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Island Life! Kent Island Waterfront with Pool-Bring your boat!

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Photo gallery for Island Life! Kent Island Waterfront with Pool-Bring your boat!

Pool
Dining
Private kitchen
Living area
Living area

Reviews

10 out of 10, Loved by Guests
Top 10% based on

Popular amenities

  • Free WiFi
  • Air conditioning
  • Laundry
$435
avg per night

Explore the area

View in a map
Stevensville, MD
  • Place, Island Dog Park
    ‪5 min drive‬
  • Place, Paul Reed Smith Guitars
    ‪5 min drive‬
  • Place, Matapeake State Park
    ‪8 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪49 min drive‬

Rooms & beds

3 bedrooms (sleeps 12)

2nd Floor Bedroom

3 Double Beds

2nd Floor Loft

2 Queen Beds

Master

1 King Bed

2 bathrooms, 1 half bathroom

2nd Floor Guest Bath

Bathtub or shower · Toilet

Main Floor

Toilet

Master

Bathtub · Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Outdoor play area
Garden
Dining area
Price is $435 avg per night

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About the neighborhood

Stevensville

Located in Stevensville, this guesthouse is on the waterfront. Queenstown Premium Outlets and Annapolis City Dock are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Matapeake State Park and Love Point State Park. Looking to enjoy an event or a game while in town? See what's happening at Alumni Hall or Navy-Marine Corps Memorial Stadium. Be sure to check out the area's animals with activities such as game walks and birdwatching.
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What's nearby

  • Island Dog Park - 5 min drive - 2.8 km
  • Paul Reed Smith Guitars - 5 min drive - 3.8 km
  • Matapeake State Park - 8 min drive - 7.3 km
  • Chesapeake Exploration Center - 9 min drive - 8.1 km
  • Love Point State Park - 9 min drive - 9.2 km

Getting around

  • Easton, MD (ESN-Easton - Newnam) - 34 min drive

Restaurants

  • ‪Chick-fil-A - ‬6 min drive
  • ‪McDonald's - ‬3 min drive
  • ‪McDonald's - ‬7 min drive
  • ‪Cracker Barrel - ‬20 min walk
  • ‪Dunkin' - ‬7 min drive

About this property

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Beautiful 2 story secluded private waterfront retreat with shared pool and hot tub access. Bring your boat and tie up to the dock for fishing or sunset cruises. 4ft average water depth at dock. Easy boat rides to local restaurants and historic towns await. 5 minute car ride to Kent Island's great restaurants and wedding venues. Convenient access to Rt 50 and only15 minutes to Annapolis. Great for Bridal parties. Bedrooms: King Bedroom Suite on main floor. Two Queen Bedroom loft area another Bedroom with three (3) full beds. Enjoy everything the Eastern Shore has to offer. The home has interior stair access from garage to the second and third floor living areas.
It does not have an elevator. Enjoy the all the conveniences and amenities this home has to offer. A great place to call homebase while you're away and enjoy Kent Island's best restaurants, dock bars and wedding venues. Nestled on 22 acres of private waterfront. Stroll on the pier or catch some crabs. Jump in the pool--relax in the hot tub. Bring your boat! This place has it all.

Need more room? There is a second home on this property listed as VRBO# 4131073 called Island Life 2 which sleeps 8 people!

Location! Location! Location! We perfectly situated near Kent Island finest Restaurants, Dock Bars and Wedding Venues:
Kent Narrows: 4.7 miles
Chesapeake Bay Beach Club-2.3 miles
Kent Island Resort-2.9 miles

Other popular destinations cities are only minutes away:
Annapolis- 15 miles
Baltimore- 40 miles
Washington DC- 45 miles
Easton- 30 miles
St. Michael's -37 miles

This is a Non-Smoking House.
Also No Pets, Parties or Large Groups (12 max).

The Space:
This Home is situated on a 22 acre private waterfront estate. Nature lovers will be in their glory with Kent Islands wildlife all around you. Bring the kids bikes--we have a 1/4 mile private drive for the to ride and explore. Bring your boat or catch some crabs off the dock!

The first floor has the Kitchen, Dining Room, Living Room, Half Bathroom, Master Bedroom, Full Bathroom and a Washer/Dryer.

Located on the second floor is Three Bedrooms:
Bedroom 2: Loft area with (2) Queen Beds
Bedroom 3: Bedroom with (3) Full Beds

Upstairs Bedrooms and Living Room have Smart TV's with streaming services.
The House also has WIFI, A/C, Heating, Washer/Dryer, Microwave, Dishwasher, Coffee Maker (Both Keurig and Drip), most common spices for the cooks in the group and a fully outfitted Kitchen with all essentials.

Blankets, pillows, linens and bath towels ARE provided with the home.

Guest Access:
You will have full access to the entire house and property, with the exception of the main home and its immediate area, garage, and exterior buildings.

Other Things to Note:
- The home has a set of stairs inside the garage which access the main floor of the guest home. There is an interior set of stairs on the interior to reach the upper floor where the additional bedrooms are located. The house has covered wrap around porches on the main level. These areas are private and for your use only. There is a grill in this area too for your use. There is a set of private stairs from the main level on the waterfront side of the home for convenient access to the pool and hot tub area.

Book Today!
Our prices include all fees. No hidden fees.

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
default

Smoking

Smoking is not permitted
Adult supervision is required for pool and hot tub use as well as for children under 13 on the pier..

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Safety features at this property include a smoke detector and a deadbolt lock

We should mention

This property does not have elevators
A car is recommended for transportation to and from this property

Frequently asked questions

Does Island Life! Kent Island Waterfront with Pool-Bring your boat! have a pool?

Yes, this property has an outdoor pool.

How much does it cost to stay at Island Life! Kent Island Waterfront with Pool-Bring your boat!?

As of Mar 26, 2026, prices found for a 1-night stay for 2 adults at Island Life! Kent Island Waterfront with Pool-Bring your boat! on Mar 29, 2026 start from $435, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Island Life! Kent Island Waterfront with Pool-Bring your boat! pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Island Life! Kent Island Waterfront with Pool-Bring your boat!?

Check-in begins at 4:00 PM.

What time is check-out at Island Life! Kent Island Waterfront with Pool-Bring your boat!?

Check-out is at 11:00 AM.

Where is Island Life! Kent Island Waterfront with Pool-Bring your boat! located?

Situated on the waterfront, this guesthouse is within 3 mi (5 km) of Paul Reed Smith Guitars, Chesapeake Bay, and Northern Chesapeake Bay. Island Dog Park and Matapeake State Park are also within 6 mi (10 km).

Island Life! Kent Island Waterfront with Pool-Bring your boat! Reviews

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 199 out of 206 reviews
Rating 8 - Good. 5 out of 206 reviews
Rating 6 - Okay. 1 out of 206 reviews
Rating 4 - Poor. 0 out of 206 reviews
Rating 2 - Terrible. 1 out of 206 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Karen M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a gorgeous place to stay! We had a wonderful time!
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

francis t.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The place is so nice .. have a lot things can do ! The owner is so helpful and they give you a peace and privacy .. will book this place again on summer for sure
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Rosina S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved this spot to spend time with our Midshipman! Kent Island is wonderful. The home is spotless, comfortably furnished, and had everything we could want. We enjoyed walking the property and want to go back when the weather is warmer.
Stayed 4 nights in Feb 2026
Verified

8/10 Good

MICHELLE C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
My overall experience was good. The host was super helpful and welcoming. The hospitality was impeccable.
Stayed 4 nights in Nov 2025
Verified

10/10 Excellent

Chuck C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great spot.
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Kimberly C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely amazing property with superb host! The place is packed with "little" details that anyone would need! Such a clean place and peaceful property! Highly recommend!Also, this place is nestled in a country-like setting but so conveniently close to nearby eats and Target! Cannot say enough about the communication with the host and overall stay!
Stayed 4 nights in Sep 2025
Verified

10/10 Excellent

Hannah L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house exceeded our expectations! The property is absolutely gorgeous, and the home is spacious, clean, and had everything we needed. We stayed here for my wedding weekend with our bridal party and it was perfect. Thank you, John!
Stayed 3 nights in Oct 2025
Verified

10/10 Excellent

Maura M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay at John’s place - it was absolutely beautiful and the property was wonderful. John was very responsive and the listing was exactly as pictured!
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Trish S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We rented the property for extended family to stay during our son’s wedding weekend and it was perfect. Beautiful property and plenty of space and amenities. John was very helpful and so easy to work with. I’d love to go back for a quiet, relaxing vacation! Highly recommend!
Stayed 5 nights in Sep 2025
Verified

10/10 Excellent

Vicki F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful and private property. Close to grocery stores and restaurants. Lots of things to do. The hosts were very welcoming and made us feel at home.
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

Janet W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Getaway

Wonderful house with great water access. Great place to relax and visit and recreate
Stayed 14 nights in Apr 2025
Verified

6/10 Okay

Katie C.

Liked: Cleanliness, check-in, communication, location
Place was clean! Hot tub was great! Only thing that would have been nice to know is that the home is above a garage that the owners actively use. During the night cars were moved from garage under us.
Stayed 3 nights in Oct 2025
Verified

8/10 Good

Ricky W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Propery

Great location, clean and everything was just like it posted. Would 100% stay here again
Stayed 7 nights in Apr 2025
Verified

10/10 Excellent

Theresa S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful place! Had everything there for a great vacation!

The place was very clean , had all the things in the home to make your stay wonderful!!!! Kitchen stocked with cooking equipment, towels for the pool, and the was owner was a great host.
Stayed 3 nights in Jul 2024
Verified

10/10 Excellent

Sharon T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Highly recommend!

We were there for son’s wedding weekend. We could not have been more pleased!
Stayed 3 nights in May 2025
Verified

10/10 Excellent

James R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Didn't use the hot tub.
Stayed 5 nights in Oct 2025
Verified

10/10 Excellent

Nicolette M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

So relaxing!!

This was our first VRBO experience and it was wonderful. The rental provided more than our expectations. It was a beautiful site and extremely clean.The host was friendly, kind and easily reachable. We highly recommend this rental location and host and will check here first for future trips to this area.
Stayed 3 nights in Jun 2025
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful

Everything about our stay was WONDERFUL!
Stayed 4 nights in Aug 2024
Verified

10/10 Excellent

Mike Y.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay on Kent Island!

We had a great stay at this vacation home. From the time we booked the vacation, communication with the host, John, was great. He is very responsive.The home exceeded our expectations. This location is beautiful, and we enjoyed exploring, swimming in the gorgeous pool, and spending time relaxing with family on the wraparound porches.We would definitely like to stay here again in the future.
Stayed 4 nights in Jul 2025
Verified

10/10 Excellent

Terri M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Stevensville

It was a great location and place to stay for the weekend of our son's wedding.
Stayed 3 nights in Sep 2024
Verified

10/10 Excellent

Michelle K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Family Get Away

My family and I thoroughly enjoyed our stay. The house was clean and inviting when we arrived. My grandchildren loved the pool and hot tub. The location was also a plus. Close to a grocery store and my granddaughters favorite, Target! We also enjoy going into Annapolis. Such a quaint town.John was a wonderful host and available to answer any questions. We certainly will return!
Stayed 9 nights in Jul 2025
Verified

10/10 Excellent

Eva S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful!

Great place!
Stayed 3 nights in Jul 2023
Verified

10/10 Excellent

Chester Y.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent stay

Beautiful property. House beautiful and so clean pool exquisite. Grounds and scenery spectacular.
Stayed 3 nights in Jun 2024
Verified

10/10 Excellent

Stacey L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for a relaxing weekend

We would highly recommend this place for a girls weekend.
Stayed 2 nights in Sep 2023
Verified

10/10 Excellent

Deborah C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family time

This property is amazing. Wonderful location to The Narrows, Annapolis, Saint Michaels, wonderful restaurants, parks and trails. The amenities were perfect. The kitchen was well stocked and there was plenty of paper products , soaps, towels, pool toys. Wonderful for a large family and great for small children. The pool was beautiful.
Stayed 5 nights in Jun 2025