Oakes Estates Vacations from $266

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Your Oakes Estates Vacation

Reserving an Oakes Estates vacation package is a great way to become acquainted with this neighborhood. From its hot spots to its lesser-known treasures, you won't be short of adventures. Wondering what to see and do during your trip to Oakes Estates? Nearby attractions such as Tiburon Golf Club, North Collier Regional Park and Sun N Fun Lagoon are good places to start. Expedia will help you turn your ideal Oakes Estates vacation into reality, whatever your budget or travel plans.

The Latest Oakes Estates 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
Price was $488, price is now $266 per person
$266
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,006 reviews)
Safe and quiet place. Easy parking. Strongly recommend.

Reviewed on Aug 23, 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
Price was $1,900, price is now $1,057 per person
$1,057
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,003 reviews)
I loved the beachfront access

Reviewed on Aug 27, 2025

Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $603, price is now $383 per person
$383
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,474 reviews)
Love this place. We have been staying here for 24 years.

Reviewed on Aug 28, 2025

Embassy Suites by Hilton Fort Myers Estero

Embassy Suites by Hilton Fort Myers Estero

3.5 out of 5
Save 100% on your flight
Price was $429, price is now $290 per person
$290
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,000 reviews)
Nice Hotel, and location. My only issue was I was charged for parking twice for everyday of my stay. The parking is only 7.00 a day, so it makes me wonder if it was deliberate. I did make them aware, and they corrected it right away.

Reviewed on Aug 28, 2025

Shell Island Beach Club

Shell Island Beach Club

4 out of 5
Save 100% on your flight
Price was $1,842, price is now $1,253 per person
$1,253
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Fort Myers (RSW)
9.6/10 Exceptional! (22 reviews)
Beautiful view and beautiful beach!

Reviewed on Aug 2, 2025

Where to stay in Oakes Estates

Find the best Oakes Estates areas and neighborhoods for the activities you enjoy most. Learn more about Oakes Estates
South Florida showing a coastal town, a marina and a bay or harbor

Old Naples

3 out of top 10 points of interest in this area
4.5/5(397 area reviews)

The stunning beaches and popular shops are just a few highlights of Old Naples. Make a stop by Fifth Avenue South or Naples Beach while you're exploring the area.

Find hotels in Old Naples

Oakes Estates Hotel Deals

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
Fully refundable
$197 nightly
The price is $219 total per night from Sep 7 to Sep 8
$219 total
Sep 7 - Sep 8
Total with taxes and fees
Naples Grande Beach Resort
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street, Fort Myers Beach, FL
$211 nightly
The price is $236 total per night from Sep 8 to Sep 9
$236 total
Sep 8 - Sep 9
Total with taxes and fees
8.8/10 Excellent! (1,411 reviews)
"Great hotel and facilities, late notice of a power cut annoying as lifts out of operation lugging suitcases up stairs and air con etc in rooms. Otherwise great stay"

Reviewed on Aug 27, 2025

Margaritaville Beach Resort Fort Myers
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
$71 nightly
The price is $79 total per night from Sep 7 to Sep 8
$79 total
Sep 7 - Sep 8
Total with taxes and fees
8.2/10 Very Good! (1,606 reviews)
"The breakfast room is very small, which causes discomfort due to too many people."

Reviewed on Aug 25, 2025

La Quinta Inn & Suites by Wyndham Naples Downtown
See all 10,209 properties in Oakes Estates
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 Oakes Estates

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.