Title: Rockland Key Vacation Packages 2026 from $913 | Expedia.com

[Rockland Key Travel Guide](https://expedia.com/Rockland-Key.dx553248635976197596)[Hotels in Rockland Key](https://expedia.com/Rockland-Key-Hotels.d553248635976197596.Travel-Guide-Hotels)[Vacation Rentals in Rockland Key](https://expedia.com/Rockland-Key-Vacation-Rentals.d553248635976197596.Travel-Guide-VacationRentals)[Flights to Rockland Key](https://expedia.com/Cheap-Flights-To-Rockland-Key.d553248635976197596.Travel-Guide-Flights)[Car Rentals in Rockland Key](https://expedia.com/Car-Rentals-In-Rockland-Key.d553248635976197596.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Rockland Key Vacations from $913

## Book a Hotel + Flight or Car together to unlock savings

## The Latest Rockland Key vacation packages

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

![Ibis Bay Beach Resort](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/4a09d86c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Ibis Bay Beach Resort

Northside Resort

Save 100% on your flight

$913

per person

Mar 12 - Mar 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.2/10 Very Good! (2,000 reviews)

Great ppl that work there!

Reviewed on Feb 5, 2026

![The Key West Hotel](https://images.trvl-media.com/lodging/9000000/8660000/8657100/8657021/bc64cbf7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,719

per person

Apr 19 - Apr 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (505 reviews)

Everything was great. I couldn’t complain about anything if I wanted to. Thanks for a great stay!

Reviewed on Jan 28, 2026

![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Southernmost Beach Resort and Guesthouses

Old Town Key West

Save 100% on your flight

$1,364

per person

Apr 19 - Apr 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (2,844 reviews)

We splurged because it was a special occasion and I assumed given the room price and the high daily amenity fees that it would be fabulous. I don’t know what I paid for. Pools weren’t heated as promised, pool bars wouldn’t open and they’d send you to the beach cafe, there was talk on the website of free yoga—never saw that. The location is great but if you are gonna charge people $65 daily in amenity fees, there should be more amenities

Reviewed on Feb 5, 2026

![Hyatt Vacation Club at Windward Pointe, Key West](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$1,103

per person

Apr 2 - Apr 6

just found

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.6/10 Exceptional! (1,002 reviews)

Said there was beach There is no beach Our initial flight was cancelled we re-rebooked for two days later The hotel would not refund the 2 nights We will reach out again to Expedia but hotel is. also very difficult to reach a live person

Reviewed on Feb 5, 2026

![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$1,294

per person

Mar 12 - Mar 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,736 reviews)

The room was spotless. The resort was quiet and well maintained. The staff was very helpful. Check in and check out went very smoothly. My only complaints were that I was unable to order in-room breakfast as the phone was never answered. Also, the edges of the mattress were pretty soft.

Reviewed on Feb 4, 2026

Don't see what you're looking for?

See all available trips from Columbus to Rockland Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Rockland Key Hotel Deals

![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundable

$530 nightly

$596 total

Feb 8 - Feb 9

Total with taxes and fees

8.6/10 Excellent! (3,047 reviews)

Always our favorite spot. Staff is wonderful. Can’t beat the views and amenities.

Reviewed on Feb 1, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F8%2F2026&endDate=2%2F9%2F2026&selected=863329&PinnedHotelID=863329&HadPinnedHotel=true&regionId=553248635976197596)

![Ibis Bay Beach Resort](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/4a09d86c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

$389 nightly

$437 total

Mar 8 - Mar 9

Total with taxes and fees

8/10 Very Good! (2,071 reviews)

Great ppl that work there!

Reviewed on Feb 5, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%2F2026&selected=4218809&PinnedHotelID=4218809&HadPinnedHotel=true&regionId=553248635976197596)

![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue Key West FL

Fully refundableReserve now, pay when you stay

$418 nightly

$471 total

Feb 9 - Feb 10

Total with taxes and fees

8.8/10 Excellent! (1,795 reviews)

The room was spotless. The resort was quiet and well maintained. The staff was very helpful. Check in and check out went very smoothly. My only complaints were that I was unable to order in-room breakfast as the phone was never answered. Also, the edges of the mattress were pretty soft.

Reviewed on Feb 4, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F9%2F2026&endDate=2%2F10%2F2026&selected=16202992&PinnedHotelID=16202992&HadPinnedHotel=true&regionId=553248635976197596)

[See all 3,312 properties in Rockland Key](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F6%2F2026&endDate=2%2F7%2F2026&regionId=553248635976197596)

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.

## Find the Best Rockland Key Vacation Packages

## Rockland Key Essential Information

| Language | English     |
| -------- | ----------- |
| Currency | U.S dollars |

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- [Flights to Big Coppitt Key ](https://www.expedia.com/Cheap-Flights-To-Big-Coppitt-Key.d553248635975850102.Travel-Guide-Flights)
- [Flights from Boca Chica Key ](https://www.expedia.com/lp/flights/553248635083916609/flights-from-boca-chica-key)
- [Flights to Raccoon Key ](https://www.expedia.com/Cheap-Flights-To-Raccoon-Key.d180164.Travel-Guide-Flights)
- [Flights from Philadelphia (PHL) to Key West (EYW) ](https://www.expedia.com/lp/flights/phl/eyw/philadelphia-to-key-west)
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- [Flights to Stock Island ](https://www.expedia.com/Cheap-Flights-To-Stock-Island.d180166.Travel-Guide-Flights)
- [Flights from Orlando (MCO) to Key West (EYW) ](https://www.expedia.com/lp/flights/mco/eyw/orlando-to-key-west)
- [Flights from Chicago to Stock Island ](https://www.expedia.com/lp/flights/178248/180166/chicago-to-stock-island)
- [Flights from Philadelphia to Stock Island ](https://www.expedia.com/lp/flights/178297/180166/philadelphia-to-stock-island)
- [Flights from Miami (MIA) to Key West (EYW) ](https://www.expedia.com/lp/flights/mia/eyw/miami-to-key-west)
- [Flights from Boston (BOS) to Key West (EYW) ](https://www.expedia.com/lp/flights/bos/eyw/boston-to-key-west)

- [Key West Vacations ](https://www.expedia.com/Key-West.d1187.Destination-Travel-Guides)
- [Boca Chica Key Vacations ](https://www.expedia.com/Boca-Chica-Key.d553248635083916609.Destination-Travel-Guides)
- [Boca Chica Nude Beach ](https://www.expedia.com/Boca-Chica-Nude-Beach-Key-West.d553248635983994034.Vacation-Attraction)
- [Saddlebunch Keys ](https://www.expedia.com/Saddlebunch-Keys-Florida.d553248635976195874.Vacation-Attraction)
- [Raccoon Key Vacations ](https://www.expedia.com/Raccoon-Key.d180164.Destination-Travel-Guides)
- [Robbie's ](https://www.expedia.com/Robbies-Key-West.d6068603.Vacation-Attraction)
- [Stock Island Vacations ](https://www.expedia.com/Stock-Island.d180166.Destination-Travel-Guides)
- [Visit Raccoon Key ](https://www.expedia.com/Raccoon-Key.dx180164)
- [Cow Key Vacations ](https://www.expedia.com/Cow-Key.d180163.Destination-Travel-Guides)
- [Visit Stock Island ](https://www.expedia.com/Stock-Island.dx180166)
- [All inclusive Vacation Packages Stock Island ](https://www.expedia.com/lp/theme-vacations/all-inclusive-vacations/180166/Stock-Island)
- [Visit Cow Key ](https://www.expedia.com/Cow-Key.dx180163)

- [Car rentals near Big Coppitt Key ](https://www.expedia.com/Car-Rentals-In-Big-Coppitt-Key.d553248635975850102.Car-Rental-Guide)
- [Car rentals near Stock Island Yacht Club & Marina ](https://www.expedia.com/Car-Rentals-In-Stock-Island-Yacht-Club-Marina.d6184527.Car-Rental-Guide)
- [Car rentals near Stock Island ](https://www.expedia.com/Car-Rentals-In-Stock-Island.d180166.Car-Rental-Guide)
- [National Car Rental Rental Cars in Stock Island ](https://www.expedia.com/National-Car-Rental-Car-Rentals-In-Stock-Island.d180166-c42.Car-Rental-Guide-Suppliers)
- [Enterprise Rental Cars in Stock Island ](https://www.expedia.com/Enterprise-Car-Rentals-In-Stock-Island.d180166-c15.Car-Rental-Guide-Suppliers)
- [Car rentals near Key West Golf Club ](https://www.expedia.com/Car-Rentals-In-Key-West-Golf-Club.d6163814.Car-Rental-Guide)
- [Van Car Rentals near Key West Golf Club ](https://www.expedia.com/Van-Car-Rentals-In-Key-West-Golf-Club.d6163814-tVan.Car-Rental-Guide-Class)
- [Mini Car Rentals near Key West Golf Club ](https://www.expedia.com/Mini-Car-Rentals-In-Key-West-Golf-Club.d6163814-tMini.Car-Rental-Guide-Class)

- [Raccoon Key Vacation Rentals ](https://www.expedia.com/Raccoon-Key-Vacation-Rentals.d180164.Travel-Guide-VacationRentals)
- [Stock Island Vacation Rentals ](https://www.expedia.com/Stock-Island-Vacation-Rentals.d180166.Travel-Guide-VacationRentals)

- [Things to do in Stock Island ](https://www.expedia.com/Things-To-Do-In-Stock-Island.d180166.Travel-Guide-Activities)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.