Hot Tub, Walk to Siesta Beach & Village
3BR+/2BA
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Sleeps 6-7
– Private Homes, Siesta Key Village #394366
$1950- $3000 weekly US & Canadian Dollars
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Beautifully Redone Condo Right on Crescent Beach!
1BR+/1BA
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Sleeps 2-4
– Crescent Arms #270616
$924- $1536/wk
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Palm Bay Club, Siesta Key, Tower G25-Newly Renovated 2BR/2BA
2BR/2BA
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Sleeps 6
– Palm Bay Club #467533
$205 - $447 per night 3 night min stay
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Panoramic Gulf and Siesta Beach Views Plus Spectacular Sunsets!
2BR/2BA
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Sleeps 4
– Our House at The Beach #424185
$950 to $1445/week
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'Siesta Sandals' Cottage Near Village and Beach
3BR/2BA
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Sleeps 6
– Private Homes, Siesta Key Village #419755
$200 - $400 per night 2 night min stay
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Steps to the Whitest Sands of #1 Beach
2BR/2BA
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Sleeps 4-6
– Crescent Arms #466036
$165 - $261 per night 2-7 night min stay
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Peppertree Bay - Relax in Paradise on Siesta Key
2BR+/2BA
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Sleeps 4-6
– Peppertree Bay #154003
From $1000/wk - 4000/mo
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Siesta Key Waterfront Home
4BR/3BA
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Sleeps 6-8
– Other Siesta Key Properties #426781
$9,000- $12,500/month
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4 Brm Across from Beach, on Canal, Gorgeous! / 5633 Cape Leyte Dr
4BR/3BA
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Sleeps 8-10
– Private Homes, Siesta Isles #449684
see above
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Siesta Key Gulf & Bay Club Bayside Condo
2BR/2BA
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Sleeps 4
– Gulf & Bay Club #405324
$895/wk - $1,355/wk
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Siesta Key Village Apartment - Sleeps 4 - One Block to Beach
1BR+/1BA
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Sleeps 2-4
– Private Homes, Siesta Key Village #399800
Overview of Siesta Key Vacation Rentals
Siesta Key Condos: Create Your Dream Vacation with Ease
Just off the coast of Sarasota, Florida, you’ll find the beautiful barrier island called Siesta Key. If you are looking for the whitest beaches and the most tropical atmosphere in Florida, then you’ll find it here. Forego bland hotels and make your vacation plan more exciting – Siesta Key condos are the perfect option for you.
Siesta Key beach rentals are an even better option if you long to hear the egrets singing and waves crashing outside your bedroom window. Of course, there are also several Siesta Key resorts to choose from as well.
Luxurious Vacations Start Here: Siesta Key Condos
Siesta Key condos come in a wide variety of options, and they definitely offer you the most in terms of amenities. If the weather might be a little chilly on your trip, don’t fret. Many of the condos have heated pools, so regardless of the weather you can still fit in some swimming time with the family. Looking for a more private getaway? Many Florida condos in Siesta Key even have their own beaches!
Other great features that many of the condos offer include beachfront property, breathtaking views and a variety of bedroom options. This makes selecting perfect Siesta Key beach rentals a breeze for a large family.
Siesta Key Beach Rentals Put You Steps from the Ocean
When you plan a family vacation to Florida, it’s all about the water, right? With all the options available in Siesta Key beach rentals, you won’t be far from sinking your toes into the gorgeous white sand and feeling the surf soak your ankles. Plus, being so close to the water provides you with an excellent view.
Another great benefit is that you are close to any action or events taking place on the beach. In May, for instance, you can see World-class sand sculptures created by amazing artists at the Siesta Key Sand Sculpture Contest.
Stay at Some of the Finest Resorts with Siesta Key Resorts
Even if you prefer having complete control over your vacation, there are times when it's great to get a little pampering at luxurious Siesta Key resorts. If you want to take in 50 miles of canals and waterways from your room balcony, then the Siesta Key resorts will allow you to do just that. You’re also not far from great dining and shopping. And, of course, you're never far from the sand - many of the resorts have private beaches where you can rent bungalows, chairs, water toys, or take advantage of the many entertainment options that may be provided by the resort. No matter which option you choose one thing is sure: Siesta Key will provide you with a vacation full of rest, relaxation and fun