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Holiday Rentals in Longboat Key

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726 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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cancellation below MKT price had cancellation $199 Aug 13-15, holiday rental in Longboat Key
cancellation below MKT price had cancellation $199 Aug 13-15, holiday rental in Longboat Key
cancellation below MKT price had cancellation $199 Aug 13-15, holiday rental in Longboat Key

cancellation below MKT price had cancellation $199 Aug 13-15

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Few days on sale 5th floor Penthouse  take a peek  100 + 5 star reviews, holiday rental in Longboat Key
Few days on sale 5th floor Penthouse  take a peek  100 + 5 star reviews, holiday rental in Longboat Key
Few days on sale 5th floor Penthouse  take a peek  100 + 5 star reviews, holiday rental in Longboat Key

Few days on sale 5th floor Penthouse take a peek 100 + 5 star reviews

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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LUXURY  UPGRADED BEACHFRONT CONDO WITH BREATHTAKING VIEWS, holiday rental in Longboat Key
LUXURY  UPGRADED BEACHFRONT CONDO WITH BREATHTAKING VIEWS, holiday rental in Longboat Key
LUXURY  UPGRADED BEACHFRONT CONDO WITH BREATHTAKING VIEWS, holiday rental in Longboat Key

LUXURY UPGRADED BEACHFRONT CONDO WITH BREATHTAKING VIEWS

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gorgeous condo on the beautiful Longboat Key beach, holiday rental in Longboat Key
Gorgeous condo on the beautiful Longboat Key beach, holiday rental in Longboat Key
Gorgeous condo on the beautiful Longboat Key beach, holiday rental in Longboat Key

Gorgeous condo on the beautiful Longboat Key beach

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Unit is a wow  take a peek  Aug & Sept sale, holiday rental in Longboat Key
Unit is a wow  take a peek  Aug & Sept sale, holiday rental in Longboat Key
Unit is a wow  take a peek  Aug & Sept sale, holiday rental in Longboat Key

Unit is a wow take a peek Aug & Sept sale

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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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
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Outrigger 9 Gulf Front first level walk out to the beach., holiday rental in Longboat Key
Outrigger 9 Gulf Front first level walk out to the beach., holiday rental in Longboat Key
Outrigger 9 Gulf Front first level walk out to the beach., holiday rental in Longboat Key

Outrigger 9 Gulf Front first level walk out to the beach.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Unit #309 great rates, 2 Bed/2 Bath, view of ocean, steps to the sandy beach., holiday rental in Longboat Key
Unit #309 great rates, 2 Bed/2 Bath, view of ocean, steps to the sandy beach., holiday rental in Longboat Key
Unit #309 great rates, 2 Bed/2 Bath, view of ocean, steps to the sandy beach., holiday rental in Longboat Key

Unit #309 great rates, 2 Bed/2 Bath, view of ocean, steps to the sandy beach.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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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, renovated Gulf Front at Sand Cay with private beach on Longboat, holiday rental in Longboat Key
Beautiful, renovated Gulf Front at Sand Cay with private beach on Longboat, holiday rental in Longboat Key
Beautiful, renovated Gulf Front at Sand Cay with private beach on Longboat, holiday rental in Longboat Key

Beautiful, 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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client said view crazy   Aug sale 13-14th only $199 really, holiday rental in Longboat Key
client said view crazy   Aug sale 13-14th only $199 really, holiday rental in Longboat Key
client said view crazy   Aug sale 13-14th only $199 really, holiday rental in Longboat Key

client said view crazy Aug sale 13-14th only $199 really

Condo/Apartment
1 bedroom
1 bathroom
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
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Upscale Beachplace Condo Gulf & Bay Views *LAST MINUTE AUGUST SPECIAL 50% OFF*, holiday rental in Longboat Key
Upscale Beachplace Condo Gulf & Bay Views *LAST MINUTE AUGUST SPECIAL 50% OFF*, holiday rental in Longboat Key
Upscale Beachplace Condo Gulf & Bay Views *LAST MINUTE AUGUST SPECIAL 50% OFF*, holiday rental in Longboat Key

Upscale Beachplace Condo Gulf & Bay Views *LAST MINUTE AUGUST SPECIAL 50% OFF*

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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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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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Incredible Panoramic Gulf View and The Most Beautiful Sunset., holiday rental in Longboat Key
Incredible Panoramic Gulf View and The Most Beautiful Sunset., holiday rental in Longboat Key
Incredible Panoramic Gulf View and The Most Beautiful Sunset., holiday rental in Longboat Key

Incredible Panoramic Gulf View and The Most Beautiful Sunset.

Condo/Apartment
1 bedroom
1 bathroom
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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Love the beach? Tennis? Swimming? This great family friendly retreat has it all!, holiday rental in Longboat Key
Love the beach? Tennis? Swimming? This great family friendly retreat has it all!, holiday rental in Longboat Key
Love the beach? Tennis? Swimming? This great family friendly retreat has it all!, holiday rental in Longboat Key

Love the beach? Tennis? Swimming? This great family friendly retreat has it all!

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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Direct Beachfront Gulf with Amazing Views, holiday rental in Longboat Key
Direct Beachfront Gulf with Amazing Views, holiday rental in Longboat Key
Direct Beachfront Gulf with Amazing Views, holiday rental in Longboat Key

Direct Beachfront Gulf with Amazing Views

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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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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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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 canal-front home with heated pool, deep water dock & walk to beach, holiday rental in Longboat Key
Tranquil canal-front home with heated pool, deep water dock & walk to beach, holiday rental in Longboat Key
Tranquil canal-front home with heated pool, deep water dock & walk to beach, holiday rental in Longboat Key

Tranquil canal-front home with heated pool, deep water dock & walk to beach

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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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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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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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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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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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Bayfront Longboat Key House with Pool and 3 min walk to the beach, holiday rental in Longboat Key
Bayfront Longboat Key House with Pool and 3 min walk to the beach, holiday rental in Longboat Key
Bayfront Longboat Key House with Pool and 3 min walk to the beach, holiday rental in Longboat Key

Bayfront Longboat Key House with Pool and 3 min walk to the beach

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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LUXURIOUS BEACHFRONT HOUSE ON EXCLUSIVE LONGBOAT KEY - DIRECTLY ON THE BEACH, holiday rental in Longboat Key
LUXURIOUS BEACHFRONT HOUSE ON EXCLUSIVE LONGBOAT KEY - DIRECTLY ON THE BEACH, holiday rental in Longboat Key
LUXURIOUS BEACHFRONT HOUSE ON EXCLUSIVE LONGBOAT KEY - DIRECTLY ON THE BEACH, holiday rental in Longboat Key

LUXURIOUS 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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Sea Grape Inn #6- BEACHFRONT Property, holiday rental in Longboat Key
Sea Grape Inn #6- BEACHFRONT Property, holiday rental in Longboat Key
Sea Grape Inn #6- BEACHFRONT Property, holiday rental in Longboat Key

Sea Grape Inn #6- BEACHFRONT Property

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Charming LBK canal home, walk to beach, Solar heated pool, boat/kids/pet welcome, holiday rental in Longboat Key
Charming LBK canal home, walk to beach, Solar heated pool, boat/kids/pet welcome, holiday rental in Longboat Key
Charming LBK canal home, walk to beach, Solar heated pool, boat/kids/pet welcome, holiday rental in Longboat Key

Charming LBK canal home, walk to beach, Solar heated pool, boat/kids/pet welcome

Holiday Rental House
3 bedrooms
3 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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*** OCEAN FRONT STUDIO SPECIAL ***  FROM $99/NIGHT, holiday rental in Longboat Key
*** OCEAN FRONT STUDIO SPECIAL ***  FROM $99/NIGHT, holiday rental in Longboat Key
*** OCEAN FRONT STUDIO SPECIAL ***  FROM $99/NIGHT, holiday rental in Longboat Key

*** OCEAN FRONT STUDIO SPECIAL *** FROM $99/NIGHT

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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The Beach on Longboat Key #227: 1 BR / 1 BA Resort by RVA, Sleeps 6, holiday rental in Longboat Key
The Beach on Longboat Key #227: 1 BR / 1 BA Resort by RVA, Sleeps 6, holiday rental in Longboat Key
The Beach on Longboat Key #227: 1 BR / 1 BA Resort by RVA, Sleeps 6, holiday rental in Longboat Key

The Beach on Longboat Key #227: 1 BR / 1 BA Resort by RVA, Sleeps 6

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Sea Grape Inn #7 - BEACHFRONT Property, holiday rental in Longboat Key
Sea Grape Inn #7 - BEACHFRONT Property, holiday rental in Longboat Key
Sea Grape Inn #7 - BEACHFRONT Property, holiday rental in Longboat Key

Sea Grape Inn #7 - BEACHFRONT Property

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Unit #201 Sand Cay Beach Resort Gulf View, holiday rental in Longboat Key
Unit #201 Sand Cay Beach Resort Gulf View, holiday rental in Longboat Key
Unit #201 Sand Cay Beach Resort Gulf View, holiday rental in Longboat Key

Unit #201 Sand Cay Beach Resort Gulf View

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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, Sun set and Sunrise view, Gulf front condo, Monthly rental, holiday rental in Longboat Key
On the beach, Sun set and Sunrise view, Gulf front condo, Monthly rental, holiday rental in Longboat Key
On the beach, Sun set and Sunrise view, Gulf front condo, Monthly rental, holiday rental in Longboat Key

On the beach, Sun set and Sunrise view, Gulf front condo, Monthly rental

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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Beachfront Villa on Serene Gulf of Mexico, holiday rental in Longboat Key
Beachfront Villa on Serene Gulf of Mexico, holiday rental in Longboat Key
Beachfront Villa on Serene Gulf of Mexico, holiday rental in Longboat Key

Beachfront Villa on Serene Gulf of Mexico

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

*** OCEAN FRONT STUDIO SPECIAL *** FROM $99/NIGHT

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Inn on the Beach 3007, holiday rental in Longboat Key
Inn on the Beach 3007, holiday rental in Longboat Key
Inn on the Beach 3007, holiday rental in Longboat Key

Inn on the Beach 3007

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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