Vacation rentals in Oakland, FL

Best Vacation rentals and Airbnb offers in Oakland, FL

Modern Private Room With Private Entrance

Holiday Home, Oakland

Modern Private Room With Private Entrance is a holiday home in Oakland, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Modern Private Room With Private Entrance

Modern Private Room With Private Entrance is a holiday home in Oakland, with 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, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $635.

From$68/night

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2nd Floor Studio Downtown Winter Garden

Apartment, Oakland

2nd Floor Studio Downtown Winter Garden is a apartment in Oakland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About 2nd Floor Studio Downtown Winter Garden

2nd Floor Studio Downtown Winter Garden is a apartment in Oakland, with 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: kitchen, with kitchen, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $781.

From$81/night

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Cozy Studio Private Entrance 30 Minute From Disney and Universal Studio All new

Apartment, Oakland

Cozy Studio Private Entrance 30 Minute From Disney and Universal Studio All new is a apartment in Oakland, with parking. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy Studio Private Entrance 30 Minute From Disney and Universal Studio All new

Cozy Studio Private Entrance 30 Minute From Disney and Universal Studio All new is a apartment in Oakland, with 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, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $759.

From$85/night

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Walkable Winter Garden Bungalow: 3 Blocks to Dtwn

Holiday Home, Oakland

Walkable Winter Garden Bungalow: 3 Blocks to Dtwn is a holiday home in Oakland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Walkable Winter Garden Bungalow: 3 Blocks to Dtwn

Walkable Winter Garden Bungalow: 3 Blocks to Dtwn is a holiday home in Oakland, with 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,078.

From$89/night

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Browse 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.

Charming Private Suite Near Scenic Trails

Apartment, Oakland

Charming Private Suite Near Scenic Trails is a apartment in Oakland, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Charming Private Suite Near Scenic Trails

Charming Private Suite Near Scenic Trails 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: free cancellation, pool, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $723.

From$85/night

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2 BR/2 bath Clermont cottage w/ Heated Olympic Pool/basketball/lake access

Condo, Oakland

2 BR/2 bath Clermont cottage w/ Heated Olympic Pool/basketball/lake access is a condo in Oakland, with pool access, parking, and room for a group. This stay gives travelers a comfortable…

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About 2 BR/2 bath Clermont cottage w/ Heated Olympic Pool/basketball/lake access

2 BR/2 bath Clermont cottage w/ Heated Olympic Pool/basketball/lake access is a condo 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, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,072.

From$111/night

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Charming Villa near Disney, pool, 4 beds, sleeps 5

Villa, Oakland

Charming Villa near Disney, pool, 4 beds, sleeps 5 is a villa in Oakland, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for…

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About Charming Villa near Disney, pool, 4 beds, sleeps 5

Charming Villa near Disney, pool, 4 beds, sleeps 5 is a villa in Oakland, with pet-friendly space, 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,078.

From$113/night

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Beautiful cottage near Lake Louisa & mins from Disney, Vehicle Rental Available

Holiday Home, Oakland

Beautiful cottage near Lake Louisa & mins from Disney, Vehicle Rental Available is a holiday home in Oakland, with pool access and parking. This stay gives travelers a comfortable base for…

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About Beautiful cottage near Lake Louisa & mins from Disney, Vehicle Rental Available

Beautiful cottage near Lake Louisa & mins from Disney, Vehicle Rental Available 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,109.

From$113/night

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Best Oakland, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Private Cozy Studio

B & B, Oakland

Private Cozy Studio is a b & b in Oakland, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Private Cozy Studio

Private Cozy Studio is a b & b in Oakland, with 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, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $617.

From$73/night

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Charming studio in superb Clermont with AC, WiFi

Apartment, Oakland

Charming studio in superb Clermont with AC, WiFi is a apartment in Oakland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Charming studio in superb Clermont with AC, WiFi

Charming studio in superb Clermont with AC, WiFi is a apartment in Oakland, with 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $833.

From$86/night

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16 Mi to Disney: Cottage w/ Deck in Winter Garden

Cottage, Oakland

16 Mi to Disney: Cottage w/ Deck in Winter Garden is a cottage in Oakland, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 16 Mi to Disney: Cottage w/ Deck in Winter Garden

16 Mi to Disney: Cottage w/ Deck in Winter Garden is a cottage in Oakland, with outdoor space, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,190.

From$138/night

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Lake Louisa Lodge near Disney

Chalet, Oakland

Lake Louisa Lodge near Disney is a chalet in Oakland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Lake Louisa Lodge near Disney

Lake Louisa Lodge near Disney is a chalet in Oakland, with 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,081.

From$108/night

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Best Pet-Friendly Vacation Rentals in Oakland, FL

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

Centrally Located Cozy studio with High WiFi speed and AC

Apartment, Oakland

Centrally Located Cozy studio with High WiFi speed and AC is a apartment in Oakland, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Centrally Located Cozy studio with High WiFi speed and AC

Centrally Located Cozy studio with High WiFi speed and AC is a apartment in Oakland, with 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, parking, free parking, fireplace, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $746.

From$82/night

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20 Mi to Disney: Condo w/ Pool Access in Clermont!

Holiday Home, Oakland

20 Mi to Disney: Condo w/ Pool Access in Clermont! is a holiday home in Oakland, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for…

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About 20 Mi to Disney: Condo w/ Pool Access in Clermont!

20 Mi to Disney: Condo w/ Pool Access in Clermont! 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 wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,044.

From$86/night

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20 Mi to Disney: Condo w/ Pool Access in Clermont!

Condo, Oakland

20 Mi to Disney: Condo w/ Pool Access in Clermont! is a condo in Oakland, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

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About 20 Mi to Disney: Condo w/ Pool Access in Clermont!

20 Mi to Disney: Condo w/ Pool Access in Clermont! is a condo in Oakland, with pet-friendly space, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,152.

From$88/night

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Cozy modern cottage garden bath

Holiday Home, Oakland

Cozy modern cottage garden bath is a holiday home in Oakland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy modern cottage garden bath

Cozy modern cottage garden bath is a holiday home in Oakland, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,026.

From$105/night

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Best Oakland, FL vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Landing Incredible 2BD Clubhouse Game Room

Apartment, Oakland

Landing Incredible 2BD Clubhouse Game Room is a apartment in Oakland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Landing Incredible 2BD Clubhouse Game Room

Landing Incredible 2BD Clubhouse Game Room is a apartment in Oakland, with 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 washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,066.

From$122/night

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Charming Lakefront Apt. Near Disney

Apartment, Oakland

Charming Lakefront Apt. Near Disney is a apartment in Oakland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Charming Lakefront Apt. Near Disney

Charming Lakefront Apt. Near Disney is a apartment in Oakland, with 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $774.

From$77/night

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Charming Lakefront Cottage Near Disney

Cottage, Oakland

Charming Lakefront Cottage Near Disney is a cottage in Oakland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Charming Lakefront Cottage Near Disney

Charming Lakefront Cottage Near Disney is a cottage in Oakland, with 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $774.

From$77/night

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Family Friendly Villa near Disney, pool, sleeps 5

Villa, Oakland

Family Friendly Villa near Disney, pool, sleeps 5 is a villa in Oakland, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Family Friendly Villa near Disney, pool, sleeps 5

Family Friendly Villa near Disney, pool, sleeps 5 is a villa in Oakland, with pool 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, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,114.

From$117/night

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Our Favorite Family-Friendly Vacation Rentals in Oakland, FL

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

Gorgeous Cottage near Lake Louisa & mins 2 Disney.

Cottage, Oakland

Gorgeous Cottage near Lake Louisa & mins 2 Disney. is a cottage in Oakland, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Gorgeous Cottage near Lake Louisa & mins 2 Disney.

Gorgeous Cottage near Lake Louisa & mins 2 Disney. 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $855.

From$88/night

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Cozy modern cottage

Holiday Home, Oakland

Cozy modern cottage is a holiday home in Oakland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Cozy modern cottage

Cozy modern cottage is a holiday home 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $937.

From$95/night

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Dtwn Winter Garden Home: 12 Mi to Disney!

Cottage, Oakland

Dtwn Winter Garden Home: 12 Mi to Disney! is a cottage in Oakland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Dtwn Winter Garden Home: 12 Mi to Disney!

Dtwn Winter Garden Home: 12 Mi to Disney! is a cottage in Oakland, with 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,684.

From$132/night

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Walkable Winter Garden Bungalow: 3 Blocks to Dtwn

Cottage, Oakland

Walkable Winter Garden Bungalow: 3 Blocks to Dtwn is a cottage in Oakland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Walkable Winter Garden Bungalow: 3 Blocks to Dtwn

Walkable Winter Garden Bungalow: 3 Blocks to Dtwn is a cottage in Oakland, with 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,177.

From$132/night

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