Photo by Gary-Heather Kobza
Open Photo by Gary-Heather Kobza
Southwest Vacations from $475
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 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
The Latest Southwest Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Marriott Hutchinson Island Resort & Beach Villas, Golf & Marina
Sep 11 - Sep 16Marriott Hutchinson Island Resort & Beach Villas, Golf & Marina + Flight
Stuart5 nights4.0 star property8.4/10 - Very Good (644 reviews)"I was extremely disappointed with my stay at this resort. Unfortunately, the experience did not match the expectations set by the description or the price. During our stay, the elevators were out of service, which was a major inconvenience, especially when we were on the top floor having to walk 3 flights of stairs . We also experienced a water outage for several hours, and the TVs never had internet access for the entire duration of our visit. The bathroom design was also disappointing, with..."Reviewed August 2, 2026Roundtrip • Boston (BOS) - West Palm Beach (PBI)BOS - MIA • 1 stop MIA - BOS • Nonstop - Capt Hiram's Resort
Oct 27 - Nov 1Capt Hiram's Resort + Flight
Sebastian5 nights3.0 star property9.2/10 - Wonderful (1,005 reviews)Roundtrip • Philadelphia (PHL) - West Palm Beach (PBI)PHL - MCO • Nonstop MCO - PHL • Nonstop - Tideline Palm Beach Ocean Resort and Spa
Oct 27 - Oct 30Tideline Palm Beach Ocean Resort and Spa + Flight
Palm Beach3 nights4.0 star property7.8/10 - Good (433 reviews)"Didn’t have enough time to explore, but will be staying here again"Reviewed August 2, 2026Roundtrip • Boston (BOS) - Fort Lauderdale (FLL)BOS - PBI • Nonstop PBI - BOS • 1 stop - Amrit Ocean Resort and Residences - Singer Island
Oct 4 - Oct 9Amrit Ocean Resort and Residences - Singer Island + Flight
Singer Island5 nights5.0 star property8.8/10 - Excellent (346 reviews)"Great amenities and service! Beach service was a bit understaffed and slower than the rest."Reviewed August 4, 2026Roundtrip • Boston (BOS) - Fort Lauderdale (FLL)BOS - FLL • Nonstop FLL - BOS • 1 stop - The Brazilian Court Hotel
Oct 27 - Oct 30The Brazilian Court Hotel + Flight
Palm Beach3 nights4.5 star property9.0/10 - Wonderful (718 reviews)"This hotel was old school lovely! Rooms were beautiful and loved that there was separate shower and bath. Pool was charming and small. Staff was friendly and brought us special treats for our birthdays. We didn’t know there was a yacht tour for free with room stay! It was out of commission or we would have done that! Food on property was yummy. Would definitely stay here again!"Reviewed August 2, 2026Roundtrip • Boston (BOS) - Fort Lauderdale (FLL)BOS - PBI • Nonstop PBI - BOS • 1 stop