Cheap Vacations in Monroe County

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Monroe County vacations

Price found within the past 48 hours. Click for updated prices.
1818 Meridian House Apartments and Suites by Eskape Collection

1818 Meridian House Apartments and Suites by Eskape Collection

3 out of 5
South Beach
Save 100% on your flight
Price was $671, price is now $433 per person
$433
per person
Aug 19 - Aug 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Villa Italia by At Mine Hospitality

Villa Italia by At Mine Hospitality

3 out of 5
South Beach
Save 100% on your flight
Price was $1,188, price is now $581 per person
$581
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Ocean Four
Save 100% on your flight
Price was $1,030, price is now $570 per person
$570
per person
Aug 19 - Aug 26
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
South Beach
Price was $12,039, price is now $6,663 per person
$6,663
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Save 100% on your flight
Price was $1,503, price is now $857 per person
$857
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
ABAE Hotel by Eskape Collection

ABAE Hotel by Eskape Collection

3.5 out of 5
South Beach
Save 100% on your flight
Price was $922, price is now $533 per person
$533
per person
Aug 19 - Aug 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
The Marlin Hotel

The Marlin Hotel

4 out of 5
South Beach
Save 100% on your flight
Price was $924, price is now $567 per person
$567
per person
Aug 19 - Aug 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Villas At Hawks Cay Resort

Villas At Hawks Cay Resort

4 out of 5
Save 100% on your flight
Price was $1,484, price is now $951 per person
$951
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
Hollywood Beachside Boutique Suites

Hollywood Beachside Boutique Suites

3 out of 5
Hollywood Beach
Save 100% on your flight
Price was $704, price is now $457 per person
$457
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Kaskades Hotel South Beach

Kaskades Hotel South Beach

2.5 out of 5
South Beach
Save 100% on your flight
Price was $733, price is now $477 per person
$477
per person
Aug 19 - Aug 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)

3-night Monroe County vacations

Price found within the past 48 hours. Click for updated prices.
Luxuri Suites

Luxuri Suites

3 out of 5
Price was $528, price is now $359 per person
$359
per person
Aug 22 - Aug 25
found 1 day 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 $12,039, price is now $6,663 per person
$6,663
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
Save 100% on your flight
Price was $1,503, price is now $857 per person
$857
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Villas At Hawks Cay Resort

Villas At Hawks Cay Resort

4 out of 5
Save 100% on your flight
Price was $1,484, price is now $951 per person
$951
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
Beach Plaza

Beach Plaza

2 out of 5
Price was $911, price is now $630 per person
$630
per person
Aug 20 - Aug 23
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
Price was $810, price is now $560 per person
$560
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $1,557, price is now $1,090 per person
$1,090
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Marenas Beach Resort

Marenas Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,986, price is now $1,395 per person
$1,395
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $1,205, price is now $848 per person
$848
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Price was $1,024, price is now $730 per person
$730
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Save 100% on your flight
Price was $916, price is now $658 per person
$658
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Price was $864, price is now $622 per person
$622
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)

4-night Monroe County vacations

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

Soleado Hotel

3 out of 5
Save 100% on your flight
Price was $585, price is now $398 per person
$398
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Villa Italia by At Mine Hospitality

Villa Italia by At Mine Hospitality

3 out of 5
Save 100% on your flight
Price was $1,188, price is now $581 per person
$581
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $15,268, price is now $8,112 per person
$8,112
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
Save 100% on your flight
Price was $1,848, price is now $985 per person
$985
per person
Aug 23 - Aug 27
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 $723, price is now $474 per person
$474
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $1,509, price is now $1,013 per person
$1,013
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Beach Plaza

Beach Plaza

2 out of 5
Save 100% on your flight
Price was $1,023, price is now $688 per person
$688
per person
Aug 19 - Aug 23
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
The Local House

The Local House

3.5 out of 5
Save 100% on your flight
Price was $995, price is now $669 per person
$669
per person
Aug 27 - Aug 31
found 23 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
Save 100% on your flight
Price was $2,013, price is now $1,372 per person
$1,372
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Hotel AKA West Palm

Hotel AKA West Palm

4 out of 5
Save 100% on your flight
Price was $765, price is now $522 per person
$522
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Lauderdale (FLL)
Private Apartment at the Congress

Private Apartment at the Congress

4 out of 5
Price was $830, price is now $571 per person
$571
per person
Aug 27 - Aug 31
found 23 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Price was $958, price is now $660 per person
$660
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)

5-night Monroe County vacations

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

Clinton Hotel South Beach

4 out of 5
Save 100% on your flight
Price was $600, price is now $366 per person
$366
per person
Aug 27 - Sep 1
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
Price was $2,151, price is now $1,023 per person
$1,023
per person
Aug 19 - Aug 24
found 1 day 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 $17,848, price is now $8,627 per person
$8,627
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
Nobu Hotel Miami Beach

Nobu Hotel Miami Beach

5 out of 5
Save 100% on your flight
Price was $1,143, price is now $652 per person
$652
per person
Aug 26 - Aug 31
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Pelican Hotel

Pelican Hotel

4 out of 5
Save 100% on your flight
Price was $947, price is now $550 per person
$550
per person
Aug 18 - Aug 23
found 6 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
Eden Roc Miami Beach

Eden Roc Miami Beach

4.5 out of 5
Save 100% on your flight
Price was $1,107, price is now $645 per person
$645
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
Save 100% on your flight
Price was $2,501, price is now $1,502 per person
$1,502
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
EAST Miami Residences

EAST Miami Residences

5 out of 5
Save 100% on your flight
Price was $1,916, price is now $1,162 per person
$1,162
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
Private Apartment at the Congress

Private Apartment at the Congress

4 out of 5
Save 100% on your flight
Price was $818, price is now $502 per person
$502
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
Barcelona Studios Guesthouse

Barcelona Studios Guesthouse

2 out of 5
Save 100% on your flight
Price was $775, price is now $476 per person
$476
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Villas At Hawks Cay Resort

Villas At Hawks Cay Resort

4 out of 5
Save 100% on your flight
Price was $2,465, price is now $1,515 per person
$1,515
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Miami (MIA)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
Save 100% on your flight
Price was $831, price is now $511 per person
$511
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)

6-7 night Monroe County vacations

Price found within the past 48 hours. Click for updated prices.
Barcelona Studios Guesthouse

Barcelona Studios Guesthouse

2 out of 5
Save 100% on your flight
Price was $893, price is now $487 per person
$487
per person
Aug 19 - Aug 26
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $20,584, price is now $10,824 per person
$10,824
per person
Aug 21 - Aug 27
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Nobu Hotel Miami Beach

Nobu Hotel Miami Beach

5 out of 5
Save 100% on your flight
Price was $1,406, price is now $759 per person
$759
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,030, price is now $570 per person
$570
per person
Aug 19 - Aug 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Save 100% on your flight
Price was $1,582, price is now $899 per person
$899
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
President Hotel Villa

President Hotel Villa

3.5 out of 5
Save 100% on your flight
Price was $893, price is now $514 per person
$514
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
Save 100% on your flight
Price was $3,169, price is now $1,831 per person
$1,831
per person
Sep 7 - Sep 14
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $922, price is now $533 per person
$533
per person
Aug 19 - Aug 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
President Hotel

President Hotel

3.5 out of 5
Save 100% on your flight
Price was $968, price is now $565 per person
$565
per person
Aug 19 - Aug 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Save 100% on your flight
Price was $1,646, price is now $969 per person
$969
per person
Sep 7 - Sep 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
The Penguin Hotel

The Penguin Hotel

3.5 out of 5
Save 100% on your flight
Price was $906, price is now $535 per person
$535
per person
Aug 19 - Aug 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $2,309, price is now $1,399 per person
$1,399
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)

Top places to visit in Monroe County

A beach with palm trees, people sunbathing, and a resort in the background.
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.

Sat, Aug 8 - Mon, Aug 10
ATL
Atlanta
MIA
Miami
$78 Roundtrip, found 3 hours ago
$78
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Aug 8 from Atlanta to Miami, returning Mon, Aug 10, priced at $78 found 3 hours ago
Mon, Aug 17 - Thu, Aug 20
PHL
Philadelphia
MIA
Miami
$108 Roundtrip, found 5 days ago
$108
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Aug 17 from Philadelphia to Miami, returning Thu, Aug 20, priced at $108 found 5 days ago
Wed, Aug 19 - Tue, Sep 1
BOS
Boston
MIA
Miami
$163 Roundtrip, found 3 days ago
$163
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Aug 19 from Boston to Miami, returning Tue, Sep 1, priced at $163 found 3 days ago

Top rated hotels for your Monroe County vacation

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
1.36 mi from city center
$202 nightly
The price is $227 total per night
$227 total
Aug 18 - Aug 19
Total with taxes and fees
When you stay at Beachside Resort & Residences in Key West, you'll be next to a golf course, a 5-minute drive from Smathers Beach and 6 minutes from Florida Keys Beaches.
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
Reserve now, pay when you stay
1.8 mi from city center
$210 nightly
The price is $237 total per night
$237 total
Aug 18 - Aug 19
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.
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
1.32 mi from city center
$150 nightly
The price is $169 total per night
$169 total
Aug 18 - Aug 19
Total with taxes and fees
In the heart of Key West, Hilton Garden Inn Key West / The Keys Collection is within a 5-minute drive of Key West Tropical Forest and Botanical Garden and Key West Art and Historical Society.
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.