Cheap Vacations in Big Pine Key

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3-night Big Pine Key vacations

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

The Penguin Hotel

3.5 out of 5
Save 100% on your flight
Price was $816, price is now $451 per person
$451
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
Price was $1,787, price is now $869 per person
$869
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
Price was $14,283, price is now $7,172 per person
$7,172
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
Save 100% on your flight
Price was $1,032, price is now $526 per person
$526
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
President Hotel

President Hotel

3.5 out of 5
Save 100% on your flight
Price was $915, price is now $496 per person
$496
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
President Hotel Villa

President Hotel Villa

3.5 out of 5
Save 100% on your flight
Price was $915, price is now $496 per person
$496
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
Park Central South Beach

Park Central South Beach

4 out of 5
Save 100% on your flight
Price was $1,415, price is now $796 per person
$796
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
Save 100% on your flight
Price was $2,795, price is now $1,606 per person
$1,606
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Save 100% on your flight
Price was $1,060, price is now $612 per person
$612
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Save 100% on your flight
Price was $1,482, price is now $865 per person
$865
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Pelican Hotel

Pelican Hotel

4 out of 5
Save 100% on your flight
Price was $1,012, price is now $597 per person
$597
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
EAST Miami

EAST Miami

5 out of 5
Save 100% on your flight
Price was $1,450, price is now $860 per person
$860
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)

4-night Big Pine Key vacations

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

President Hotel Villa

3.5 out of 5
Price was $734, price is now $362 per person
$362
per person
Jan 19 - Jan 23
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
Price was $2,899, price is now $1,344 per person
$1,344
per person
Jan 15 - Jan 19
found 10 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $1,330, price is now $633 per person
$633
per person
Jan 8 - Jan 12
found 15 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
Price was $16,352, price is now $7,836 per person
$7,836
per person
Jan 10 - Jan 14
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Pelican Hotel

Pelican Hotel

4 out of 5
Price was $1,246, price is now $620 per person
$620
per person
Jan 15 - Jan 19
found 10 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
6080 Design Hotel by Eskape Collection

6080 Design Hotel by Eskape Collection

4 out of 5
Save 100% on your flight
Price was $692, price is now $374 per person
$374
per person
Jan 15 - Jan 19
found 10 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
Price was $3,554, price is now $1,977 per person
$1,977
per person
Jan 15 - Jan 19
found 10 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
Save 100% on your flight
Price was $1,066, price is now $613 per person
$613
per person
Jan 9 - Jan 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Save 100% on your flight
Price was $1,199, price is now $691 per person
$691
per person
Jan 6 - Jan 10
found 11 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
Save 100% on your flight
Price was $736, price is now $424 per person
$424
per person
Jan 15 - Jan 19
found 10 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
President Hotel

President Hotel

3.5 out of 5
Save 100% on your flight
Price was $643, price is now $384 per person
$384
per person
Jan 6 - Jan 10
found 11 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
The Penguin Hotel

The Penguin Hotel

3.5 out of 5
Save 100% on your flight
Price was $617, price is now $369 per person
$369
per person
Jan 6 - Jan 10
found 11 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)

5-night Big Pine Key vacations

Price found within the past 48 hours. Click for updated prices.
Beacon Hotel South Beach

Beacon Hotel South Beach

3.5 out of 5
Save 100% on your flight
Price was $634, price is now $337 per person
$337
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
Price was $1,431, price is now $670 per person
$670
per person
Jan 30 - Feb 4
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
Price was $19,349, price is now $9,253 per person
$9,253
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Pelican Hotel

Pelican Hotel

4 out of 5
Price was $1,374, price is now $657 per person
$657
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Price was $1,893, price is now $926 per person
$926
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $2,169, price is now $1,090 per person
$1,090
per person
Jan 15 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
Beach Place Hotel

Beach Place Hotel

2 out of 5
Price was $769, price is now $388 per person
$388
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
6080 Design Hotel by Eskape Collection

6080 Design Hotel by Eskape Collection

4 out of 5
Save 100% on your flight
Price was $724, price is now $367 per person
$367
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
President Hotel Villa

President Hotel Villa

3.5 out of 5
Save 100% on your flight
Price was $1,066, price is now $543 per person
$543
per person
Jan 30 - Feb 4
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Solara Surfside

Solara Surfside

3.5 out of 5
Price was $907, price is now $466 per person
$466
per person
Jan 10 - Jan 15
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
The Penguin Hotel

The Penguin Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,114, price is now $574 per person
$574
per person
Jan 15 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
EAST Miami

EAST Miami

5 out of 5
Price was $2,296, price is now $1,242 per person
$1,242
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)

6-7 night Big Pine Key vacations

Price found within the past 48 hours. Click for updated prices.
6080 Design Hotel by Eskape Collection

6080 Design Hotel by Eskape Collection

4 out of 5
Price was $1,030, price is now $502 per person
$502
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Pelican Hotel

Pelican Hotel

4 out of 5
Price was $1,781, price is now $817 per person
$817
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
President Hotel Villa

President Hotel Villa

3.5 out of 5
Price was $1,728, price is now $808 per person
$808
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
Price was $31,145, price is now $14,937 per person
$14,937
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $2,303, price is now $1,140 per person
$1,140
per person
Jan 7 - Jan 14
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Flow Fort Lauderdale Hotel

Flow Fort Lauderdale Hotel

3.5 out of 5
Price was $1,718, price is now $861 per person
$861
per person
Jan 13 - Jan 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
President Hotel

President Hotel

3.5 out of 5
Price was $1,579, price is now $797 per person
$797
per person
Jan 11 - Jan 18
found 6 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Park Central South Beach

Park Central South Beach

4 out of 5
Price was $2,633, price is now $1,362 per person
$1,362
per person
Jan 11 - Jan 18
found 7 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
The Penguin Hotel

The Penguin Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,270, price is now $657 per person
$657
per person
Jan 11 - Jan 18
found 6 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
Save 100% on your flight
Price was $2,173, price is now $1,148 per person
$1,148
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Solara Surfside

Solara Surfside

3.5 out of 5
Save 100% on your flight
Price was $1,509, price is now $798 per person
$798
per person
Jan 11 - Jan 18
found 6 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Villas At Hawks Cay Resort

Villas At Hawks Cay Resort

4 out of 5
Price was $2,529, price is now $1,338 per person
$1,338
per person
Jan 17 - Jan 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)

Flight deals to Big Pine Key

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Dec 20 - Tue, Dec 23
ATL
Atlanta
MIA
Miami
$51 Roundtrip, just found
$51
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Dec 20 from Atlanta to Miami, returning Tue, Dec 23, priced at $51 just found
Mon, Jan 12 - Fri, Jan 30
DTW
Detroit
MIA
Miami
$59 Roundtrip, found 4 days ago
$59
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Jan 12 from Detroit to Miami, returning Fri, Jan 30, priced at $59 found 4 days ago
Tue, Jan 6 - Sat, Jan 10
PHL
Philadelphia
MIA
Miami
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jan 6 from Philadelphia to Miami, returning Sat, Jan 10, priced at $63 found 1 day ago

Top rated hotels for your Big Pine Key vacation

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

2.5 out of 5
1791 Bogie Drive Big Pine Key FL
1.94 mi from city center
$254 nightly
The price is $286 total per night
$286 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
With a stay at Old Wooden Bridge Resort and Marina in Big Pine Key (Punta Brisa), you'll be within a 15-minute drive of Florida Keys Beaches and Blue Hole.
Pool
Pet friendly
Barnacle Resort

Barnacle Resort

3 out of 5
1557 Long Beach Dr Big Pine Key FL
2.36 mi from city center
$251 nightly
The price is $283 total per night
$283 total
Dec 8 - Dec 9
Total with taxes and fees
With a stay at Barnacle Resort in Big Pine Key (Long Beach Estates), you'll be steps from Florida Keys Beaches and Coupon Bight Aquatic Preserve.
Parking included
Free WiFi
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Charming 3-bedroom house in Big Pine Key near Beach and Key West

Big Pine Key FL
0.85 mi from city center
$567 nightly
The price is $628 total per night
$628 total
Dec 7 - Dec 8
Total with taxes and fees
With a stay at this vacation home in Big Pine Key (Sands), you'll be within a 15-minute drive of Florida Keys Beaches and Bahia Honda State Park.
Kitchen
Washer
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.