House vacation rentals in Kent Island
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Top-rated house rentals in Kent Island
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Kent Island house rentals
House rentals with a pool
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Apr 4 – 11
Home in Edgewater
4.95 out of 5 average rating, 118 reviewsHouse in Edgewater Maryland
Jan 31 – Feb 7
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
Jul 7 – 14
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
Jan 8 – 15
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Mar 28 – Apr 4
Home in Stevensville
5.0 out of 5 average rating, 34 reviewsThe Pool House in Romancoke On The Bay
Apr 3 – 10
Home in Stevensville
4.98 out of 5 average rating, 61 reviewsBeautiful Kent Island Getaway with Pool
Mar 26 – Apr 2
Home in Stevensville
4.7 out of 5 average rating, 217 reviewsSpectacular Water View Bay House
Aug 18 – 25
Weekly house rentals
Home in Chester
4.88 out of 5 average rating, 137 reviewsKent Island Beautiful 4 BR home, central location!
Aug 7 – 14
Home in Annapolis
4.89 out of 5 average rating, 182 reviewsCountry House on the Bay
Jan 20 – 27
Home in Lusby
4.98 out of 5 average rating, 261 reviewsCove Point Beach Cabin
Sep 24 – Oct 1
Home in Stevensville
5.0 out of 5 average rating, 39 reviewsModern Island Escape by the Bay
Jun 18 – 25
Home in Chester
5.0 out of 5 average rating, 12 reviews*Waterfront Sunset Bayview* sleeps 6
Oct 17 – 24
Home in Stevensville
4.97 out of 5 average rating, 97 reviewsThe Kent Island House
Aug 27 – Sep 3
Home in Stevensville
4.85 out of 5 average rating, 48 reviewsCheerful & Spacious Shore Life Beauty!
Mar 6 – 13
Home in Stevensville
5.0 out of 5 average rating, 30 reviewsBayview Bungalow - Water view, EV charging station
Dec 8 – 15
Private house rentals
Home in Edgewater
4.95 out of 5 average rating, 38 reviewsRelaxing Turkey Point Retreat-Steps to the marina!
Feb 5 – 12
Home in Stevensville
5.0 out of 5 average rating, 22 reviewsAway at the Bay: New Home on the Chesapeake Bay!
Apr 10 – 17
Home in Chester
5.0 out of 5 average rating, 40 reviewsChester Delight- Fireplace/Deck&Patio+fenced yard
Oct 12 – 19
Home in Grasonville
5.0 out of 5 average rating, 22 reviewsBay Breeze-Chester River Retreat
Apr 20 – 27
Home in Arnold
4.94 out of 5 average rating, 48 reviewsBring A Boat! Waterfront home-w/basement apt+dock!
Dec 2 – 9
Home in Chester
4.94 out of 5 average rating, 35 reviewsWaterfront Paradise to Work or Rest
Jun 14 – 21
Home in Stevensville
5.0 out of 5 average rating, 51 reviewsLove Point Idyll - 240' Private Beachfront
Mar 11 – 18
Home in Greensboro
4.96 out of 5 average rating, 47 reviewsCozy 2 bedroom home on wooded private lane
Oct 31 – Nov 7
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- Monthly Rentals Kent Island
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