Cheap Vacations in Monroe County

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Monroe County vacations

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

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
Price was $790, price is now $467 per person
$467
per person
Jul 4 - Jul 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
3BR Pool House Sleeps 8

3BR Pool House Sleeps 8

3 out of 5
Driftwood
Price was $2,209, price is now $744 per person
$744
per person
Jul 15 - Jul 19
found 22 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
East Fort Lauderdale
Price was $1,788, price is now $658 per person
$658
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Brickell Bay 3318

Brickell Bay 3318

3 out of 5
Brickell
Price was $1,794, price is now $743 per person
$743
per person
Jul 8 - Jul 13
found 10 hours ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
Family Pool Home by Hollywood Beach

Family Pool Home by Hollywood Beach

2.5 out of 5
Hollywood Hills
Save 100% on your flight
Price was $1,570, price is now $861 per person
$861
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,544, price is now $1,434 per person
$1,434
per person
Jun 27 - Jul 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
Price was $1,159, price is now $655 per person
$655
per person
Jul 4 - Jul 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
The 27 Wynwood

The 27 Wynwood

4 out of 5
Wynwood Art District
Save 100% on your flight
Price was $1,428, price is now $821 per person
$821
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
President Hotel

President Hotel

3.5 out of 5
South Beach
Save 100% on your flight
Price was $794, price is now $471 per person
$471
per person
Jul 4 - Jul 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
The Crosby Miami World Center

The Crosby Miami World Center

4 out of 5
Downtown Miami
Save 100% on your flight
Price was $1,405, price is now $846 per person
$846
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)

3-night Monroe County vacations

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

Cavalier Hotel South Beach

3.5 out of 5
Save 100% on your flight
Price was $790, price is now $467 per person
$467
per person
Jul 4 - Jul 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
3BR Pool House Sleeps 8

3BR Pool House Sleeps 8

3 out of 5
Price was $1,833, price is now $648 per person
$648
per person
Jul 16 - Jul 19
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
Price was $1,788, price is now $658 per person
$658
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Brickell Bay 3505

Brickell Bay 3505

3 out of 5
Price was $1,546, price is now $592 per person
$592
per person
Jul 16 - Jul 19
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Brickell Bay 3318

Brickell Bay 3318

3 out of 5
Price was $1,427, price is now $598 per person
$598
per person
Jul 17 - Jul 20
found 18 hours ago
Roundtrip flight included
New York (NYC) 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 $17,108, price is now $9,171 per person
$9,171
per person
Jul 17 - Jul 20
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Family Pool Home by Hollywood Beach

Family Pool Home by Hollywood Beach

2.5 out of 5
Save 100% on your flight
Price was $1,570, price is now $861 per person
$861
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Save 100% on your flight
Price was $1,159, price is now $655 per person
$655
per person
Jul 4 - Jul 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
The 27 Wynwood

The 27 Wynwood

4 out of 5
Save 100% on your flight
Price was $1,428, price is now $821 per person
$821
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
President Hotel

President Hotel

3.5 out of 5
Save 100% on your flight
Price was $794, price is now $471 per person
$471
per person
Jul 4 - Jul 7
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
Save 100% on your flight
Price was $1,061, price is now $653 per person
$653
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip non-stop 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 $985, price is now $616 per person
$616
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)

4-night Monroe County 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 $875, price is now $503 per person
$503
per person
Jul 11 - Jul 15
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
3BR Pool House Sleeps 8

3BR Pool House Sleeps 8

3 out of 5
Price was $2,209, price is now $744 per person
$744
per person
Jul 15 - Jul 19
found 22 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
Price was $1,957, price is now $854 per person
$854
per person
Jul 1 - Jul 5
found 15 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 $19,721, price is now $11,096 per person
$11,096
per person
Jun 25 - Jun 29
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
Save 100% on your flight
Price was $1,187, price is now $672 per person
$672
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
Save 100% on your flight
Price was $1,326, price is now $765 per person
$765
per person
Jul 3 - Jul 7
found 13 hours ago
Roundtrip flight included
Islip (ISP) to Miami (MIA)
President Hotel

President Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,267, price is now $742 per person
$742
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Save 100% on your flight
Price was $1,361, price is now $805 per person
$805
per person
Jun 28 - Jul 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
The 27 Wynwood

The 27 Wynwood

4 out of 5
Save 100% on your flight
Price was $1,402, price is now $835 per person
$835
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
The Crosby Miami World Center

The Crosby Miami World Center

4 out of 5
Save 100% on your flight
Price was $1,405, price is now $846 per person
$846
per person
Jul 2 - Jul 6
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 $2,113, price is now $1,287 per person
$1,287
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
May-Dee Suites

May-Dee Suites

2.5 out of 5
Save 100% on your flight
Price was $1,107, price is now $682 per person
$682
per person
Jul 15 - Jul 19
found 22 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)

5-night Monroe County 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 $1,082, price is now $615 per person
$615
per person
Jun 29 - Jul 4
found 5 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
Price was $2,292, price is now $819 per person
$819
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
Brickell Bay 3318

Brickell Bay 3318

3 out of 5
Price was $1,794, price is now $743 per person
$743
per person
Jul 8 - Jul 13
found 10 hours ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
Family Pool Home by Hollywood Beach

Family Pool Home by Hollywood Beach

2.5 out of 5
Price was $1,938, price is now $895 per person
$895
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
Price was $2,938, price is now $1,405 per person
$1,405
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
The Avenue Hotel Coral Gables

The Avenue Hotel Coral Gables

2.5 out of 5
Save 100% on your flight
Price was $1,737, price is now $933 per person
$933
per person
Jul 8 - Jul 13
found 10 hours ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
The Landon Bay Harbor - Miami Beach

The Landon Bay Harbor - Miami Beach

3.5 out of 5
Save 100% on your flight
Price was $2,164, price is now $1,199 per person
$1,199
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Save 100% on your flight
Price was $2,544, price is now $1,434 per person
$1,434
per person
Jun 27 - Jul 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
Save 100% on your flight
Price was $3,101, price is now $1,750 per person
$1,750
per person
Jun 28 - Jul 3
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
President Hotel

President Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,241, price is now $703 per person
$703
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
Save 100% on your flight
Price was $1,212, price is now $700 per person
$700
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Lime Tree Bay Resort

Lime Tree Bay Resort

3.5 out of 5
Save 100% on your flight
Price was $1,397, price is now $810 per person
$810
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
New York (NYC) to Miami (MIA)

6-7 night Monroe County vacations

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

Riverside Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,257, price is now $696 per person
$696
per person
Jul 14 - Jul 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
Price was $3,029, price is now $1,112 per person
$1,112
per person
Jul 5 - Jul 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Family Pool Home by Hollywood Beach

Family Pool Home by Hollywood Beach

2.5 out of 5
Price was $2,664, price is now $1,205 per person
$1,205
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Price was $3,916, price is now $1,825 per person
$1,825
per person
Jul 3 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
Price was $34,234, price is now $17,732 per person
$17,732
per person
Jun 26 - Jul 3
found 22 hours ago
Roundtrip flight included
Los Angeles (LAX) to Miami (MIA)
President Hotel Villa

President Hotel Villa

3.5 out of 5
Save 100% on your flight
Price was $1,569, price is now $822 per person
$822
per person
Jul 6 - Jul 13
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Miami (MIA)
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
Price was $2,007, price is now $1,051 per person
$1,051
per person
Jul 5 - Jul 12
found 1 day ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
The Landon Bay Harbor - Miami Beach

The Landon Bay Harbor - Miami Beach

3.5 out of 5
Price was $3,002, price is now $1,620 per person
$1,620
per person
Jun 25 - Jul 2
found 22 hours ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
President Hotel

President Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,652, price is now $893 per person
$893
per person
Jun 29 - Jul 6
found 1 day ago
Roundtrip non-stop 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 $1,551, price is now $858 per person
$858
per person
Jul 5 - Jul 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
Save 100% on your flight
Price was $1,482, price is now $831 per person
$831
per person
Jul 14 - Jul 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

4 out of 5
Save 100% on your flight
Price was $2,015, price is now $1,133 per person
$1,133
per person
Jul 11 - Jul 18
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)

Top places to visit in Monroe County

FlightsFlightsHotelsHotels

Key West

Key West

Flight deals to Monroe County

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

Sun, Aug 16 - Thu, Aug 20
PHL
Philadelphia
MIA
Miami
$87 Roundtrip, found 1 day ago
$87
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Aug 16 from Philadelphia to Miami, returning Thu, Aug 20, priced at $87 found 1 day ago
Mon, Jul 6 - Thu, Jul 9
ATL
Atlanta
MIA
Miami
$88 Roundtrip, found 4 days ago
$88
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Jul 6 from Atlanta to Miami, returning Thu, Jul 9, priced at $88 found 4 days ago
Tue, Sep 15 - Sat, Sep 19
DTW
Detroit
MIA
Miami
$157 Roundtrip, just found
$157
Roundtrip
just found
Select American Airlines flight, departing Tue, Sep 15 from Detroit to Miami, returning Sat, Sep 19, priced at $157 just found

Top rated hotels for your Monroe County vacation

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
1.26 mi from city center
$184 nightly
The price is $207 total per night
$207 total
May 27 - May 28
Total with taxes and fees
A stay at Blue Flamingo Resort Key West places you in the heart of Key West, within a 10-minute drive of Stock Island Yacht Club & Marina and Key West Lighthouse and Keeper's Quarters Museum.
Pool
Hot Tub
Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
Free Cancellation
Reserve now, pay when you stay
94.82 mi from city center
$259 nightly
The price is $286 total per night
$286 total
Jun 21 - Jun 22
Total with taxes and fees
When you stay at Reefhouse Resort & Marina in Key Largo, you'll be on the waterfront, within a 5-minute drive of Florida Keys Visitor Center - Key Largo and John Pennekamp Coral Reef State Park.
On private beach
Pool
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Free Cancellation
1.8 mi from city center
$261 nightly
The price is $294 total per night
$294 total
Jun 8 - Jun 9
Total with taxes and fees
With a stay at Southernmost Beach Resort and Guesthouses, you'll be centrally located in Key West, steps from South Beach and within a 5-minute walk of Southernmost Point.
Pool
Spa
Don't see what you're looking for?
See all available properties in Monroe County
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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.