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Reviews
8.8 out of 10
Excellent
Popular amenities
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Showing 11 of 11 rooms
View all photos for Resort View Queen Family Suite w/ Kitchen

Resort View Queen Family Suite w/ Kitchen
10.0 out of 10
Exceptional
(1 review)
Highlights
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Kitchen
Full-sized refrigerator/freezer
Flat-screen TV
2 bedrooms
View all photos for Oceanfront King Suite w/ Beach Walkout & Kitchen

Oceanfront King Suite w/ Beach Walkout & Kitchen
9.6 out of 10
Exceptional
(11 reviews)
Highlights
Deck/patio
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Kitchen
Full-sized refrigerator/freezer
Flat-screen TV
View all photos for Oceanfront Trailer

Oceanfront Trailer
8.0 out of 10
Very good
(8 reviews)
Highlights
Patio
Separate dining area
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Kitchenette
Full-sized refrigerator/freezer
View all photos for Ocean View Double Queen w/ Kitchen & Private Balcony

Ocean View Double Queen w/ Kitchen & Private Balcony
9.6 out of 10
Exceptional
(5 reviews)
Highlights
Balcony
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Kitchen
Flat-screen TV
Separate bedroom
View all photos for Oceanfront Queen Room

Oceanfront Queen Room
Highlights
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
Premium bedding
View all photos for Resort View ADA King Room

Resort View ADA King Room
Highlights
Patio
Yard
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Refrigerator
Flat-screen TV
View all photos for Resort View Queen Room w/ Kitchen & Private Porch

Resort View Queen Room w/ Kitchen & Private Porch
9.4 out of 10
Exceptional
(6 reviews)
Highlights
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Kitchen
Full-sized refrigerator/freezer
Flat-screen TV
Separate bedroom
View all photos for Resort View Family Suite w/ Kitchen

Resort View Family Suite w/ Kitchen
7.4 out of 10
Good
(3 reviews)
Highlights
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Kitchen
Full-sized refrigerator/freezer
Flat-screen TV
Separate bedroom
View all photos for Ocean View Double Queen Room

Ocean View Double Queen Room
8.8 out of 10
Excellent
(15 reviews)
Highlights
Balcony
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
View all photos for Oceanfront King Suite w/ Kitchen & Private Balcony

Oceanfront King Suite w/ Kitchen & Private Balcony
10.0 out of 10
Exceptional
(18 reviews)
Highlights
Balcony
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Kitchenette
Full-sized refrigerator/freezer
Flat-screen TV
View all photos for Oceanfront Family Suite w/ Kitchen

Oceanfront Family Suite w/ Kitchen
Highlights
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Kitchen
Full-sized refrigerator/freezer
Flat-screen TV
2 bedrooms
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Ad

Chesapeake Beach Resort
Matecumbe
- On private beach
- Pool
- Breakfast included
- Pet-friendly
9.2 out of 10, Wonderful, 1,498 reviews
The price is CA $208
CA $311 total
includes taxes & fees
Aug 17 - Aug 18
Sign in to view eligible discounts and perks. More rewards for more adventures!
About the area

84959 Overseas Highway, 222, Islamorada, FL, 33036
About this property
Property amenities
Room amenities
Policies
Important information
Fees
You'll be asked to pay the following charges at the property. Fees may include applicable taxes:
- Resort fee: USD 35 per accommodation, per night
The resort fee includes:
- Beach access
- Beach loungers
- Beach towels
- Housekeeping
- In-room coffee
- Pool access
We have included all charges provided to us by the property.
Optional extras
- Pet fee: USD 25 per pet, per day
- Service animals are exempt from fees
The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards, debit cards, and cash
Safety features at this property include a carbon monoxide detector, a fire extinguisher, and a smoke detector
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
We should mention
This property does not have elevators
Pool access available from 7:30 AM to 6:30 PM
The property has connecting/adjoining rooms, which are subject to availability and can be requested by contacting the property using the number on the booking confirmation
Property is also known as
Drop Anchor
Drop Anchor Islamorada
Drop Anchor Resort
Drop Anchor Resort Islamorada
Drop Anchor Hotel Islamorada
Drop Anchor Hotel
Drop Anchor Islamorada
Hotel Drop Anchor Islamorada
Islamorada Drop Anchor Hotel
Hotel Drop Anchor
Drop Anchor Islamorada
Drop Anchor Resort Marina
Drop Anchor Hotel Islamorada
Drop Anchor Hotel
Drop Anchor Islamorada
Drop Anchor
Hotel Drop Anchor Islamorada
Islamorada Drop Anchor Hotel
Hotel Drop Anchor
Drop Anchor Islamorada
Drop Anchor Resort Marina
Drop Anchor Hotel
Drop Anchor Islamorada
Drop Anchor Hotel Islamorada
Frequently asked questions
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Drop Anchor Reviews
Reviews
8.8
Excellent
9.0/10
Cleanliness
9.2/10
Staff & service
8.6/10
Amenities
8.4/10
Property conditions & facilities
8.6/10
Eco-friendliness
Reviews
Aug 12, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Stayed 1 night in Aug 2025
8/10 Good
Raul
Aug 11, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Raul
Stayed 3 nights in Aug 2025
10/10 Excellent
Travis
Jul 18, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Travis
Stayed 2 nights in Jul 2025
8/10 Good
Jack
Jul 14, 2025
Liked: Cleanliness, amenities, property conditions & facilities
Jack
Stayed 2 nights in Jun 2025
10/10 Excellent
Silvia
Aug 4, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities



Silvia
Stayed 1 night in Aug 2025
10/10 Excellent
Morgan
Jul 9, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Morgan
Stayed 2 nights in Jun 2025
8/10 Good
Anthony
Jun 19, 2025
Liked: Cleanliness, property conditions & facilities
Disliked: Amenities


Anthony
Stayed 1 night in Jun 2025
8/10 Good
Paolo
Jul 21, 2025
Liked: Cleanliness, property conditions & facilities
Paolo
Stayed 3 nights in Jul 2025
10/10 Excellent
Dixiana
Jun 8, 2025
Liked: Cleanliness, amenities, property conditions & facilities
Dixiana
Stayed 2 nights in Jun 2025
8/10 Good
David
Jun 19, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
David
Stayed 1 night in Feb 2025
10/10 Excellent
ellie
Jul 3, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
ellie
Stayed 1 night in Jul 2025
10/10 Excellent
Michael
May 4, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Michael
Stayed 1 night in May 2025
8/10 Good
Verified traveller
May 5, 2025
Liked: Cleanliness, staff & service, property conditions & facilities
Nice ocean views
Verified traveller
Stayed 1 night in Apr 2025
6/10 Okay
Niurka
Jul 7, 2025
Disliked: Amenities
Niurka
Stayed 2 nights in Jul 2025
4/10 Poor
Tanya
Jul 28, 2025
Disliked: Staff & service, property conditions & facilities
Tanya
Stayed 1 night in Jul 2025
6/10 Okay
Cathy
Jul 7, 2025
Liked: Cleanliness, staff & service, property conditions & facilities
Cathy
Stayed 1 night in Jul 2025
10/10 Excellent
hevelin
May 26, 2025
Liked: Cleanliness, amenities, property conditions & facilities
hevelin
Stayed 3 nights in May 2025
8/10 Good
Morayma P.
Apr 9, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Morayma P.
Stayed 2 nights in Apr 2025
10/10 Excellent
Nicole
Mar 8, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nicole
Stayed 4 nights in Feb 2025
10/10 Excellent
Kim
Apr 23, 2025
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Good price and clean

Kim
Stayed 1 night in Apr 2025
10/10 Excellent
Tom
Feb 15, 2025
Liked: Cleanliness, staff & service, property conditions & facilities
Tom
Stayed 2 nights in Feb 2025
10/10 Excellent
Judith
Feb 17, 2025
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Judith
Stayed 2 nights in Jan 2025
10/10 Excellent
Da
Aug 19, 2024
Liked: Cleanliness, staff & service, property conditions & facilities
Disliked: Amenities
Da
Stayed 1 night in Aug 2024
8/10 Good
PETER
Mar 15, 2025
Liked: Cleanliness, staff & service, property conditions & facilities
PETER
Stayed 7 nights in Mar 2025
10/10 Excellent
jose
Dec 27, 2024
Liked: Staff & service, property conditions & facilities
jose
Stayed 2 nights in Dec 2024