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Top hotels in Cross Key Waterways

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $228 total per night from Sep 7 to Sep 8
$228 total
Sep 7 - Sep 8
Total with taxes and fees
A private beach, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind ...
"Amazing breakfast, clean room and very friendly staff."

Reviewed on Aug 21, 2026

Opens in a new windowChesapeake Beach Resort
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $149 total per night from Aug 24 to Aug 25
$149 total
Aug 24 - Aug 25
Total with taxes and fees
A marina and an outdoor pool are featured at this smoke-free hotel. WiFi in public areas is free. A terrace, a picnic area, and luggage storage are also on ...
"Great stay overall !!! ⭐️⭐️⭐️⭐️⭐️"

Reviewed on Aug 21, 2026

Opens in a new windowWaterside Suites & Marina
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

4.5 out of 5
97450 Overseas Highway Key Largo FL
Fully refundableReserve now, pay when you stay
$296 nightly
The price is $333 total per night from Sep 20 to Sep 21
$333 total
Sep 20 - Sep 21
Total with taxes and fees
This luxury resort features a full-service spa, a marina, and 3 restaurants. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Enjoy the ...
"We had a wonderful stay at Playa Largo Resort & Spa. The resort is absolutely beautiful, with breathtaking views, a relaxing atmosphere, and excellent amenities. The staff was friendly, attentive, and made us feel welcome throughout our entire stay. We truly enjoyed every moment and created beautiful ..."

Reviewed on Aug 21, 2026

Opens in a new windowPlaya Largo Resort & Spa, Autograph Collection
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$272 nightly
The price is $306 total per night from Aug 30 to Aug 31
$306 total
Aug 30 - Aug 31
Total with taxes and fees
This Art Deco resort features a private beach, a marina, and 4 restaurants. Enjoy a day at the beach snorkeling, or relax with sun loungers. Families will appreciate ...
"Shuttle driver was driving while in personal FaceTime call. Did not move to help with van door which was hard to close. The resort is beautiful and we really enjoyed the amenities."

Reviewed on Aug 19, 2026

Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay

2.5 out of 5
102400 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $147 total per night from Aug 31 to Sep 1
$147 total
Aug 31 - Sep 1
Total with taxes and fees
A private beach and an outdoor pool are featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi ...
"While the property itself was clean and the staff was polite, our stay was completely derailed by the unacceptable condition of the beds in Room 148. At 72 years old, after driving all the way down from Palm Beach County, working a physically demanding job for several hours and dealing with an injured ..."

Reviewed on Aug 20, 2026

Opens in a new windowHampton Inn Key Largo Manatee Bay
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

4 out of 5
97000 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$302 nightly
The price is $340 total per night from Sep 21 to Sep 22
$340 total
Sep 21 - Sep 22
Total with taxes and fees
A private beach, 2 restaurants, and 2 outdoor pools are all featured at this resort. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...
Opens in a new windowBaker's Cay Resort Key Largo, Curio Collection by Hilton
Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$259 nightly
The price is $286 total per night from Aug 23 to Aug 24
$286 total
Aug 23 - Aug 24
Total with taxes and fees
This luxury hotel features a private beach, a full-service spa, and a marina. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Family-friendly ...
Opens in a new windowReefhouse Resort & Marina
Bayside Inn Key Largo

Bayside Inn Key Largo

3 out of 5
99490 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $171 total per night from Aug 31 to Sep 1
$171 total
Aug 31 - Sep 1
Total with taxes and fees
A private beach, a 24-hour gym, and a restaurant are all featured at this hotel. Enjoy a day at the beach snorkeling, or relax with sun loungers. Enjoy the outdoor ...
Opens in a new windowBayside Inn Key Largo
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

2 out of 5
99340 Overseas Highway Key Largo FL
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $103 total per night from Aug 25 to Aug 26
$103 total
Aug 25 - Aug 26
Total with taxes and fees
This smoke-free hotel's private beach and marina are among the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. ...
Opens in a new windowThe Pelican Key Largo Cottages
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Cross Key Waterways Hotel Guide

Don’t keep your travel plans on repeat year after year. The same city with the same hotel every season will bore you and give you an itch to go looking for something new. Expand your geographical horizons to more than just those five blocks around your usual haunt.

Nowhere else can you find better deals on Cross Key Waterways area hotels. You’ll find the best prices on the quirky, the haunted, the old, the new, and the legendary. If you’re wondering what side of the pricing scale some of these hotels fall on, you need not to worry. Compare cheap hotels near Cross Key Waterways to find the perfect one to will fit your budget.

Leave the ordinary routine you’re set on behind and go. Go anywhere you want. Anywhere that makes you think, “I wonder what that’s like?” Part of Travelocity’s mission is to get you off-the-beaten path and the hotels near Cross Key Waterways are perfect for that. Find your new favorite watering hole on a quiet street. Discover a place to escape for the weekend with tasty local fare and unique sights. We want you to consider the places outside your normal comfort zone. Browse our selection and find the ideal hotel, in a place you’d like to explore.

Recent Cross Key Waterways hotel reviews by fellow wanderers

Chesapeake Beach Resort

Chesapeake Beach Resort

5 out of 5
Posted 3 hours ago
Travelocity Verified Review
"Amazing breakfast, clean room and very friendly staff."
A verified traveler stayed at Chesapeake Beach Resort
Chesapeake Beach Resort

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