Vacation rentals in Chipley, FL

Best Vacation rentals and Airbnb offers in Chipley, FL

Lovely 2-bedroom house with AC in charming Chipley. Mixed nationalities

Holiday Home, Chipley

Lovely 2-bedroom house with AC in charming Chipley. Mixed nationalities is a holiday home in Chipley, with room for a group. This stay gives travelers a comfortable base for exploring the…

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About Lovely 2-bedroom house with AC in charming Chipley. Mixed nationalities

Lovely 2-bedroom house with AC in charming Chipley. Mixed nationalities is a holiday home in Chipley, 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.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $850.

From$80/night

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Countryside Duplex 2 Bedroom 1.5 bath Family Friendly No Pets

Apartment, Chipley

Countryside Duplex 2 Bedroom 1.5 bath Family Friendly No Pets is a apartment in Chipley, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base…

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About Countryside Duplex 2 Bedroom 1.5 bath Family Friendly No Pets

Countryside Duplex 2 Bedroom 1.5 bath Family Friendly No Pets is a apartment in Chipley, 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, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $675.

From$83/night

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Cozy Studio Apt in quiet & charming Greenwood close to Caverns SP. No pet fee.

Apartment, Chipley

Cozy Studio Apt in quiet & charming Greenwood close to Caverns SP. No pet fee. is a apartment in Chipley, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Cozy Studio Apt in quiet & charming Greenwood close to Caverns SP. No pet fee.

Cozy Studio Apt in quiet & charming Greenwood close to Caverns SP. No pet fee. is a apartment in Chipley, 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 $892.

From$98/night

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Come Stay At the Blue House! Entire Home In The Country With Lots Of Space

Holiday Home, Chipley

Come Stay At the Blue House! Entire Home In The Country With Lots Of Space is a holiday home in Chipley, with pet-friendly space. This stay gives travelers a comfortable base for exploring…

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About Come Stay At the Blue House! Entire Home In The Country With Lots Of Space

Come Stay At the Blue House! Entire Home In The Country With Lots Of Space is a holiday home in Chipley, 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, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $924.

From$99/night

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Browse Vacation Rentals with a Pool in Chipley, FL

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

Relaxing in Nature Retreat - Indoor heated pool, Spa, Art Studio, 5-star Bkfst.

B & B, Chipley

Relaxing in Nature Retreat - Indoor heated pool, Spa, Art Studio, 5-star Bkfst. is a b & b in Chipley, with pool access and a quieter setting. This stay gives travelers a comfortable base…

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About Relaxing in Nature Retreat - Indoor heated pool, Spa, Art Studio, 5-star Bkfst.

Relaxing in Nature Retreat - Indoor heated pool, Spa, Art Studio, 5-star Bkfst. is a b & b in Chipley, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,093.

From$121/night

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Relaxing Retreat Pool, Spa, Art Studio, Breakfast

B & B, Chipley

Relaxing Retreat Pool, Spa, Art Studio, Breakfast is a b & b in Chipley, with pool access and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Relaxing Retreat Pool, Spa, Art Studio, Breakfast

Relaxing Retreat Pool, Spa, Art Studio, Breakfast is a b & b in Chipley, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,066.

From$127/night

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Hampton Inn Marianna I-10

Guest House, Chipley

Hampton Inn Marianna I-10 is a guest house in Chipley, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Hampton Inn Marianna I-10

Hampton Inn Marianna I-10 is a guest house in Chipley, 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: free breakfast, pool, gym, and ourdoor pool.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,630.

From$207/night

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Best Chipley, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

An entire house for getaway, totally private with a private parking

Holiday Home, Chipley

An entire house for getaway, totally private with a private parking is a holiday home in Chipley, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About An entire house for getaway, totally private with a private parking

An entire house for getaway, totally private with a private parking is a holiday home in Chipley, 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, ac, air conditioning, internet, and non smoking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,443.

From$161/night

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Country Cabin in Private Setting

Cabin, Chipley

Country Cabin in Private Setting is a cabin in Chipley, 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 Country Cabin in Private Setting

Country Cabin in Private Setting is a cabin in Chipley, 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 $1,447.

From$164/night

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Merritt's Mill Pond Hideaway - 2.5 acres of waterfront paradise

Holiday Home, Chipley

Merritt's Mill Pond Hideaway - 2.5 acres of waterfront paradise is a holiday home in Chipley, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable…

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About Merritt's Mill Pond Hideaway - 2.5 acres of waterfront paradise

Merritt's Mill Pond Hideaway - 2.5 acres of waterfront paradise is a holiday home in Chipley, 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: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,542.

From$293/night

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Caverns Crossing --- CLOSE to Chipola , MERE ball field & the Caverns State Park

Holiday Home, Chipley

Caverns Crossing --- CLOSE to Chipola , MERE ball field & the Caverns State Park is a holiday home in Chipley, with pet-friendly space and parking. This stay gives travelers a comfortable…

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About Caverns Crossing --- CLOSE to Chipola , MERE ball field & the Caverns State Park

Caverns Crossing --- CLOSE to Chipola , MERE ball field & the Caverns State Park is a holiday home in Chipley, 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 cancellation, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,019.

From$319/night

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Our Favorite Family-Friendly Vacation Rentals in Chipley, FL

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

New cozy 1-bedroom cottage in quaint Vernon with AC, 30 min to Panama city beach

Cottage, Chipley

New cozy 1-bedroom cottage in quaint Vernon with AC, 30 min to Panama city beach is a cottage in Chipley, with pet-friendly space, easy beach access, and parking. This stay gives travelers…

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About New cozy 1-bedroom cottage in quaint Vernon with AC, 30 min to Panama city beach

New cozy 1-bedroom cottage in quaint Vernon with AC, 30 min to Panama city beach is a cottage in Chipley, 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, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,429.

From$150/night

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Cabin close to FL Caverns! Pool, WI-FI, & Firepit

Cabin, Chipley

Cabin close to FL Caverns! Pool, WI-FI, & Firepit is a cabin in Chipley, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cabin close to FL Caverns! Pool, WI-FI, & Firepit

Cabin close to FL Caverns! Pool, WI-FI, & Firepit is a cabin in Chipley, 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, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,385.

From$157/night

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Outdoor Entertainment Area: Fountain Family Home!

Cabin, Chipley

Outdoor Entertainment Area: Fountain Family Home! is a cabin in Chipley, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Outdoor Entertainment Area: Fountain Family Home!

Outdoor Entertainment Area: Fountain Family Home! is a cabin in Chipley, with parking, 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,147.

From$279/night

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