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.
6080 Design Hotel by Eskape Collection

6080 Design Hotel by Eskape Collection

4 out of 5
Save 100% on your flight
Price was $557, price is now $279 per person
$279
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Pelican Hotel

Pelican Hotel

4 out of 5
Price was $851, price is now $395 per person
$395
per person
Feb 7 - Feb 10
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 $701, price is now $333 per person
$333
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
President Hotel

President Hotel

3.5 out of 5
Price was $770, price is now $380 per person
$380
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Creekside Inn

Creekside Inn

2.5 out of 5
Save 100% on your flight
Price was $984, price is now $511 per person
$511
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Save 100% on your flight
Price was $1,066, price is now $557 per person
$557
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Price was $1,345, price is now $717 per person
$717
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
EAST Miami

EAST Miami

5 out of 5
Save 100% on your flight
Price was $1,379, price is now $766 per person
$766
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Save 100% on your flight
Price was $866, price is now $489 per person
$489
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
BEST DEAL! 2BR Modern Beachfront Ocean Drive WiFi

BEST DEAL! 2BR Modern Beachfront Ocean Drive WiFi

3 out of 5
Save 100% on your flight
Price was $1,039, price is now $588 per person
$588
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,181, price is now $690 per person
$690
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Clarion Inn & Suites Miami International Airport

Clarion Inn & Suites Miami International Airport

2.5 out of 5
Save 100% on your flight
Price was $503, price is now $297 per person
$297
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)

4-night Big Pine Key vacations

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites Miami Exec Airport - Kendall by IHG

Candlewood Suites Miami Exec Airport - Kendall by IHG

2.5 out of 5
Save 100% on your flight
Price was $434, price is now $246 per person
$246
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Pelican Hotel

Pelican Hotel

4 out of 5
Price was $1,175, price is now $524 per person
$524
per person
Jan 29 - Feb 2
found 7 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
Price was $1,014, price is now $486 per person
$486
per person
Jan 24 - Jan 28
found 18 hours 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
Price was $1,230, price is now $644 per person
$644
per person
Feb 2 - Feb 6
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton

Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton

4 out of 5
Save 100% on your flight
Price was $1,031, price is now $571 per person
$571
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Clarion Inn & Suites Miami International Airport

Clarion Inn & Suites Miami International Airport

2.5 out of 5
Save 100% on your flight
Price was $872, price is now $485 per person
$485
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Save 100% on your flight
Price was $3,147, price is now $1,770 per person
$1,770
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Save 100% on your flight
Price was $1,762, price is now $1,001 per person
$1,001
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
President Hotel

President Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,125, price is now $646 per person
$646
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
Price was $3,452, price is now $1,990 per person
$1,990
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 out of 5
Save 100% on your flight
Price was $1,769, price is now $1,025 per person
$1,025
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Miami (MIA)

5-night Big Pine Key vacations

Price found within the past 48 hours. Click for updated prices.
BEST DEAL! 2BR Modern Beachfront Ocean Drive WiFi

BEST DEAL! 2BR Modern Beachfront Ocean Drive WiFi

3 out of 5
Save 100% on your flight
Price was $838, price is now $409 per person
$409
per person
Feb 1 - Feb 6
found 10 hours ago
Roundtrip flight included
Chicago (ORD) 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 $20,914, price is now $9,374 per person
$9,374
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
Pelican Hotel

Pelican Hotel

4 out of 5
Price was $1,391, price is now $624 per person
$624
per person
Jan 30 - Feb 4
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 $1,756, price is now $805 per person
$805
per person
Feb 5 - Feb 10
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
Price was $992, price is now $464 per person
$464
per person
Jan 19 - Jan 24
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Broadmore Miami Beach

Broadmore Miami Beach

3.5 out of 5
Price was $882, price is now $437 per person
$437
per person
Feb 5 - Feb 10
found 3 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 $1,316, price is now $658 per person
$658
per person
Feb 7 - Feb 12
found 13 hours ago
Roundtrip non-stop 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 $1,190, price is now $603 per person
$603
per person
Feb 7 - Feb 12
found 13 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
ABAE Hotel by Eskape Collection

ABAE Hotel by Eskape Collection

3.5 out of 5
Save 100% on your flight
Price was $938, price is now $480 per person
$480
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Barnacle Resort

Barnacle Resort

3 out of 5
Price was $1,339, price is now $689 per person
$689
per person
Jan 22 - Jan 27
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Beach Place Hotel

Beach Place Hotel

2 out of 5
Save 100% on your flight
Price was $961, price is now $506 per person
$506
per person
Feb 7 - Feb 12
found 13 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
Save 100% on your flight
Price was $1,048, price is now $555 per person
$555
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Miami (MIA)

6-7 night Big Pine Key vacations

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

Broadmore Miami Beach

3.5 out of 5
Save 100% on your flight
Price was $1,040, price is now $543 per person
$543
per person
Feb 1 - Feb 7
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $1,986, price is now $839 per person
$839
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Price was $2,312, price is now $1,006 per person
$1,006
per person
Feb 4 - Feb 11
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
President Hotel

President Hotel

3.5 out of 5
Price was $1,678, price is now $762 per person
$762
per person
Feb 4 - Feb 11
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
The Penguin Hotel

The Penguin Hotel

3.5 out of 5
Price was $1,456, price is now $667 per person
$667
per person
Feb 4 - Feb 11
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Beach Place Hotel

Beach Place Hotel

2 out of 5
Price was $1,210, price is now $569 per person
$569
per person
Feb 4 - Feb 11
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Park Central South Beach

Park Central South Beach

4 out of 5
Price was $2,015, price is now $965 per person
$965
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
6080 Design Hotel by Eskape Collection

6080 Design Hotel by Eskape Collection

4 out of 5
Price was $1,195, price is now $573 per person
$573
per person
Feb 4 - Feb 11
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Solara Surfside

Solara Surfside

3.5 out of 5
Price was $1,470, price is now $716 per person
$716
per person
Feb 4 - Feb 11
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Nomada Residences

Nomada Residences

4 out of 5
Price was $1,773, price is now $898 per person
$898
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Price was $2,089, price is now $1,060 per person
$1,060
per person
Feb 1 - Feb 7
found 20 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
Barnacle Resort

Barnacle Resort

3 out of 5
Price was $1,584, price is now $824 per person
$824
per person
Jan 21 - Jan 27
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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, Jan 12 - Thu, Jan 15
PHL
Philadelphia
MIA
Miami
$59 Roundtrip, found 3 days ago
$59
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Mon, Jan 12 from Philadelphia to Miami, returning Thu, Jan 15, priced at $59 found 3 days ago
Tue, Dec 16 - Sun, Dec 21
ATL
Atlanta
MIA
Miami
$59 Roundtrip, found 5 days ago
$59
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Dec 16 from Atlanta to Miami, returning Sun, Dec 21, priced at $59 found 5 days ago
Thu, Jan 22 - Wed, Jan 28
BOS
Boston
MIA
Miami
$62 Roundtrip, found 3 days ago
$62
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, Jan 22 from Boston to Miami, returning Wed, Jan 28, priced at $62 found 3 days 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
$294 nightly
The price is $331 total per night
$331 total
Jan 10 - Jan 11, 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
$256 nightly
The price is $288 total per night
$288 total
Dec 16 - Dec 17
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
$685 nightly
The price is $761 total per night
$761 total
Dec 21 - Dec 22
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.