Whispering Pines Vacation Packages

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Top Holiday Package Deals in Whispering Pines

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

Creekside Inn

2.5 out of 5
Price was CA $2,301, price is now CA $1,035 per person
CA $1,035
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
7.8/10 Good! (1,013 reviews)
Room was clean. I recommend washing down the walls in the bathroom and around light fixtures. Staff was excellent. Pool was good.

Reviewed on Mar 6, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was CA $25,977, price is now CA $12,127 per person
CA $12,127
per person
Apr 26 - May 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very Good! (1 review)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was CA $3,030, price is now CA $1,607 per person
CA $1,607
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Miami (MIA)
8.6/10 Excellent! (1,002 reviews)
The Cavalier is a quirky, fun hotel in the art deco district. It’s near the quieter end, so it’s perfect for adults, they provide beach access and free chairs, the restaurant is great- a mix of American and Italian. The employees are nice, Philip checked us in and Lester was our wonderful bar tender and server and had our drinks waiting! We should be back in six months for our bi annual girls trip! The rooms are quirky and cute and really loved the stylized feel with the older touches they preserved! Room was super clean, breakfast cost less than Starbucks and was so much better! Loved the original elevator- a must try- and just the whole vibe! This is old Miami at its best!

Reviewed on Mar 5, 2026

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was CA $3,104, price is now CA $1,698 per person
CA $1,698
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Miami (MIA)
8.4/10 Very Good! (2,048 reviews)
I really liked the location — it was very convenient. The room was pretty big and very clean, which made the stay comfortable. The staff was friendly and welcoming. The breakfast was okay, nothing special, but it was fine.

Reviewed on Mar 1, 2026

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was CA $2,550, price is now CA $1,452 per person
CA $1,452
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Miami (MIA)
8.4/10 Very Good! (1,701 reviews)
The staff and service plus the location has made this my new Miami Beach place of stay. Luggage holding and early check in is a godsend with vacation traveling. The walk to the beach was short and near the Art Deco section of the beach. Police are near and keep the area relatively safe at night. Unlike other beach spots this area does calm down and able to sleep at night without a club jamming music

Reviewed on Mar 3, 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
Aerial view from Venture Out on Cudjoe Key Florida., Shutterstock ID 757510879, Purchase Order: Wave 0 First Batch, Order Number: , Client/Licensee: Hotels.com / BEX, Other: Mixed Budget

Long Beach Estates

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

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Whispering Pines Hotel Deals

Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

5 out of 5
1 Knights Key Boulevard Marathon FL
Fully refundableReserve now, pay when you stay
The price is CA $742 per night from Mar 8 to Mar 9
CA $742
CA $932 total
Mar 8 - Mar 9
includes taxes & fees
9.2/10 Wonderful! (1,100 reviews)
Nice resort,,great staff ,but main restaurant dinnr service is terribly slow and food isnt great ,also cold ,,breakfast food is good ,but takes forever!,,

Reviewed on Mar 5, 2026

Isla Bella Beach Resort & Spa
Kingsail Resort

Kingsail Resort

2 out of 5
7050 Overseas Highway Marathon FL
The price is CA $282 per night from Apr 6 to Apr 7
CA $282
CA $317 total
Apr 6 - Apr 7
includes taxes & fees
8.6/10 Excellent! (1,036 reviews)
Old school Key West motel, with a nice pool and comfortable, clean rooms. Our room was spotless, and kept clean every day. Free coffee every morning at the outdoor Tiki Hut by the water, and a handy microwave and refrigerator in the room. Everyone we interacted with was friendly, helpful, and welcoming. ...

Reviewed on Mar 5, 2026

Kingsail Resort
Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

3 out of 5
2146 Overseas Hwy Marathon FL
Fully refundableReserve now, pay when you stay
The price is CA $417 per night from Apr 5 to Apr 6
CA $417
CA $523 total
Apr 5 - Apr 6
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
Chair in front the desk look like someone went to the bathroom in it and was NEVER cleaned during our week long stay. Plus 20.00 a day to park and 35.00 a day resort fee was nothing but a joke. We won't be back.

Reviewed on Feb 28, 2026

Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys
See all 1,432 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.
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Frequently asked questions

How much does a Whispering Pines vacation package cost?
The cheapest Whispering Pines vacation package is CA $1,035, so your dream trip can become a reality — without burning a hole in your pocket. Combine flights, hotels and car rentals to tailor make a package that's perfect for you.
How do I get a cheap travel package to Whispering Pines?
Search for flights that fit in with your schedule, add a hotel room to your booking and watch how much you save with a Whispering Pines vacation package. It's as simple as that! From flights and hotels to rental cars and activities, Expedia is where your cheap vacation begins. And with over 550 partner airlines and 1,000,000 hotel options worldwide to select from, you won't be short of choice.
Where should I stay in Whispering Pines?
You'll want to stay where the action is. Many travelers book hotels around popular sights, such as National Key Deer Refuge Visitor Center, Big Pine Key Flea Market and Blue Hole.
How far in advance should I book my Whispering Pines vacation?
Travelers are normally able to look up international flights on Expedia within 12 months of departure. Booking at the last minute? With a stroke of luck, it's still possible to score a cheaper ticket only weeks before your journey.
What does an Expedia Whispering Pines travel package include?
Expedia has all you need to lock in Whispering Pines escape, but how your package is structured is your call. Choose from a combination of hotels, flights and rental cars. After some activities to keep you entertained? Once you've made your booking, you can add them too. Whatever your style or budget, there's a package deal to match your needs.
What should I know before booking a Whispering Pines travel package?
Whether it's adventure or relaxation you're craving, a Whispering Pines vacation package lets you organize your escape your way. Plus, you'll get access to great discounts when you combine your accommodations with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Whispering Pines Expedia vacation package?
With a vacation package, you're the one in charge. Whether you're looking to fly to Whispering Pines in coach or business class, simply pick from the available airline options. Expedia has access to more than 550 partner airlines around the world.
If I'm not able to travel, can I cancel my Whispering Pines vacation package?
Whether it's your flight or hotel, you can cancel or change it. Locked in your Whispering Pines vacation package in the last 24 hours? You may be able to make changes at no cost. If it's been longer than that, you may be charged a fee by your hotel, airline or car rental company. For more information, visit our Customer Service Portal. We'll help you every step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.