Kent Island vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Kent Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Apartment in Stevensville

4.97 out of 5 average rating, 239 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Aug 16 – 23

$173 per night
Guest favorite

Home in Stevensville

4.94 out of 5 average rating, 185 reviews

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Enjoy your vacation in this Stylish Coastal-Country 3+ Bedroom Home w/3 acres of outdoor living! Perfect for Families & sleeps 14. We are conveniently located to many areas/cities: Annapolis- 15 miles Baltimore- 40 Wash. DC- 45 Easton- 30 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions, including Chesapeake Beaches. This is a Non-Smoking House. Also No Pets, Parties or Large Groups (14 max.). Book Today!

Feb 17 – 24

$192 per night
Guest favorite

Apartment in Pasadena

4.99 out of 5 average rating, 542 reviews

Sea Dreamer aka Phenomenal Hospitality

Stunning sunrises free in a tranquil, riverfront, apartment with front entrance. Split foyer home, I am upstairs, you are downstairs. 2 separate bedrooms, one overlooking the river. Living room includes dining area, office space, comfy seating, and a massage chair!. Full bath, best showerhead, soaps, shampoos, and towels. Pull out sofa bed for larger parties. Kitchenette has everything necessary to cook with. BWI 20 min, 40 Annapolis, 60 to DC. Patio, fire pit, grill, deck and beach walks.

Nov 16 – 23

$83 per night

Popular amenities for Kent Island vacation rentals

Other great vacation rentals in Kent Island

Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 113 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

Mar 18 – 25

$417 per night
Guest favorite

Home in Annapolis

4.96 out of 5 average rating, 103 reviews

Historic Downtown in-law suite

Jan 9 – 16

$106 per night
Superhost

Bungalow in Deale

4.86 out of 5 average rating, 353 reviews

Cozy waterfront getaway on the Bay

Jan 24 – 31

$158 per night
Superhost

Cottage in Wittman

4.9 out of 5 average rating, 134 reviews

"Wittman Cottage"

Dec 27 – Jan 3

$185 per night
Guest favorite

Guesthouse in Annapolis

4.97 out of 5 average rating, 195 reviews

RECENTLY RENOVATED Cottage Near Downtown Annapolis

Oct 18 – 25

$107 per night
Guest favorite

Home in Rock Hall

5.0 out of 5 average rating, 102 reviews

Bayside Beach House

Jun 1 – 8

$137 per night
Guest favorite

Guesthouse in Annapolis

4.99 out of 5 average rating, 102 reviews

Coastal Waterfront 1 Bedroom Cottage

Apr 29 – May 6

$332 per night
Guest favorite

Cottage in Edgewater

4.99 out of 5 average rating, 123 reviews

Waterfront Chesapeake Bay Getaway Firepit & Pier!

Nov 11 – 18

$279 per night
Guest favorite

Cottage in Annapolis

4.96 out of 5 average rating, 328 reviews

Relaxing Water Views - Mill Creek Cottage

Dec 21 – 28

$170 per night
Guest favorite

Apartment in Edgewater

4.92 out of 5 average rating, 396 reviews

Pet Friendly Garden Apartment Near Annapolis

Aug 2 – 9

$96 per night
Guest favorite

Guesthouse in Riva

4.99 out of 5 average rating, 273 reviews

The Riva House

Mar 2 – 9

$133 per night
Guest favorite

Apartment in North Beach

4.97 out of 5 average rating, 100 reviews

Bayside Oasis of Southern Maryland

Nov 4 – 11

$113 per night

Other great vacation rentals in Kent Island

Guest favorite

Cottage in Stevensville

4.93 out of 5 average rating, 15 reviews

Cozy, Waterfront Getaway “The Great Nest”

Oct 9 – 16

$325 per night
Guest favorite

Home in Stevensville

5.0 out of 5 average rating, 20 reviews

Away at the Bay: New Home on the Chesapeake Bay!

Mar 12 – 19

$450 per night
Guest favorite

Home in Stevensville

4.95 out of 5 average rating, 40 reviews

25-50% Off~Private Beach~Hot Tub~Fire Table~

Oct 5 – 12

$477 per night
Guest favorite

Home in Stevensville

4.98 out of 5 average rating, 61 reviews

Beautiful Kent Island Getaway with Pool

Nov 12 – 19

$650 per night
Guest favorite

Guesthouse in Chester

5.0 out of 5 average rating, 39 reviews

Waterfront Guest Cottage: Sunsets, Pool, Pier

Jan 11 – 18

$599 per night
Guest favorite

Home in Stevensville

5.0 out of 5 average rating, 15 reviews

Impressive Waterfront Home - Pool, Pier, & Sunsets

Apr 8 – 15

$990 per night
Guest favorite

Home in Stevensville

5.0 out of 5 average rating, 34 reviews

The Pool House in Romancoke On The Bay

Oct 22 – 29

$700 per night
Guest favorite

Home in Stevensville

5.0 out of 5 average rating, 99 reviews

Chesapeake Bay Waterfront ARTectural Home w/ Pool!

Aug 15 – 22

$833 per night
Guest favorite

Home in Stevensville

5.0 out of 5 average rating, 28 reviews

Bayview Bungalow - Water view, EV charging station

Sep 18 – 25

$384 per night
Guest favorite

Home in Stevensville

4.97 out of 5 average rating, 95 reviews

The Kent Island House

May 2 – 9

$226 per night
Guest favorite

Barn in Queenstown

5.0 out of 5 average rating, 40 reviews

Waterfront Modern Guest Barn

Aug 23 – 30

$540 per night
Guest favorite

Home in Stevensville

4.85 out of 5 average rating, 48 reviews

Cheerful & Spacious Shore Life Beauty!

Nov 28 – Dec 5

$209 per night

Destinations to explore