Entire home
Bayside: Bayfront villa W/ free onsite boat ramp marina & trailer parking.
Islamorada villa in Matecumbe area
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Reviews
9.8 out of 10
Exceptional
Entire home
2 bedrooms2 bathroomsSleeps 470 sq m
Popular amenities
Explore the area

Islamorada, FL
- Place, Islamorada Brewery & Distillery1 min walk
- Place, Keys History & Discovery Center8 min walk
- Place, Florida Keys Brewing Co.18 min walk
- Airport, Marathon, FL (MTH-Florida Keys Marathon)50 min drive
Room options
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About the area
About this property
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Chesapeake Beach Resort
Matecumbe
Chesapeake Beach Resort
- On private beach
- Pool
- Breakfast included
- Pet friendly
4.6 out of 5, Wonderful, 1,682 reviews
The price is CA $288
CA $403 total
includes taxes & fees
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Property amenities
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Bayside: Bayfront villa W/ free onsite boat ramp marina & trailer parking. Reviews
Reviews
9.8
Exceptional
10/10
Cleanliness
Reviews
Mar 21, 2026
Liked: Cleanliness
Stayed 7 nights in Mar 2026
10/10 Excellent
James S.
Aug 19, 2024
Liked: Cleanliness
Boaters paradise
James S.
Stayed 4 nights in Aug 2024
10/10 Excellent
Carmen K.
Jul 23, 2024
Liked: Cleanliness
Slice of Paradise
Carmen K.
Stayed 7 nights in Jul 2024
10/10 Excellent
Mike H., Saint Simons Island, GA
May 22, 2024
Liked: Cleanliness
Fantastic week
Mike H.
Stayed 7 nights in May 2024
10/10 Excellent
Cindi W.
Nov 21, 2023
Liked: Cleanliness
Overall Fantastic Place!
Cindi W.
Stayed 7 nights in Nov 2023
10/10 Excellent
Bruce J., Melbourne, Florida
May 9, 2023
Liked: Cleanliness
Amazing View … Keys Charm
Bruce J.
Stayed 7 nights in Apr 2023
10/10 Excellent
Cindy L.
Jan 29, 2023
Liked: Cleanliness
Two weeks in paradise!
Cindy L.
Stayed 14 nights in Jan 2023
10/10 Excellent
Patrick E., Dallas Texas
Jul 18, 2022
Liked: Cleanliness
Bayside Villa 2022
Patrick E.
Stayed 7 nights in Jul 2022
10/10 Excellent
Frederick D.
May 31, 2022
Liked: Cleanliness
Keep Coming Back
Frederick D.
Stayed 7 nights in May 2022
10/10 Excellent
Ron K.
Mar 2, 2021
Liked: Cleanliness
Perfect
Ron K.
Stayed 14 nights in Feb 2021
10/10 Excellent
Benjamin R.
Jan 17, 2021
Liked: Cleanliness
Best place in the Keys.
Benjamin R.
Stayed 7 nights in Jan 2021
10/10 Excellent
Trisha F., Tyler, TX
Jan 13, 2021
Liked: Cleanliness
Much Better Than the Pics!!
Trisha F.
Stayed 7 nights in Jan 2021
10/10 Excellent
George D.
Sep 14, 2019
Liked: Cleanliness
Everything we needed in one spot.
George D.
10/10 Excellent
FP S.
Jul 29, 2019
Liked: Cleanliness
7 years in Islamorada
FP S.
Stayed 21 nights in Jul 2019
10/10 Excellent
John L.
Jul 6, 2019
Liked: Cleanliness
Cozy getaway perfect for two.
John L.
Stayed 7 nights in Jun 2019
10/10 Excellent
Verified traveller
Jul 2, 2019
Liked: Cleanliness
KEYS KOTTAGE - JUNE 2019
Verified traveller
Stayed 7 nights in Jun 2019
10/10 Excellent
Mary Jo D.
Jun 11, 2019
Our happy place
Mary Jo D.
Stayed 7 nights in Jun 2019
10/10 Excellent
Joel A.
May 22, 2019
"Siten" on the dock of the bay
Joel A.
Stayed 7 nights in May 2019
8/10 Good
Randall R.
May 7, 2019
Bayside at Islamorada
Randall R.
Stayed 14 nights in Apr 2019
10/10 Excellent
Jim S.
Apr 23, 2019
Paradise
Jim S.
Stayed 7 nights in Apr 2019
10/10 Excellent
Verified traveller
Apr 16, 2019
Key cottage villa
Verified traveller
Stayed 14 nights in Mar 2019
10/10 Excellent
Ed M.
Mar 23, 2019
Another great vacation
Ed M.
Stayed 7 nights in Mar 2019
10/10 Excellent
Laurie S.
Feb 25, 2019
Paradise
Laurie S.
Stayed 7 nights in Feb 2019
10/10 Excellent
stephen d.
Jan 15, 2019
Sunset serenity
stephen d.
Stayed 7 nights in Jan 2019
10/10 Excellent
Marc L.
Dec 15, 2018
Beautiful location and accommodations
Marc L.
Stayed 7 nights in Dec 2018

















