Name: Old Wooden Bridge Resort and Marina
Price range: $286 total
Rating: 8.6

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Your Lower Keys Vacation

Make planning your next big getaway quick and easy with a Lower Keys vacation package. Whether it's history, nature or something else entirely that brings you here, our package deals will help you discover the best of it. A trip to Lower Keys wouldn't be complete without spending a day or two in Cudjoe Key. This city is one of the most well-known places to visit here. When you're ready to stop dreaming and start packing, Expedia will help turn your Lower Keys vacation into reality.

The Latest Lower Keys vacation packages

Price found within the past 48 hours. Click for updated prices.

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$1,105

per person

Jul 15 - Jul 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,079 reviews)

The property staff wasn’t as attentive as I would have hoped at a resort like this. The rooms were spacious and clean.

Reviewed on May 12, 2026

Hyatt Vacation Club at Sunset Harbor, Key West

Old Town Key West

Save 100% on your flight

$1,625

per person

Jul 30 - Aug 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (367 reviews)

Stayed in a one bedroom unit. Good size kitchen/living room, however bathroom was tiny. Bedroom was ok.. lots of closet/storage, however bed could have been bigger. Location was awesome… just a couple blocks to everything!

Reviewed on May 6, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,686

per person

Jul 30 - Aug 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (552 reviews)

The staff at the hotel were excellent. Very friendly and helpful. Room was very clean and comfortable. We were right in the middle of the old district which had many many places to explore. Hotel had a wonderful hidden pool with live music/bar next to it in case we just wanted to relax after exploring all day.

Reviewed on Apr 21, 2026

The Gardens Hotel

Old Town Key West

Save 100% on your flight

$1,759

per person

Jul 30 - Aug 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,001 reviews)

I have rarely been so positively surprised by a hotel. The outdoor areas (pool, gardens, bar) were more spacious than I expected, and impeccably maintained. It is so tranquil and peaceful, yet so close to the action. The Master Suite was super nice - large balcony, private sauna, and 2 bathrooms. Would definitely come back.

Reviewed on May 14, 2026

Hyatt Vacation Club at Beach House, Key West

Save 100% on your flight

$1,114

per person

Jul 15 - Jul 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,045 reviews)

This property is amazing! The rooms are like little apartments and very clean. The staff was extremely kind and helpful. We will be back again next year because our experience was sooo wonderful!

Reviewed on May 15, 2026

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Where to stay in Lower Keys

Find the best Lower Keys areas and neighborhoods for the activities you enjoy most. Learn more about Lower Keys

Bahia Honda State Park beach in the Florida Keys near the overseas highway bridge.

Big Coppitt Key

If you're spending some time in Big Coppitt Key, Shark Key and Wilhelmina Harvey Park are top sights worth seeing.

Discover the most popular places to visit in Lower Keys

Calusa Beach

Why not spend a lazy afternoon at Calusa Beach during your trip to Big Pine Key? While you're in the area, wander around the natural setting.

Boca Chica Marina Key West Florida damaged by Hurricane Irma

Boca Chica Beach

Why not spend a lazy afternoon at Boca Chica Beach during your trip to Key West? Stroll along the area's seaside, or simply savor its lively bars.

Sugarloaf Beach

Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?

What to do in Lower Keys

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

$45

per adult

94% of travellers recommend

Key West Sunset Sail with Live Music, Drinks and Appetizers!

$80

per traveler

92% of travellers recommend

12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

$27

per adult

88% of travellers recommend

See all activities in Lower Keys

Lower Keys Hotel Deals

Parmer's Resort

565 Barry Avenue Summerland Key FL

Fully refundableReserve now, pay when you stay

$169 nightly

$190 total

May 20 - May 21

Total with taxes and fees

9/10 Wonderful! (1,000 reviews)

Breakfast was a nice continental assortment. We had a partial ocean view.

Reviewed on May 13, 2026

Sugarloaf Key Hotel at KOA Resort

251 Co Rd 939 Summerland Key FL

9.8/10 Exceptional! (569 reviews)

Would recommend to anyone! Love this place!

Reviewed on May 12, 2026

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Old Wooden Bridge Resort and Marina

1791 Bogie Drive Big Pine Key FL

$254 nightly

$286 total

May 21 - May 22

Total with taxes and fees

8.6/10 Excellent! (336 reviews)

No soap, no nothing. Marina and Aqualodge smelled soooo bad like sewage. We could not stay in there. Moved to a house. Beds were really lumpy. Pool was closed the entire time we were there. Deer are adorable.

Reviewed on May 7, 2026

See all 820 properties in Lower Keys

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.