Vacation rentals in Oakland, FL

Best vacation rentals and Airbnb offers in Oakland, FL

10 ★ 1 reviews

Lakefront Retreat w/ Kayaks & Fire Pit in Clermont

Cottage, Oakland

Lakefront Retreat w/ Kayaks & Fire Pit in Clermont is a cottage in Oakland, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring…

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About Lakefront Retreat w/ Kayaks & Fire Pit in Clermont

Lakefront Retreat w/ Kayaks & Fire Pit in Clermont is a cottage in Oakland, with parking, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,851.

From$212/night

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Studio near Universal Studios with great view

Apartment, Oakland

Studio near Universal Studios with great view is a apartment in Oakland, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Studio near Universal Studios with great view

Studio near Universal Studios with great view is a apartment in Oakland, with 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: pool, hot tub, and free wifi.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $858.

From$97/night

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Near Disney cozy quiet place, 2 rooms with queen bed up to 4 people

Homestay, Oakland

Near Disney cozy quiet place, 2 rooms with queen bed up to 4 people is a homestay in Oakland, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a…

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About Near Disney cozy quiet place, 2 rooms with queen bed up to 4 people

Near Disney cozy quiet place, 2 rooms with queen bed up to 4 people is a homestay in Oakland, with pet-friendly space, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $503.

From$59/night

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Modern Studio on I-Drive: parking + pool included

Apartment, Oakland

Modern Studio on I-Drive: parking + pool included is a apartment in Oakland, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Modern Studio on I-Drive: parking + pool included

Modern Studio on I-Drive: parking + pool included is a apartment in Oakland, with pool 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, hot tub, and free wifi.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $858.

From$97/night

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Family-friendly vacation rentals in Oakland, FL

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

10 ★ 1 reviews

Apopka Single-story Home w/ Private Lanai + Pool!

Cottage, Oakland

Apopka Single-story Home w/ Private Lanai + Pool! is a cottage in Oakland, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Apopka Single-story Home w/ Private Lanai + Pool!

Apopka Single-story Home w/ Private Lanai + Pool! is a cottage in Oakland, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,198.

From$218/night

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3BR Disney Escape for Families - 8990

Holiday Home, Oakland

3BR Disney Escape for Families - 8990 is a holiday home in Oakland, with pool access, parking, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About 3BR Disney Escape for Families - 8990

3BR Disney Escape for Families - 8990 is a holiday home in Oakland, with pool access, parking, 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, free wifi, parking, and free parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,128.

From$131/night

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Sunny Clermont Retreat w/ Lanai: 12 Mi to Disney!

Cottage, Oakland

Sunny Clermont Retreat w/ Lanai: 12 Mi to Disney! is a cottage in Oakland, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Sunny Clermont Retreat w/ Lanai: 12 Mi to Disney!

Sunny Clermont Retreat w/ Lanai: 12 Mi to Disney! is a cottage in Oakland, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,706.

From$196/night

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~ 12 Mi to Disney: Downtown Winter Garden Cottage!

Cottage, Oakland

~ 12 Mi to Disney: Downtown Winter Garden Cottage! is a cottage in Oakland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About ~ 12 Mi to Disney: Downtown Winter Garden Cottage!

~ 12 Mi to Disney: Downtown Winter Garden Cottage! is a cottage in Oakland, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,917.

From$212/night

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Pet-friendly vacation rentals in Oakland, FL

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

Serene Mountain Retreat With Pool

Holiday Home, Oakland

Serene Mountain Retreat With Pool is a holiday home in Oakland, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Serene Mountain Retreat With Pool

Serene Mountain Retreat With Pool is a holiday home in Oakland, with pet-friendly space, pool 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, free wifi, pet friendly, pets friendly, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,802.

From$315/night

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The Piano House

Villa, Oakland

The Piano House is a villa in Oakland, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About The Piano House

The Piano House is a villa in Oakland, with pet-friendly space 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, pet friendly, pets friendly, parking, and paid parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,709.

From$192/night

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Pool Access! Spacious Home Near Wekiwa Springs

Cottage, Oakland

Pool Access! Spacious Home Near Wekiwa Springs is a cottage in Oakland, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Pool Access! Spacious Home Near Wekiwa Springs

Pool Access! Spacious Home Near Wekiwa Springs is a cottage in Oakland, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,944.

From$218/night

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1-acre Backyard & Gym: Spacious Apopka Escape!

Cottage, Oakland

1-acre Backyard & Gym: Spacious Apopka Escape! is a cottage in Oakland, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About 1-acre Backyard & Gym: Spacious Apopka Escape!

1-acre Backyard & Gym: Spacious Apopka Escape! is a cottage in Oakland, with pet-friendly space. 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,757.

From$273/night

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Vacation rentals with a pool in Oakland, FL

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

Sunny Clermont Retreat w/ Lanai: 12 Mi to Disney!

Holiday Home, Oakland

Sunny Clermont Retreat w/ Lanai: 12 Mi to Disney! is a holiday home in Oakland, with pool access and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Sunny Clermont Retreat w/ Lanai: 12 Mi to Disney!

Sunny Clermont Retreat w/ Lanai: 12 Mi to Disney! is a holiday home in Oakland, with pool 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, hot tub, and free wifi.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,645.

From$162/night

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Apopka Single-Story Home w/ Private Lanai + Pool!

Holiday Home, Oakland

Apopka Single-Story Home w/ Private Lanai + Pool! is a holiday home in Oakland, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Apopka Single-Story Home w/ Private Lanai + Pool!

Apopka Single-Story Home w/ Private Lanai + Pool! is a holiday home in Oakland, with pool 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, pool, free wifi, parking, and paid parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,117.

From$183/night

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Pool Therapy - New Pool Home

Holiday Home, Oakland

Pool Therapy - New Pool Home is a holiday home in Oakland, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Pool Therapy - New Pool Home

Pool Therapy - New Pool Home is a holiday home in Oakland, with pool 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, pool, parking, paid parking, and ourdoor pool.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,503.

From$157/night

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12 Mi to Disney: Home w/ Pool & Spa in Clermont

Holiday Home, Oakland

12 Mi to Disney: Home w/ Pool & Spa in Clermont is a holiday home in Oakland, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 12 Mi to Disney: Home w/ Pool & Spa in Clermont

12 Mi to Disney: Home w/ Pool & Spa in Clermont is a holiday home in Oakland, with pool 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, free wifi, parking, and paid parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,014.

From$206/night

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