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Holiday Rentals in Longboat Key

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597 rentals in Longboat Key.
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One-of-a-kind home right on the gulf of Mexi, holiday rental in Longboat Key
One-of-a-kind home right on the gulf of Mexi, holiday rental in Longboat Key
One-of-a-kind home right on the gulf of Mexi, holiday rental in Longboat Key

One-of-a-kind home right on the gulf of Mexi

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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ZILLI VILLA, holiday rental in Longboat Key
ZILLI VILLA, holiday rental in Longboat Key
ZILLI VILLA, holiday rental in Longboat Key

ZILLI VILLA

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Luxury unit $149 2 days next Saturday& Sunday  Private Island  beach open, holiday rental in Longboat Key
Luxury unit $149 2 days next Saturday& Sunday  Private Island  beach open, holiday rental in Longboat Key
Luxury unit $149 2 days next Saturday& Sunday  Private Island  beach open, holiday rental in Longboat Key

Luxury unit $149 2 days next Saturday& Sunday Private Island beach open

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Welcome back  rate $175 Penthouse  Superior decor  private island beach open, holiday rental in Longboat Key
Welcome back  rate $175 Penthouse  Superior decor  private island beach open, holiday rental in Longboat Key
Welcome back  rate $175 Penthouse  Superior decor  private island beach open, holiday rental in Longboat Key

Welcome back rate $175 Penthouse Superior decor private island beach open

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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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, holiday rental in Longboat Key
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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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This unit is a wow $175 amazing   decor  private island beach open, holiday rental in Longboat Key
This unit is a wow $175 amazing   decor  private island beach open, holiday rental in Longboat Key
This unit is a wow $175 amazing   decor  private island beach open, holiday rental in Longboat Key

This unit is a wow $175 amazing decor private island beach open

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
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!, holiday rental in Longboat Key
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!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Zilli Tower 503, holiday rental in Longboat Key
Zilli Tower 503, holiday rental in Longboat Key
Zilli Tower 503, holiday rental in Longboat Key

Zilli Tower 503

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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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, holiday rental in Longboat Key
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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Last minute CXL  $169   2 day min inquire with in   private island beach open, holiday rental in Longboat Key
Last minute CXL  $169   2 day min inquire with in   private island beach open, holiday rental in Longboat Key
Last minute CXL  $169   2 day min inquire with in   private island beach open, holiday rental in Longboat Key

Last minute CXL $169 2 day min inquire with in private island beach open

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Hidden Bay/Beach Paradise, holiday rental in Longboat Key
Hidden Bay/Beach Paradise, holiday rental in Longboat Key
Hidden Bay/Beach Paradise, holiday rental in Longboat Key

Hidden Bay/Beach Paradise

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful, newly renovated Gulf Front at Sand Cay with private beach on Longboat, holiday rental in Longboat Key
Beautiful, newly renovated Gulf Front at Sand Cay with private beach on Longboat, holiday rental in Longboat Key
Beautiful, newly renovated Gulf Front at Sand Cay with private beach on Longboat, holiday rental in Longboat Key

Beautiful, newly renovated Gulf Front at Sand Cay with private beach on Longboat

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Zilli Ocean Front 101, holiday rental in Longboat Key
Zilli Ocean Front 101, holiday rental in Longboat Key
Zilli Ocean Front 101, holiday rental in Longboat Key

Zilli Ocean Front 101

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

Breathtaking Beach Front Property Ground Floor Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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*, holiday rental in Longboat Key
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*

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Private Island Retreat with Private Beach,  Dock, Palm Trees & Glorious Sunsets, holiday rental in Longboat Key
Private Island Retreat with Private Beach,  Dock, Palm Trees & Glorious Sunsets, holiday rental in Longboat Key
Private Island Retreat with Private Beach,  Dock, Palm Trees & Glorious Sunsets, holiday rental in Longboat Key

Private Island Retreat with Private Beach, Dock, Palm Trees & Glorious Sunsets

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Amazing Panoramic Gulf View and The Most Beautiful Sunset In The World., holiday rental in Longboat Key
Amazing Panoramic Gulf View and The Most Beautiful Sunset In The World., holiday rental in Longboat Key
Amazing Panoramic Gulf View and The Most Beautiful Sunset In The World., holiday rental in Longboat Key

Amazing Panoramic Gulf View and The Most Beautiful Sunset In The World.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Penthouse Condo with Awesome Views !, holiday rental in Longboat Key
Penthouse Condo with Awesome Views !, holiday rental in Longboat Key
Penthouse Condo with Awesome Views !, holiday rental in Longboat Key

Penthouse Condo with Awesome Views !

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beautiful Updated Beachfront Condo on the Gulf of Mexico, holiday rental in Longboat Key
Beautiful Updated Beachfront Condo on the Gulf of Mexico, holiday rental in Longboat Key
Beautiful Updated Beachfront Condo on the Gulf of Mexico, holiday rental in Longboat Key

Beautiful Updated Beachfront Condo on the Gulf of Mexico

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beautiful Beachfront Condo With Balcony, View of the Gulf, holiday rental in Longboat Key
Beautiful Beachfront Condo With Balcony, View of the Gulf, holiday rental in Longboat Key
Beautiful Beachfront Condo With Balcony, View of the Gulf, holiday rental in Longboat Key

Beautiful Beachfront Condo With Balcony, View of the Gulf

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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!, holiday rental in Longboat Key
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!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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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, holiday rental in Longboat Key
Unit #218 Sand Cay Beach Resort  Gulf Front, holiday rental in Longboat Key

Unit #218 Sand Cay Beach Resort Gulf Front

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beach is Open - Direct Beachfront Gulf of Mexico, Amazing Views, holiday rental in Longboat Key
Beach is Open - Direct Beachfront Gulf of Mexico, Amazing Views, holiday rental in Longboat Key
Beach is Open - Direct Beachfront Gulf of Mexico, Amazing Views, holiday rental in Longboat Key

Beach is Open - Direct Beachfront Gulf of Mexico, Amazing Views

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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, holiday rental in Longboat Key
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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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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, holiday rental in Longboat Key
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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beachcomber unit 303, holiday rental in Longboat Key
Beachcomber unit 303, holiday rental in Longboat Key
Beachcomber unit 303, holiday rental in Longboat Key

Beachcomber unit 303

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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, holiday rental in Longboat Key
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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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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, holiday rental in Longboat Key
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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Updated Beach Style Condo at Sand Cay with Great Ocean Views., holiday rental in Longboat Key
Updated Beach Style Condo at Sand Cay with Great Ocean Views., holiday rental in Longboat Key
Updated Beach Style Condo at Sand Cay with Great Ocean Views., holiday rental in Longboat Key

Updated Beach Style Condo at Sand Cay with Great Ocean Views.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Panoramic beach View and amazing Sunset., holiday rental in Longboat Key
Panoramic beach View and amazing Sunset., holiday rental in Longboat Key
Panoramic beach View and amazing Sunset., holiday rental in Longboat Key

Panoramic beach View and amazing Sunset.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Beach view. Year around Balcony Sunsets., holiday rental in Longboat Key
Beach view. Year around Balcony Sunsets., holiday rental in Longboat Key
Beach view. Year around Balcony Sunsets., holiday rental in Longboat Key

Beach view. Year around Balcony Sunsets.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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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, holiday rental in Longboat Key
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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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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, holiday rental in Longboat Key
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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Bayfront Longboat Key House with Pool and Beach Access, holiday rental in Longboat Key
Bayfront Longboat Key House with Pool and Beach Access, holiday rental in Longboat Key
Bayfront Longboat Key House with Pool and Beach Access, holiday rental in Longboat Key

Bayfront Longboat Key House with Pool and Beach Access

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Unit #120 Sand Cay Beach Resort Gulf View, holiday rental in Longboat Key
Unit #120 Sand Cay Beach Resort Gulf View, holiday rental in Longboat Key
Unit #120 Sand Cay Beach Resort Gulf View, holiday rental in Longboat Key

Unit #120 Sand Cay Beach Resort Gulf View

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Charming beach house on Longboat Key, with private pool&beach access, pool, pet, holiday rental in Longboat Key
Charming beach house on Longboat Key, with private pool&beach access, pool, pet, holiday rental in Longboat Key
Charming beach house on Longboat Key, with private pool&beach access, pool, pet, holiday rental in Longboat Key

Charming beach house on Longboat Key, with private pool&beach access, pool, pet

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Sea Grape Inn #6-Beautiful! BEACHVIEW, steps from ocean., holiday rental in Longboat Key
Sea Grape Inn #6-Beautiful! BEACHVIEW, steps from ocean., holiday rental in Longboat Key
Sea Grape Inn #6-Beautiful! BEACHVIEW, steps from ocean., holiday rental in Longboat Key

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

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

Longboat Key Beachfront - Beautifully Updated with Prime Location

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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, holiday rental in Longboat Key
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

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
More info
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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, holiday rental in Longboat Key
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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Sea Grape Inn #7-Beautiful BEACHVIEW property, steps from ocean., holiday rental in Longboat Key
Sea Grape Inn #7-Beautiful BEACHVIEW property, steps from ocean., holiday rental in Longboat Key
Sea Grape Inn #7-Beautiful BEACHVIEW property, steps from ocean., holiday rental in Longboat Key

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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Pet Friendly Longboat Key Condo with View of Gulf, holiday rental in Longboat Key
Pet Friendly Longboat Key Condo with View of Gulf, holiday rental in Longboat Key
Pet Friendly Longboat Key Condo with View of Gulf, holiday rental in Longboat Key

Pet Friendly Longboat Key Condo with View of Gulf

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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, holiday rental in Longboat Key
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

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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On the beach! Luxury gulf front condo, 2B/2B, pool, tennis, WiFi. Amazing view., holiday rental in Longboat Key
On the beach! Luxury gulf front condo, 2B/2B, pool, tennis, WiFi. Amazing view., holiday rental in Longboat Key
On the beach! Luxury gulf front condo, 2B/2B, pool, tennis, WiFi. Amazing view., holiday rental in Longboat Key

On the beach! Luxury gulf front condo, 2B/2B, pool, tennis, WiFi. Amazing view.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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~ SPECIALS FROM $99 ~ OCEAN FRONT DLX STUDIO  ~, holiday rental in Longboat Key
~ SPECIALS FROM $99 ~ OCEAN FRONT DLX STUDIO  ~, holiday rental in Longboat Key
~ SPECIALS FROM $99 ~ OCEAN FRONT DLX STUDIO  ~, holiday rental in Longboat Key

~ SPECIALS FROM $99 ~ OCEAN FRONT DLX STUDIO ~

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Cabana Beach Club #7: 2BR+Den / 2 BA Resort on Longboat Key by RVA, Sleeps 6, holiday rental in Longboat Key
Cabana Beach Club #7: 2BR+Den / 2 BA Resort on Longboat Key by RVA, Sleeps 6, holiday rental in Longboat Key
Cabana Beach Club #7: 2BR+Den / 2 BA Resort on Longboat Key by RVA, Sleeps 6, holiday rental in Longboat Key

Cabana Beach Club #7: 2BR+Den / 2 BA Resort on Longboat Key by RVA, Sleeps 6

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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~ SPECIALS FROM $99 ~ OCEAN FRONT DLX STUDIO  ~, holiday rental in Longboat Key
~ SPECIALS FROM $99 ~ OCEAN FRONT DLX STUDIO  ~, holiday rental in Longboat Key
~ SPECIALS FROM $99 ~ OCEAN FRONT DLX STUDIO  ~, holiday rental in Longboat Key

~ SPECIALS FROM $99 ~ OCEAN FRONT DLX STUDIO ~

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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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!, holiday rental in Longboat Key
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!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Beach is Open - Beachfront Villa on Serene Gulf of Mexico, holiday rental in Longboat Key
Beach is Open - Beachfront Villa on Serene Gulf of Mexico, holiday rental in Longboat Key
Beach is Open - Beachfront Villa on Serene Gulf of Mexico, holiday rental in Longboat Key

Beach is Open - Beachfront Villa on Serene Gulf of Mexico

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Silver Sands #255: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4, holiday rental in Longboat Key
Silver Sands #255: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4, holiday rental in Longboat Key
Silver Sands #255: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4, holiday rental in Longboat Key

Silver Sands #255: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Frequently Asked Questions about Longboat Key