Whispering Pines Vacation Packages 2026 from $483

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Your Whispering Pines Vacation

Organizing your next exciting getaway just got a whole lot simpler with a vacation package to Whispering Pines. Enjoy the very best this neighborhood has to offer while creating wonderful memories you'll remember for years. Free up some time for sightseeing activities during your trip to Whispering Pines. Nearby Big Pine Key Flea Market and Blue Hole are on the must-visit lists of many tourists. Don't just dream it — do it! Reserve your ultimate Whispering Pines vacation with Expedia and travel your way.

The Latest Whispering Pines Vacation Packages

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

President Hotel Villa

South Beach

Save 100% on your flight

$483

per person

Oct 3 - Oct 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,005 reviews)

Casablanca Miami Beach

North Beach

$2,856

per person

Oct 13 - Oct 16

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

5.8/10 (327 reviews)

Valet parking 10/10, safety 10/10 room description not the same as what I got, dirty towels and blanket bad experience.

Reviewed on Aug 12, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,298

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

The Key West Hotel

Key West Historic District

$6,091

per person

Oct 18 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (561 reviews)

This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!

Reviewed on Jul 27, 2026

Pantera Rosa

South Beach

Save 100% on your flight

$908

per person

Sep 30 - Oct 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.8/10 Excellent! (74 reviews)

The property is great. The location is perfect. The room was outstanding. Checkin is an absolute nightmare!!! Took us an hour from arrival to get our room. It's all done online, nobody to greet you. I saw one person in 4 days on the property. Requested fresh towels sent a text message had to send it again 8 hours later. Finally, got our towels.

Reviewed on Jun 26, 2026

Where to stay in Whispering Pines

Find the best Whispering Pines areas and neighborhoods for the activities you enjoy most. Learn more about Whispering Pines

A tropical island with clear blue waters, palm trees, and a thatched-roof hut.

Long Beach Estates

While visiting Long Beach Estates, you might make a stop by sights like Florida Keys Beaches and Coupon Bight Aquatic Preserve.

A steel bridge over turquoise water with a clear sky.

Sands

Though Sands might not have many top sights, you can venture to the surrounding area to see attractions like Big Pine Key Flea Market and Calusa Beach.

A long, rusted bridge over a body of water with a cloudy sky.

Pine Channel Estates

While there might not be top attractions in Pine Channel Estates, you can explore the larger area and discover places like Big Pine Key Flea Market and Coupon Bight Aquatic Preserve.

A coastal scene with a pier extending into the ocean, surrounded by palm trees and greenery.

Eden Pines

While there might not be top attractions in Eden Pines, you can explore the larger area and discover places like Big Pine Key Flea Market and Coupon Bight Aquatic Preserve.

A sign for 'No Name Pub' with a parrot illustration and text stating it's the oldest bar built in 1936.

Doctor's Arm

Though Doctor's Arm might not have many top sights, you can venture to the surrounding area to see attractions like Big Pine Key Flea Market and Coupon Bight Aquatic Preserve.

Whispering Pines Hotel Deals

Isla Bella Beach Resort & Spa

1 Knights Key Boulevard Marathon FL

Fully refundableReserve now, pay when you stay

$288 nightly

$324 total

Sep 1 - Sep 2

Total with taxes and fees

Tranquility Bay Beachfront Hotel and Resort

2600 Overseas Hwy Marathon FL

Fully refundableReserve now, pay when you stay

$264 nightly

$297 total

Sep 13 - Sep 14

Total with taxes and fees

8.8/10 Excellent! (1,001 reviews)

"awesome resort in Marathon, beach, pool and all the resort has to offer. Great location"

Reviewed on Aug 12, 2026

Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

2146 Overseas Hwy Marathon FL

Fully refundableReserve now, pay when you stay

$170 nightly

$191 total

Sep 1 - Sep 2

Total with taxes and fees

See all 1,449 properties in Whispering Pines

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.