Caldecott Vacations from $260

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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.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Price was $439, price is now $260 per person
$260
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,003 reviews)
Safe and quiet place. Easy parking. Strongly recommend.

Reviewed on Aug 23, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $881, price is now $508 per person
$508
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (398 reviews)
Great property with welcoming staff

Reviewed on Aug 28, 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
Price was $1,022, price is now $608 per person
$608
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,004 reviews)
Ants in room-service was just okay-place needs updating-prices very high for what you get. Lack of attention to detail-Balleen was just fair-signature grouper dish highly recommended by server was warm (not hot) and risotto cake was undercooked (and for $65 per portion ????? ) overall price for value received was WAY TO HIGH).

Reviewed on Aug 29, 2025

Hyatt Place Fort Myers/at The Forum

Hyatt Place Fort Myers/at The Forum

3 out of 5
The Forum
Price was $449, price is now $274 per person
$274
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.2/10 Very Good! (1,006 reviews)
There is not truly a restaurant or cafe in this hotel.

Reviewed on Aug 24, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
Price was $1,295, price is now $810 per person
$810
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,001 reviews)
Great hotel at great location , ill be back!

Reviewed on Aug 28, 2025

Where to stay in Caldecott

Find the best Caldecott areas and neighborhoods for the activities you enjoy most. Learn more about Caldecott
South Florida showing a coastal town, a marina and a bay or harbor

Old Naples

3 out of top 10 points of interest in this area
4.5/5(397 area reviews)

The stunning beaches and popular shops are just a few highlights of Old Naples. Make a stop by Fifth Avenue South or Naples Beach while you're exploring the area.

Find hotels in Old Naples

Caldecott Hotel Deals

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
Fully refundable
$197 nightly
The price is $219 total per night from Sep 7 to Sep 8
$219 total
Sep 7 - Sep 8
Total with taxes and fees
Naples Grande Beach Resort
La Quinta Inn & Suites by Wyndham Naples Downtown

La Quinta Inn & Suites by Wyndham Naples Downtown

2.5 out of 5
1555 5th Ave S, Naples, FL
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $79 total per night from Sep 8 to Sep 9
$79 total
Sep 8 - Sep 9
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Naples Downtown
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 Sep 5 to Sep 6
$141 total
Sep 5 - Sep 6
Total with taxes and fees
Hyatt House Naples/5th Avenue
See all 10,371 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

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

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

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

$70
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.