Ole Vacations from $598

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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.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was $901, price is now $598 per person
$598
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (788 reviews)
Food was great, two pools (family and adults only) the room was clean which is extremely important and a great view

Reviewed on May 7, 2026

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 $2,187, price is now $1,199 per person
$1,199
per person
Jul 16 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Fort Myers (RSW)
9/10 Wonderful! (1,005 reviews)
Great resort. Beautiful beach. Great restaurant. Close to 5th Ave South

Reviewed on May 9, 2026

Shell Island Beach Club

Shell Island Beach Club

4 out of 5
East End
Save 100% on your flight
Price was $2,145, price is now $1,379 per person
$1,379
per person
Jul 11 - Jul 18
found 21 hours ago
Roundtrip flight included
New York (JFK) to Fort Myers (RSW)
9.6/10 Exceptional! (23 reviews)
Beautiful view and beautiful beach!

Reviewed on Aug 2, 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 $1,359, price is now $899 per person
$899
per person
Jul 18 - Jul 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (846 reviews)
It is not on the beach but a 30 minute drive to get there by golf cart. There is no restaurant for dinner. The lunch cafe closes at 7:30p.m so after that there is nothing! Or you could drive somewhere to eat! The Lazy River closes at 6:30p.m. It is light until 8:30p.m? The resort itself is very beautiful and the landscape is gorgeous.

Reviewed on May 10, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Save 100% on your flight
Price was $1,113, price is now $742 per person
$742
per person
Jul 18 - Jul 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (1,192 reviews)
Very clean and high spec. Lots more room for your money than at a comparable hotel

Reviewed on May 10, 2026

Where to stay in Ole

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

East Naples

4/5(175 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

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
$262 nightly
The price is $291 total per night from May 20 to May 21
$291 total
May 20 - May 21
Total with taxes and fees
9/10 Wonderful! (1,780 reviews)
We really enjoyed our stay the only thing to criticize (and there’s nothing anyone could do about it), is there are drainage grates throughout the pool deck and every so often you could smell sewage. It was very unpleasant. Our room was comfy and clean and all the food we had here was really good. ...

Reviewed on May 10, 2026

Hilton Marco Island Beach Resort and Spa
Great Wolf Lodge Naples

Great Wolf Lodge Naples

3 out of 5
3900 City Gate Blvd N. Naples FL
Fully refundableReserve now, pay when you stay
$220 nightly
The price is $244 total per night from May 25 to May 26
$244 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (782 reviews)
Es muy buena opción para niños. En general todo muy limpio.

Reviewed on May 11, 2026

Great Wolf Lodge Naples
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
$79 nightly
The price is $88 total per night from May 21 to May 22
$88 total
May 21 - May 22
Total with taxes and fees
8.2/10 Very Good! (1,952 reviews)
Everything great. 👍

Reviewed on May 9, 2026

La Quinta Inn & Suites by Wyndham Naples Downtown
See all 9,769 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

Pristine and idyllic beach at sunset in a bright day, Naples, Florida, USA

Naples Beach

4.5/5(1,422 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
Fifth Avenue South

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
Vanderbilt beach in Naples, Florida

Vanderbilt Beach

4.5/5(319 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

Things to do

Naples Sightseeing Boat Tour

Naples Sightseeing Boat Tour

$53
per adult
96% of travellers recommend
Naples Sightseeing Boat Tour
Gulf of Mexico Sunset Cruise from Naples

Gulf of Mexico Sunset Cruise from Naples

$73
per adult
88% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
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
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.