
Lower Florida Keys Vacation Packages
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3.5-star property
Ridley House - Key West Historic Inns
Key West Historic District
9.2/10 Wonderful! (819 reviews)
Dec 27 - Jan 1
5 night stay
Detroit (DTW) to Key West (EYW)
American Airlines • Non-stop • Coach
Key West (EYW) to Detroit (DTW)
Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,533, price is now $1,503 per person
$1,503
per person
found 1 day ago
Breakfasts with Chef Andrew were amazing
Reviewed on Feb 19, 2025

3.5-star property
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
9/10 Wonderful! (791 reviews)
Dec 27 - Jan 1
5 night stay
Detroit (DTW) to Key West (EYW)
American Airlines • Non-stop • Coach
Key West (EYW) to Detroit (DTW)
Southwest Airlines • Non-stop • Coach
Price was $3,397, price is now $1,744 per person
$1,744
per person
found 1 day ago
This place is a much better place to stay than places closer to the cruise ship pier or off or whitehead or duval
Reviewed on Sep 22, 2024

4.0-star property
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
9.2/10 Wonderful! (1,005 reviews)
Dec 27 - Jan 1
5 night stay
Detroit (DTW) to Key West (EYW)
American Airlines • Non-stop • Coach
Key West (EYW) to Detroit (DTW)
Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,931, price is now $1,594 per person
$1,594
per person
found 1 day ago
Friendly staff. Tasty breakfast. Comfortable pools. Nice rooms.
Reviewed on Jul 15, 2025

3.5-star property
Fitch Lodge - Key West Historic Inns
Key West Historic District
8.8/10 Excellent! (484 reviews)
Dec 27 - Jan 1
5 night stay
Detroit (DTW) to Key West (EYW)
American Airlines • Non-stop • Coach
Key West (EYW) to Detroit (DTW)
Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,847, price is now $1,557 per person
$1,557
per person
found 1 day ago
My only complaint is. “Pet friendly” property shouldn’t charge $100 to bring said pet. A deposit fine, but otherwise it’s ripoff
Reviewed on Jun 21, 2024

3.5-star property
Ella's Cottages - Key West Historic Inns
Old Town Key West
9.4/10 Exceptional! (375 reviews)
Dec 27 - Jan 1
5 night stay
Detroit (DTW) to Key West (EYW)
American Airlines • Non-stop • Coach
Key West (EYW) to Detroit (DTW)
Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $3,687, price is now $2,101 per person
$2,101
per person
found 1 day ago
We chose this historic inn based on central location to everything we wanted in less than 15 min. Front desk staff (Dwight and others) are fantastic and always willing to listen and provide assistance. Fort Zachary Taylor Beach Park is walkable - 25 min (beach water shoes recommended due to rocks). We didn't need to rent any transportation as it was easier for us to walk it out, so I can't comment on parking since I didn't use it (it is limited at most places). We felt very safe walking around, even at night. We used a taxi to and from Key West airport (both drivers familiar with this inn). Room is clean. Both night stands have power and USB charging outlets. Excellent daily room service and Sunshine Breakfast basket hand delivered to your room. Duval Loop bus stop 14 (free) in front of inn (bus route loop is an hour long and two buses running to ensure next bus in 30 min), so this is another convenient option if walking isn't your thing.
Reviewed on Dec 17, 2024
Top rated hotels for your Lower Florida Keys vacation package

Parmer's Resort
565 Barry Avenue, Summerland Key, FL
Free Cancellation
Reserve now, pay when you stay
15.31 mi from city center
$158 nightly
The price is $178 total per night
$178 total
Oct 7 - Oct 8
Total with taxes and fees
Guests of Parmer's Resort have access to a private beach, a marina, and an outdoor pool. A stay here includes free parking. The front desk has multilingual staff that can help with tours/tickets and luggage storage. Other amenities at this beach motel include free WiFi in public areas, coffee/tea in a common area, and a microwave in a common area.
On private beach
Pool

Sugar Loaf Lodge
17001 Overseas Hwy, Summerland Key, FL
Free Cancellation
Reserve now, pay when you stay
4.06 mi from city center
$99 nightly
The price is $111 total per night
$111 total
Oct 7 - Oct 8
Total with taxes and fees
Guests staying at Sugar Loaf Lodge enjoy access to a marina, an outdoor pool, and outdoor tennis courts. If you drive, take advantage of free parking. Front-desk staff can help with tours or tickets, and provide local restaurant recommendations. Additional amenities include free WiFi in public areas, a garden, and a vending machine.
Pool
Parking included

Looe Key Reef Resort
27340 Overseas Highway, Summerland Key, FL
Free Cancellation
Reserve now, pay when you stay
14.08 mi from city center
$145 nightly
The price is $163 total per night
$163 total
Oct 8 - Oct 9
Total with taxes and fees
Guests staying at Looe Key Reef Resort enjoy karaoke, an outdoor pool, and free WiFi in public areas. If you drive, put free parking to good use. Front-desk staff can assist with luggage storage and tours/tickets. Additional amenities include express check-in, a vending machine, and a picnic area.
Pool
Pet friendly
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