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
Jun 19 – 26
Home in Edgewater
4.95 out of 5 average rating, 119 reviewsHouse in Edgewater Maryland
Feb 1 – 8
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
Jan 27 – Feb 3
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
Oct 28 – Nov 4
Home in Stevensville
4.98 out of 5 average rating, 61 reviewsBeautiful Kent Island Getaway with Pool
Mar 26 – Apr 2
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
4.7 out of 5 average rating, 217 reviewsSpectacular Water View Bay House
Jan 30 – Feb 6
Weekly house rentals
Home in Annapolis
4.89 out of 5 average rating, 182 reviewsCountry House on the Bay
Sep 28 – Oct 5
Home in Cambridge
4.99 out of 5 average rating, 141 reviewsSunset Breezes - quiet waterfront retreat
Nov 21 – 28
Home in Chester
5.0 out of 5 average rating, 12 reviews*Waterfront Sunset Bayview* sleeps 6
Oct 17 – 24
Home in Stevensville
5.0 out of 5 average rating, 39 reviewsModern Island Escape by the Bay
Jan 12 – 19
Home in Stevensville
4.97 out of 5 average rating, 97 reviewsThe Kent Island House
Nov 14 – 21
Home in Stevensville
4.85 out of 5 average rating, 48 reviewsCheerful & Spacious Shore Life Beauty!
Mar 18 – 25
Home in Stevensville
5.0 out of 5 average rating, 30 reviewsBayview Bungalow - Water view, EV charging station
Nov 17 – 24
Home in Stevensville
5.0 out of 5 average rating, 80 reviewsKent Island Waterfront Home with Amazing Sunsets
Nov 21 – 28
Private house rentals
Home in Chester
5.0 out of 5 average rating, 40 reviewsChester Delight- Fireplace/Deck&Patio+fenced yard
Oct 13 – 20
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
4.94 out of 5 average rating, 35 reviewsWaterfront Paradise to Work or Rest
Jun 14 – 21
Home in Arnold
4.94 out of 5 average rating, 48 reviewsBring A Boat! Waterfront home-w/basement apt+dock!
Nov 1 – 8
Home in Stevensville
5.0 out of 5 average rating, 51 reviewsLove Point Idyll - 240' Private Beachfront
Feb 27 – Mar 6
Home in Greensboro
4.96 out of 5 average rating, 47 reviewsCozy 2 bedroom home on wooded private lane
Oct 31 – Nov 7
Home in Stevensville
4.98 out of 5 average rating, 53 reviewsCozy home with Screened Porch, Min from Weddings
Dec 4 – 11
Home in Chester
5.0 out of 5 average rating, 7 reviewsA Shore Thing waterfront home with private pier
Jan 16 – 23
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