Caldecott Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Holiday Package Deals in Caldecott

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $1,385, price is now CA $856 per person
CA $856
per person
Jul 3 - Jul 7
found 19 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Fort Myers (RSW)
9.4/10 Exceptional! (776 reviews)
Food was great, two pools (family and adults only) the room was clean which is extremely important and a great view

Reviewed on May 7, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was CA $3,749, price is now CA $2,120 per person
CA $2,120
per person
Jun 15 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9/10 Wonderful! (1,001 reviews)
Nice, high end facility with friendly staff. Check in was easy, check out was easy, going to the beach was easy… very relaxing stay.

Reviewed on May 4, 2026

Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

3 out of 5
South Island
Price was CA $2,019, price is now CA $1,378 per person
CA $1,378
per person
Jul 20 - Jul 27
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
10/10 Exceptional! (1 review)
Hurricane Ian decimated the area but the residents are working hard to bring it back to its glory days. This resort has undergone an amazing renovation and they are doing more and more every day. Their new pool and Jacuzzi is stunning. The location is perfect. The staff is wonderful!

Reviewed on Apr 29, 2026

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Price was CA $1,810, price is now CA $1,239 per person
CA $1,239
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Fort Myers (RSW)
8.6/10 Excellent! (1,003 reviews)
View from room was amazing.

Reviewed on May 7, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Price was CA $1,257, price is now CA $902 per person
CA $902
per person
Jul 3 - Jul 7
found 19 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Fort Myers (RSW)
9.8/10 Exceptional! (1,192 reviews)
place was immaculate beds for super comfy

Reviewed on May 5, 2026

Where to stay in Caldecott

Find the best Caldecott areas and neighborhoods for the activities you enjoy most. Learn more about Caldecott
East Naples

East Naples

4/5(11 area reviews)

Beaches, shopping, and restaurants are just a few things travelers enjoy about East Naples. Check out Fifth Avenue South or Naples Botanical Garden while you're exploring the area.

Find hotels in East Naples

Caldecott Hotel Deals

Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

4 out of 5
560 S Collier Blvd Marco Island FL
Fully refundableReserve now, pay when you stay
The price is CA $302 per night from May 20 to May 21
CA $302
CA $411 total
May 20 - May 21
includes taxes & fees
9/10 Wonderful! (1,775 reviews)
Yes

Reviewed on May 8, 2026

Hilton Marco Island Beach Resort and Spa
Great Wolf Lodge Naples

Great Wolf Lodge Naples

3 out of 5
3900 City Gate Blvd N. Naples FL
Fully refundableReserve now, pay when you stay
The price is CA $354 per night from May 11 to May 12
CA $354
CA $393 total
May 11 - May 12
includes taxes & fees
9.4/10 Exceptional! (776 reviews)
Nice.

Reviewed on May 8, 2026

Great Wolf Lodge Naples
Hyatt House Naples/5th Avenue

Hyatt House Naples/5th Avenue

3.5 out of 5
1345 5th Avenue South Naples FL
Fully refundableReserve now, pay when you stay
The price is CA $272 per night from May 17 to May 18
CA $272
CA $302 total
May 17 - May 18
includes taxes & fees
9/10 Wonderful! (1,740 reviews)
Had an issue with the rooms cleanliness, guest manager blew me off. Second one made it right. Girl checking us in was so extremely unfriendly.

Reviewed on May 8, 2026

Hyatt House Naples/5th Avenue
See all 10,528 properties in Caldecott
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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Frequently asked questions

How much does a Caldecott vacation package cost?
From as little as CA $856, you can build your own Caldecott package the way you want. Simply bundle hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Caldecott?
Crafting your own Caldecott vacation package with Expedia is one of the best ways to save. We have more than 550 airlines and 1,000,000 hotel options spread across the globe. With such a wonderful range to pick from, you'll have no difficulty creating your next dream escape.
Where should I stay in Caldecott?
There's loads to do in Caldecott, so spend your evenings near its best sights and allow yourself more time sightseeing. Eagle Lakes Community Park is one place to put on your must-see list.
What are the top hotels in Caldecott?
Model Home In Lely Resort Naples Florida is one of Caldecott's most well-known hotels. Reserve a room here and you'll be able to rest easy knowing you're in capable hands.
How far in advance should I book my Caldecott vacation?
It's tricky picking the ideal time for airfares, but we usually say the earlier, the better. Many international journeys on Expedia become available to compare up to 12 months in advance. If you're booking last minute, fear not. Bargain prices occasionally appear just weeks before departure dates.
What does an Expedia Caldecott travel package include?
That depends on what sort of getaway you're contemplating. Caldecott travel deals can include car rentals, hotels and flights. You can mix and match to create the bundle that suits your needs. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking a Caldecott travel package?
Bundling your bookings into a Caldecott vacation package is the most convenient way to organize your trip. Not only that, you'll save just for combining your flights, hotels and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Caldecott Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines globally. Our vacation packages give you the flexibility to pick from available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Caldecott vacation package?
If your travel plans in Caldecott have changed, it's a relief to know that it's possible to cancel your booking. If you booked less than 24 hours ago, you may be eligible for a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose a fee. For more details, check our Customer Service Portal.

Discover the most popular places to visit in Caldecott

Pristine and idyllic beach at sunset in a bright day, Naples, Florida, USA

Naples Beach

4.5/5(102 reviews)

Why not spend a carefree afternoon at Naples Beach during your travels in Naples? Stroll along the seaside or visit the shops while you're in the area.

Naples Beach
Fifth Avenue South

Fifth Avenue South

Enjoy many happy hours exploring the variety of shops, dining options and cultural attractions of this popular shopping district in Naples, Florida.

Fifth Avenue South
Vanderbilt beach in Naples, Florida

Vanderbilt Beach

4.5/5(26 reviews)

If a restful vacation is part of your travel plans, Vanderbilt Beach might be the perfect place to seek out during your trip to North Naples.

Vanderbilt Beach

Things to do

Naples Sightseeing Boat Tour

Naples Sightseeing Boat Tour

CA $74
per adult
96% of travellers recommend
Naples Sightseeing Boat Tour
Naples Florida: Downtown Electric Trike Tour

Naples Florida: Downtown Electric Trike Tour - Family Fun

CA $68
per adult
100% of travellers recommend
Naples Florida: Downtown Electric Trike Tour - Family Fun
Gulf of Mexico Sunset Cruise from Naples

Gulf of Mexico Sunset Cruise from Naples

CA $101
per adult
88% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
See all activities in Naples
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.