Vacation rentals in Highland Beach, MD

65 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Highland Beach, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat' - Highland Beach, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Holiday Home, Highland Beach

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Highland Beach, 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 Highland Beach, 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 $1,789.

From$144/night
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Steps to Chesapeake Bay! 'Callaway Drive Retreat' - Highland Beach, MD

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Holiday Home, Highland Beach

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

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About Steps to Chesapeake Bay! 'Callaway Drive Retreat'

Steps to Chesapeake Bay! 'Callaway Drive Retreat' is a holiday home in Highland Beach, 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 $1,720.

From$155/night
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Charming 1-bedroom cottage with AC in cozy Harwood - Highland Beach, MD

Charming 1-bedroom cottage with AC in cozy Harwood

Cottage, Highland Beach

Charming 1-bedroom cottage with AC in cozy Harwood is a cottage in Highland Beach, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Charming 1-bedroom cottage with AC in cozy Harwood

Charming 1-bedroom cottage with AC in cozy Harwood is a cottage in Highland 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: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,525.

From$158/night
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Studio Apartment in Downtown Annapolis - Highland Beach, MD

Studio Apartment in Downtown Annapolis

Apartment, Highland Beach

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

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About Studio Apartment in Downtown Annapolis

Studio Apartment in Downtown Annapolis is a apartment in Highland 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, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,972.

From$209/night
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Browse Waterfront Vacation Rentals in Highland Beach, MD

Discover vacation rentals close to the coast, water, and beach areas around Highland Beach, MD.

Carriage House on 42 Acres in West River. Just 17 Miles from Annapolis. - Highland Beach, MD

Carriage House on 42 Acres in West River. Just 17 Miles from Annapolis.

Guest House, Highland Beach

Carriage House on 42 Acres in West River. Just 17 Miles from Annapolis. is a guest house in Highland Beach, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Carriage House on 42 Acres in West River. Just 17 Miles from Annapolis.

Carriage House on 42 Acres in West River. Just 17 Miles from Annapolis. is a guest house in Highland 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 $1,843.

From$181/night
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Waterfront private In-law apartment, 10 minutes from Downtown Annapolis. - Highland Beach, MD

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

Apartment, Highland Beach

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

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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 Highland Beach, 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 $3,190.

From$350/night
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Edgewater's Shelby on the Bay - Highland Beach, MD

Edgewater's Shelby on the Bay

Holiday Home, Highland Beach

Edgewater's Shelby on the Bay is a holiday home in Highland Beach, 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 Highland Beach, 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 $3,880.

From$397/night
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Cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown - Highland Beach, MD

Cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown

Holiday Home, Highland Beach

Cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown is a holiday home in Highland Beach, with easy beach access, outdoor space, and kitchen access. This stay gives travelers a…

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About Cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown

Cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown is a holiday home in Highland Beach, with easy beach access, 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, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,463.

From$681/night
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Browse Vacation Rentals with a Pool in Highland Beach, 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 - Highland Beach, MD

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Holiday Home, Highland Beach

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

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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 Highland Beach, 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 $3,850.

From$385/night
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Modern Bay Dream - Highland Beach, MD

Modern Bay Dream

Holiday Home, Highland Beach

Modern Bay Dream is a holiday home in Highland Beach, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Modern Bay Dream

Modern Bay Dream is a holiday home in Highland Beach, 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 $4,738.

From$495/night
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USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR - Highland Beach, MD

USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR

Holiday Home, Highland Beach

USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR is a holiday home in Highland Beach, with pool access and kitchen access. This stay gives travelers a…

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About USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR

USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR is a holiday home in Highland Beach, 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 $8,027.

From$802/night
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The Inn at Tacaro Estate - Highland Beach, MD

The Inn at Tacaro Estate

B & B, Highland Beach

The Inn at Tacaro Estate is a b & b in Highland Beach, 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 The Inn at Tacaro Estate

The Inn at Tacaro Estate is a b & b in Highland Beach, 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,583.

From$449/night
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Best Highland Beach, MD vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Perfect Waterview Cottage - St. Michaels Getaway - Highland Beach, MD

Perfect Waterview Cottage - St. Michaels Getaway

Cottage, Highland Beach

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

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About Perfect Waterview Cottage - St. Michaels Getaway

Perfect Waterview Cottage - St. Michaels Getaway is a cottage in Highland 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 $2,056.

From$239/night
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Relax on Kent Island in a 4 Bedroom Home w/Waterview! - Highland Beach, MD

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Holiday Home, Highland Beach

Relax on Kent Island in a 4 Bedroom Home w/Waterview! is a holiday home in Highland Beach, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview! is a holiday home in Highland 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 $2,621.

From$287/night
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Enchanting West River Retreat - Highland Beach, MD

Enchanting West River Retreat

Cottage, Highland Beach

Enchanting West River Retreat is a cottage in Highland Beach, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Enchanting West River Retreat

Enchanting West River Retreat is a cottage in Highland Beach, with parking, 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,312.

From$338/night
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Panoramic Bay Views, Wraparound Decks, 1-Minute Walk to Beach - Highland Beach, MD

Panoramic Bay Views, Wraparound Decks, 1-Minute Walk to Beach

Holiday Home, Highland Beach

Panoramic Bay Views, Wraparound Decks, 1-Minute Walk to Beach is a holiday home in Highland Beach, with easy beach access, outdoor space, and parking. This stay gives travelers a…

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About Panoramic Bay Views, Wraparound Decks, 1-Minute Walk to Beach

Panoramic Bay Views, Wraparound Decks, 1-Minute Walk to Beach is a holiday home in Highland Beach, with easy beach access, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $11,040.

From$1,151/night
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Best Pet-Friendly Vacation Rentals in Highland Beach, 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 - Highland Beach, MD

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

Apartment, Highland Beach

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis is a apartment in Highland Beach, 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 Highland Beach, 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 $1,513.

From$154/night
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Lovely bay views with kayaks, bikes, fire pit, crabbing & more - Highland Beach, MD

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

Holiday Home, Highland Beach

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

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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 Highland Beach, 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 $2,412.

From$257/night
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Pet Friendly Hideaway for 4 Close to Annapolis - Highland Beach, MD

Pet Friendly Hideaway for 4 Close to Annapolis

Holiday Home, Highland Beach

Pet Friendly Hideaway for 4 Close to Annapolis is a holiday home in Highland Beach, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Pet Friendly Hideaway for 4 Close to Annapolis

Pet Friendly Hideaway for 4 Close to Annapolis is a holiday home in Highland 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 $2,987.

From$299/night
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Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital - Highland Beach, MD

Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital

Holiday Home, Highland Beach

Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital is a holiday home in Highland Beach, with pet-friendly space, parking, and room for a group. This stay gives…

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About Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital

Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital is a holiday home in Highland Beach, 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, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,762.

From$414/night
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Best Highland Beach, MD vacation rentals with a kitchen

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

Room for an Island getaway - Highland Beach, MD

Room for an Island getaway

Holiday Home, Highland Beach

Room for an Island getaway is a holiday home in Highland Beach, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Room for an Island getaway

Room for an Island getaway is a holiday home in Highland 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, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,325.

From$280/night
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Renovated 3BR | Near Sandy Point Beach - Highland Beach, MD

Renovated 3BR | Near Sandy Point Beach

Holiday Home, Highland Beach

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

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About Renovated 3BR | Near Sandy Point Beach

Renovated 3BR · Near Sandy Point Beach is a holiday home in Highland Beach, 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 $3,516.

From$369/night
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Pet Friendly, 4 Bedrooms in Annapolis, MD less than 2 miles to Naval Academy. - Highland Beach, MD

Pet Friendly, 4 Bedrooms in Annapolis, MD less than 2 miles to Naval Academy.

Holiday Home, Highland Beach

Pet Friendly, 4 Bedrooms in Annapolis, MD less than 2 miles to Naval Academy. is a holiday home in Highland Beach, with pet-friendly space, kitchen access, and room for a group. This stay…

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About Pet Friendly, 4 Bedrooms in Annapolis, MD less than 2 miles to Naval Academy.

Pet Friendly, 4 Bedrooms in Annapolis, MD less than 2 miles to Naval Academy. is a holiday home in Highland 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: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,772.

From$495/night
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Ahoy! Game Room, Screened Porch, Yard Mins to DTA - Highland Beach, MD

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

Holiday Home, Highland Beach

Ahoy! Game Room, Screened Porch, Yard Mins to DTA is a holiday home in Highland Beach, 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 Highland 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 $4,823.

From$498/night
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