Ole Vacations from $329

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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.
Days Inn by Wyndham Port Charlotte/Punta Gorda

Days Inn by Wyndham Port Charlotte/Punta Gorda

3 out of 5
Save 100% on your flight
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
7.8/10 Good! (1,009 reviews)
Very good stay good customer service

Reviewed on Sep 23, 2024

South Seas Resort

South Seas Resort

3.5 out of 5
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.4/10 Very Good! (1,001 reviews)
Property was good still a lot of construction going on to repair damage from the hurricane. Staff was very nice great service overall experience was nice and easy walkable to pool and the private beach.

Reviewed on Sep 22, 2024

Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
per person
Nov 15 - Nov 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (2,025 reviews)
Excellent location, friendly staff, beautiful property excellent gourmet food, phenomenal cocktails. highly recommended will definitely is a comeback place to visit.

Reviewed on Sep 24, 2024

Doubletree by Hilton Fort Myers at Bell Tower Shops

Doubletree by Hilton Fort Myers at Bell Tower Shops

4 out of 5
Villas
Save 100% on your flight
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,000 reviews)
The TVs were not working during our stay. Apparently, that was the case throughout the hotel. Very disappointing as we were looking forward to watching college football that afternoon and evening. At checkout I asked about a credit and was told they wouldn't give a credit because we booked through Expedia. In today's computerized world it should be easy for the hotel to issue a credit back through Expedia or by some other means. I hesitate to use Expedia in the future if it's true that no credit can be given if there is a problem with the travel experience.

Reviewed on Sep 24, 2024

Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Save 100% on your flight
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.4/10 Very Good! (1,000 reviews)
Amazing property and staff!!!

Reviewed on Sep 10, 2024

Where to stay in Ole

Find the best Ole areas and neighborhoods for the activities you enjoy most. Learn more about Ole
Naples Zoo at Caribbean Gardens which includes wildflowers

Central Naples

1 out of top 10 points of interest in this area
4/5(21 area reviews)

If you're spending some time in Central Naples, Naples Grande Golf Club and Naples Zoo at Caribbean Gardens are top sights worth seeing.

Find hotel + flight trips in Central Naples

Ole Hotel Deals

Naples Grande Beach Resort
Naples Grande Beach Resort
4.5 out of 5
475 Seagate Drive, Naples, FL
The price is $270 per night from Sep 29 to Sep 30
$270
includes taxes & fees
$243 per night
Sep 29 - Sep 30
8.8/10 Excellent! (1,279 reviews)
"This resort is top shelf. From the employees to the amenities all were excellent. The beach is one of the nicest beaches on the Gulf of Mexico. The breakfasts were delicious and the servers were outstanding. We loved the availability of the lounges, towels and umbrellas at both the pools and beach. ..."

Reviewed on Sep 25, 2024

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
The price is $88 per night from Oct 6 to Oct 7
$88
includes taxes & fees
$79 per night
Oct 6 - Oct 7
8/10 Very Good! (1,213 reviews)
"Very nice place-convenient to shopping and great restaurants."

Reviewed on Sep 25, 2024

La Quinta Inn & Suites by Wyndham Naples Downtown
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
The price is $265 per night from Oct 2 to Oct 3
$265
includes taxes & fees
$238 per night
Oct 2 - Oct 3
8.6/10 Excellent! (1,279 reviews)
"Great access to the beach. Nice beach and pool."

Reviewed on Sep 24, 2024

Hilton Marco Island Beach Resort and Spa
See all 9,062 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

Frequently asked questions

How much does an Ole vacation package cost?
From as little as $329. Yes, you read that right. Our Ole packages are the best way to stretch your budget further. Bundle your favorite flights, hotels and rental car and get out and see this vibrant destination.
How do I get a cheap travel package to Ole?
Bundling your flight and hotel with Expedia won’t just save valuable time — it’ll save you a tidy sum too. An Ole vacation package makes it easy to create your perfect trip. With more than 550 airlines around the world to pick from, finding flights that suit your schedule will be no sweat. In addition to that, we have over 1,000,000 properties globally to select from. Talk about choice! No matter who you are, Expedia brings the world within your reach.
Where should I stay in Ole?
A getaway to Ole wouldn’t be complete without paying a visit to Eagle Lakes Community Park. Why not choose a hotel within walking distance of this much-loved tourist attraction?
What are the top hotels in Ole?
Get your escape off to a great start by staying at Beautiful Pool View Condo. It’s one of most popular properties in Ole. Another top option is Quiet Lely Resort Condo With Pool.
How far in advance should I book my Ole vacation?
It can be difficult to know when is the ideal time to book your vacation to Ole. But usually the earlier you book, the cheaper the prices. Sometimes, you can reserve your flights and hotels up to 12 months prior to departure. If you’re hoping for a last-minute getaway, no need to worry! There are fabulous deals posted on Expedia all the time.
What does an Expedia Ole travel package include?
Car rentals, hotels and flights — we connect you to all the best deals. All you have to do is figure out your favorite combination. Once you’ve made your booking, you can add on the exciting stuff like tours and experiences. Our travel packages make it easy to create an unforgettable Ole trip.
What should I know before booking an Ole travel package?
Booking all the parts of your getaway together is one of the best ways to save. Bundle your flights, car rentals and hotels into one package. But you’re not limited to hotels. Expedia features all kinds of properties, including vacation rentals like mountain cabins and spacious residences. The list goes on!
Can I choose my airline with an Ole Expedia vacation package?
You can, and with more than 550 airlines to select from all over the world, you have plenty of choice. Browse the available options and see which airline fits your needs and budget.
If I'm not able to travel, can I cancel my Ole vacation package?
It’s impossible to predict what the future holds, so it’s comforting to know that you can cancel or change your Ole vacation package. If your booking was made in the last 24 hours, you may be eligible for a refund. If it’s an older booking, your airline, hotel or car rental company may charge a fee. Check our Customer Service Portal for further details.

Discover the most popular places to visit in Ole

Image for 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
Image for 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
Image for 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

Things to do

Image for Gulf of Mexico Sunset Cruise from Naples

Gulf of Mexico Sunset Cruise from Naples

$65
Per adult
86% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
Image for Everglades: Mangrove Maze Airboat Tour and Boardwalk

Everglades: Mangrove Maze Airboat Tour and Boardwalk

$59
Per adult
Everglades: Mangrove Maze Airboat Tour and Boardwalk
Image for Naples Sightseeing Boat Tour

Naples Sightseeing Boat Tour

$60
Per adult
100% of travellers recommend
Naples Sightseeing 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.