- Arbomar
- Banyan Bay Club
- Bay Harbour
- Bay Isles
- Bay Isles, Harbour Oaks
- Bayport Beach & Tennis Club
- Beach Castle Resort
- Beach Harbor Club
- Beachcomber
- Beachcomber II
- Beachplace
- Cabana Beach Club
- Casa del Mar
- Castillian
- Cedars Tennis Resort
- Cedars West
- Club Longboat
- Covert II
- Covert III
- Diplomat
- Fairway Bay
- Grand Bay
- Inn on the Beach
- Islander Club
- Islands West
- La Playa
- Longbeach Condominiums
- Longboat Arms
- Longboat Bay Club
- Longboat Harbour
- Longboat Harbour Towers
- Longboat Key Club
- Longboat Key Towers
- Longboat Key Yacht & Tennis Mark I
- Longboat Key Yacht & Tennis Mark II
- Longboat Landing
- Longboat Terrace
- Neptune
- Outrigger Resort
- Pelican Harbour
- Pierre
- Portobello
- Private Homes
- Private Homes, Cannons By The Sea
- Private Homes, Conrad Beach
- Private Homes, Country Club Shores
- Private Homes, Hideaway Bay
- Private Homes, Laguna Yacht Village
- Private Homes, Longbeach Village
- Private Homes, Sleepy Lagoon
- Private Homes, Triton Cove
- Private Homes, Twin Shores
- Privateer
- Promenade
- Salty Acres
- Sand Cay Beach
- Sands Point
- Sea Club I
- Sea Grape Inn
- Sea Oats
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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Longboat Key Vacation Rentals Show this location only Back to top
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Silver Sands #249
2BR/1BA
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Sleeps 6
– Other Longboat Key Properties #3190773ha
$250 - $425 per night
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Silver Sands #245s
2BR/2BA
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Sleeps 6
– Other Longboat Key Properties #3190767ha
$230 - $395 per night
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Bay Winds
2BR/3BA
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Sleeps 6
– Other Longboat Key Properties #3240687ha
$1283 - $1900 per week
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Silver Sands #257s
2BR/2BA
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Sleeps 6
– Other Longboat Key Properties #3190789ha
$230 - $395 per night
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Silver Sands #253a
1BR/1BA
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Sleeps 2
– Other Longboat Key Properties #3190780ha
$125 - $170 per night
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Silver Sands #256
1BR/1BA
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Sleeps 4
– Other Longboat Key Properties #3190786ha
$175 - $295 per night
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The Beach on Longboat Key #227
1BR/1BA
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Sleeps 5
– Other Longboat Key Properties #3190901ha
$190 - $295 per night
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Cedars East #845
2BR/2BA
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Sleeps 4
– Other Longboat Key Properties #3464023ha
$700 - $1900 per week
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Relaxing, Charming & Tropical Beach Retreat with Private Pool
2BR+/2BA
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Sleeps 4-8
– Private Homes #308831
$1450-$1850/wk - $4640-$5920/mo
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Beautiful Home with Pool On Bay / Boat Lift Available
2BR+/2BA
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Sleeps 4-6
– Private Homes, Sleepy Lagoon #196485
$350 per night 14 night min stay
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Amazing Oceanfront Condominium on Second Floor with Balcony
Studio/1BA
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Sleeps 2-3
– Diplomat #141858
$120 - $175 per night 2-7 night min stay
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Relaxing Small Resort on the Beach - Condo on Longboat Key
2BR+/2BA
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Sleeps 4-5
– Sand Cay Beach #242620
$980- $1650/wk
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Longboat Key Beachfront - Newly Updated with Prime Location
2BR+/2BA
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Sleeps 4-6
– Cedars West #320426
$2600-$3300/2 wks - $3500-$5400/mo
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Bay Front Condo-Free Boat Slip & Across Street from the Beach
2BR+/2BA
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Sleeps 8
– Longboat Key Yacht & Tennis Mark I #370463
"From $2,500- $4,200/mo"
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Remodeled Condo on Canal - Close to Beach!
1BR/1BA
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Sleeps 2-4
– Other Longboat Key Properties #252057
From $1100/2wks - $1800/month
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Panoramic View of Gulf of Mexico Private Beach
2BR+/2BA
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Sleeps 2-6
– Arbomar #255709
$3500- $5500/mo
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Beautiful Condo on Garden Level in Gulf-to-Bay Resort.
2BR+/2BA
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Sleeps 4-6
– Banyan Bay Club #430991
$2400 - $3600 per month
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1st Floor Unit Steps from the Beach. No Need to Climb Stairs
Studio+/1BA
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Sleeps 4-5
– Diplomat #160494
$113-$185/nt - $649- $1160/wk
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Beautifully Renovated Villa - Steps from Beach & Pool
1BR+/1BA
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Sleeps 2-4
– Whitney Beach #46059
$2000- $3200/mo
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Steps from the Beach & Bay - Beautiful Whitney Beach Villa
2BR+/2BA
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Sleeps 4-6
– Whitney Beach #55302
$2200- $3500/mo
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Just Steps Away from the Gulf & Bay
3BR/2BA
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Sleeps 7
– Private Homes #64692
$1,050-$1,600/wk - $3230-$4930/mo
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Beautiful Beachfront Retreat on Longboat Key
3BR/2BA
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Sleeps 6
– Covert III #266788
$1400-$1500/wk - $5600-$6000/mo
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Vacation Paradise Waterfront Home Walk to Beack Pool&Boat Dock
3BR/2BA
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Sleeps 5
– Other Longboat Key Properties #257978ha
$950 - $1125 per week 7-28 night min stay
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Old Florida, Private, Quiet, All the Modern Conveniences.
2BR/1BA
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Sleeps 3
– Private Homes, Longbeach Village #361750
$800.00/wk
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Can't Get Closer to the Beach Without Getting Your Feet Wet!
2BR/2BA
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Sleeps 4
– Covert III #401362
$1400/wk or $4500/mo
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Relaxing Updated Cottage with New Private Hot Tub ~ Pet Friendly!
1BR/1BA
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Sleeps 2-3
– Private Homes #395073
$90- $105.00/nt
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Charming Beach House Private Pool, Dock, Beach Access in Longboat Key
3BR/2BA
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Sleeps 6
– Other Longboat Key Properties #3013714ha
$700 - $1650 per week
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Luxurious Longboat Vacation Home W/ Gorgeous View- Walk to Beach
5BR/5BA
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Sleeps 10
– Private Homes, Sleepy Lagoon #373016
$3,800- $3,900/wk
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Condo with Own Beautiful Beach. Great Reductions Great Review,Aug/Sep Special
2BR+/2BA
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Sleeps 4-5
– Sand Cay Beach #207443
$798- $1547/wk
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Jul 1-July7(2013)One wk Special at $1500 All Inclusive.
3BR+/2BA
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Sleeps 6-8
– Private Homes #299453
$1200-$1500/wk - $2000/mo
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Longboat Key Paradise on the Bay
3BR+/2BA
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Sleeps 4-6
– Longboat Landing #264212
$4800/mo
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Longboat Key Beach
2BR/2BA
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Sleeps 4
– Covert III #234425
$1050 per week 7 night min stay
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Up to 20% Discount 2013, Condo Directly on/View Sandy Beach
1BR+/1BA
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Sleeps 2-4
– Diplomat #296875
From $174/nt or $1096/wk
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Beach Living Comfort and Style on Longboat Key
2BR/2BA
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Sleeps 4
– Beachplace #475939
$1225 - $1260 per week 7-10 night min stay
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Fabulous Recently Updated Cedars Tennis Resort Townhouse
2BR/2BA
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Sleeps 4
– Cedars Tennis Resort #168178
$875 - $1500
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Paradise on the Beach
2BR+/2BA
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Sleeps 6-7
– Sea Pines #255714
$5000- $6000/mo
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Direct Water View, Luxury 2 Bedroom, 2 Bath, Condominium
2BR+/2BA
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Sleeps 4-6
– Islander Club #317645
$4000- $5500/mo
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Reduced $ Vacation on the White Sands of the Gulf of Mexico!
3BR+/3BA
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Sleeps 6-8
– Banyan Bay Club #377875
Jan-Apr $7250/month; May-Dec $4300/month
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Elevator Equipped Luxury Canalfront Home Short Stroll to Beach
3BR+/4BA
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Sleeps 6-10
– Private Homes #171511
$2500- $3500/wk
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Longboat Key Vacation Get Away
2BR/2BA
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Sleeps 4
– Longboat Harbour Towers #381462
$5,500/Month US
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Prestigious Canal Front Home with Private Pool and Hot Tub
3BR+/2BA
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Sleeps 6-10
– Bay Isles #318904
$4900- $6600/mo
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Beautiful Beach Front, 2/2 Newly Remodeled, Gorgeous Views
2BR/2BA
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Sleeps 2-4
– Longboat Terrace #474602
$5400 per month 30 night min stay
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Whitney Beach: Legendary White Sand Beaches Are Calling You
1BR+/1BA
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Sleeps 2-4
– Whitney Beach #286463
$1700- $3100/mo
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Longboat Key Fl, Bayport Beach & Tennis Club
2BR+/2BA
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Sleeps 4-6
– Bayport Beach & Tennis Club #412128
1450- 4800/mo
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Longboat Key Luxury Condo for Rent
3BR+/2BA
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Sleeps 6
– Other Longboat Key Properties #249621
$3000/2wks - $4000- $6000mo
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Longboat Key Paradise - Luxury Rental
3BR+/3BA
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Sleeps 8
– Private Homes #323467
$1500-$2300/wk - $5000-$6500/mo
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Updated Condo in Serene Setting with Beach and Bay Access
2BR+/2BA
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Sleeps 4-6
– Bayport Beach & Tennis Club #379348
From $1500/mo to $5000/mo
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The Ocean is Your Backyard!
2BR/2BA
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Sleeps 4
– Portobello #432766
$2500- 5800/Monthly rental only
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Spring,Summer Fall Retrat Looking at Gulf of Mexico
2BR/2BA
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Sleeps 4-6
– Privateer #441625
open U.S dollars
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Have the Best of Both Worlds
2BR+/2BA
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Sleeps 4-6
– Bay Harbour #267039
$3000- $4000/mo
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Beach Condo Directly on the Gulf of Mexico
2BR/2BA
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Sleeps 4
– Other Longboat Key Properties #3494747ha
$4000 - $6000 per month
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Sea Grape Inn in Longboat Key
2BR/2BA
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Sleeps 2-6
– Sea Grape Inn #291276
From $177/night
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Gulf Front Condo (1st Floor), 2 Bed/Bathrooms, Heated Pool, Tennis
2BR/2BA
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Sleeps 4-6
– Longboat Key #3495801ha
$3000 - $5500 per month
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Direct Water View, Beach, Tasteful/Large W/Granite Kitchen & Fireplace
Studio/0BA
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Sleeps 6
– Fairway Bay #447102
2,500 to 6,000
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Beautiful Complex on the Beach. Family-Friendly and Family Fun
2BR/2BA
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Sleeps 4
– Sand Cay Beach #479376
$183 - $236 per night 5-7 night min stay
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Beachplace 8-301
2BR/2BA
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Sleeps 4
– Other Longboat Key Properties #3190599ha
$3500 - $7000 per month
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Silver Sands #238
3BR/2BA
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Sleeps 8
– Other Longboat Key Properties #3190754ha
$275 - $450 per night
- The Pierre 2BR/3BA – Sleeps 4 – Other Longboat Key Properties #3190738ha
- Sunset Pointe Home 3BR/3BA – Sleeps 6 – Other Longboat Key Properties #3190814ha
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The Beach on Longboat Key #220
1BR/1BA
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Sleeps 2
– Other Longboat Key Properties #3190894ha
$115 - $170 per night
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Jessmyth Estate
4BR/4BA
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Sleeps 8
– Other Longboat Key Properties #3199771ha
$11000 - $13500 per month
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Cedars East #658
2BR/2BA
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Sleeps 6
– Other Longboat Key Properties #3231118ha
$513 - $1500 per week
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Buttonwood Home
3BR/2BA
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Sleeps 6
– Other Longboat Key Properties #3240678ha
$642 - $1750 per week
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Longboat Beach House #401
2BR/2BA
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Sleeps 4
– Other Longboat Key Properties #3190605ha
$2500 - $5200 per month
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Whitney Beach #333
2BR/2BA
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Sleeps 6
– Longboat Key #3191016ha
$2900 - $6000 per month
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Grants Getaway
3BR/3BA
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Sleeps 6
– Other Longboat Key Properties #3190650ha
$840 - $1800 per week
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Outrigger #4
2BR/2BA
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Sleeps 4
– Other Longboat Key Properties #3190692ha
$1100 - $1495 per week
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Island Paradise
3BR/2BA
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Sleeps 8
– Longboat Key #3190659ha
$817 - $1800 per week
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Azure Sky Emerald Sea Home
3BR/2BA
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Sleeps 6
– Other Longboat Key Properties #3195726ha
$120 - $271 per night
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Beach Castle Resort #17
1BR/1BA
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Sleeps 4
– Other Longboat Key Properties #3244176ha
$114 - $225 per night
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Ragland-Lewis Estate
6BR/5BA
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Sleeps 14
– Other Longboat Key Properties #3240679ha
$5833 - $10000 per week
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Beach Castle Resort #8
2BR/2BA
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Sleeps 6
– Other Longboat Key Properties #3231115ha
$171 - $350 per night
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Rachel's Paradise
3BR/2BA
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Sleeps 6
– Other Longboat Key Properties #3190741ha
$863 - $1400 per week
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The Beach on Longboat Key #104
1BR/1BA
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Sleeps 4
– Other Longboat Key Properties #3190891ha
$155 - $200 per night
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Longboat Beach House #203
2BR/2BA
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Sleeps 4
– Other Longboat Key Properties #3190666ha
$3200 - $5950 per month
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Castillian #109
2BR/2BA
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Sleeps 4
– Other Longboat Key Properties #3190618ha
$183 per night
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The Beach on Longboat Key #223
1BR/1BA
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Sleeps 4
– Other Longboat Key Properties #3190897ha
$170 - $230 per night
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Eb & Phiff's Place
3BR/2BA
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Sleeps 6-8
– Other Longboat Key Properties #3190639ha
$933 - $1900 per week
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Cabana Beach Club #12
1BR/1BA
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Sleeps 4
– Other Longboat Key Properties #3190621ha
$100 - $165 per night
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The Beach on Longboat Key #226
1BR/1BA
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Sleeps 4
– Other Longboat Key Properties #3190900ha
$155 - $210 per night
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The Beach on Longboat Key #107
1BR/1BA
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Sleeps 4
– Other Longboat Key Properties #3190604ha
$155 - $200 per night
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Castillian #111
2BR/2BA
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Sleeps 4
– Other Longboat Key Properties #3190619ha
$3000 - $5400 per month
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Idle Time
2BR/2BA
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Sleeps 6
– Other Longboat Key Properties #3231122ha
$537 - $1700 per week
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Beach to Bay Home
4BR/2BA
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Sleeps 8
– Other Longboat Key Properties #3190610ha
$1517 - $3300 per week
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Cabana Beach Club #4
2BR/2BA
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Sleeps 6
– Other Longboat Key Properties #3190625ha
$175 - $325 per night
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Cedars East #804
2BR/2BA
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Sleeps 4
– Other Longboat Key Properties #3252759ha
$700 - $1900 per week
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Cedars East #661
3BR/2BA
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Sleeps 8
– Other Longboat Key Properties #3252754ha
$1050 - $2300 per week
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Whitney Beach #319
2BR/2BA
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Sleeps 4
– Other Longboat Key Properties #3484683ha
$3000 - $5500 per month
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Cedars East #854
2BR/2BA
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Sleeps 4
– Other Longboat Key Properties #3252779ha
$817 - $2100 per week
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Whitney Beach #110
2BR/2BA
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Sleeps 6
– Other Longboat Key Properties #3252801ha
$3700 per month
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Cedars East #820
2BR/2BA
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Sleeps 4
– Other Longboat Key Properties #3252767ha
$863 - $2200 per week
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Sea Lion Cottage
3BR/2BA
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Sleeps 7
– Other Longboat Key Properties #3252797ha
$607 - $2200 per week
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208 Beach Property, Family Friendly, Beautiful Updated Condo, Heated Pool
2BR+/2BA
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Sleeps 6
– Sand Cay Beach #225394
$143 - $219 per night
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Stunning Key West-Style Home on Longboat Key with Gulf Views
3BR+/3BA
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Sleeps 5-8
– Private Homes, Triton Cove #14033
$6650- $10,000/mo
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Best Waterfront Value-One Bdrm-Nature Lover Retreat!
1BR+/1BA
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Sleeps 4
– Other Longboat Key Properties #51385
$700wk - $1450- $1950/mo
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Rare Bay Isles 3 Bedroom with 1st Class Comfort & Convenience
3BR/2BA
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Sleeps 6
– Harbour Oaks #38752
From $1870/wk - $7550/mo plus tax
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French Country Cottage - Historic Village on Lbk North End
3BR/2BA
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Sleeps 6
– Private Homes, Longbeach Village #196003
From $900/wk - $3500/mo
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Buttonwood Harbour Private Pool Home - Walk to Beach
2BR/2BA
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Sleeps 4
– Private Homes #35326
$3200- $4800/mo
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Longboat Key Retreat
2BR+/2BA
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Sleeps 4-8
– Cedars Tennis Resort #50109
From $700/wk - $4100/4 wks
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Private Pool, Beach, 3/2 Canal Front Home - Perfect Getaway
3BR/2BA
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Sleeps 8
– Private Homes, Sleepy Lagoon #271096
$1,500-$2500/wk - $3200-$5800/mo
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Silver Sands #249
2BR/1BA
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Sleeps 6
– Other Longboat Key Properties #3190773ha
Overview of Longboat Key Vacation Rentals
Enjoy Stunning Beauty with Longboat Key Vacation Rentals
Stunning beaches and golden sunsets await you when you enjoy Longboat Key vacation rentals. There is so much to do and see. Visit the snow white sands of Coquina Beach, which has free parking and public access or visit the only undeveloped beach in the 32 acres of Joan Durante Park, where you can watch birds or travel down one of the many nature trails. If you enjoy fishing then visit New Pass where you can take part in saltwater fishing or just enjoying one of the beautiful sunsets as you sit on the soft sand.
Catch Up on Cultural Activities with Longboat Key Condos
You don't have to miss out on culture and cultural activities when you visit Longboat Key condos. There are many art galleries, museums and entertainment such as ballet and opera. Visit Wyland Galleries or Exit Art in Sarasota, just a short drive away. Experience Circus Sarasota, the Sarasota Ballet of Florida or the Sarasota Opera. You can even enjoy dinner theater at Golden Apple Dinner Theater or take in a movie at Regal 20 Cinema Movielines.
Savor Local Cuisine with Southwest Florida Beach Rentals
Southwest Florida has plenty to offer when it comes to local cuisine and fine dining. You can enjoy a mouth watering dinner at the Lazy Lobster or dine dockside at Mar Vista Dockside Restaurant and Pub. If it's world class cuisine you're after then try out Maison Blanche Restaurant with unbelievable French food or Euphemia Haye Restaurant where they serve American, Continental and International dishes. If you and your family enjoy a home-cooked meal, why not try out a charter boat with deep-sea fishing so you can serve it right in your condo? Southwest Florida beach rentals allow you to experience all of the many flavors of Florida.