Caldecott Vacations from $543

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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.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $1,035, price is now $543 per person
$543
per person
Mar 9 - Mar 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
We enjoyed meeting Penny and really liked our little spot on the water :)

Reviewed on Dec 13, 2025

Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Price was $1,318, price is now $617 per person
$617
per person
Feb 28 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
Great amenities, pool and spa, clean room, beautiful lobby and good on site restaurant

Reviewed on Dec 9, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $2,270, price is now $1,169 per person
$1,169
per person
Feb 22 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (477 reviews)
Great hotel! Beautiful area and views, stunning pool and lounge area, wonderful staff and very warm and welcoming!

Reviewed on Dec 9, 2025

Innovation Hotel

Innovation Hotel

4 out of 5
Price was $2,165, price is now $1,117 per person
$1,117
per person
Feb 5 - Feb 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (527 reviews)
Nice, spacious rooms. Good bar and restaurant. Great gym. Also, no children!

Reviewed on Dec 4, 2025

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was $2,502, price is now $1,304 per person
$1,304
per person
Feb 28 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (704 reviews)
Room great clean, staff great.loved pool

Reviewed on Dec 10, 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 Fifth Avenue South or Naples Botanical Garden 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 refundableReserve now, pay when you stay
$411 nightly
The price is $457 total per night from Jan 4 to Jan 5
$457 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.8/10 Excellent! (1,970 reviews)
Enjoyed beach, pools, view from balcony.

Reviewed on Dec 11, 2025

Naples Grande Beach Resort
Fairways Inn of Naples

Fairways Inn of Naples

3 out of 5
103 Palm River Blvd Naples FL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $119 total per night from Dec 15 to Dec 16
$119 total
Dec 15 - Dec 16
Total with taxes and fees
9.4/10 Exceptional! (1,114 reviews)
Everything was great really enjoyed the ambiance

Reviewed on Dec 9, 2025

Fairways Inn of Naples
Inn on Fifth

Inn on Fifth

4 out of 5
699 5th Ave S Naples FL
Fully refundable
$363 nightly
The price is $403 total per night from Jan 4 to Jan 5
$403 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2/10 Wonderful! (1,008 reviews)
Lovely and well located!

Reviewed on Dec 12, 2025

Inn on Fifth
See all 10,748 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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Kid Friendly Vacations
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Discover the most popular places to visit in Caldecott

Vanderbilt Beach

Vanderbilt Beach

4.5/5(313 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
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 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

Things to do

Sunset Tour in Naples Bay on a New Godfrey- All included

Naples Sunset Cruise - Complimentary Charcuterie and wine

$110
per adult
100% of travellers recommend
Naples Sunset Cruise - Complimentary Charcuterie and wine
Naples Florida: Downtown Electric Trike Tour

Naples Florida: Downtown Electric Trike Tour - Family Fun

$46
per adult
100% of travellers recommend
Naples Florida: Downtown Electric Trike Tour - Family Fun
Wild Dolphin Boat Tour

Best of Marco Dolphin Tour

$100
per adult
Best of Marco Dolphin 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.