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Chesapeake Beach Resort

2.5 star property
Hotel on the beach, with 2 outdoor pools

Photo gallery for Chesapeake Beach Resort

Private beach, white sand, sun-loungers, beach towels
Hypo-allergenic bedding, pillow-top beds, laptop workspace
Water view
Outdoor spa tub
Balcony

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • Pet-friendly
  • 24/7 front desk
  • Housekeeping
  • Air conditioning
The current price is NZ$488
includes taxes & fees
20 Apr - 21 Apr

Explore the area

Map
83409 Overseas Hwy, Islamorada, FL, 33036
  • History of Diving Museum
    ‪11 min walk‬
  • Theater of the Sea
    ‪2 min drive‬
  • Windley Key Fossil Reef Geological State Park
    ‪2 min drive‬

Room options

View all photos for 2-Bedroom Villa

2-Bedroom Villa

2-Bedroom Villa

Highlights

Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dishwasher
HDTV
Hypo-allergenic bedding
  • 60 sq m
  • Resort view
  • Sleeps 6
  • 1 King Bed, 1 Double Bed and 1 Double Sofa Bed

View all photos for Standard King

Standard King

Standard King

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 25 sq m
  • Sleeps 3
  • 1 King Bed

View all photos for King Efficiency Villa

King Efficiency Villa

King Efficiency Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
Dishwasher
  • 48 sq m
  • Resort view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Doubles

Standard Doubles

Standard Doubles

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 25 sq m
  • Sleeps 4
  • 2 Double Beds

View all photos for Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

Standard King with Sleeper Sofa

Highlights

Deck/patio
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Sofa bed - double
  • 29 sq m
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Hearing Impaired Ocean View Queens

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Hearing Impaired Ocean View Queens

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

View all photos for Hearing Impaired Ocean View King Suite

43-inch flat-screen TV with cable channels, TV

Hearing Impaired Ocean View King Suite

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 50 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for ADA King Efficiency Villa

ADA King Efficiency Villa

ADA King Efficiency Villa

Highlights

Separate dining area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
HDTV
Hypo-allergenic bedding
  • 48 sq m
  • Resort view
  • Sleeps 3
  • 1 King Bed

View all photos for Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa

Premium 1-Bedroom Ocean View Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
Dishwasher
  • 65 sq m
  • Ocean view
  • Sleeps 6
  • 2 Double Beds and 1 Double Sofa Bed

View all photos for Deluxe Ocean View Two Queen Suite

Balcony

Deluxe Ocean View Two Queen Suite

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
  • 60 sq m
  • Ocean view
  • Sleeps 6
  • 2 Queen Beds

View all photos for Ocean View King

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Sofa bed - double
  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

View all photos for Ocean View King Suite

Hypo-allergenic bedding, pillow-top beds, laptop workspace

Ocean View King Suite

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 49 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Ocean View Queens

Terrace/patio

Ocean View Queens

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

Ocean View King Efficiency Villa

Highlights

Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dishwasher
HDTV
  • 48 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Standard Queens

Standard Queens

Standard Queens

Highlights

Deck/patio
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 29 sq m
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard King Villa

Standard King Villa

Standard King Villa

Highlights

Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 30 sq m
  • Resort view
  • Sleeps 3
  • 1 King Bed

View all photos for Premium Ocean View King Villa

Premium Ocean View King Villa | Living area

Premium Ocean View King Villa

Highlights

Patio
Separate dining area
Separate sitting area
Air conditioning
Free cots/infant beds
Kitchenette
Full-sized fridge/freezer
Dining table
  • 77 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed and 1 Double Sofa Bed

View all photos for ADA Ocean View Queens

ADA Ocean View Queens

ADA Ocean View Queens

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Ceiling fan
  • 34 sq m
  • Ocean view
  • Sleeps 4
  • 2 Queen Beds

View all photos for ADA Ocean View King Suite

ADA Ocean View King Suite | Balcony

ADA Ocean View King Suite

Highlights

Balcony
Separate sitting area
Air conditioning
Free cots/infant beds
Mini-fridge
Dining table
HDTV
Hypo-allergenic bedding
  • 50 sq m
  • Ocean view
  • Sleeps 4
  • 1 King Bed

View all photos for ADA Ocean View King

Hypo-allergenic bedding, pillow-top beds, laptop workspace

ADA Ocean View King

Highlights

Balcony
Air conditioning
Free cots/infant beds
Mini-fridge
HDTV
Hypo-allergenic bedding
Renovated in 2020
Blackout curtains
  • 34 sq m
  • Ocean view
  • Sleeps 3
  • 1 King Bed

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About the area

Islamorada

At Chesapeake Beach Resort you'll be within a 15-minute walk of History of Diving Museum and 1.8 km (1.1 mi) from Windley Key Fossil Reef Geological State Park. Highlights at this beachfront hotel include 2 outdoor swimming pools and a private beach. .This beach hotel offers concierge services, a 24-hour front desk and a computer station. Plus you'll find multilingual staff. .With a stay at this Matecumbe hotel, you'll be 2 km (1.2 mi) from Islamorada Brewery & Distillery and 2.7 km (1.7 mi) from Keys History & Discovery Center.

What's nearby

  • History of Diving Museum - 11 min walk - 1.0 km
  • Theater of the Sea - 2 min drive - 1.8 km
  • Windley Key Fossil Reef Geological State Park - 2 min drive - 1.8 km
  • Islamorada Brewery & Distillery - 2 min drive - 2.0 km
  • Florida Keys Brewing Co. - 3 min drive - 3.5 km

Getting around

  • Miami International Airport (MIA) - 91 min drive

Restaurants

  • ‪Lorelei Restaurant & Cabana Bar - ‬3 min drive
  • ‪Hog Heaven - ‬3 min drive
  • ‪Wahoo's Bar & Grill - ‬2 min walk
  • ‪Florida Keys Brewing Co. - ‬3 min drive
  • ‪Whale Harbor Restaurant Marina - ‬2 min walk

About this property

Chesapeake Beach Resort

Hotel on the beach, with 2 outdoor pools
Simply walk outside to smell the salty air and watch the ocean waves from the white sand beach. Cool off in one of the 2 outdoor swimming pools at Chesapeake Beach Resort, and enjoy summer activities such as kayaking.

A complete renovation of Chesapeake Beach Resort was completed in January 2020.

This Islamorada hotel is smoke free.

  • 60 guestrooms or units
  • 2 levels
  • 9 buildings
  • Built in 2020
  • Beach lounge chairs
  • Towels for the beach
  • Poolside lounge chairs
  • Front desk (24 hours)
  • Staff members are multilingual
  • Concierge
  • Computer for guest use
  • No smoking on site
Chesapeake Beach Resort offers 60 air-conditioned accommodations, which are accessible via exterior corridors, and features coffee/tea makers and designer toiletries. Beds feature pillowtop mattresses. 43-inch flat-screen televisions come with cable channels.

Bathrooms include a shower, complimentary toiletries and hairdryers. Business-friendly amenities include telephones along with free local calls (restrictions may apply). Additionally, rooms include an iron/ironing board and a ceiling fan. Housekeeping is offered on a daily basis and hypo-allergenic bedding can be requested.

Languages

English, Spanish

Similar properties

Exterior

Amara Cay Resort

  • On private beach
  • Pool
  • Pet-friendly
  • Parking included
4.4 out of 5, Excellent, 1,197 reviews
The price is NZ$495
includes taxes & fees
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Property amenities

Parking and transport

  • Wheelchair-accessible parking available
  • Onsite parking includes off-street options

Things to do

  • 2 outdoor pools
  • Kayaking

Family friendly

  • 2 outdoor pools
  • Fenced pool
  • In-room microwave
  • Pool gate

Conveniences

  • 24-hour front desk

Guest services

  • Concierge services
  • Housekeeping (daily)
  • Multilingual staff

Business services

  • Computer station

Outdoors

  • Beach loungers
  • Beach towels
  • On a private beach
  • Pool loungers

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Assistive listening devices
  • Braille/raised signage
  • Handrails in hallways
  • Handrails in stairways
  • Lever door handles
  • Pool hoist on site
  • Upper floors accessible by stairs only
  • Visual alarms in hallways
  • Well-lit path to entrance
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible parking
  • Wheelchair-accessible pool
  • Wheelchair-accessible public bathroom

Room amenities

Bedroom

  • Bedsheets provided
  • Blackout drapes
  • Hypo-allergenic bedding
  • Pillowtop mattress

Bathroom

  • Designer toiletries
  • Hair dryer
  • Private bathroom
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • 43-inch flat-screen TV with cable channels

Food and drink

  • Coffee/tea maker
  • Microwave

More

  • Access via exterior corridors
  • Air conditioning
  • Ceiling fan
  • Free local calls
  • Iron/ironing board
  • Laptop workspace
  • Phone

Policies

Check-in

Check-in start time: 4:00 PM; check-in end time: midnight
Early check-in subject to availability
Contactless check-in and check-out are available
Late check-in subject to availability
Minimum check-in age - 18

Check-out

Check-out before 11 AM
Contactless check-out
Late check-out subject to availability
A late check-out fee will be charged

Special check-in instructions

Front desk staff will greet guests on arrival at the property

Access methods

Staffed front desk

Pets

  • Pets: USD 50.00 per accommodation, per night, plus a deposit of USD 50.00 per stay
  • Maximum 2 (weight limit: 50 lb per pet)
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
    • Service animals are exempt from fees.

Children and extra beds

  • Children are welcome.
  • Rollaway/extra beds are not available.

Payment types

Important information

Optional extras

The fees and deposits listed below will be charged at the time of service, check-in, or check-out.

  • Pet deposit: USD 50.00 per stay
  • Pet fee: USD 50.00 per accommodation, per night
  • Service animals are exempt from fees
  • Late check-out is available for a fee (subject to availability)

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card 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
Minimum Spring Break check-in age is 21 years old.
This property accepts credit cards; cash is not accepted
Charges for extra guests may apply and vary according to property policy.
A credit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. Minimum Spring Break check-in age is 21 years old. This property accepts Visa, Mastercard, American Express and Discover. Cash is not accepted. 

We should mention

  • Pool access available from 7:00 AM to 10:30 PM
  • Certain facilities might have restricted access. For details, you can contact the property at the number on the booking confirmation.
  • Guests may experience noise disturbance due to nearby construction work.
  • To make arrangements to bring your pet, contact the property directly at the number on your booking confirmation (please see the Fees section for related charges).

Property is also known as

Chesapeake Beach Islamorada
Chesapeake Beach Resort
Chesapeake Beach Resort Islamorada
Chesapeake Resort
Chesapeake Beach Hotel Islamorada
Chesapeake Beach Resort Hotel
Chesapeake Beach Resort Islamorada
Chesapeake Beach Resort Hotel Islamorada

Frequently asked questions

What is the cancellation policy at Chesapeake Beach Resort?

Chesapeake Beach Resort offers free cancellation on select room rates. Check out the cancellation policy for more info.

How much does it cost to stay at Chesapeake Beach Resort?

As of 15 Apr 2025, prices found for a 1-night stay for 2 adults at Chesapeake Beach Resort on 20 Apr 2025 start from NZ$488.01, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Are there any beaches close to Chesapeake Beach Resort?

The closest beach to Chesapeake Beach Resort is Anne's Beach (16.1 km).

Does Chesapeake Beach Resort have a pool?

Yep, and guests love it! Chesapeake Beach Resort has 2 outdoor swimming pools. Grab your bathers and lounge poolside while enjoying on a lounger. The pool is open 7:00 AM to 10:30 PM.

What makes Chesapeake Beach Resort a romantic place to stay?

A private beach, plus pillowtop beds in the guestrooms, help set the scene for a romantic weekend at Chesapeake Beach Resort.

Is there a free airport shuttle available at Chesapeake Beach Resort?

No, Chesapeake Beach Resort does not offer an airport shuttle service.

What time are check-in & check-out at Chesapeake Beach Resort?

Check-in begins at 4:00 PM. Check-out time is 11 AM.

Chesapeake Beach Resort Reviews

Reviews

9.0

Wonderful

Rating 10 - Excellent. 1007 out of 1430 reviews
Rating 8 - Good. 240 out of 1430 reviews
Rating 6 - Okay. 102 out of 1430 reviews
Rating 4 - Poor. 46 out of 1430 reviews
Rating 2 - Terrible. 35 out of 1430 reviews

9.2/10

Cleanliness

9.2/10

Staff & service

8.8/10

Amenities

9.2/10

Property conditions & facilities

8.8/10

Eco-friendliness

Reviews

10/10 Excellent

Holly

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
So beautiful, quiet, warm pools, excellent breakfast, views, and reception was amazing! Highly recommend!
Stayed 1 night in Jan 2025

10/10 Excellent

Riceldys

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very nice property. Staff was nice, room was nice and clean, beach area was beautiful, pool was warm, dinning options near
Stayed 1 night in Jan 2025

8/10 Good

Sean

Liked: Cleanliness, property conditions & facilities
Disliked: Staff & service
Stayed 2 nights in Dec 2024

2/10 Terrible

Heidi

Travelled with partner
Liked: Cleanliness
Disliked: Staff & service, amenities, property conditions & facilities
The front desk staff were so unfriendly. No safe in the room. Grounds were so ugly. We had a garden view that was a parking lot with sand so we had to upgrade to am ocean view for an extra $50.00. Pool staff were also not friendly and when i asked for a towel she said she would brink me one and never did.
Stayed 2 nights in Nov 2024

10/10 Excellent

Manuela

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Jan 2025

10/10 Excellent

Angela

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Not sure when they clean, but they do a good job. Good breakfast. Could use few more employees there in the morning.
Stayed 2 nights in Dec 2024

10/10 Excellent

Michele

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Jan 2025

10/10 Excellent

Karen

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful location, helpful friendly staff, great breakfast , comfy robes, pools, jacuzzi, kayaks and paddle boards.
Stayed 1 night in Jan 2025

6/10 Okay

Danielle

Travelled with family
Liked: Staff & service
Disliked: Property conditions & facilities
Christmas disappointment
We stayed over Christmas for 2 nights so it is our own fault that we severely overpaid for this resort. The guy working breakfast was awesome, however, there was never any juice selection, one day it was only cartons of egg whites, just not great options. Our room smelled like gas station bathroom air freshener and gave me a sore throat even with leaving patio door open it was so strong They did offer to move us but that room smelled similar, guessing they use really toxic cleaning supplies. Our socks were literally black from the room and it felt slippery like a film on the floor. Dont let beach pictures fool you- there is seaweed and soda bottles everywhere. I would never stay here again even if it was two hundred a night, this place needs some major TLC.
Stayed 2 nights in Dec 2024

10/10 Excellent

Joseph

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Awesome place to stay in islamorada. Quiet private beach for relaxation
Stayed 2 nights in Dec 2024

10/10 Excellent

claudia

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The rooms, including the bathroom, were recently renovated and were very clean. The staff were very friendly. I received a text shortly after check in to make sure my room was ok and if we needed anything to let them know- nice touch! They had a breakfast room with pancakes, waffles, omelets made to order, yogurts and fruits, bagels, toast, coffee and teas, cereals etc all complimentary. And speaking of complimentary, they had bikes, kayaks, paddle boards etc for your use. I would definitely recommend Chesapeake Beach Resort.
Stayed 2 nights in Dec 2024

10/10 Excellent

Marli da

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Stayed 2 nights in Jan 2025

10/10 Excellent

Margaret

Liked: Property conditions & facilities
Really lovely property, nice updated room. Bathroom could use improved lighting for mirrors, but overall very nice! Front desk staff seemed a bit frazzled & slightly unprofessional, but some customer service training could easily improve that. The bar/breakfast service and staff were very good! Cleaning and ground crew really friendly and helpful.
Stayed 2 nights in Dec 2024

10/10 Excellent

Jeannie, Girard

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved the location, beach area, breakfast and STAFF
Stayed 4 nights in Dec 2024

10/10 Excellent

Amy

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Dec 2024

10/10 Excellent

Viorel

Liked: Cleanliness, staff & service, property conditions & facilities
Great front desk staff, clean property overall. Some things never change fortunately.
Stayed 1 night in Nov 2024

10/10 Excellent

Viorel

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I'm a routine guest at this property for over 25 years. One of the best in the Keys, price and money. Great location, nearby Whale Harbour, the Sandbar, Boat rentals, 3 restaurants and one rooftop bar within a 1 minute walk, and Islamorada attractions just over the bridge. Great front desk staff, clean property overall. Some things never change fortunately.
Stayed 1 night in Dec 2024

8/10 Good

Luca

Travelled with family
Liked: Cleanliness, amenities, property conditions & facilities
Great beach and clean big well furnished rooms
Stayed 2 nights in Dec 2024

10/10 Excellent

Samara

Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful
Stayed 1 night in Sep 2024

10/10 Excellent

Bing Yi

Stayed 1 night in Dec 2024

10/10 Excellent

Jack

Liked: Staff & service, property conditions & facilities
Loved our room & view (Ocean-view King suite) and LOVED the hot tub. It saved our trip! It rained A LOT during our trip - and we very much enjoyed going from the hot tub to the heated swimming pool during the rain : )
Stayed 3 nights in Dec 2024

4/10 Poor

Lori

Travelled with family
Disliked: Cleanliness, staff & service
Very disappointing, considering hotel rate. No room for bags, no room for towels in bathroom, stains on sheets. Had to call front desk twice and then had to go to reception for change of sheets. Balcony looked out on parking area. What do you want for 700/per night. Total rip-off.
Stayed 2 nights in Dec 2024

8/10 Good

Verified traveller

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Dec 2024

10/10 Excellent

Saravanan

Liked: Cleanliness, staff & service, property conditions & facilities
Good
Stayed 1 night in Dec 2024

6/10 Okay

Michele

Disliked: Property conditions & facilities
We stayed one night at CHESAPEAKE BEACH resort en route to the keys and I would not recommend to fellow travelers. The hotel is right off a very busy road so you will hear traffic if you are situated near the front of the property. More problematic are the paper thin walls that allow you to hear every word of the conversation in the room next door as well as their 6:30 am alarm and 3:30 pm margarita party. There was very limited hot water - my husband took a cold shower and I opted to wait until our next stop as I don't enjoy a cold plunge shower. My son and I walked over to breakfast at 7 am only to be told they had run out of eggs so the "make your personalized omelette" was not in order. We had cold cereal out of plastic cups (no bowls) and a piece of toast. Upon checking out, I was informed "you'll get a receipt from Expedia" - no thank you, no how was your stay, no common courtesy. I would definitely NOT recommend this resort to others. Especially with a $600/night price tag over the holidays.
Stayed 1 night in Dec 2024