Ole Vacations from $432

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Your Ole Vacation

Take in everything this neighborhood has to offer with a tailor-made Ole vacation package. However you picture yourself spending your time here, you'll find countless opportunities for relaxation, fun and adventure. Some popular nearby attractions to check out during your trip to Ole include Flamingo Island Course - Lely Resort, TPC Treviso Bay and Mustang Course - Lely Resort. Expedia will help turn your dream Ole vacation into reality, whatever your travel plans or budget.

The Latest Ole Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $682, price is now $432 per person
$432
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (521 reviews)
Very nice hotel. Good service and great rooms.

Reviewed on Aug 31, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was $1,166, price is now $547 per person
$547
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (417 reviews)
Great all around 10/10 ; tigress restaurant is worth checking out as well

Reviewed on Sep 28, 2025

Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
Price was $1,059, price is now $656 per person
$656
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (2,219 reviews)
Joyful, relax and exceptional place in the center of the town. People at reception thanks to Tesse and her coworker was pleasant and welcoming , menu at Claw Bar and the London Club superbly delicious , service above and beyond accommodating , dream team of the cleaning crew (spotless clean, but invisible) , valet people friendly and entertaining . Whole experience during our stay was just perfect . Thank you , Bellasera , we will be back

Reviewed on Sep 29, 2025

Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $810, price is now $507 per person
$507
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,499 reviews)
Very clean rooms and the staff was great! Especially Ms Annie ….. she was wonderful!

Reviewed on Oct 1, 2025

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Save 100% on your flight
Price was $884, price is now $560 per person
$560
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (639 reviews)
Had a great time, the pools and lazy river were more than welcome on the hot days. The water shuttle to the private beach is a great feature, just be sure to signup in advance. Having our own vehicle gave us the chance to explore more of the areas activities and restaurants. The Only downsides were communication with having our room being cleaned or fresh towels, and the pesky room keys that would randomly stop working. Would visit again and had a great time.

Reviewed on Oct 2, 2025

Where to stay in Ole

Find the best Ole areas and neighborhoods for the activities you enjoy most. Learn more about Ole
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

Ole Hotel Deals

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
Fully refundable
$254 nightly
The price is $282 total per night from Oct 13 to Oct 14
$282 total
Oct 13 - Oct 14
Total with taxes and fees
9/10 Wonderful! (1,825 reviews)
"Wonderful staff and fast elevators!! Clean facilities and room service was phenomenal"

Reviewed on Sep 30, 2025

Naples Grande Beach Resort
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
$236 nightly
The price is $262 total per night from Oct 5 to Oct 6
$262 total
Oct 5 - Oct 6
Total with taxes and fees
8.8/10 Excellent! (1,605 reviews)
"exelent"

Reviewed on Sep 24, 2025

Hilton Marco Island Beach Resort and Spa
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
$169 nightly
The price is $188 total per night from Oct 26 to Oct 27
$188 total
Oct 26 - Oct 27
Total with taxes and fees
9/10 Wonderful! (1,475 reviews)
"Excellent."

Reviewed on Sep 26, 2025

Hyatt House Naples/5th Avenue
See all 9,785 properties in Ole
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 Ole

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

Wild Dolphin Boat Tour

Best of Marco Dolphin Tour

$100
per adult
Best of Marco Dolphin Tour
Naples, FL: Manatee, Dolphin, 10,000 Islands Beach Eco Tour

Naples, FL: Manatee, Dolphin, 10,000 Islands Beach Eco Tour

$127
per adult
Naples, FL: Manatee, Dolphin, 10,000 Islands Beach Eco Tour
Everglades National Park: 2 hour Dolphin & Birding Boat Tour

Everglades: 2 hour Manatee, Dolphin & Birding Boat Tour

$110
per adult
Everglades: 2 hour Manatee, Dolphin & Birding Boat 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.