Lower Keys Vacation Packages for 2026

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Top Hotel Deals

Looe Key Reef Resort

Looe Key Reef Resort

2.5 out of 5
27340 Overseas Highway Summerland Key FL
9.13 km from city center
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Parmer's Resort

Parmer's Resort

2.5 out of 5
565 Barry Avenue Summerland Key FL
10.76 km from city center
Book a stay at this beach motel in Summerland Key. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

2.5 out of 5
1791 Bogie Drive Big Pine Key FL
14.91 km from city center
Stay at this cottage in Big Pine Key. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Bahia ...
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 out of 5
17001 Overseas Hwy Summerland Key FL
8.16 km from city center
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
251 Co Rd 939 Summerland Key FL
3.36 km from city center
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Barnacle Resort

Barnacle Resort

3 out of 5
1557 Long Beach Dr Big Pine Key FL
15.59 km from city center
Book a stay at this beach B&B in Big Pine Key. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Bahia Honda State Park and Coupon Bight ...
Little Torch Cottages

Little Torch Cottages

2 out of 5
28501 Channel View Drive Summerland Key FL
10.98 km from city center
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Big Pine Key Flea Market and Blue Hole are located ...
Sunshine Key RV Resort & Marina

Sunshine Key RV Resort & Marina

2 out of 5
38801 Overseas Highway Big Pine Key FL
25.09 km from city center
Enjoy a private beach, a marina, and laundry facilities. Popular attractions Bahia Honda State Park and Sandspur Beach are located nearby.
Don't see what you're looking for?
See all available properties in Lower Keys
View all properties
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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Sat, Jan 17 - Wed, Jan 21
TPA
Tampa Intl.
EYW
Key West Intl.
$230 Roundtrip, found 3 days ago
$230
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Jan 17 from Tampa Intl. to Key West Intl., returning Wed, Jan 21, priced at $230 found 3 days ago
American Airlines
Wed, Apr 1 - Tue, Apr 7
ORD
O'Hare Intl.
EYW
Key West Intl.
$249 Roundtrip, found 3 days ago
$249
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Apr 1 from O'Hare Intl. to Key West Intl., returning Tue, Apr 7, priced at $249 found 3 days ago
Delta
Wed, Mar 4 - Tue, Mar 10
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$259 Roundtrip, found 3 days ago
$259
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Mar 4 from Baltimore Washington Intl. Thurgood Marshall to Key West Intl., returning Tue, Mar 10, priced at $259 found 3 days ago
United
Sat, Jan 31 - Tue, Feb 3
ORD
O'Hare Intl.
EYW
Key West Intl.
$272 Roundtrip, found 5 days ago
$272
Roundtrip
found 5 days ago
Select United flight, departing Sat, Jan 31 from O'Hare Intl. to Key West Intl., returning Tue, Feb 3, priced at $272 found 5 days ago
Spirit Airlines
Wed, Apr 1 - Tue, Apr 7
ORD
O'Hare Intl.
EYW
Key West Intl.
$319 Roundtrip, found 3 days ago
$319
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Apr 1 from O'Hare Intl. to Key West Intl., returning Tue, Apr 7, priced at $319 found 3 days ago