Caldecott Vacations from $285

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Your Caldecott Vacation

Book a Caldecott vacation package and immerse yourself in the way of life and vibe of this interesting neighborhood. With all your travel plans worked out, the only thing you need to concentrate on here is having a great time. When it's time to see the sights, you'll find a lot of awesome attractions nearby including Flamingo Island Course - Lely Resort, TPC Treviso Bay and Mustang Course - Lely Resort. Visit one, two or more during your trip to Caldecott. Whatever your ideal Caldecott vacation looks like, you can make it a reality with Expedia.

The Latest Caldecott Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
The Forum
Save 100% on your flight
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
8.2/10 Very Good! (1,001 reviews)
Good value, clean rooms, a bit dated and could use some updating, but overall not a bad place. It is convenient to many locations in the Fort Meyers/SW FL area, and the bed was comfortable.

Reviewed on Jul 13, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
8.8/10 Excellent! (1,002 reviews)
Beautiful property, beautiful clean rooms. Wasn’t informed of extra charges that were being applied after being told “it’s included.” Would have been nice to know. Wasn’t informed of holding fee of an extra $200 a night for “amenities” until we arrived. When booking it just looked like a $120 fee. The food is not kid friendly or budget friendly. Decided to splurge and order room service one morning and the bacon was nasty and the waffle was raw. Not to mention the guy who delivered it walked right in, not a comfortable situation. Overall a nice place, but did have some down falls.

Reviewed on Jul 14, 2025

Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Save 100% on your flight
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
8.6/10 Excellent! (1,010 reviews)
It was very clean and pretty decent, room service was great. Breakfast was great as well

Reviewed on Jul 10, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
9.4/10 Exceptional! (1,000 reviews)
A very nice hotel in the heart of downtown Naples. Clean modern rooms, attentive staff and a sunny pool deck. Naples’ best dining steps from your door.

Reviewed on Jul 9, 2025

Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
per person
Aug 20 - Aug 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
9.4/10 Exceptional! (1,405 reviews)
Allowing smoking on the property was definitely the one factor that brought myrsteing down.

Reviewed on Jul 13, 2025

Where to stay in Caldecott

Find the best Caldecott areas and neighborhoods for the activities you enjoy most. Learn more about Caldecott
Naples Botanical Garden showing a garden and a pond

East Naples

4/5(171 area reviews)

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

Find hotels in East Naples

Caldecott Hotel Deals

Naples Grande Beach Resort
Naples Grande Beach Resort
4.5 out of 5
475 Seagate Drive, Naples, FL
Fully refundable
$176 nightly
The price is $196 total per night from Aug 10 to Aug 11
$196 total
Aug 10 - Aug 11
Total includes taxes and fees
9/10 Wonderful! (1,583 reviews)
"Front desk service was great. Emily made our check in smooth and helpful. The pool area had to be shut down twice for lightning as well as the beach, which was the only downside to the stay."

Reviewed on Jul 13, 2025

Naples Grande Beach Resort
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
$127 nightly
The price is $141 total per night from Aug 3 to Aug 4
$141 total
Aug 3 - Aug 4
Total includes taxes and fees
8.8/10 Excellent! (1,318 reviews)
"Beatifil hotel and location"

Reviewed on Jul 13, 2025

Hyatt House Naples/5th Avenue
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
$260 nightly
The price is $289 total per night from Aug 10 to Aug 11
$289 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (1,435 reviews)
"We have been coming here literally a few times a year for quite a few years and the property, hotel, staff, restaurants, and shops are all amazing. Can't wait to book our next trip!!"

Reviewed on Jul 14, 2025

Hilton Marco Island Beach Resort and Spa
See all 10,239 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

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Discover the most popular places to visit in Caldecott

Naples Beach

Naples Beach

4.5/5(1,407 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
5th Avenue Shopping District which includes markets, street scenes and a city

Fifth Avenue South

4.5/5(45 reviews)

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
Naples Pier featuring a sandy beach and landscape views as well as a large group of people

Naples Pier

4.5/5(1,161 reviews)

Visit this beloved Naples destination to experience the simple charms of the beachfront on a dock that has served the city for more than 100 years.

Naples Pier

Things to do

SEAS The Day with Pure Florida

Naples Sightseeing Boat Tour

$64
per adult
98% of travellers recommend
Naples Sightseeing Boat Tour
Cute Manatee

Manatee Sightseeing and Wildlife Boat Tour

$70
per adult
90% of travellers recommend
Manatee Sightseeing and Wildlife Boat Tour
Naples Florida: Downtown Electric Moped Tour

Naples Florida: Downtown Electric Moped Tour

$60
per adult
100% of travellers recommend
Naples Florida: Downtown Electric Moped Tour
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.