Vacation rentals in Kent Island, MD

66 available vacation rental offers

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Best vacation rentals and Airbnb offers in Kent Island, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat' - Kent Island, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Holiday Home, Kent Island

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Kent Island, with easy beach access, parking, and a quieter setting. This stay gives travelers a comfortable base for…

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About Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Kent Island, with easy beach 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 $1,684.

From$150/night
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'callaway Drive Retreat' 3BR Home Near Water - Kent Island, MD

'callaway Drive Retreat' 3BR Home Near Water

Cottage, Kent Island

'callaway Drive Retreat' 3BR Home Near Water is a cottage in Kent Island, with kitchen access, room for a group, and a quieter setting. This stay gives travelers a comfortable base for…

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About 'callaway Drive Retreat' 3BR Home Near Water

'callaway Drive Retreat' 3BR Home Near Water is a cottage in Kent Island, with kitchen access, room for a group, 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, kitchen, with kitchen, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,747.

From$184/night
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Studio Apartment in Downtown Annapolis - Kent Island, MD

Studio Apartment in Downtown Annapolis

Apartment, Kent Island

Studio Apartment in Downtown Annapolis is a apartment in Kent Island, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Studio Apartment in Downtown Annapolis

Studio Apartment in Downtown Annapolis is a apartment in Kent 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, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,686.

From$241/night
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Perfect Waterview Cottage - St. Michaels Getaway - Kent Island, MD

Perfect Waterview Cottage - St. Michaels Getaway

Cottage, Kent Island

Perfect Waterview Cottage - St. Michaels Getaway is a cottage in Kent Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Perfect Waterview Cottage - St. Michaels Getaway

Perfect Waterview Cottage - St. Michaels Getaway is a cottage in Kent 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 $1,876.

From$268/night
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Waterfront vacation rentals in Kent Island, MD

Discover vacation rentals close to the coast, water, and beach areas around Kent Island, MD.

Steps to Chesapeake Bay! 'Callaway Drive Retreat' - Kent Island, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Holiday Home, Kent Island

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Kent Island, with easy beach access, kitchen access, and a quieter setting. This stay gives travelers a comfortable…

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About Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Kent Island, with easy beach 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, kitchen, with kitchen, washer, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,520.

From$217/night
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Waterfront private In-law apartment, 10 minutes from Downtown Annapolis. - Kent Island, MD

Waterfront private In-law apartment, 10 minutes from Downtown Annapolis.

Apartment, Kent Island

Waterfront private In-law apartment, 10 minutes from Downtown Annapolis. is a apartment in Kent Island, with easy beach access and parking. This stay gives travelers a comfortable base for…

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About Waterfront private In-law apartment, 10 minutes from Downtown Annapolis.

Waterfront private In-law apartment, 10 minutes from Downtown Annapolis. is a apartment in Kent Island, with 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, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,798.

From$400/night
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Renovated 3BR | Near Sandy Point Beach - Kent Island, MD

Renovated 3BR | Near Sandy Point Beach

Holiday Home, Kent Island

Renovated 3BR · Near Sandy Point Beach is a holiday home in Kent Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Renovated 3BR | Near Sandy Point Beach

Renovated 3BR · Near Sandy Point Beach is a holiday home in Kent Island, 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: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,125.

From$446/night
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Love Point Waterfront Home....Chesapeake Bay views....Pets OK - Kent Island, MD

Love Point Waterfront Home....Chesapeake Bay views....Pets OK

Holiday Home, Kent Island

Love Point Waterfront Home....Chesapeake Bay views....Pets OK is a holiday home in Kent Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a…

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About Love Point Waterfront Home....Chesapeake Bay views....Pets OK

Love Point Waterfront Home....Chesapeake Bay views....Pets OK is a holiday home in Kent 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 $4,043.

From$578/night
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Vacation rentals with a pool in Kent Island, MD

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

Annapolis Home | Fenced Yard | Pool Table | 10 Guests - Kent Island, MD

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Holiday Home, Kent Island

Annapolis Home · Fenced Yard · Pool Table · 10 Guests is a holiday home in Kent Island, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for…

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About Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home · Fenced Yard · Pool Table · 10 Guests is a holiday home in Kent Island, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,297.

From$471/night
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Chesapeake Bay Waterfront ARTectural Home - Kent Island, MD

Chesapeake Bay Waterfront ARTectural Home

Holiday Home, Kent Island

Chesapeake Bay Waterfront ARTectural Home is a holiday home in Kent Island, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area,…

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About Chesapeake Bay Waterfront ARTectural Home

Chesapeake Bay Waterfront ARTectural Home is a holiday home in Kent 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 $8,130.

From$1,161/night
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Inn at Huntingfield Creek - Kent Island, MD

Inn at Huntingfield Creek

B & B, Kent Island

Inn at Huntingfield Creek is a b & b in Kent Island, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Inn at Huntingfield Creek

Inn at Huntingfield Creek is a b & b in Kent Island, 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 cancellation, free breakfast, pool, free wifi, and for couples.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,497.

From$320/night
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Inn at Huntingfield Creek - Kent Island, MD

Inn at Huntingfield Creek

B & B, Kent Island

Inn at Huntingfield Creek is a b & b in Kent Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Inn at Huntingfield Creek

Inn at Huntingfield Creek is a b & b in Kent 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 breakfast, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,490.

From$320/night
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Vacation rentals with parking in Kent Island, MD

Find vacation rentals that make arriving by car easier.

Charming 3-bedroom in Village of Claiborne BOOK 3 NIGHTS GET 4TH FREE STRN26-6 - Kent Island, MD

Charming 3-bedroom in Village of Claiborne BOOK 3 NIGHTS GET 4TH FREE STRN26-6

Holiday Home, Kent Island

Charming 3-bedroom in Village of Claiborne BOOK 3 NIGHTS GET 4TH FREE STRN26-6 is a holiday home in Kent Island, with parking, kitchen access, and room for a group. This stay gives…

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About Charming 3-bedroom in Village of Claiborne BOOK 3 NIGHTS GET 4TH FREE STRN26-6

Charming 3-bedroom in Village of Claiborne BOOK 3 NIGHTS GET 4TH FREE STRN26-6 is a holiday home in Kent Island, 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 $2,544.

From$363/night
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2BR Historic District Gem w/Parking Near City Dock - Kent Island, MD

2BR Historic District Gem w/Parking Near City Dock

Holiday Home, Kent Island

2BR Historic District Gem w/Parking Near City Dock is a holiday home in Kent Island, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About 2BR Historic District Gem w/Parking Near City Dock

2BR Historic District Gem w/Parking Near City Dock is a holiday home in Kent Island, 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 $2,785.

From$398/night
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Edgewater's Shelby on the Bay - Kent Island, MD

Edgewater's Shelby on the Bay

Holiday Home, Kent Island

Edgewater's Shelby on the Bay is a holiday home in Kent Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Edgewater's Shelby on the Bay

Edgewater's Shelby on the Bay is a holiday home in Kent Island, 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: free cancellation, kitchen, with kitchen, parking, and onsite parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,374.

From$482/night
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Port of Call: 5BR Modern Nautical Luxury - Kent Island, MD

Port of Call: 5BR Modern Nautical Luxury

Holiday Home, Kent Island

Port of Call: 5BR Modern Nautical Luxury is a holiday home in Kent Island, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Port of Call: 5BR Modern Nautical Luxury

Port of Call: 5BR Modern Nautical Luxury is a holiday home in Kent Island, 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 $3,513.

From$502/night
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Pet-friendly vacation rentals in Kent Island, MD

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

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis - Kent Island, MD

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Apartment, Kent Island

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis is a apartment in Kent Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis is a apartment in Kent 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 $1,329.

From$190/night
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Lovely bay views with kayaks, bikes, fire pit, crabbing & more - Kent Island, MD

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Holiday Home, Kent Island

Lovely bay views with kayaks, bikes, fire pit, crabbing & more is a holiday home in Kent Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a…

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About Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Lovely bay views with kayaks, bikes, fire pit, crabbing & more is a holiday home in Kent 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 $2,079.

From$297/night
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Family Home on Mayo Peninsula | Deck | Sleeps 10 - Kent Island, MD

Family Home on Mayo Peninsula | Deck | Sleeps 10

Holiday Home, Kent Island

Family Home on Mayo Peninsula · Deck · Sleeps 10 is a holiday home in Kent Island, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

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About Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula · Deck · Sleeps 10 is a holiday home in Kent Island, with pet-friendly space, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,552.

From$365/night
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Sunny and spacious water view/access home in Annapolis. - Kent Island, MD

Sunny and spacious water view/access home in Annapolis.

Holiday Home, Kent Island

Sunny and spacious water view/access home in Annapolis. is a holiday home in Kent Island, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area,…

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About Sunny and spacious water view/access home in Annapolis.

Sunny and spacious water view/access home in Annapolis. is a holiday home in Kent Island, 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 $3,739.

From$534/night
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Vacation rentals with a kitchen in Kent Island, MD

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

Minutes from Downtown St. Michaels | Character Filled - Kent Island, MD

Minutes from Downtown St. Michaels | Character Filled

Holiday Home, Kent Island

Minutes from Downtown St. Michaels · Character Filled is a holiday home in Kent Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Minutes from Downtown St. Michaels | Character Filled

Minutes from Downtown St. Michaels · Character Filled is a holiday home in Kent Island, 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 $2,610.

From$373/night
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Ahoy! Game Room, Screened Porch, Yard Mins to DTA - Kent Island, MD

Ahoy! Game Room, Screened Porch, Yard Mins to DTA

Holiday Home, Kent Island

Ahoy! Game Room, Screened Porch, Yard Mins to DTA is a holiday home in Kent Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Ahoy! Game Room, Screened Porch, Yard Mins to DTA

Ahoy! Game Room, Screened Porch, Yard Mins to DTA is a holiday home in Kent Island, 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 $4,260.

From$609/night
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Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach - Kent Island, MD

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Holiday Home, Kent Island

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach is a holiday home in Kent Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach is a holiday home in Kent 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,630.

From$661/night
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Charming 3 Bedroom 3 Bath Beach Front Property - Kent Island, MD

Charming 3 Bedroom 3 Bath Beach Front Property

Holiday Home, Kent Island

Charming 3 Bedroom 3 Bath Beach Front Property is a holiday home in Kent Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Charming 3 Bedroom 3 Bath Beach Front Property

Charming 3 Bedroom 3 Bath Beach Front Property is a holiday home in Kent Island, 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: free cancellation, kitchen, with kitchen, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,706.

From$672/night
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