Vacation rentals in Holly Bluff Island, VA

46 available vacation rental offers

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Best vacation rentals and Airbnb offers in Holly Bluff Island, VA

Farmhouse Sunset | Renovated Duplex - A Boater - Holly Bluff Island, VA

Farmhouse Sunset | Renovated Duplex - A Boater

Apartment, Holly Bluff Island

Farmhouse Sunset · Renovated Duplex - A Boater is a apartment in Holly Bluff Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Farmhouse Sunset | Renovated Duplex - A Boater

Farmhouse Sunset · Renovated Duplex - A Boater is a apartment in Holly Bluff Island, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,096.

From$299/night
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Sweet Virginia Breeze - Chesapeake Properties - Holly Bluff Island, VA

Sweet Virginia Breeze - Chesapeake Properties

Holiday Home, Holly Bluff Island

Sweet Virginia Breeze - Chesapeake Properties is a holiday home in Holly Bluff Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Sweet Virginia Breeze - Chesapeake Properties

Sweet Virginia Breeze - Chesapeake Properties is a holiday home in Holly Bluff Island, 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 $2,151.

From$307/night
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Charming luxurious 2-bedroom house in enchanting Cape Charles - Holly Bluff Island, VA

Charming luxurious 2-bedroom house in enchanting Cape Charles

Holiday Home, Holly Bluff Island

Charming luxurious 2-bedroom house in enchanting Cape Charles is a holiday home in Holly Bluff Island, with pet-friendly space, parking, and room for a group. This stay gives travelers a…

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About Charming luxurious 2-bedroom house in enchanting Cape Charles

Charming luxurious 2-bedroom house in enchanting Cape Charles is a holiday home in Holly Bluff Island, with pet-friendly space, 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, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,247.

From$321/night
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Southern Breezes Nor'wester - close to beach, park, and shops; pet-friendly - Holly Bluff Island, VA

Southern Breezes Nor'wester - close to beach, park, and shops; pet-friendly

Holiday Home, Holly Bluff Island

Southern Breezes Nor'wester - close to beach, park, and shops; pet-friendly is a holiday home in Holly Bluff Island, with pet-friendly space, easy beach access, and kitchen access. This…

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About Southern Breezes Nor'wester - close to beach, park, and shops; pet-friendly

Southern Breezes Nor'wester - close to beach, park, and shops; pet-friendly is a holiday home in Holly Bluff Island, with pet-friendly space, 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: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,296.

From$328/night
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Waterfront vacation rentals in Holly Bluff Island, VA

Discover vacation rentals close to the coast, water, and beach areas around Holly Bluff Island, VA.

Virginia Lee | Rooftop Terrace, Fireplace, Skylights, Walk to Beach & Downtown Cape Charles - Holly Bluff Island, VA

Virginia Lee | Rooftop Terrace, Fireplace, Skylights, Walk to Beach & Downtown Cape Charles

Condo, Holly Bluff Island

Virginia Lee · Rooftop Terrace, Fireplace, Skylights, Walk to Beach & Downtown Cape Charles is a condo in Holly Bluff Island, with easy beach access and kitchen access. This stay gives…

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About Virginia Lee | Rooftop Terrace, Fireplace, Skylights, Walk to Beach & Downtown Cape Charles

Virginia Lee · Rooftop Terrace, Fireplace, Skylights, Walk to Beach & Downtown Cape Charles is a condo in Holly Bluff Island, 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: free wifi, kitchen, with kitchen, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,197.

From$457/night
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Ocean Breeze - Chesapeake Properties - Holly Bluff Island, VA

Ocean Breeze - Chesapeake Properties

Holiday Home, Holly Bluff Island

Ocean Breeze - Chesapeake Properties is a holiday home in Holly Bluff Island, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Ocean Breeze - Chesapeake Properties

Ocean Breeze - Chesapeake Properties is a holiday home in Holly Bluff Island, 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: free cancellation, hot tub, kitchen, with kitchen, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,346.

From$478/night
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Pebble Beach East - Chesapeake Properties - Holly Bluff Island, VA

Pebble Beach East - Chesapeake Properties

Holiday Home, Holly Bluff Island

Pebble Beach East - Chesapeake Properties is a holiday home in Holly Bluff Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Pebble Beach East - Chesapeake Properties

Pebble Beach East - Chesapeake Properties is a holiday home in Holly Bluff Island, with pool access, 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: free cancellation, pool, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,266.

From$609/night
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Modern Coastal Retreat in Bay Creek Featuring Access to Club Amenities! - Holly Bluff Island, VA

Modern Coastal Retreat in Bay Creek Featuring Access to Club Amenities!

Condo, Holly Bluff Island

Modern Coastal Retreat in Bay Creek Featuring Access to Club Amenities! is a condo in Holly Bluff Island, with pool access, easy beach access, and parking. This stay gives travelers a…

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About Modern Coastal Retreat in Bay Creek Featuring Access to Club Amenities!

Modern Coastal Retreat in Bay Creek Featuring Access to Club Amenities! is a condo in Holly Bluff Island, with pool access, 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,554.

From$651/night
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Vacation rentals with a pool in Holly Bluff Island, VA

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

Bay Creek Getaway + Pool + Game Rm + Bikes + Beach - Holly Bluff Island, VA

Bay Creek Getaway + Pool + Game Rm + Bikes + Beach

Condo, Holly Bluff Island

Bay Creek Getaway + Pool + Game Rm + Bikes + Beach is a condo in Holly Bluff Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About Bay Creek Getaway + Pool + Game Rm + Bikes + Beach

Bay Creek Getaway + Pool + Game Rm + Bikes + Beach is a condo in Holly Bluff Island, with pool access, 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: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,936.

From$419/night
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Saratoga Charmer.w/Communtiy Pool and Private Beach - Holly Bluff Island, VA

Saratoga Charmer.w/Communtiy Pool and Private Beach

Holiday Home, Holly Bluff Island

Saratoga Charmer.w/Communtiy Pool and Private Beach is a holiday home in Holly Bluff Island, with pool access and easy beach access. This stay gives travelers a comfortable base for…

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About Saratoga Charmer.w/Communtiy Pool and Private Beach

Saratoga Charmer.w/Communtiy Pool and Private Beach is a holiday home in Holly Bluff Island, with pool access and easy beach 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,047.

From$435/night
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Bay Creek Meets Historic Cape Charles! pool access! - Holly Bluff Island, VA

Bay Creek Meets Historic Cape Charles! pool access!

Holiday Home, Holly Bluff Island

Bay Creek Meets Historic Cape Charles! pool access! is a holiday home in Holly Bluff Island, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base…

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About Bay Creek Meets Historic Cape Charles! pool access!

Bay Creek Meets Historic Cape Charles! pool access! is a holiday home in Holly Bluff Island, with pool access, 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,424.

From$489/night
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Spacious 4BR Coastal Retreat in Bay Creek – Beach & Golf - Holly Bluff Island, VA

Spacious 4BR Coastal Retreat in Bay Creek – Beach & Golf

Holiday Home, Holly Bluff Island

Spacious 4BR Coastal Retreat in Bay Creek – Beach & Golf is a holiday home in Holly Bluff Island, with pool access, easy beach access, and room for a group. This stay gives travelers a…

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About Spacious 4BR Coastal Retreat in Bay Creek – Beach & Golf

Spacious 4BR Coastal Retreat in Bay Creek – Beach & Golf is a holiday home in Holly Bluff Island, with pool access, easy beach 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, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,503.

From$500/night
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Vacation rentals with parking in Holly Bluff Island, VA

Find vacation rentals that make arriving by car easier.

Fully Renovated in 2023 - Siren of the Cape - Holly Bluff Island, VA

Fully Renovated in 2023 - Siren of the Cape

Holiday Home, Holly Bluff Island

Fully Renovated in 2023 - Siren of the Cape is a holiday home in Holly Bluff Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Fully Renovated in 2023 - Siren of the Cape

Fully Renovated in 2023 - Siren of the Cape is a holiday home in Holly Bluff Island, 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, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,942.

From$420/night
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THE LIGHTHOUSE INN..Imagine Walking 2 Blocks And Having Your Feet In The Sand!!! - Holly Bluff Island, VA

THE LIGHTHOUSE INN..Imagine Walking 2 Blocks And Having Your Feet In The Sand!!!

Holiday Home, Holly Bluff Island

THE LIGHTHOUSE INN..Imagine Walking 2 Blocks And Having Your Feet In The Sand!!! is a holiday home in Holly Bluff Island, with parking and kitchen access. This stay gives travelers a…

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About THE LIGHTHOUSE INN..Imagine Walking 2 Blocks And Having Your Feet In The Sand!!!

THE LIGHTHOUSE INN..Imagine Walking 2 Blocks And Having Your Feet In The Sand!!! is a holiday home in Holly Bluff Island, 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: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,832.

From$547/night
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come enjoy this true EsCape from reality! - Holly Bluff Island, VA

come enjoy this true EsCape from reality!

Condo, Holly Bluff Island

come enjoy this true EsCape from reality! is a condo in Holly Bluff Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About come enjoy this true EsCape from reality!

come enjoy this true EsCape from reality! is a condo in Holly Bluff Island, 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 $4,554.

From$651/night
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The Nest on the Shore - Holly Bluff Island, VA

The Nest on the Shore

Holiday Home, Holly Bluff Island

The Nest on the Shore is a holiday home in Holly Bluff Island, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About The Nest on the Shore

The Nest on the Shore is a holiday home in Holly Bluff Island, 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 fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,626.

From$661/night
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Pet-friendly vacation rentals in Holly Bluff Island, VA

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

New to Vacation Rentals! Coastal Comfort at Bay Creek Golf Resort! - Holly Bluff Island, VA

New to Vacation Rentals! Coastal Comfort at Bay Creek Golf Resort!

Holiday Home, Holly Bluff Island

New to Vacation Rentals! Coastal Comfort at Bay Creek Golf Resort! is a holiday home in Holly Bluff Island, with pool access, easy beach access, and parking. This stay gives travelers a…

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About New to Vacation Rentals! Coastal Comfort at Bay Creek Golf Resort!

New to Vacation Rentals! Coastal Comfort at Bay Creek Golf Resort! is a holiday home in Holly Bluff Island, with pool access, 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: pool, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,410.

From$487/night
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Perfect Location in the heart of Cape Charles - Holly Bluff Island, VA

Perfect Location in the heart of Cape Charles

Holiday Home, Holly Bluff Island

Perfect Location in the heart of Cape Charles is a holiday home in Holly Bluff Island, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Perfect Location in the heart of Cape Charles

Perfect Location in the heart of Cape Charles is a holiday home in Holly Bluff Island, 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 wifi, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,529.

From$504/night
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Near Beach & Trails: Elegant Home in Cape Charles! - Holly Bluff Island, VA

Near Beach & Trails: Elegant Home in Cape Charles!

Holiday Home, Holly Bluff Island

Near Beach & Trails: Elegant Home in Cape Charles! is a holiday home in Holly Bluff Island, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable…

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About Near Beach & Trails: Elegant Home in Cape Charles!

Near Beach & Trails: Elegant Home in Cape Charles! is a holiday home in Holly Bluff Island, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,758.

From$537/night
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Relaxing Condo in Golf Community With Access to Club Amenities! - Holly Bluff Island, VA

Relaxing Condo in Golf Community With Access to Club Amenities!

Condo, Holly Bluff Island

Relaxing Condo in Golf Community With Access to Club Amenities! is a condo in Holly Bluff Island, with pet-friendly space, pool access, and a quieter setting. This stay gives travelers a…

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About Relaxing Condo in Golf Community With Access to Club Amenities!

Relaxing Condo in Golf Community With Access to Club Amenities! is a condo in Holly Bluff Island, with pet-friendly space, 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,554.

From$651/night
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Vacation rentals with a kitchen in Holly Bluff Island, VA

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

Maryland | Rooftop Terrace w/ Marina Views, Walk Downtown Cape Charles + Cozy Fireplace - Holly Bluff Island, VA

Maryland | Rooftop Terrace w/ Marina Views, Walk Downtown Cape Charles + Cozy Fireplace

Condo, Holly Bluff Island

Maryland · Rooftop Terrace w/ Marina Views, Walk Downtown Cape Charles + Cozy Fireplace is a condo in Holly Bluff Island, with kitchen access. This stay gives travelers a comfortable base…

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About Maryland | Rooftop Terrace w/ Marina Views, Walk Downtown Cape Charles + Cozy Fireplace

Maryland · Rooftop Terrace w/ Marina Views, Walk Downtown Cape Charles + Cozy Fireplace is a condo in Holly Bluff Island, 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 wifi, kitchen, with kitchen, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,197.

From$457/night
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Above it All - Chesapeake Properties - Holly Bluff Island, VA

Above it All - Chesapeake Properties

Condo, Holly Bluff Island

Above it All - Chesapeake Properties is a condo in Holly Bluff Island, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Above it All - Chesapeake Properties

Above it All - Chesapeake Properties is a condo in Holly Bluff Island, 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, hot tub, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,502.

From$500/night
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Beautiful Condo in Golf Community Featuring Access to Club Amenities! - Holly Bluff Island, VA

Beautiful Condo in Golf Community Featuring Access to Club Amenities!

Condo, Holly Bluff Island

Beautiful Condo in Golf Community Featuring Access to Club Amenities! is a condo in Holly Bluff Island, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About Beautiful Condo in Golf Community Featuring Access to Club Amenities!

Beautiful Condo in Golf Community Featuring Access to Club Amenities! is a condo in Holly Bluff Island, 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 $4,450.

From$636/night
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Spacious First Floor Condo in Golf Community With Access to Club Amenities! - Holly Bluff Island, VA

Spacious First Floor Condo in Golf Community With Access to Club Amenities!

Condo, Holly Bluff Island

Spacious First Floor Condo in Golf Community With Access to Club Amenities! is a condo in Holly Bluff Island, with pool access and kitchen access. This stay gives travelers a comfortable…

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About Spacious First Floor Condo in Golf Community With Access to Club Amenities!

Spacious First Floor Condo in Golf Community With Access to Club Amenities! is a condo in Holly Bluff Island, 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 $4,554.

From$651/night
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