Discover Your Perfect Smith Island Vacation Homes

Smith Island Luxury Rentals

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Home of the Terrapin King
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  • Pet Friendly
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Why Choose Rent By Owner for your Smith Island Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Smith Island

When should you plan your Vacation Rentals stay?

Choosing the right time to visit can enhance your experience here, allowing you to enjoy the area's natural beauty and tranquility at its best, whether you prefer the quieter months or the lively peak season.

Peak Season Highlights

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Summer (June to August)

During the warm summer months, you'll enjoy ideal conditions for outdoor activities and water-based adventures around this destination.

Average Temperature Daytime: 85°F - Nighttime: 70°F
autumn
Fall (September to November)

Early fall offers pleasant weather and fewer crowds, making it a great time to explore the region's natural beauty and relax in your chosen property.

Average Temperature Daytime: 75°F - Nighttime: 55°F

Off-Season Highlights

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Winter (December to February)

In the winter months, you can find quieter surroundings and more affordable rental options, perfect for a peaceful retreat away from the busy season.

Average Temperature Daytime: 40°F - Nighttime: 30°F
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Spring (March to May)

Early spring sees fewer visitors, offering a calm environment where you can enjoy the area's scenic views and comfortable temperatures.

Average Temperature Daytime: 60°F - Nighttime: 45°F

Weekly Weather Forecast for Smith Island

How to Book Your Smith Island Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Smith Island

More Top-Rated Vacation Rentals in Smith Island Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining with a patio or deck area, perfect for savoring the fresh regional air.
  • Take advantage of scenic water views from private balconies or outdoor seating spaces.
  • Benefit from access to outdoor fire pits, ideal for cozy evenings after a day exploring the region.
  • Make the most of spacious yards or gardens for relaxation or outdoor activities during your stay.
  • Utilize shared or private docks to enhance your experience by the water, if available.
  • Relax in outdoor lounge areas designed for soaking in the tranquil surroundings of this coastal area.
  • Explore nearby trails or nature paths accessible directly from your rental property, offering a great way to explore the region’s natural beauty.

Top Attractions Around Smith Island

What attractions are nearby?

In this charming destination, you can enjoy a variety of outdoor activities such as boating, fishing, and exploring scenic nature trails that showcase the area's natural beauty and tranquility.

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Family Activities

  • Smith Island Wildlife Sanctuary: Explore the diverse bird and marine life at this wildlife sanctuary, offering family-friendly nature walks and educational programs tailored for all ages.
  • Beachcombing and Picnicking: Enjoy relaxing days on the pristine shores with opportunities for beachcombing along the coastline and family picnics in scenic, shaded areas.
  • Water Activities: Engage in kayaking, paddleboarding, or boat rentals to discover the tranquil waters surrounding here, providing safe and fun options for families seeking outdoor adventure.
  • Community Events and Markets: Experience local culture through seasonal festivals and markets, perfect for families to enjoy regional crafts, fresh seafood, and entertainment in the area.
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Adult Activities

  • Bird Watching Tours: Experience the region’s rich avian diversity by joining guided bird watching tours that showcase the area's unique habitats and migratory patterns.
  • Kayaking Adventures: Explore the scenic waterways surrounding this destination, where tranquil kayaking provides a peaceful way to enjoy the natural beauty of the region.
  • Crabbing and Fishing: Engage in traditional crabbing or fishing activities, offering an authentic taste of local life along the shoreline and marshes.
  • Historical Site Visits: Discover the area's history by visiting local historical sites and museums that highlight the region's cultural heritage and maritime legacy.

Other Places to Stay in Smith Island, MD

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Smith Island Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead: Book your Smith Island vacation rentals early to secure the best properties and enjoy a more relaxed arrival experience in this charming destination.
  • Explore the Outdoors: Take advantage of the region’s natural beauty by engaging in local outdoor activities that showcase the area's unique landscape and environment.
  • Discover Local Flavors: Savor the region's authentic cuisine by visiting local establishments or preparing meals in your vacation rental’s fully equipped kitchen.
  • Respect the Environment: Practice sustainable tourism by minimizing waste and respecting the natural surroundings, ensuring the preservation of the area’s pristine qualities for future visitors.

Transportation Options

  • Ferries: You can rely on ferry services to access the island, providing a scenic and authentic way to arrive at this charming destination.
  • Private Boat Charters: For a personalized experience, private boat charters offer flexible transportation options directly from nearby ports.
  • Water Taxis: Water taxis serve as convenient and quick routes across the region’s waterways, connecting you efficiently to your vacation rental.
  • Personal Vehicles: If you bring your own vehicle or rent one locally, driving is a practical option once you're on the island, with limited road access for visitors.

Local Customs Options

  • Clamming Traditions: Engaging in the time-honored practice of clam digging is a cherished custom here, reflecting the area's rich maritime heritage.
  • Seafood Festivals: Participating in local seafood festivals allows visitors to enjoy freshly caught delicacies and celebrate the region's fishing culture.
  • Boat Races: Watching or taking part in traditional boat races showcases the community’s connection to its waterways and seafaring history.
  • Island Folk Music: Listening to and preserving island folk music remains a vibrant custom that keeps local traditions alive within this coastal destination.

Frequently Asked Questions About Smith Island?

1. What are the top vacation rentals in Smith Island?

There are a lot of options in Smith Island. If you plan on staying in the Smith Island area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Smith Island:

2. How many vacation rentals have private pools in Smith Island?

There are 1 vacation rentals with private pools near Smith Island. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Smith Island are best for families?

If you are looking for a family-friendly vacation home in Smith Island, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Smith Island:

4. How many Rentbyowner vacation rentals are available in Smith Island?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 60 in the Smith Island area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Smith Island. 

5. What is the cancellation policy for vacation rentals in Smith Island, Maryland?

Cancellation policies vary by property. You should check the specific listing details or contact the owner directly to understand the terms and any applicable fees before finalizing your booking.

6. Are pets allowed in vacation rentals on Smith Island, Maryland?

Pet policies differ among properties. Please review the individual listing or reach out to the host to confirm if pets are permitted during your stay.

7. How do I know if a vacation rental in the area has suitable amenities?

Each listing provides detailed information about available amenities. Be sure to read the description carefully and contact the owner if you have specific requirements.

8. What are the check-in and check-out times for vacation rentals here?

Check-in and check-out times can vary by property. You should refer to the listing details or communicate with the owner to confirm these times for your reservation.

9. Is there a secure way to pay for my booking in Maryland's region?

Payments are generally handled through trusted platforms that offer secure processing. Always verify payment methods listed on the property page and avoid direct transfers to ensure safety.