Cow Key Vacations from $247
Book a Hotel + Flight or Car together to unlock savings
Your Cow Key Vacation
When you book a vacation package to Cow Key, you can relax and enjoy your escape knowing that all your travel arrangements have been worked out ahead of time. Uncover the wonders of this lively city from your base in a neighborhood like Sunset Key, which is good for coastal beaches. If your trip to Cow Key includes some sightseeing, check out famous attractions like Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Your ideal Cow Key vacation is only clicks away. Explore hotels, flights and more on Expedia for an adventure that's tailored to suit your travel style.
The Latest Cow Key vacation packages
Price found within the past 48 hours. Click for updated prices.
Avalon Hotel
South Beach
Save 100% on your flight
Price was $510, price is now $247 per person
$247
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (1,018 reviews)
Cross street to the beach. Very popular and busy area. Staffs are nice.
Reviewed on Aug 25, 2025
Cow Key Hotel Deals
Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $207 total per night from Aug 27 to Aug 28
$207 total
Aug 27 - Aug 28
Total with taxes and fees
8.4/10 Very Good! (1,479 reviews)
"The property was excellent, located in the heart of everything!! 😍"
Reviewed on Aug 23, 2025
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $247 total per night from Sep 2 to Sep 3
$247 total
Sep 2 - Sep 3
Total with taxes and fees
8.8/10 Excellent! (1,729 reviews)
"Excellent service"
Reviewed on Aug 25, 2025
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $149 total per night from Sep 2 to Sep 3
$149 total
Sep 2 - Sep 3
Total with taxes and fees
7.8/10 Good! (1,070 reviews)
"Most excellent facility with very accommodating staff."
Reviewed on Aug 18, 2025
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.
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Flights to Key West
- Flights from Philadelphia (PHL) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Miami (MIA) to Key West (EYW)
- Flights from Boston (BOS) to Key West (EYW)
- Flights from New York (JFK) to Key West (EYW)
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Flights from Fort Myers (RSW) to Key West (EYW)
- Flights from Chicago (ORD) to Key West (EYW)
- Flights from Atlanta (ATL) to Key West (EYW)
- Flights from Baltimore (BWI) to Key West (EYW)
- Flights from Charlotte (CLT) to Key West (EYW)
- Flights from Key West Intl.
- Flights from Detroit (DTW) to Key West (EYW)
- Flights from Washington (DCA) to Key West (EYW)
- Flights from Jacksonville (JAX) to Key West (EYW)
- Flights from Dallas (DFW) to Key West (EYW)
- Flights from Raleigh (RDU) to Key West (EYW)
- Flights from Indianapolis (IND) to Key West (EYW)
- Flights from Minneapolis (MSP) to Key West (EYW)
- Flights from Pittsburgh (PIT) to Key West (EYW)
- Flights from St. Louis (STL) to Key West (EYW)
- Flights from Columbus (CMH) to Key West (EYW)
- Flights from Nashville (BNA) to Key West (EYW)
- Flights from Cleveland (CLE) to Key West (EYW)
- Flights from West Palm Beach (PBI) to Key West (EYW)
- Flights from Pensacola (PNS) to Key West (EYW)
- Flights from Cincinnati (CVG) to Key West (EYW)
- Flights from Houston (IAH) to Key West (EYW)
- Flights from New Orleans (MSY) to Key West (EYW)
- Flights from Charleston (CHS) to Key West (EYW)
- Flights from Kansas City (MCI) to Key West (EYW)
- Flights from Milwaukee (MKE) to Key West (EYW)
- Flights from Richmond (RIC) to Key West (EYW)
- Flights from Louisville (SDF) to Key West (EYW)
- Flights from Hartford (BDL) to Key West (EYW)
- Flights from Albany (ALB) to Key West (EYW)
- Flights from Sarasota (SRQ) to Key West (EYW)
- Flights from Grand Rapids (GRR) to Key West (EYW)
- Flights from Buffalo (BUF) to Key West (EYW)
- Flights from Norfolk (ORF) to Key West (EYW)
- Flights from Providence (PVD) to Key West (EYW)
- Flights from Denver (DEN) to Key West (EYW)
- Flights from St. Petersburg (PIE) to Key West (EYW)
- Flights from Memphis (MEM) to Key West (EYW)
- Flights from Naples (APF) to Key West (EYW)
- Flights from Los Angeles (LAX) to Key West (EYW)
- Flights from Omaha (OMA) to Key West (EYW)
- Flights from Knoxville (TYS) to Key West (EYW)
- Flights from Tulsa (TUL) to Key West (EYW)
- Flights from Myrtle Beach (MYR) to Key West (EYW)
- Flights from Savannah (SAV) to Key West (EYW)
- Flights from Greenville (GSP) to Key West (EYW)
- Flights from Punta Gorda Airport (PGD) to Key West (EYW)
- Flights from Austin (AUS) to Key West (EYW)
- Flights from Phoenix (PHX) to Key West (EYW)
- Flights from Rochester (ROC) to Key West (EYW)
- Flights from Springfield (SGF) to Key West (EYW)
- Flights from Syracuse (SYR) to Key West (EYW)
- Flights from Tallahassee (TLH) to Key West (EYW)
- Flights from Wilmington (ILM) to Key West (EYW)
- Flights from Des Moines (DSM) to Key West (EYW)
- Flights from Harrisburg (MDT) to Key West (EYW)
- Flights from Washington (IAD) to Key West (EYW)
- Flights from Birmingham (BHM) to Key West (EYW)
- Flights from Daytona Beach (DAB) to Key West (EYW)
- Flights from Seattle (SEA) to Key West (EYW)
- Flights from Gainesville (GNV) to Key West (EYW)
- Flights from Oklahoma City (OKC) to Key West (EYW)
- Flights from Panama City (ECP) to Key West (EYW)
- Flights from Chattanooga (CHA) to Key West (EYW)
- Flights from San Francisco (SFO) to Key West (EYW)
- Flights from Las Vegas (LAS) to Key West (EYW)
- Flights from San Antonio (SAT) to Key West (EYW)
- Flights from Portland (PDX) to Key West (EYW)
- Flights from South Bend (SBN) to Key West (EYW)
- Flights from Sioux Falls (FSD) to Key West (EYW)
- Flights from Manchester (MHT) to Key West (EYW)
- Flights from Asheville (AVL) to Key West (EYW)
- Flights from Huntsville (HSV) to Key West (EYW)
- Flights from Madison (MSN) to Key West (EYW)
- Flights from Portland (PWM) to Key West (EYW)
- Flights from San Diego (SAN) to Key West (EYW)
- Flights from Little Rock (LIT) to Key West (EYW)
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.