Vacation rentals in Portland, MO

114 available vacation rental offers

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Best vacation rentals and Airbnb offers in Portland, MO

Country Container Tiny House. Experience peace by the water & native wildlife! - Portland, MO

Country Container Tiny House. Experience peace by the water & native wildlife!

Cabin, Portland

Country Container Tiny House. Experience peace by the water & native wildlife! is a cabin in Portland, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Country Container Tiny House. Experience peace by the water & native wildlife!

Country Container Tiny House. Experience peace by the water & native wildlife! is a cabin in Portland, 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 $715.

From$102/night
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Gipfel Suite - Himmel Haus Bed & Breakfast - Portland, MO

Gipfel Suite - Himmel Haus Bed & Breakfast

Holiday Home, Portland

Gipfel Suite - Himmel Haus Bed & Breakfast is a holiday home in Portland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Gipfel Suite - Himmel Haus Bed & Breakfast

Gipfel Suite - Himmel Haus Bed & Breakfast is a holiday home in Portland, 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 $964.

From$138/night
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The Venue at Hermann - Portland, MO

The Venue at Hermann

Apartment, Portland

The Venue at Hermann is a apartment in Portland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About The Venue at Hermann

The Venue at Hermann is a apartment in Portland, 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, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $976.

From$139/night
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The Venue at Hermann - Portland, MO

The Venue at Hermann

Apartment, Portland

The Venue at Hermann is a apartment in Portland. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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About The Venue at Hermann

The Venue at Hermann is a apartment in Portland. 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 internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $976.

From$139/night
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Vacation rentals with a pool in Portland, MO

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

Cozy Missouri Retreat w/ Pool, Pond & Fire Pit! - Portland, MO

Cozy Missouri Retreat w/ Pool, Pond & Fire Pit!

Apartment, Portland

Cozy Missouri Retreat w/ Pool, Pond & Fire Pit! is a apartment in Portland, with pool access, parking, and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About Cozy Missouri Retreat w/ Pool, Pond & Fire Pit!

Cozy Missouri Retreat w/ Pool, Pond & Fire Pit! is a apartment in Portland, with pool access, parking, 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, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $997.

From$99/night
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Charming Berger Apt on 42-Acre Farm w/ Pool Access - Portland, MO

Charming Berger Apt on 42-Acre Farm w/ Pool Access

Apartment, Portland

Charming Berger Apt on 42-Acre Farm w/ Pool Access is a apartment in Portland, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Charming Berger Apt on 42-Acre Farm w/ Pool Access

Charming Berger Apt on 42-Acre Farm w/ Pool Access is a apartment in Portland, 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, free wifi, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,002.

From$106/night
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Cozy Missouri Retreat w/ Pool, Pond & Fire Pit! - Portland, MO

Cozy Missouri Retreat w/ Pool, Pond & Fire Pit!

Apartment, Portland

Cozy Missouri Retreat w/ Pool, Pond & Fire Pit! is a apartment in Portland, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Cozy Missouri Retreat w/ Pool, Pond & Fire Pit!

Cozy Missouri Retreat w/ Pool, Pond & Fire Pit! is a apartment in Portland, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $997.

From$124/night
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Cozy Missouri Retreat w/ Pool, Pond & Fire Pit! - Portland, MO

Cozy Missouri Retreat w/ Pool, Pond & Fire Pit!

Apartment, Portland

Cozy Missouri Retreat w/ Pool, Pond & Fire Pit! is a apartment in Portland, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Cozy Missouri Retreat w/ Pool, Pond & Fire Pit!

Cozy Missouri Retreat w/ Pool, Pond & Fire Pit! is a apartment in Portland, with pool 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $917.

From$131/night
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Vacation rentals with parking in Portland, MO

Find vacation rentals that make arriving by car easier.

Cozy Cabin in the woods near charming Hermann - Portland, MO

Cozy Cabin in the woods near charming Hermann

Cabin, Portland

Cozy Cabin in the woods near charming Hermann is a cabin in Portland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy Cabin in the woods near charming Hermann

Cozy Cabin in the woods near charming Hermann is a cabin in Portland, 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 $1,040.

From$149/night
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Secluded 2 bedroom home close to Hermann - Portland, MO

Secluded 2 bedroom home close to Hermann

Holiday Home, Portland

Secluded 2 bedroom home close to Hermann is a holiday home in Portland, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Secluded 2 bedroom home close to Hermann

Secluded 2 bedroom home close to Hermann is a holiday home in Portland, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,312.

From$187/night
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Cobbler Suite, Private Entrance and Private bath, 100% NO SMOKING PROPERTY! - Portland, MO

Cobbler Suite, Private Entrance and Private bath, 100% NO SMOKING PROPERTY!

Holiday Home, Portland

Cobbler Suite, Private Entrance and Private bath, 100% NO SMOKING PROPERTY! is a holiday home in Portland, with parking. This stay gives travelers a comfortable base for exploring the area,…

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About Cobbler Suite, Private Entrance and Private bath, 100% NO SMOKING PROPERTY!

Cobbler Suite, Private Entrance and Private bath, 100% NO SMOKING PROPERTY! is a holiday home in Portland, 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: parking, free parking, fireplace, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,372.

From$196/night
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Captain Wohlt Inn Bed & Breakfast - Portland, MO

Captain Wohlt Inn Bed & Breakfast

B & B, Portland

Captain Wohlt Inn Bed & Breakfast is a b & b in Portland, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Captain Wohlt Inn Bed & Breakfast

Captain Wohlt Inn Bed & Breakfast is a b & b in Portland, 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 wifi, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,631.

From$203/night
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Pet-friendly vacation rentals in Portland, MO

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

Dog-Friendly Cabin w/ Yard Near Auxvasse Creek! - Portland, MO

Dog-Friendly Cabin w/ Yard Near Auxvasse Creek!

Cabin, Portland

Dog-Friendly Cabin w/ Yard Near Auxvasse Creek! is a cabin in Portland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Dog-Friendly Cabin w/ Yard Near Auxvasse Creek!

Dog-Friendly Cabin w/ Yard Near Auxvasse Creek! is a cabin in Portland, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,091.

From$156/night
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Bank Loft with Original Vault in River Town - Portland, MO

Bank Loft with Original Vault in River Town

Apartment, Portland

Bank Loft with Original Vault in River Town is a apartment in Portland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Bank Loft with Original Vault in River Town

Bank Loft with Original Vault in River Town is a apartment in Portland, 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 $1,230.

From$176/night
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Wine Alley East suite - Portland, MO

Wine Alley East suite

Apartment, Portland

Wine Alley East suite is a apartment in Portland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Wine Alley East suite

Wine Alley East suite is a apartment in Portland, 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 $1,401.

From$200/night
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Wine Alley West Suite - Portland, MO

Wine Alley West Suite

Apartment, Portland

Wine Alley West Suite is a apartment in Portland, 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 Wine Alley West Suite

Wine Alley West Suite is a apartment in Portland, 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 $1,401.

From$200/night
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Vacation rentals with a kitchen in Portland, MO

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

Charming Berger Apt on 42-acre Farm w/ Pool Access - Portland, MO

Charming Berger Apt on 42-acre Farm w/ Pool Access

Apartment, Portland

Charming Berger Apt on 42-acre Farm w/ Pool Access is a apartment in Portland, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Charming Berger Apt on 42-acre Farm w/ Pool Access

Charming Berger Apt on 42-acre Farm w/ Pool Access is a apartment in Portland, 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 $1,055.

From$132/night
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The Bloom Suite - Portland, MO

The Bloom Suite

Apartment, Portland

The Bloom Suite is a apartment in Portland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family…

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About The Bloom Suite

The Bloom Suite is a apartment in Portland, 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, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,199.

From$171/night
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Nature`s Nook by Zia, Hermann - Portland, MO

Nature`s Nook by Zia, Hermann

Apartment, Portland

Nature`s Nook by Zia, Hermann is a apartment in Portland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Nature`s Nook by Zia, Hermann

Nature`s Nook by Zia, Hermann is a apartment in Portland, 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 $1,475.

From$211/night
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Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!! - Portland, MO

Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!

Holiday Home, Portland

Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!! is a holiday home in Portland, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!!

Beautiful historic 3 bed 3 bath Guest House w old stone wine cellar!! is a holiday home in Portland, 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 $1,510.

From$216/night
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Family-friendly vacation rentals in Portland, MO

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

Hanna's Cottage in the Downtown Historic District of Hermann, Missouri - Portland, MO

Hanna's Cottage in the Downtown Historic District of Hermann, Missouri

Cottage, Portland

Hanna's Cottage in the Downtown Historic District of Hermann, Missouri is a cottage in Portland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Hanna's Cottage in the Downtown Historic District of Hermann, Missouri

Hanna's Cottage in the Downtown Historic District of Hermann, Missouri is a cottage in Portland, 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 $1,174.

From$168/night
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Century Old Farmhouse in Fulton: 6 Mi to Town! - Portland, MO

Century Old Farmhouse in Fulton: 6 Mi to Town!

Cottage, Portland

Century Old Farmhouse in Fulton: 6 Mi to Town! is a cottage in Portland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Century Old Farmhouse in Fulton: 6 Mi to Town!

Century Old Farmhouse in Fulton: 6 Mi to Town! is a cottage in Portland, 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 $1,609.

From$189/night
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2 Mi to Dtwn Fulton: 'meadowlark' Home w/ Deck! - Portland, MO

2 Mi to Dtwn Fulton: 'meadowlark' Home w/ Deck!

Cottage, Portland

2 Mi to Dtwn Fulton: 'meadowlark' Home w/ Deck! is a cottage in Portland, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

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About 2 Mi to Dtwn Fulton: 'meadowlark' Home w/ Deck!

2 Mi to Dtwn Fulton: 'meadowlark' Home w/ Deck! is a cottage in Portland, with pet-friendly space, outdoor 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 $1,735.

From$196/night
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Cottage located in Hermann, MO. Historic District. 100% NO SMOKING PROPERTY! - Portland, MO

Cottage located in Hermann, MO. Historic District. 100% NO SMOKING PROPERTY!

Cottage, Portland

Cottage located in Hermann, MO. Historic District. 100% NO SMOKING PROPERTY! is a cottage in Portland, with parking. This stay gives travelers a comfortable base for exploring the area,…

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About Cottage located in Hermann, MO. Historic District. 100% NO SMOKING PROPERTY!

Cottage located in Hermann, MO. Historic District. 100% NO SMOKING PROPERTY! is a cottage in Portland, 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: parking, free parking, fireplace, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,445.

From$206/night
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