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Longboat Key Holiday Rentals with Pools

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384 rentals in Longboat Key.
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1 bedroom single story ocean view
1 bedroom
1 bathroom
Sleeps 4
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~ BEACH FRONT APARTMENT ~
1 bedroom
1 bathroom
Sleeps 3
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Beachfront Unit 4, Cozy Getaway for two
0 bedrooms
1 bathroom
Sleeps 2
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ZILLI VILLA
2 bedrooms
2 bathrooms
Sleeps 10
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Beautiful Beach Views that will let you see 2020 in a whole new perspective
2 bedrooms
2 bathrooms
Sleeps 6
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Zilli Tower 503
1 bedroom
1 bathroom
Sleeps 6
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Unit #309 Enjoy great rates, just steps to the sandy beach!
2 bedrooms
2 bathrooms
Sleeps 5
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Outrigger 9 Gulf Front first level walk out to the beach Oct-Nov $195 per night
1 bedroom
1 bathroom
Sleeps 2
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Hidden Bay/Beach Paradise
4 bedrooms
4 bathrooms
Sleeps 8
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Upscale Beachplace Condo w/ Gulf & Bay Views *DEC 2020 OPEN*
2 bedrooms
2 bathrooms
Sleeps 4
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Beachfront Studio #1 Longboat Key
0 bedrooms
1 bathroom
Sleeps 4
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Las Hermanas/Starfish #3 Beach front Longboat Key
1 bedroom
1 bathroom
Sleeps 4
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Breathtaking Beach Front Property Ground Floor Condo
2 bedrooms
2 bathrooms
Sleeps 6
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Love the Beach? Love tennis? The pool? Great family home with many amenities!
4 bedrooms
3 bathrooms
Sleeps 9
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Unit #208 Sand Cay Beach Resort Pool and Garden View
2 bedrooms
2 bathrooms
Sleeps 6
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Tranquil waterfront with heated pool, dock and walk to beach
4 bedrooms
4 bathrooms
Sleeps 8
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Penthouse Condo with Awesome Views !
2 bedrooms
2 bathrooms
Sleeps 6
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Ground Floor 2 Beds 1 bath beach cottage short walk to beach on North end LBK
2 bedrooms
2 bathrooms
Sleeps 4
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Las Hermanas/Starfish #2 Beachfront Longboat Key
1 bedroom
1 bathroom
Sleeps 4
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Beachcomber unit 303
1 bedroom
1 bathroom
Sleeps 4
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PRIVATE BEACHFRONT HOUSE ON EXCLUSIVE LONGBOAT KEY - DIRECTLY ON THE BEACH
4 bedrooms
4 bathrooms
Sleeps 8
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Zilli Ocean Front 101
1 bedroom
1 bathroom
Sleeps 6
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Private Beach Cottage On The North End Of LBK. 2 Bedrooms 1 Bath On 2nd Floor
2 bedrooms
1 bathroom
Sleeps 4
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Unit #218 Sand Cay Beach Resort Gulf Front
2 bedrooms
2 bathrooms
Sleeps 6
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Luxurious Longboat Vacation Home w/ gorgeous views- Walk to Beach
5 bedrooms
7 bathrooms
Sleeps 10
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Bayfront Longboat Key House with Pool and Beach Access
3 bedrooms
4 bathrooms
Sleeps 6
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Sea Grape Inn #6-Beautiful! BEACHVIEW, steps from ocean.
2 bedrooms
2 bathrooms
Sleeps 6
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Cabana Beach Club #2: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6
2 bedrooms
2 bathrooms
Sleeps 6
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Sea Grape Inn #7-Beautiful BEACHVIEW property, steps from ocean.
2 bedrooms
2 bathrooms
Sleeps 4
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Longboat Key Beachfront - Beautifully Updated with Prime Location
2 bedrooms
2 bathrooms
Sleeps 6
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Pet Friendly Longboat Key Condo with View of Gulf
1 bedroom
1 bathroom
Sleeps 4
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Silver Sands #256: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4
1 bedroom
1 bathroom
Sleeps 4
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The Beach on Longboat Key #227: 1 BR / 1 BA Resort by RVA, Sleeps 5
1 bedroom
1 bathroom
Sleeps 6
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Can't Get Closer to the Beach Without Getting Your Feet Wet!
2 bedrooms
2 bathrooms
Sleeps 4
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Cedars East Unit #521 2BR/2.5BA Condo Longboat Key- updated- 1440 sqft
2 bedrooms
3 bathrooms
Sleeps 6
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Silver Sands #255: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4
1 bedroom
1 bathroom
Sleeps 4
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Silver Sands #252: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4
1 bedroom
1 bathroom
Sleeps 4
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~ SPECIALS FROM $99 ~ OCEAN FRONT DLX STUDIO ~
2 bedrooms
1 bathroom
Sleeps 3
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NO REGRETS! Bright elevated beautiful sunny home. Quick walk to beach and bay.
4 bedrooms
4 bathrooms
Sleeps 8
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Cabana Beach Club #7: 2BR+Den / 2 BA Resort on Longboat Key by RVA, Sleeps 6
2 bedrooms
2 bathrooms
Sleeps 6
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Pet Friendly Longboat Key Condo - Steps from Beach !!
1 bedroom
1 bathroom
Sleeps 4
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Tropical Waterfront Retreat In Historic Longboat Village
3 bedrooms
3 bathrooms
Sleeps 6
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Beach Castle #3: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6
2 bedrooms
2 bathrooms
Sleeps 6
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Sea Grape Inn #1-Beautiful BEACHFRONT property, steps from ocean.
2 bedrooms
2 bathrooms
Sleeps 6
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Beach Escape to Longboat Key, Waterfront Sunrises/Sunsets, Gulf Beach Access
2 bedrooms
3 bathrooms
Sleeps 5
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Unit #304 Sand Cay Beach Resort Gulf Front 5 night minimum
3 bedrooms
3 bathrooms
Sleeps 8
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Unit #217 Sand Cay Beach Resort Gulf Front
2 bedrooms
2 bathrooms
Sleeps 6
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Beachcomber unit 205
1 bedroom
1 bathroom
Sleeps 4
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Beach Castle #1: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6
2 bedrooms
2 bathrooms
Sleeps 6
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Beach Castle #16: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6
2 bedrooms
2 bathrooms
Sleeps 6
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