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 $634, price is now $366 per person
$366
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Iberostar Waves Berkeley Shore

Iberostar Waves Berkeley Shore

4 out of 5
Price was $1,006, price is now $456 per person
$456
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
Price was $1,500, price is now $680 per person
$680
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $1,011, price is now $459 per person
$459
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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)
Flow Brickell

Flow Brickell

3 out of 5
Save 100% on your flight
Price was $813, price is now $433 per person
$433
per person
Jan 27 - Jan 30
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Flow Fort Lauderdale Hotel

Flow Fort Lauderdale Hotel

3.5 out of 5
Save 100% on your flight
Price was $701, price is now $388 per person
$388
per person
Jan 12 - Jan 15
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Sentral Wynwood

Sentral Wynwood

4 out of 5
Save 100% on your flight
Price was $682, price is now $384 per person
$384
per person
Jan 27 - Jan 30
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
EAST Miami

EAST Miami

5 out of 5
Price was $1,374, price is now $775 per person
$775
per person
Jan 27 - Jan 30
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Save 100% on your flight
Price was $1,192, price is now $680 per person
$680
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Key West (EYW)
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Save 100% on your flight
Price was $1,020, price is now $585 per person
$585
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
President Hotel

President Hotel

3.5 out of 5
Save 100% on your flight
Price was $661, price is now $380 per person
$380
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)

4-night Big Pine Key vacations

Price found within the past 48 hours. Click for updated prices.
Hollywood by the Sea Hotel

Hollywood by the Sea Hotel

3 out of 5
Price was $1,096, price is now $327 per person
$327
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $1,061, price is now $471 per person
$471
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 $2,943, price is now $1,411 per person
$1,411
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $16,199, price is now $8,028 per person
$8,028
per person
Jan 22 - Jan 26
found 21 hours ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
Save 100% on your flight
Price was $1,291, price is now $647 per person
$647
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Miami (MIA)
President Hotel

President Hotel

3.5 out of 5
Price was $1,214, price is now $613 per person
$613
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
The Penguin Hotel

The Penguin Hotel

3.5 out of 5
Save 100% on your flight
Price was $988, price is now $512 per person
$512
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
President Hotel Villa

President Hotel Villa

3.5 out of 5
Save 100% on your flight
Price was $1,135, price is now $608 per person
$608
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Miami (MIA)
Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Save 100% on your flight
Price was $826, price is now $452 per person
$452
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Amara Cay Resort

Amara Cay Resort

4 out of 5
Save 100% on your flight
Price was $976, price is now $543 per person
$543
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Pelican Hotel

Pelican Hotel

4 out of 5
Save 100% on your flight
Price was $1,213, price is now $680 per person
$680
per person
Jan 22 - Jan 26
found 21 hours ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Save 100% on your flight
Price was $1,277, price is now $721 per person
$721
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)

5-night Big Pine Key vacations

Price found within the past 48 hours. Click for updated prices.
Hollywood by the Sea Hotel

Hollywood by the Sea Hotel

3 out of 5
Price was $1,129, price is now $348 per person
$348
per person
Jan 11 - Jan 16
found 16 hours ago
Roundtrip flight included
Baltimore (BWI) 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 6 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 21 hours 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 21 hours 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 $1,386, price is now $676 per person
$676
per person
Jan 11 - Jan 16
found 19 hours ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $1,720, price is now $840 per person
$840
per person
Jan 11 - Jan 16
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
Price was $1,039, price is now $509 per person
$509
per person
Jan 11 - Jan 16
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Key West (EYW)
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 6 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 Key West Hotel

The Key West Hotel

2.5 out of 5
Price was $2,830, price is now $1,501 per person
$1,501
per person
Jan 11 - Jan 16
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Key West (EYW)
EAST Miami

EAST Miami

5 out of 5
Price was $2,289, price is now $1,232 per person
$1,232
per person
Jan 24 - Jan 29
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
President Hotel

President Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,274, price is now $693 per person
$693
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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
Save 100% on your flight
Price was $915, price is now $443 per person
$443
per person
Jan 8 - Jan 15
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 20 hours 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)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
Price was $1,716, price is now $814 per person
$814
per person
Jan 15 - Jan 22
found 24 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Le Particulier Miami

Le Particulier Miami

3.5 out of 5
Price was $1,177, price is now $567 per person
$567
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Renzzi Wynwood Apartments

Renzzi Wynwood Apartments

4 out of 5
Price was $1,140, price is now $556 per person
$556
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $1,971, price is now $983 per person
$983
per person
Jan 7 - Jan 13
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Flow Brickell

Flow Brickell

3 out of 5
Price was $1,651, price is now $827 per person
$827
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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)
Prestige Retreat by Renzzi

Prestige Retreat by Renzzi

3 out of 5
Price was $1,243, price is now $635 per person
$635
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Solara Surfside

Solara Surfside

3.5 out of 5
Price was $1,118, price is now $580 per person
$580
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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.

Mon, Dec 22 - Thu, Dec 25
ATL
Atlanta
MIA
Miami
$51 Roundtrip, just found
$51
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, Dec 22 from Atlanta to Miami, returning Thu, Dec 25, 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
$545 nightly
The price is $604 total per night
$604 total
Dec 8 - Dec 9
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
Don't see what you're looking for?
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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.