Cheap Vacations in Islamorada

Choose two or more items and save on your trip:

3-night Islamorada vacations

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
Price was $12,296, price is now $7,047 per person
per person
Oct 27 - Oct 30
Roundtrip flight included
New York (LGA) to Miami (MIA)
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

4 out of 5
Price was $1,011, price is now $610 per person
per person
Oct 29 - Nov 1
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Kimpton Fitch Lodge, an IHG Hotel

Kimpton Fitch Lodge, an IHG Hotel

3.5 out of 5
Price was $801, price is now $516 per person
per person
Oct 29 - Nov 1
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
NYAH Key West - Adults Only

NYAH Key West - Adults Only

3 out of 5
Price was $817, price is now $531 per person
per person
Oct 29 - Nov 1
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
Price was $881, price is now $575 per person
per person
Oct 29 - Nov 1
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Southwinds Motel

Southwinds Motel

2 out of 5
Price was $860, price is now $571 per person
per person
Oct 29 - Nov 1
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Fairfield Inn and Suites by Marriott Key West

Fairfield Inn and Suites by Marriott Key West

3 out of 5
Price was $787, price is now $535 per person
per person
Oct 29 - Nov 1
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $792, price is now $542 per person
per person
Oct 29 - Nov 1
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4 out of 5
Price was $1,227, price is now $839 per person
per person
Oct 29 - Nov 1
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Fairfield Inn & Suites Key West at The Keys Collection

Fairfield Inn & Suites Key West at The Keys Collection

3.5 out of 5
Price was $793, price is now $543 per person
per person
Oct 29 - Nov 1
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Eden House

Eden House

3.5 out of 5
Price was $1,000, price is now $686 per person
per person
Oct 29 - Nov 1
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Westwinds Inn

Westwinds Inn

3.5 out of 5
Price was $969, price is now $667 per person
per person
Oct 29 - Nov 1
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Prices and availability subject to change. Additional terms may apply.

4-night Islamorada vacations

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
Price was $9,284, price is now $5,017 per person
per person
Nov 13 - Nov 17
Roundtrip flight included
New York (JFK) to Miami (MIA)
W South Beach

W South Beach

5 out of 5
Save 100% on your flightPrice was $1,534, price is now $910 per person
per person
Nov 13 - Nov 17
Roundtrip flight included
New York (JFK) to Miami (MIA)
Hampton Inn Miami Beach - Mid Beach, FL

Hampton Inn Miami Beach - Mid Beach, FL

2.5 out of 5
Save 100% on your flightPrice was $542, price is now $402 per person
per person
Oct 27 - Oct 31
Roundtrip flight included
Philadelphia (PHL) to Miami (MIA)
Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Price was $1,305, price is now $969 per person
per person
Nov 2 - Nov 6
Roundtrip flight included
New York (JFK) to Miami (MIA)
Kimpton EPIC Hotel, an IHG Hotel

Kimpton EPIC Hotel, an IHG Hotel

5 out of 5
Save 100% on your flightPrice was $1,180, price is now $892 per person
per person
Oct 27 - Oct 31
Roundtrip flight included
Philadelphia (PHL) to Miami (MIA)
The Tony Hotel South Beach

The Tony Hotel South Beach

4 out of 5
Save 100% on your flightPrice was $772, price is now $592 per person
per person
Oct 27 - Oct 31
Roundtrip flight included
Philadelphia (PHL) to Miami (MIA)
Key West Marriott Beachside Hotel

Key West Marriott Beachside Hotel

3.5 out of 5
Price was $1,788, price is now $1,398 per person
per person
Nov 15 - Nov 19
Roundtrip non-stop flight included
Philadelphia (PHL) to Key West (EYW)
Pullman Miami Airport

Pullman Miami Airport

4 out of 5
Price was $587, price is now $461 per person
per person
Nov 5 - Nov 9
Roundtrip flight included
New York (JFK) to Miami (MIA)
The Confidante Miami Beach, part of Hyatt

The Confidante Miami Beach, part of Hyatt

4.5 out of 5
Save 100% on your flightPrice was $905, price is now $716 per person
per person
Oct 27 - Oct 31
Roundtrip flight included
Philadelphia (PHL) to Miami (MIA)
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

5 out of 5
Save 100% on your flightPrice was $5,402, price is now $4,297 per person
per person
Nov 2 - Nov 6
Roundtrip non-stop flight included
Philadelphia (PHL) to Key West (EYW)
Creekside Inn Islamorada

Creekside Inn Islamorada

2.5 out of 5
Save 100% on your flightPrice was $434, price is now $347 per person
per person
Nov 4 - Nov 8
Roundtrip flight included
Philadelphia (PHL) to Miami (MIA)
Beach Place Hotel

Beach Place Hotel

2 out of 5
Price was $485, price is now $388 per person
per person
Nov 2 - Nov 6
Roundtrip flight included
New York (JFK) to Miami (MIA)
Prices and availability subject to change. Additional terms may apply.

5-night Islamorada vacations

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
Price was $13,178, price is now $7,208 per person
per person
Nov 4 - Nov 9
Roundtrip flight included
New York (LGA) to Miami (MIA)
W South Beach

W South Beach

5 out of 5
Price was $5,655, price is now $3,677 per person
per person
Nov 4 - Nov 9
Roundtrip flight included
New York (LGA) to Miami (MIA)
Key West Marriott Beachside Hotel

Key West Marriott Beachside Hotel

3.5 out of 5
Save 100% on your flightPrice was $1,436, price is now $1,018 per person
per person
Nov 10 - Nov 15
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Kimpton Angler's Hotel, an IHG Hotel

Kimpton Angler's Hotel, an IHG Hotel

4 out of 5
Save 100% on your flightPrice was $586, price is now $446 per person
per person
Oct 27 - Nov 1
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
National Hotel, An Adult Only Oceanfront Resort

National Hotel, An Adult Only Oceanfront Resort

4 out of 5
Save 100% on your flightPrice was $683, price is now $521 per person
per person
Oct 27 - Nov 1
Roundtrip flight included
Chicago (CHI) to Miami (MIA)
Hotel AKA Brickell

Hotel AKA Brickell

5 out of 5
Price was $1,211, price is now $976 per person
per person
Nov 4 - Nov 9
Roundtrip flight included
New York (LGA) to Miami (MIA)
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
Price was $1,174, price is now $991 per person
per person
Oct 31 - Nov 5
Roundtrip non-stop flight included
New York (JFK) to Key West (EYW)
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool

Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool

4.5 out of 5
Price was $1,898, price is now $1,689 per person
per person
Oct 31 - Nov 5
Roundtrip non-stop flight included
New York (JFK) to Key West (EYW)
Kimpton Winslow's Bungalows, an IHG Hotel

Kimpton Winslow's Bungalows, an IHG Hotel

4 out of 5
Price was $1,313, price is now $1,170 per person
per person
Oct 31 - Nov 5
Roundtrip non-stop flight included
New York (JFK) to Key West (EYW)
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $1,220, price is now $1,088 per person
per person
Oct 31 - Nov 5
Roundtrip non-stop flight included
New York (JFK) to Key West (EYW)
The Gates Hotel Key West

The Gates Hotel Key West

4 out of 5
Price was $923, price is now $829 per person
per person
Oct 31 - Nov 5
Roundtrip non-stop flight included
New York (JFK) to Key West (EYW)
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

5 out of 5
Save 100% on your flightPrice was $4,833, price is now $4,358 per person
per person
Nov 10 - Nov 15
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Prices and availability subject to change. Additional terms may apply.

6-7 night Islamorada vacations

Key West Marriott Beachside Hotel

Key West Marriott Beachside Hotel

3.5 out of 5
Save 100% on your flightPrice was $1,908, price is now $1,305 per person
per person
Nov 4 - Nov 11
Roundtrip non-stop flight included
New York (JFK) to Key West (EYW)
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

5 out of 5
Save 100% on your flightPrice was $9,025, price is now $6,750 per person
per person
Nov 4 - Nov 11
Roundtrip non-stop flight included
New York (JFK) to Key West (EYW)
Cambria Hotel Fort Lauderdale Beach

Cambria Hotel Fort Lauderdale Beach

3 out of 5
Price was $1,133, price is now $853 per person
per person
Nov 7 - Nov 13
Roundtrip non-stop flight included
Sacramento (SMF) to Miami (MIA)
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

4 out of 5
Save 100% on your flightPrice was $1,551, price is now $1,209 per person
per person
Oct 31 - Nov 6
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Eden House

Eden House

3.5 out of 5
Save 100% on your flightPrice was $1,304, price is now $1,040 per person
per person
Oct 31 - Nov 6
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Save 100% on your flightPrice was $1,765, price is now $1,411 per person
per person
Oct 31 - Nov 6
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
B Ocean Resort

B Ocean Resort

4 out of 5
Price was $1,099, price is now $895 per person
per person
Nov 7 - Nov 13
Roundtrip non-stop flight included
Sacramento (SMF) to Miami (MIA)
The Galleria by Brightwild

The Galleria by Brightwild

3 out of 5
Save 100% on your flightPrice was $1,309, price is now $1,088 per person
per person
Oct 31 - Nov 6
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
NYAH Key West - Adults Only

NYAH Key West - Adults Only

3 out of 5
Price was $1,989, price is now $1,672 per person
per person
Nov 4 - Nov 11
Roundtrip non-stop flight included
New York (JFK) to Key West (EYW)
Icon Residences By Sunnyside Hotel and Resorts

Icon Residences By Sunnyside Hotel and Resorts

4 out of 5
Price was $1,170, price is now $987 per person
per person
Nov 7 - Nov 13
Roundtrip non-stop flight included
Sacramento (SMF) to Miami (MIA)
Island City House Hotel

Island City House Hotel

3 out of 5
Save 100% on your flightPrice was $1,660, price is now $1,404 per person
per person
Oct 31 - Nov 6
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
Save 100% on your flightPrice was $1,091, price is now $930 per person
per person
Oct 31 - Nov 6
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Prices and availability subject to change. Additional terms may apply.

Where is Islamorada?

Cheap, cheap, cheap! No matter what you're searching for, we've got the best deals for your amazing vacation in Islamorada.

994 miles to the north of Islamorada is Washington. Key Largo is another nearby city, just 16 miles to the north-east.

Ready to meet some of the locals? 7,100 people call this part of Monroe County home.

Cheap Things t