
Rockland Key Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Rockland Key

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is S$301 per night from 25 May to 26 May
S$301
25 May - 26 May
includes taxes & fees
8.4/10 Very Good! (2,212 reviews)
Was probably one of our favorite hotels in the keys definitely coming back
Reviewed on 10 May, 2026

Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is S$349 per night from 8 Jun to 9 Jun
S$349
8 Jun - 9 Jun
includes taxes & fees
8.8/10 Excellent! (1,812 reviews)
Staff was very helpful with all our needs. I would only recommend that the hot tub had hot water. It was cold and the jets were weak. Otherwise it was a perfect spot for us. We will be back.
Reviewed on 7 May, 2026

Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundable
The price is S$404 per night from 25 May to 26 May
S$404
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (3,293 reviews)
Amazing beach access, multiple pools, great food and bar options. Staff was exceptionally friendly and helpful. I would definitely stay there again.
Reviewed on 9 May, 2026
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.
Explore a world of travel with Expedia
- Flights to Raccoon Key
- Delta Fort Wayne (FWA) to Key West (EYW) flights
- Delta Orlando (MCO) to Key West (EYW) flights
- Delta Philadelphia (PHL) to Key West (EYW) flights
- Flights from Boca Chica Key
- Flights from Key Haven
- Flights from Albuquerque (ABQ) to Key West (EYW)
- Flights from Albany (ALB) to Key West (EYW)
- Flights from Anchorage (ANC) to Key West (EYW)
- Flights from Auburn (AUO) to Key West (EYW)
- Flights from Bridgeport (BDR) to Key West (EYW)
- Flights from Birmingham (BHM) to Key West (EYW)
- Flights from Bluefield (BLF) to Key West (EYW)
- Flights from Bonaire (BON) to Key West (EYW)
- Flights from Boston (BOS) to Key West (EYW)
- Flights from Basel (BSL) to Key West (EYW)
- Flights from Buffalo (BUF) to Key West (EYW)
- Flights from Baubau (BUW) to Key West (EYW)
- Flights from Charlottesville (CHO) to Key West (EYW)
- Flights from Clearwater (CLW) to Key West (EYW)
- Flights from Casablanca (CMN) to Key West (EYW)
- Flights from Corinth (CRX) to Key West (EYW)
- Flights from Mosinee (CWA) to Key West (EYW)
- Flights from Denver (DEN) to Key West (EYW)
- Flights from Deauville (DOL) to Key West (EYW)
- Flights from Doncaster (DSA) to Key West (EYW)
- Flights from Devils Lake (DVL) to Key West (EYW)
- Flights from Davenport (DVN) to Key West (EYW)
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Flights from Florence (FLO) to Key West (EYW)
- Flights from Farmington (FMN) to Key West (EYW)
- Flights from Flint (FNT) to Key West (EYW)
- Flights from Gaithersburg (GAI) to Key West (EYW)
- Flights from Spokane (GEG) to Key West (EYW)
- Flights from Green Bay (GRB) to Key West (EYW)
- Flights from Grand Rapids (GRR) to Key West (EYW)
- Flights from Greenville (GSP) to Key West (EYW)
- Flights from Gulf Shores (GUF) to Key West (EYW)
- Flights from Helena (HLN) to Key West (EYW)
- Flights from Huntington (HTS) to Key West (EYW)
- Flights from Washington (IAD) to Key West (EYW)
- Flights from Islip (ISP) to Key West (EYW)
- Flights from New York (JFK) to Key West (EYW)
- Flights from Laconia (LCI) to Key West (EYW)
- Flights from Columbus (LCK) to Key West (EYW)
- Flights from Lexington (LEX) to Key West (EYW)
- Flights from New York (LGA) to Key West (EYW)
- Flights from London (LON) to Key West (EYW)
- Flights from Kansas City (MCI) to Key West (EYW)
- Flights from Harrisburg (MDT) to Key West (EYW)
- Flights from Chicago (MDW) to Key West (EYW)
- Flights from Madison (MSN) to Key West (EYW)
- Flights from Metlakatla (MTM) to Key West (EYW)
- Flights from Omaha (OMA) to Key West (EYW)
- Flights from Gold Coast (OOL) to Key West (EYW)
- Flights from Norfolk (ORF) to Key West (EYW)
- Flights from Orlando (ORL) to Key West (EYW)
- Flights from Owensboro (OWB) to Key West (EYW)
- Flights from Peppimenarti (PEP) to Key West (EYW)
- Flights from Philadelphia (PHL) to Key West (EYW)
- Flights from Port Elizabeth (PLZ) to Key West (EYW)
- Flights from Pensacola (PNS) to Key West (EYW)
- Flights from Pompano Beach (PPM) to Key West (EYW)
- Flights from Pasco (PSC) to Key West (EYW)
- Flights from Providence (PVD) to Key West (EYW)
- Flights from Richmond (RIC) to Key West (EYW)
- Flights from San Diego (SAN) to Key West (EYW)
- Flights from Sao Paulo (SAO) to Key West (EYW)
- Flights from Steamboat Springs (SBS) to Key West (EYW)
- Flights from Louisville (SDF) to Key West (EYW)
- Flights from Singapore (SIN) to Key West (EYW)
- Flights from Sacramento (SMF) to Key West (EYW)
- Flights from Orange County (SNA) to Key West (EYW)
- Flights from Santa Cruz de la Palma (SPC) to Key West (EYW)
- Flights from Santa Rosa (STS) to Key West (EYW)
- Flights from St. Louis (SUS) to Key West (EYW)
- Flights from Tallahassee (TLH) to Key West (EYW)
- Flights from Turtle Island (TTL) to Key West (EYW)
- Flights from Queenstown (UEE) to Key West (EYW)
- Flights from Wales (WAA) to Key West (EYW)
- Flights from Shirley (WSH) to Key West (EYW)
- Flights from Fort Frances (YAG) to Key West (EYW)
- Flights from Montreal (YUL) to Key West (EYW)
- Flights from Whale Cove (YXN) to Key West (EYW)
- Flights from St. John's (YYT) 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
