Vacation rentals in Longboat Key, FL

65 available vacation rental offers

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Best vacation rentals and Airbnb offers in Longboat Key, FL

It's A Shore Thing 1 Bedroom Condo by RedAwning - Longboat Key, FL
10 ★ 1 reviews

It's A Shore Thing 1 Bedroom Condo by RedAwning

Condo, Longboat Key

It's A Shore Thing 1 Bedroom Condo by RedAwning is a condo in Longboat Key, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About It's A Shore Thing 1 Bedroom Condo by RedAwning

It's A Shore Thing 1 Bedroom Condo by RedAwning is a condo in Longboat Key, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, tv, and smart tv.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,813.

From$228/night
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Heated Pool, Mini Golf & Cabana: Bradenton Retreat - Longboat Key, FL
10 ★ 1 reviews

Heated Pool, Mini Golf & Cabana: Bradenton Retreat

Cottage, Longboat Key

Heated Pool, Mini Golf & Cabana: Bradenton Retreat is a cottage in Longboat Key, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Heated Pool, Mini Golf & Cabana: Bradenton Retreat

Heated Pool, Mini Golf & Cabana: Bradenton Retreat is a cottage in Longboat Key, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,956.

From$316/night
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Mins From Anna Maria Island: Bright Home w/ Pool! - Longboat Key, FL
9.4 ★ 3 reviews

Mins From Anna Maria Island: Bright Home w/ Pool!

Cottage, Longboat Key

Mins From Anna Maria Island: Bright Home w/ Pool! is a cottage in Longboat Key, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Mins From Anna Maria Island: Bright Home w/ Pool!

Mins From Anna Maria Island: Bright Home w/ Pool! is a cottage in Longboat Key, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,436.

From$144/night
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Sea Club I Beach Resort - Longboat Key, FL
9.2 ★ 341 reviews

Sea Club I Beach Resort

Apartment, Longboat Key

Sea Club I Beach Resort is a apartment in Longboat Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Sea Club I Beach Resort

Sea Club I Beach Resort is a apartment in Longboat Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,175.

From$260/night
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Family-friendly vacation rentals in Longboat Key, FL

Plan a trip with stays that give families more room to spread out.

Manatee River House - Longboat Key, FL

Manatee River House

Holiday Home, Longboat Key

Manatee River House is a holiday home in Longboat Key, with room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Manatee River House

Manatee River House is a holiday home in Longboat Key, with room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, ac, air conditioning, heating, and family friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,846.

From$134/night
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2 Mi to Riverwalk: Gem w/ Private Pool & Yard! - Longboat Key, FL

2 Mi to Riverwalk: Gem w/ Private Pool & Yard!

Cottage, Longboat Key

2 Mi to Riverwalk: Gem w/ Private Pool & Yard! is a cottage in Longboat Key, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 2 Mi to Riverwalk: Gem w/ Private Pool & Yard!

2 Mi to Riverwalk: Gem w/ Private Pool & Yard! is a cottage in Longboat Key, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,953.

From$212/night
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'the City Oasis' Near IMG & Anna Maria Island! - Longboat Key, FL

'the City Oasis' Near IMG & Anna Maria Island!

Cottage, Longboat Key

'the City Oasis' Near IMG & Anna Maria Island! is a cottage in Longboat Key, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About 'the City Oasis' Near IMG & Anna Maria Island!

'the City Oasis' Near IMG & Anna Maria Island! is a cottage in Longboat Key, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,505.

From$273/night
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3706 Gulf Dr 2 Bedroom Home by RedAwning - Longboat Key, FL

3706 Gulf Dr 2 Bedroom Home by RedAwning

Cottage, Longboat Key

3706 Gulf Dr 2 Bedroom Home by RedAwning is a cottage in Longboat Key, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About 3706 Gulf Dr 2 Bedroom Home by RedAwning

3706 Gulf Dr 2 Bedroom Home by RedAwning is a cottage in Longboat Key, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and heating.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,586.

From$384/night
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Pet-friendly vacation rentals in Longboat Key, FL

Bring your pet along with stays that welcome four-legged travelers.

LaPlaya 202E Catch the gentle Gulf breezes on your private balcony beneath the swaying palms - Longboat Key, FL

LaPlaya 202E Catch the gentle Gulf breezes on your private balcony beneath the swaying palms

Apartment, Longboat Key

LaPlaya 202E Catch the gentle Gulf breezes on your private balcony beneath the swaying palms is a apartment in Longboat Key, with pool access, easy beach access, and outdoor space. This…

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About LaPlaya 202E Catch the gentle Gulf breezes on your private balcony beneath the swaying palms

LaPlaya 202E Catch the gentle Gulf breezes on your private balcony beneath the swaying palms is a apartment in Longboat Key, with pool access, easy beach access, and outdoor space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, beachfront, and beach front.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,883.

From$339/night
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Sand Dollar Beach Side Villa - Longboat Key, FL

Sand Dollar Beach Side Villa

Villa, Longboat Key

Sand Dollar Beach Side Villa is a villa in Longboat Key, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Sand Dollar Beach Side Villa

Sand Dollar Beach Side Villa is a villa in Longboat Key, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, parking, and paid parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,817.

From$183/night
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LaPlaya 104E Perfectly located near the path to the beach just steps from the pool - Longboat Key, FL

LaPlaya 104E Perfectly located near the path to the beach just steps from the pool

Apartment, Longboat Key

LaPlaya 104E Perfectly located near the path to the beach just steps from the pool is a apartment in Longboat Key, with pool access and easy beach access. This stay gives travelers a…

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About LaPlaya 104E Perfectly located near the path to the beach just steps from the pool

LaPlaya 104E Perfectly located near the path to the beach just steps from the pool is a apartment in Longboat Key, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, and ourdoor pool.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,883.

From$339/night
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Stroll to Bradenton Riverwalk! Stylish Apartment - Longboat Key, FL

Stroll to Bradenton Riverwalk! Stylish Apartment

Apartment, Longboat Key

Stroll to Bradenton Riverwalk! Stylish Apartment is a apartment in Longboat Key, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Stroll to Bradenton Riverwalk! Stylish Apartment

Stroll to Bradenton Riverwalk! Stylish Apartment is a apartment in Longboat Key, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,245.

From$126/night
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Vacation rentals with a pool in Longboat Key, FL

Add a pool to the search when you want an easy place to cool off between outings.

Amazing Panoramic Beach View and The Most Beautiful Sunset - Longboat Key, FL

Amazing Panoramic Beach View and The Most Beautiful Sunset

Apartment, Longboat Key

Amazing Panoramic Beach View and The Most Beautiful Sunset is a apartment in Longboat Key, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring…

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About Amazing Panoramic Beach View and The Most Beautiful Sunset

Amazing Panoramic Beach View and The Most Beautiful Sunset is a apartment in Longboat Key, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, beachfront, and beach front.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,750.

From$326/night
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LaPlaya 101E-Relax on your private lanai under the palms! - Longboat Key, FL

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

Apartment, Longboat Key

LaPlaya 101E-Relax on your private lanai under the palms! is a apartment in Longboat Key, with pool access, easy beach access, and a quieter setting. This stay gives travelers a comfortable…

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

LaPlaya 101E-Relax on your private lanai under the palms! is a apartment in Longboat Key, with pool access, easy beach access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, beachfront, and beach front.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,883.

From$339/night
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LaPlaya 102E-Tropical garden view near the pool! - Longboat Key, FL

LaPlaya 102E-Tropical garden view near the pool!

Apartment, Longboat Key

LaPlaya 102E-Tropical garden view near the pool! is a apartment in Longboat Key, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area,…

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About LaPlaya 102E-Tropical garden view near the pool!

LaPlaya 102E-Tropical garden view near the pool! is a apartment in Longboat Key, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, beachfront, beach front, and ourdoor pool.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,883.

From$339/night
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Pura Vida 2 Bedroom Condo by RedAwning - Longboat Key, FL

Pura Vida 2 Bedroom Condo by RedAwning

Condo, Longboat Key

Pura Vida 2 Bedroom Condo by RedAwning is a condo in Longboat Key, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Pura Vida 2 Bedroom Condo by RedAwning

Pura Vida 2 Bedroom Condo by RedAwning is a condo in Longboat Key, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, tv, and smart tv.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,486.

From$283/night
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Vacation rentals with parking in Longboat Key, FL

Find vacation rentals that make arriving by car easier.

Gulfview Lido Key Gem - Walk to Beach & Shops - Longboat Key, FL

Gulfview Lido Key Gem - Walk to Beach & Shops

Holiday Home, Longboat Key

Gulfview Lido Key Gem - Walk to Beach & Shops is a holiday home in Longboat Key, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Gulfview Lido Key Gem - Walk to Beach & Shops

Gulfview Lido Key Gem - Walk to Beach & Shops is a holiday home in Longboat Key, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, parking, paid parking, and heating.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,900.

From$185/night
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Gulfview Lido Key Gem - Walk to Beach & Shops - Longboat Key, FL

Gulfview Lido Key Gem - Walk to Beach & Shops

Apartment, Longboat Key

Gulfview Lido Key Gem - Walk to Beach & Shops is a apartment in Longboat Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Gulfview Lido Key Gem - Walk to Beach & Shops

Gulfview Lido Key Gem - Walk to Beach & Shops is a apartment in Longboat Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,142.

From$242/night
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7th Heaven condo - Longboat Key, FL

7th Heaven condo

Apartment, Longboat Key

7th Heaven condo is a apartment in Longboat Key, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About 7th Heaven condo

7th Heaven condo is a apartment in Longboat Key, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: beachfront, beach front, parking, paid parking, and ac.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,188.

From$364/night
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Waters Edge 104S condo - Longboat Key, FL

Waters Edge 104S condo

Apartment, Longboat Key

Waters Edge 104S condo is a apartment in Longboat Key, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Waters Edge 104S condo

Waters Edge 104S condo is a apartment in Longboat Key, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, beachfront, beach front, parking, and paid parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $5,058.

From$550/night
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