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Holiday Rentals in Longboat Key

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
931 rentals in Longboat Key.
***Bermuda-esque Island Cottage! Steps to Sand!***, holiday rental in Longboat Key
***Bermuda-esque Island Cottage! Steps to Sand!***, holiday rental in Longboat Key
***Bermuda-esque Island Cottage! Steps to Sand!***, holiday rental in Longboat Key

***Bermuda-esque Island Cottage! Steps to Sand!***

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Take a Peek  fabulous unit, holiday rental in Longboat Key
Take a Peek  fabulous unit, holiday rental in Longboat Key
Take a Peek  fabulous unit, holiday rental in Longboat Key

Take a Peek fabulous unit

Condo/Apartment
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, 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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Luxury Beach Condo with Breathtaking Views PROMO SUPER PROMO 106 August 2023, holiday rental in Longboat Key
Luxury Beach Condo with Breathtaking Views PROMO SUPER PROMO 106 August 2023, holiday rental in Longboat Key
Luxury Beach Condo with Breathtaking Views PROMO SUPER PROMO 106 August 2023, holiday rental in Longboat Key

Luxury Beach Condo with Breathtaking Views PROMO SUPER PROMO 106 August 2023

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beach Front One Bedroom Condo Paradise. Fully Renovated. Ground Floor., holiday rental in Longboat Key
Beach Front One Bedroom Condo Paradise. Fully Renovated. Ground Floor., holiday rental in Longboat Key
Beach Front One Bedroom Condo Paradise. Fully Renovated. Ground Floor., holiday rental in Longboat Key

Beach Front One Bedroom Condo Paradise. Fully Renovated. Ground Floor.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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1 bedroom single story ocean view, holiday rental in Longboat Key
1 bedroom single story ocean view, holiday rental in Longboat Key
1 bedroom single story ocean view, holiday rental in Longboat Key

1 bedroom single story ocean view

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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1 bedroom single story condo near pool, holiday rental in Longboat Key
1 bedroom single story condo near pool, holiday rental in Longboat Key
1 bedroom single story condo near pool, holiday rental in Longboat Key

1 bedroom single story condo near pool

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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 6
Match: Sleeps
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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
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Gulf Condo with Heated Pool - Open Thursday, Friday, $185/nt!, holiday rental in Longboat Key
Gulf Condo with Heated Pool - Open Thursday, Friday, $185/nt!, holiday rental in Longboat Key
Gulf Condo with Heated Pool - Open Thursday, Friday, $185/nt!, holiday rental in Longboat Key

Gulf Condo with Heated Pool - Open Thursday, Friday, $185/nt!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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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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
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Georgeous Condo Directly On The Beautiful Longboat Key!!!!, holiday rental in Longboat Key
Georgeous Condo Directly On The Beautiful Longboat Key!!!!, holiday rental in Longboat Key
Georgeous Condo Directly On The Beautiful Longboat Key!!!!, holiday rental in Longboat Key

Georgeous Condo Directly On The Beautiful Longboat Key!!!!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Island Hideaway! Bermuda-esque Guest House! Steps to the Sand!, holiday rental in Longboat Key
Island Hideaway! Bermuda-esque Guest House! Steps to the Sand!, holiday rental in Longboat Key
Island Hideaway! Bermuda-esque Guest House! Steps to the Sand!, holiday rental in Longboat Key

Island Hideaway! Bermuda-esque Guest House! Steps to the Sand!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Just had  cancel July 29-Aug 5 Rare 5th floor Penthouse160 + 5 star reviews, holiday rental in Longboat Key
Just had  cancel July 29-Aug 5 Rare 5th floor Penthouse160 + 5 star reviews, holiday rental in Longboat Key
Just had  cancel July 29-Aug 5 Rare 5th floor Penthouse160 + 5 star reviews, holiday rental in Longboat Key

Just had cancel July 29-Aug 5 Rare 5th floor Penthouse160 + 5 star reviews

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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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.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Direct walk out 50 feet from the sand private island, holiday rental in Longboat Key
Direct walk out 50 feet from the sand private island, holiday rental in Longboat Key
Direct walk out 50 feet from the sand private island, holiday rental in Longboat Key

Direct walk out 50 feet from the sand private island

Condo/Apartment
1 bedroom
1 bathroom
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
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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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The Beach on Longboat Key #106: STUDIO / 1 BA Resort by RVA, Sleeps 2, holiday rental in Longboat Key
The Beach on Longboat Key #106: STUDIO / 1 BA Resort by RVA, Sleeps 2, holiday rental in Longboat Key
The Beach on Longboat Key #106: STUDIO / 1 BA Resort by RVA, Sleeps 2, holiday rental in Longboat Key

The Beach on Longboat Key #106: STUDIO / 1 BA Resort by RVA, Sleeps 2

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH, holiday rental in Longboat Key
GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH, holiday rental in Longboat Key
GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH, holiday rental in Longboat Key

GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
0 bedrooms
1 bathroom
Sleeps 3
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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2/2 GULF SIDE UPDATED APARTMENT (look for seasonal specials on select dates), holiday rental in Longboat Key
2/2 GULF SIDE UPDATED APARTMENT (look for seasonal specials on select dates), holiday rental in Longboat Key
2/2 GULF SIDE UPDATED APARTMENT (look for seasonal specials on select dates), holiday rental in Longboat Key

2/2 GULF SIDE UPDATED APARTMENT (look for seasonal specials on select dates)

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Wonderful Canal Front Condo! Bring Your Boat!UNIT 11, holiday rental in Longboat Key
Wonderful Canal Front Condo! Bring Your Boat!UNIT 11, holiday rental in Longboat Key
Wonderful Canal Front Condo! Bring Your Boat!UNIT 11, holiday rental in Longboat Key

Wonderful Canal Front Condo! Bring Your Boat!UNIT 11

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Silver Sands #257A Resort by RVA, holiday rental in Longboat Key
Silver Sands #257A Resort by RVA, holiday rental in Longboat Key
Silver Sands #257A Resort by RVA, holiday rental in Longboat Key

Silver Sands #257A Resort by RVA

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Client texted me said View Crazy, holiday rental in Longboat Key
Client texted me said View Crazy, holiday rental in Longboat Key
Client texted me said View Crazy, holiday rental in Longboat Key

Client texted me said View Crazy

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Silver Sands #242 Resort by RVA, holiday rental in Longboat Key
Silver Sands #242 Resort by RVA, holiday rental in Longboat Key
Silver Sands #242 Resort by RVA, holiday rental in Longboat Key

Silver Sands #242 Resort by RVA

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Direct Oceanview Condo on Peaceful Longboat Key!, holiday rental in Longboat Key
Direct Oceanview Condo on Peaceful Longboat Key!, holiday rental in Longboat Key
Direct Oceanview Condo on Peaceful Longboat Key!, holiday rental in Longboat Key

Direct Oceanview Condo on Peaceful Longboat Key!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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THE BEACH, condo #107, PRIVATE BEACH, holiday rental in Longboat Key
THE BEACH, condo #107, PRIVATE BEACH, holiday rental in Longboat Key
THE BEACH, condo #107, PRIVATE BEACH, holiday rental in Longboat Key

THE BEACH, condo #107, PRIVATE BEACH

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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LaPlaya 101E-Relax on your private lanai under the palms!, holiday rental in Longboat Key
LaPlaya 101E-Relax on your private lanai under the palms!, holiday rental in Longboat Key
LaPlaya 101E-Relax on your private lanai under the palms!, holiday rental in Longboat Key

LaPlaya 101E-Relax on your private lanai under the palms!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Silver Sands #255A Resort by RVA, holiday rental in Longboat Key
Silver Sands #255A Resort by RVA, holiday rental in Longboat Key
Silver Sands #255A Resort by RVA, holiday rental in Longboat Key

Silver Sands #255A Resort by RVA

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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The Beach on Longboat Key #226: STUDIO / 1 BA Resort by RVA, Sleeps 4, holiday rental in Longboat Key
The Beach on Longboat Key #226: STUDIO / 1 BA Resort by RVA, Sleeps 4, holiday rental in Longboat Key
The Beach on Longboat Key #226: STUDIO / 1 BA Resort by RVA, Sleeps 4, holiday rental in Longboat Key

The Beach on Longboat Key #226: STUDIO / 1 BA Resort by RVA, Sleeps 4

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Beach Front Condo Paradise. Ground Floor. Fully Renovated with a full Kitchen., holiday rental in Longboat Key
Beach Front Condo Paradise. Ground Floor. Fully Renovated with a full Kitchen., holiday rental in Longboat Key
Beach Front Condo Paradise. Ground Floor. Fully Renovated with a full Kitchen., holiday rental in Longboat Key

Beach Front Condo Paradise. Ground Floor. Fully Renovated with a full Kitchen.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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The Beach on Longboat Key #104: STUDIO / 1 BA Resort by RVA, Sleeps 4, holiday rental in Longboat Key
The Beach on Longboat Key #104: STUDIO / 1 BA Resort by RVA, Sleeps 4, holiday rental in Longboat Key
The Beach on Longboat Key #104: STUDIO / 1 BA Resort by RVA, Sleeps 4, holiday rental in Longboat Key

The Beach on Longboat Key #104: STUDIO / 1 BA Resort by RVA, Sleeps 4

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Silver Sands #232 Resort by RVA, holiday rental in Longboat Key
Silver Sands #232 Resort by RVA, holiday rental in Longboat Key
Silver Sands #232 Resort by RVA, holiday rental in Longboat Key

Silver Sands #232 Resort by RVA

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Exquisite Beachfront Villa with Private Pool & Stunning Gulf Views!, holiday rental in Longboat Key
Exquisite Beachfront Villa with Private Pool & Stunning Gulf Views!, holiday rental in Longboat Key
Exquisite Beachfront Villa with Private Pool & Stunning Gulf Views!, holiday rental in Longboat Key

Exquisite Beachfront Villa with Private Pool & Stunning Gulf Views!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Silver Sands #243A: HOTEL / 1 BA on Longboat Key by RVA, Sleeps 2, holiday rental in Longboat Key
Silver Sands #243A: HOTEL / 1 BA on Longboat Key by RVA, Sleeps 2, holiday rental in Longboat Key
Silver Sands #243A: HOTEL / 1 BA on Longboat Key by RVA, Sleeps 2, holiday rental in Longboat Key

Silver Sands #243A: HOTEL / 1 BA on Longboat Key by RVA, Sleeps 2

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Beachfront Condo at Prestigious Long Boat Key Club, holiday rental in Longboat Key
Beachfront Condo at Prestigious Long Boat Key Club, holiday rental in Longboat Key
Beachfront Condo at Prestigious Long Boat Key Club, holiday rental in Longboat Key

Beachfront Condo at Prestigious Long Boat Key Club

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Wonderful Bay Front Condo! See Manatees Right From Your Doorstep!, holiday rental in Longboat Key
Wonderful Bay Front Condo! See Manatees Right From Your Doorstep!, holiday rental in Longboat Key
Wonderful Bay Front Condo! See Manatees Right From Your Doorstep!, holiday rental in Longboat Key

Wonderful Bay Front Condo! See Manatees Right From Your Doorstep!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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The Beach on Longboat Key #225 Resort by RVA, holiday rental in Longboat Key
The Beach on Longboat Key #225 Resort by RVA, holiday rental in Longboat Key
The Beach on Longboat Key #225 Resort by RVA, holiday rental in Longboat Key

The Beach on Longboat Key #225 Resort by RVA

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Beach Castle Resort 6, holiday rental in Longboat Key
Beach Castle Resort 6, holiday rental in Longboat Key
Beach Castle Resort 6, holiday rental in Longboat Key

Beach Castle Resort 6

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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LaPlaya 202E-Catch the gentle Gulf breezes on your private balcony beneath the s, holiday rental in Longboat Key
LaPlaya 202E-Catch the gentle Gulf breezes on your private balcony beneath the s, holiday rental in Longboat Key
LaPlaya 202E-Catch the gentle Gulf breezes on your private balcony beneath the s, holiday rental in Longboat Key

LaPlaya 202E-Catch the gentle Gulf breezes on your private balcony beneath the s

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Sunny Gulf Coast Villa: Direct Beach & Pool Access, holiday rental in Longboat Key
Sunny Gulf Coast Villa: Direct Beach & Pool Access, holiday rental in Longboat Key
Sunny Gulf Coast Villa: Direct Beach & Pool Access, holiday rental in Longboat Key

Sunny Gulf Coast Villa: Direct Beach & Pool Access

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Beautiful canal front unit!See manatees playing from your living room.Cabana #12, holiday rental in Longboat Key
Beautiful canal front unit!See manatees playing from your living room.Cabana #12, holiday rental in Longboat Key
Beautiful canal front unit!See manatees playing from your living room.Cabana #12, holiday rental in Longboat Key

Beautiful canal front unit!See manatees playing from your living room.Cabana #12

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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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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Spacious 2Bdrm Longboat Key Condo, holiday rental in Longboat Key
Spacious 2Bdrm Longboat Key Condo, holiday rental in Longboat Key
Spacious 2Bdrm Longboat Key Condo, holiday rental in Longboat Key

Spacious 2Bdrm Longboat Key Condo

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 8
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, holiday rental in Longboat Key
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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cabana Beach Club #7 Resort by RVA, holiday rental in Longboat Key
Cabana Beach Club #7 Resort by RVA, holiday rental in Longboat Key
Cabana Beach Club #7 Resort by RVA, holiday rental in Longboat Key

Cabana Beach Club #7 Resort by RVA

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Showing results 1-50 of 931
Frequently Asked Questions about Longboat Key