Ole Vacations from $301

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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.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Save 100% on your flight
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,004 reviews)
The matress was hard and wasnt able to get a good night sleep

Reviewed on Aug 16, 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
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,007 reviews)
Just what we wanted beach and golf. Restaurant services could do better, food was overpriced.

Reviewed on Aug 14, 2025

Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (2,202 reviews)
The hotel is nice, it’s just that the restaurants were not open a lot of the time. If you want breakfast you have to leave the hotel

Reviewed on Aug 15, 2025

Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
per person
Oct 24 - Oct 27
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (505 reviews)
Ultra modern and clean. Friendly staff

Reviewed on Aug 10, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (365 reviews)
The property is beautiful and well-run with excellent amenities. The staff are friendly and extremely helpful. The room was pristine and spacious. The pool areas are gorgeous. Located in close proximity to many shopping/dining options. Highly recommend.

Reviewed on Aug 16, 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
$208 nightly
The price is $231 total per night from Sep 7 to Sep 8
$231 total
Sep 7 - Sep 8
Total includes taxes and fees
9/10 Wonderful! (1,699 reviews)
"Easy check in. Our room lack oean views bu5 still very nice."

Reviewed on Aug 13, 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
$189 nightly
The price is $210 total per night from Aug 19 to Aug 20
$210 total
Aug 19 - Aug 20
Total includes taxes and fees
8.8/10 Excellent! (1,492 reviews)
"My family and I had a wonderful summer vacation."

Reviewed on Aug 11, 2025

Hilton Marco Island Beach Resort and Spa
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
$68 nightly
The price is $75 total per night from Sep 1 to Sep 2
$75 total
Sep 1 - Sep 2
Total includes taxes and fees
8.2/10 Very Good! (1,583 reviews)
"Good"

Reviewed on Aug 16, 2025

La Quinta Inn & Suites by Wyndham Naples Downtown
See all 9,620 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

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.