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Holiday Homes in Longboat Key

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436 rentals in Longboat Key.
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Las Hermanas/Starfish #3 Beach front Longboat Key, holiday rental in Longboat Key

Las Hermanas/Starfish #3 Beach front Longboat Key

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beach condo, holiday rental in Longboat Key

Beach condo

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beachfront Studio #1 Longboat Key, holiday rental in Longboat Key

Beachfront Studio #1 Longboat Key

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beachfront Unit 4, Cozy Getaway for two, holiday rental in Longboat Key

Beachfront Unit 4, Cozy Getaway for two

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Unit #105 Sand Cay Beach Resort Gulf View, holiday rental in Longboat Key

Unit #105 Sand Cay Beach Resort Gulf View

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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~ BEACH FRONT APARTMENT ~, holiday rental in Longboat Key

~ BEACH FRONT APARTMENT ~

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beautiful Beach Views that will let you see 2020 in a whole new perspective, holiday rental in Longboat Key

Beautiful Beach Views that will let you see 2020 in a whole new perspective

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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ZILLI VILLA, holiday rental in Longboat Key

ZILLI VILLA

2 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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DOLPHIN HOUSE  Luxury on Water - Canal - Dock - boat lift, holiday rental in Longboat Key

DOLPHIN HOUSE Luxury on Water - Canal - Dock - boat lift

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pet Friendly on Longboat Key, holiday rental in Longboat Key

Pet Friendly on Longboat Key

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Zilli Tower 503, holiday rental in Longboat Key

Zilli Tower 503

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Breathtaking Beach Front Property Ground Floor Condo, holiday rental in Longboat Key

Breathtaking Beach Front Property Ground Floor Condo

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Steps from Beach or Bay, holiday rental in Longboat Key

Steps from Beach or Bay

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Outrigger 9 Gulf Front first level walk out to the beach  Oct-Nov $195 per night, holiday rental in Longboat Key

Outrigger 9 Gulf Front first level walk out to the beach Oct-Nov $195 per night

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Hidden Bay/Beach Paradise, holiday rental in Longboat Key

Hidden Bay/Beach Paradise

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Unit #208 Sand Cay Beach Resort Pool and Garden View, holiday rental in Longboat Key

Unit #208 Sand Cay Beach Resort Pool and Garden View

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Upscale Beachplace Condo w/ Gulf & Bay Views *DEC 2020 OPEN*, holiday rental in Longboat Key

Upscale Beachplace Condo w/ Gulf & Bay Views *DEC 2020 OPEN*

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Unit #309 Enjoy great rates, just steps to the sandy beach!, holiday rental in Longboat Key

Unit #309 Enjoy great rates, just steps to the sandy beach!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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PRIVATE BEACHFRONT HOUSE ON EXCLUSIVE LONGBOAT KEY - DIRECTLY ON THE BEACH, holiday rental in Longboat Key

PRIVATE BEACHFRONT HOUSE ON EXCLUSIVE LONGBOAT KEY - DIRECTLY ON THE BEACH

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Penthouse Condo with Awesome Views !, holiday rental in Longboat Key

Penthouse Condo with Awesome Views !

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Condo in Longboat Key Resort: Pool, Tennis, Bikes, Beach Access!!, holiday rental in Longboat Key

Spacious Condo in Longboat Key Resort: Pool, Tennis, Bikes, Beach Access!!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beachcomber unit 303, holiday rental in Longboat Key

Beachcomber unit 303

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tranquil waterfront with heated pool, dock and walk to beach, holiday rental in Longboat Key

Tranquil waterfront with heated pool, dock and walk to beach

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Las Hermanas/Starfish #2 Beachfront Longboat Key, holiday rental in Longboat Key

Las Hermanas/Starfish #2 Beachfront Longboat Key

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Fine Living Relaxation and Enjoyment! Enjoy Beach and Sunsets, holiday rental in Longboat Key

Fine Living Relaxation and Enjoyment! Enjoy Beach and Sunsets

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Love the Beach? Love tennis? The pool? Great family home with many amenities!, holiday rental in Longboat Key

Love the Beach? Love tennis? The pool? Great family home with many amenities!

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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A little piece of Paradise! Exceptional Reviews!, holiday rental in Longboat Key

A little piece of Paradise! Exceptional Reviews!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private Beach Cottage On The North End Of LBK. 2 Bedrooms 1 Bath On 2nd Floor, holiday rental in Longboat Key

Private Beach Cottage On The North End Of LBK. 2 Bedrooms 1 Bath On 2nd Floor

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Ground Floor 2 Beds 1 bath beach cottage short walk to beach on North end LBK, holiday rental in Longboat Key

Ground Floor 2 Beds 1 bath beach cottage short walk to beach on North end LBK

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxurious Longboat Vacation Home w/ gorgeous views-  Walk to Beach, holiday rental in Longboat Key

Luxurious Longboat Vacation Home w/ gorgeous views- Walk to Beach

5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Unit #218 Sand Cay Beach Resort  Gulf Front, holiday rental in Longboat Key

Unit #218 Sand Cay Beach Resort Gulf Front

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cabana Beach Club #2: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6, holiday rental in Longboat Key

Cabana Beach Club #2: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Longboat Key Beachfront - Beautifully Updated with Prime Location, holiday rental in Longboat Key

Longboat Key Beachfront - Beautifully Updated with Prime Location

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sea Grape Inn #6-BEACHVIEW Condo, steps from ocean., holiday rental in Longboat Key

Sea Grape Inn #6-BEACHVIEW Condo, steps from ocean.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Zilli Ocean Front 101, holiday rental in Longboat Key

Zilli Ocean Front 101

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Can't Get Closer to the Beach Without Getting Your Feet Wet!, holiday rental in Longboat Key

Can't Get Closer to the Beach Without Getting Your Feet Wet!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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NO REGRETS! Bright elevated beautiful sunny home.  Quick walk to beach and bay., holiday rental in Longboat Key

NO REGRETS! Bright elevated beautiful sunny home. Quick walk to beach and bay.

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Sea Grape Inn #7-BEACHVIEW Condo, steps from ocean., holiday rental in Longboat Key

Sea Grape Inn #7-BEACHVIEW Condo, steps from ocean.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2 BED/2 BATH GROUND FLOOR BEACHFRONT CONDO ON THE GULF OF MEXICO, holiday rental in Longboat Key

2 BED/2 BATH GROUND FLOOR BEACHFRONT CONDO ON THE GULF OF MEXICO

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cedars East Unit #521 2BR/2.5BA Condo Longboat Key- updated- 1440 sqft, holiday rental in Longboat Key

Cedars East Unit #521 2BR/2.5BA Condo Longboat Key- updated- 1440 sqft

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Exquisite 2BR/2BA Condo with Beach/Gulf View, holiday rental in Longboat Key

Exquisite 2BR/2BA Condo with Beach/Gulf View

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beach Escape to Longboat Key, Waterfront Sunrises/Sunsets, Gulf Beach Access, holiday rental in Longboat Key

Beach Escape to Longboat Key, Waterfront Sunrises/Sunsets, Gulf Beach Access

2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Beach Place 6th floor penthouse with ocean and bay views., holiday rental in Longboat Key

Beach Place 6th floor penthouse with ocean and bay views.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Unit #217 Sand Cay Beach Resort Gulf Front, holiday rental in Longboat Key

Unit #217 Sand Cay Beach Resort Gulf Front

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Silver Sands #254: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4, holiday rental in Longboat Key

Silver Sands #254: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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~ SPECIALS FROM $99 ~ OCEAN FRONT DLX STUDIO  ~, holiday rental in Longboat Key

~ SPECIALS FROM $99 ~ OCEAN FRONT DLX STUDIO ~

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Your Vacation Oasis Awaits on Beautiful Longboat Key!, holiday rental in Longboat Key

Your Vacation Oasis Awaits on Beautiful Longboat Key!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Beach View, Heated Pool, Tennis Courts, holiday rental in Longboat Key

Spectacular Beach View, Heated Pool, Tennis Courts

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Beach on Longboat Key #227: 1 BR / 1 BA Resort by RVA, Sleeps 5, holiday rental in Longboat Key

The Beach on Longboat Key #227: 1 BR / 1 BA Resort by RVA, Sleeps 5

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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WATERFRONT  PRIVATE DOCK, LONGBOAT KEY FLORIDA 1000 FEET TO THE BEACH, holiday rental in Longboat Key

WATERFRONT PRIVATE DOCK, LONGBOAT KEY FLORIDA 1000 FEET TO THE BEACH

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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