House holiday 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.
Holiday rentals for every style
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Popular amenities for house rentals in Kent Island
House rentals with a pool
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
5–12 Dec
Home in Edgewater
4.95 out of 5 average rating, 119 reviewsHouse in Edgewater Maryland
21–28 Mar
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
13–20 Jul
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
5–12 Jul
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
12–19 Dec
Home in Stevensville
5.0 out of 5 average rating, 34 reviewsThe Pool House in Romancoke On The Bay
9–16 Dec
Home in Stevensville
4.98 out of 5 average rating, 62 reviewsBeautiful Kent Island Getaway with Pool
1–8 Apr
Home in Stevensville
4.7 out of 5 average rating, 217 reviewsSpectacular Water View Bay House
5–12 Mar
Weekly house rentals
Home in Silver Spring
4.99 out of 5 average rating, 153 reviewsEntire Guest Suite/Apt in Silver Spring/FDA
6–13 Mar
Home in Cambridge
4.99 out of 5 average rating, 142 reviewsSunset Breezes - quiet waterfront retreat
28 Mar – 4 Apr
Home in Lusby
4.98 out of 5 average rating, 261 reviewsCove Point Beach Cabin
27 Feb – 6 Mar
Home in Stevensville
5.0 out of 5 average rating, 40 reviewsModern Island Escape by the Bay
4–11 Sep
Home in Chester
5.0 out of 5 average rating, 14 reviews*Waterfront Sunset Bayview* sleeps 6
8–15 Nov
Home in Stevensville
4.97 out of 5 average rating, 97 reviewsThe Kent Island House
3–10 Oct
Home in Stevensville
4.86 out of 5 average rating, 49 reviewsCheerful & Spacious Shore Life Beauty!
15–22 Feb
Home in Stevensville
5.0 out of 5 average rating, 10 reviewsBeachside Dream
27 Dec – 3 Jan
Private house rentals
Home in Grasonville
5.0 out of 5 average rating, 23 reviewsBay Breeze-Chester River Retreat
28 Jan – 4 Feb
Home in Chester
4.94 out of 5 average rating, 36 reviewsWaterfront Paradise to Work or Rest
14–21 Jun
Home in Chester
5.0 out of 5 average rating, 40 reviewsChester Delight- Fireplace/Deck&Patio+fenced yard
18–25 Oct
Home in Stevensville
5.0 out of 5 average rating, 23 reviewsAway at the Bay: New Home on the Chesapeake Bay!
10–17 Apr
Home in Greensboro
4.96 out of 5 average rating, 48 reviewsCozy 2 bedroom home on wooded private lane
16–23 Feb
Home in Stevensville
5.0 out of 5 average rating, 51 reviewsLove Point Idyll - 240' Private Beachfront
20–27 Mar
Home in Pasadena
5.0 out of 5 average rating, 17 reviewsWaterfront CHeerful 2 with Private home
22–29 Jan
Home in Stevensville
4.98 out of 5 average rating, 55 reviewsCozy home with Screened Porch, Min from Weddings
10–17 Jan
Destinations to explore
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- Rentals with beach access Kent Island
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