Gleneagles Vacations from $266

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Your Gleneagles Vacation

Organizing your next getaway just got simpler with a vacation package to Gleneagles. Immerse yourself in the best this neighborhood has to offer while making beautiful memories that will last forever. Can't wait to head out and see the sights during your trip to Gleneagles? Make sure you check out nearby attractions like Flamingo Island Course - Lely Resort, Naples Botanical Garden and TPC Treviso Bay. No matter what your dream Gleneagles vacation looks like, you can make it a reality with Expedia.

The Latest Gleneagles 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 $563, price is now $266 per person
$266
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,003 reviews)
People so helpful and friendly ~ communication very good. Room was really nice.

Reviewed on Sep 2, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was $2,462, price is now $1,051 per person
$1,051
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,004 reviews)
The overall experience at the hotel was excellent.

Reviewed on Sep 2, 2025

Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $1,058, price is now $559 per person
$559
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,474 reviews)
Right on the beach and there are several shops and restaurants/bars with in close walking distance!

Reviewed on Sep 2, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Save 100% on your flight
Price was $1,119, price is now $615 per person
$615
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.4/10 Exceptional! (1,001 reviews)
Location, service and amenities are excellent

Reviewed on Aug 31, 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 $726, price is now $418 per person
$418
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (606 reviews)
Lazy river was awesome.

Reviewed on Sep 2, 2025

Where to stay in Gleneagles

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

Gleneagles 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 15 to Sep 16
$219 total
Sep 15 - Sep 16
Total with taxes and fees
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
$192 nightly
The price is $213 total per night from Sep 10 to Sep 11
$213 total
Sep 10 - Sep 11
Total with taxes and fees
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
$127 nightly
The price is $141 total per night from Sep 11 to Sep 12
$141 total
Sep 11 - Sep 12
Total with taxes and fees
Hyatt House Naples/5th Avenue
See all 10,506 properties in Gleneagles
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 Gleneagles

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

$60
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.