Vacation rentals in Oak Street Beach, IL

71 available vacation rental offers

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Best vacation rentals and Airbnb offers in Oak Street Beach, IL

Hyde Park Shared Apartments - Oak Street Beach, IL

Hyde Park Shared Apartments

Apartment, Oak Street Beach

Hyde Park Shared Apartments is a apartment in Oak Street Beach. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family…

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About Hyde Park Shared Apartments

Hyde Park Shared Apartments is a apartment in Oak Street Beach. 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $847.

From$101/night
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Kenwood Apartments, Downtown Hyde Park - Oak Street Beach, IL

Kenwood Apartments, Downtown Hyde Park

Homestay, Oak Street Beach

Kenwood Apartments, Downtown Hyde Park is a homestay in Oak Street Beach, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Kenwood Apartments, Downtown Hyde Park

Kenwood Apartments, Downtown Hyde Park is a homestay in Oak Street Beach, 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 $935.

From$134/night
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A secluded bedroom with a private full bathroom - Oak Street Beach, IL

A secluded bedroom with a private full bathroom

Homestay, Oak Street Beach

A secluded bedroom with a private full bathroom is a homestay in Oak Street Beach, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About A secluded bedroom with a private full bathroom

A secluded bedroom with a private full bathroom is a homestay in Oak Street Beach, with 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, free wifi, parking, paid parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,147.

From$134/night
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Private Workspace • Sleeps4 • Modern Stylish Stay - Oak Street Beach, IL

Private Workspace • Sleeps4 • Modern Stylish Stay

Apartment, Oak Street Beach

Private Workspace · Sleeps4 · Modern Stylish Stay is a apartment in Oak Street Beach, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Private Workspace • Sleeps4 • Modern Stylish Stay

Private Workspace · Sleeps4 · Modern Stylish Stay is a apartment in Oak Street Beach, with pet-friendly space, 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: pet friendly, pets friendly, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,092.

From$156/night
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Waterfront vacation rentals in Oak Street Beach, IL

Discover vacation rentals close to the coast, water, and beach areas around Oak Street Beach, IL.

Cozy 2BD 2BA Apt! Steps to Lake with Gym & Parking - Oak Street Beach, IL

Cozy 2BD 2BA Apt! Steps to Lake with Gym & Parking

Apartment, Oak Street Beach

Cozy 2BD 2BA Apt! Steps to Lake with Gym & Parking is a apartment in Oak Street Beach, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy 2BD 2BA Apt! Steps to Lake with Gym & Parking

Cozy 2BD 2BA Apt! Steps to Lake with Gym & Parking is a apartment in Oak Street Beach, 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, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,024.

From$289/night
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The Belcroft - By Oak Street Beach & Luxury Shops - Oak Street Beach, IL

The Belcroft - By Oak Street Beach & Luxury Shops

Apartment, Oak Street Beach

The Belcroft - By Oak Street Beach & Luxury Shops is a apartment in Oak Street Beach, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring…

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About The Belcroft - By Oak Street Beach & Luxury Shops

The Belcroft - By Oak Street Beach & Luxury Shops is a apartment in Oak Street Beach, with 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: kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,618.

From$374/night
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Chicago Gem: Wrigley - Lakefront - Red Line Train - Oak Street Beach, IL

Chicago Gem: Wrigley - Lakefront - Red Line Train

Condo, Oak Street Beach

Chicago Gem: Wrigley - Lakefront - Red Line Train is a condo in Oak Street Beach, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Chicago Gem: Wrigley - Lakefront - Red Line Train

Chicago Gem: Wrigley - Lakefront - Red Line Train is a condo in Oak Street Beach, 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 $2,785.

From$398/night
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Downtown Guild #3 Mag Mile Gold Coast The Lake! - Oak Street Beach, IL

Downtown Guild #3 Mag Mile Gold Coast The Lake!

Apartment, Oak Street Beach

Downtown Guild #3 Mag Mile Gold Coast The Lake! is a apartment in Oak Street Beach, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Downtown Guild #3 Mag Mile Gold Coast The Lake!

Downtown Guild #3 Mag Mile Gold Coast The Lake! is a apartment in Oak Street Beach, 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, gym, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,289.

From$470/night
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Vacation rentals with parking in Oak Street Beach, IL

Find vacation rentals that make arriving by car easier.

Walk to Train l Near attractions and ORD l Free Parking l Patio - Oak Street Beach, IL

Walk to Train l Near attractions and ORD l Free Parking l Patio

Apartment, Oak Street Beach

Walk to Train l Near attractions and ORD l Free Parking l Patio is a apartment in Oak Street Beach, with outdoor space and parking. This stay gives travelers a comfortable base for…

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About Walk to Train l Near attractions and ORD l Free Parking l Patio

Walk to Train l Near attractions and ORD l Free Parking l Patio is a apartment in Oak Street Beach, with outdoor 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, free wifi, parking, paid parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,692.

From$178/night
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Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI - Oak Street Beach, IL

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Apartment, Oak Street Beach

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI is a apartment in Oak Street Beach, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI is a apartment in Oak Street Beach, 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 $1,318.

From$188/night
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Comfortable and Trendy Design 1BR in Lincoln Square - Oak Street Beach, IL

Comfortable and Trendy Design 1BR in Lincoln Square

Apartment, Oak Street Beach

Comfortable and Trendy Design 1BR in Lincoln Square is a apartment in Oak Street Beach, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Comfortable and Trendy Design 1BR in Lincoln Square

Comfortable and Trendy Design 1BR in Lincoln Square is a apartment in Oak Street Beach, 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 $1,483.

From$212/night
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Cozy and Intimate 1BR in Lively Lincoln Square - Oak Street Beach, IL

Cozy and Intimate 1BR in Lively Lincoln Square

Apartment, Oak Street Beach

Cozy and Intimate 1BR in Lively Lincoln Square is a apartment in Oak Street Beach, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Cozy and Intimate 1BR in Lively Lincoln Square

Cozy and Intimate 1BR in Lively Lincoln Square is a apartment in Oak Street Beach, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,595.

From$228/night
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Pet-friendly vacation rentals in Oak Street Beach, IL

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

2BR Fitness Pad • Private Gym • Sleeps 7 - Oak Street Beach, IL

2BR Fitness Pad • Private Gym • Sleeps 7

Apartment, Oak Street Beach

2BR Fitness Pad · Private Gym · Sleeps 7 is a apartment in Oak Street Beach, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About 2BR Fitness Pad • Private Gym • Sleeps 7

2BR Fitness Pad · Private Gym · Sleeps 7 is a apartment in Oak Street Beach, with pet-friendly space, 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: pet friendly, pets friendly, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,460.

From$209/night
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Elegant Style Loft Montrose|13 mins DT|4 mins Lake - Oak Street Beach, IL

Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Apartment, Oak Street Beach

Elegant Style Loft Montrose · 13 mins DT · 4 mins Lake is a apartment in Oak Street Beach, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Elegant Style Loft Montrose · 13 mins DT · 4 mins Lake is a apartment in Oak Street Beach, 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: pet friendly, pets friendly, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,514.

From$216/night
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CHICAGO Portage Park Pad - Oak Street Beach, IL

CHICAGO Portage Park Pad

Apartment, Oak Street Beach

CHICAGO Portage Park Pad is a apartment in Oak Street Beach, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About CHICAGO Portage Park Pad

CHICAGO Portage Park Pad is a apartment in Oak Street Beach, 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 $1,536.

From$219/night
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Sleeps 7 • Huge Projector • Designated Workspace - Oak Street Beach, IL

Sleeps 7 • Huge Projector • Designated Workspace

Apartment, Oak Street Beach

Sleeps 7 · Huge Projector · Designated Workspace is a apartment in Oak Street Beach, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 · Huge Projector · Designated Workspace is a apartment in Oak Street Beach, with pet-friendly space, 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: pet friendly, pets friendly, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,545.

From$221/night
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Vacation rentals with a kitchen in Oak Street Beach, IL

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

Cozy Studio Getaway Walk to Dining and Shops + Laundry - Oak Street Beach, IL

Cozy Studio Getaway Walk to Dining and Shops + Laundry

Apartment, Oak Street Beach

Cozy Studio Getaway Walk to Dining and Shops + Laundry is a apartment in Oak Street Beach, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cozy Studio Getaway Walk to Dining and Shops + Laundry

Cozy Studio Getaway Walk to Dining and Shops + Laundry is a apartment in Oak Street Beach, 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 $1,226.

From$175/night
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Explore Northside from Modern Studio Apartment with Washer and Dryer - Oak Street Beach, IL

Explore Northside from Modern Studio Apartment with Washer and Dryer

Apartment, Oak Street Beach

Explore Northside from Modern Studio Apartment with Washer and Dryer is a apartment in Oak Street Beach, with kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Explore Northside from Modern Studio Apartment with Washer and Dryer

Explore Northside from Modern Studio Apartment with Washer and Dryer is a apartment in Oak Street Beach, 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 $1,291.

From$184/night
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Beautiful and Comfy 1BR in Lincoln Square - Oak Street Beach, IL

Beautiful and Comfy 1BR in Lincoln Square

Holiday Home, Oak Street Beach

Beautiful and Comfy 1BR in Lincoln Square is a holiday home in Oak Street Beach, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Beautiful and Comfy 1BR in Lincoln Square

Beautiful and Comfy 1BR in Lincoln Square is a holiday home in Oak Street Beach, 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 $1,737.

From$248/night
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Bridgeport Place -free parking, McCormick-Sox Park - Oak Street Beach, IL

Bridgeport Place -free parking, McCormick-Sox Park

Apartment, Oak Street Beach

Bridgeport Place -free parking, McCormick-Sox Park is a apartment in Oak Street Beach, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Bridgeport Place -free parking, McCormick-Sox Park

Bridgeport Place -free parking, McCormick-Sox Park is a apartment in Oak Street Beach, 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 $1,741.

From$249/night
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Family-friendly vacation rentals in Oak Street Beach, IL

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

The Chic Urban Oasis Near the Lake! - Oak Street Beach, IL

The Chic Urban Oasis Near the Lake!

Condo, Oak Street Beach

The Chic Urban Oasis Near the Lake! is a condo in Oak Street Beach, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About The Chic Urban Oasis Near the Lake!

The Chic Urban Oasis Near the Lake! is a condo in Oak Street Beach, 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 kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,552.

From$222/night
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McCormick 2BR Family Retreat Near Museum Campus & Soldier Field - Oak Street Beach, IL

McCormick 2BR Family Retreat Near Museum Campus & Soldier Field

Apartment, Oak Street Beach

McCormick 2BR Family Retreat Near Museum Campus & Soldier Field is a apartment in Oak Street Beach, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About McCormick 2BR Family Retreat Near Museum Campus & Soldier Field

McCormick 2BR Family Retreat Near Museum Campus & Soldier Field is a apartment in Oak Street Beach, 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, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,437.

From$348/night
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Chicago Getaway: Family-Friendly 2BD 2BA Apartment - Oak Street Beach, IL

Chicago Getaway: Family-Friendly 2BD 2BA Apartment

Apartment, Oak Street Beach

Chicago Getaway: Family-Friendly 2BD 2BA Apartment is a apartment in Oak Street Beach, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring…

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About Chicago Getaway: Family-Friendly 2BD 2BA Apartment

Chicago Getaway: Family-Friendly 2BD 2BA Apartment is a apartment in Oak Street Beach, with 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 dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,446.

From$349/night
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The Polo Inn Bridgeport U.S.A. - Oak Street Beach, IL

The Polo Inn Bridgeport U.S.A.

B & B, Oak Street Beach

The Polo Inn Bridgeport U.S.A. is a b & b in Oak Street Beach, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About The Polo Inn Bridgeport U.S.A.

The Polo Inn Bridgeport U.S.A. is a b & b in Oak Street Beach, 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 breakfast, kids friendly, kids meal, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,845.

From$360/night
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