Best Vacation Homes in Gleneagles
New
House
9.8(20 Reviews)
3 Bedrooms
2 Baths
6 Guests
1600 ft²
Private Pool
Fireplace/Heating
Pool
Ocean View
US $277/Night
7 Nights - US $1,936
Apartment
10.0(23 Reviews)
2 Bedrooms
2 Baths
4 Guests
1011.81 ft²
Oceanfront
Hot Tub- Fireplace/Heating
- Pool
US $181/Night
7 Nights - US $1,267
Condo
10.0(1 Review)
1 Bedroom
1 Bath
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $518/Night
7 Nights - US $3,626
Condo
3 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
Air Conditioner
Internet
Child Friendly
US $413/Night
7 Nights - US $2,891
House
10.0(7 Reviews)
3 Bedrooms
2 Baths
8 Guests
1840.63 ft²
- Oceanfront
- Pool
- Ocean View
View
US $504/Night
7 Nights - US $3,526
Condo
3 Bedrooms
2 Baths
6 Guests
1454 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $392/Night
7 Nights - US $2,746
Condo
3 Bedrooms
2 Baths
6 Guests
1454 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $341/Night
7 Nights - US $2,390
New
Condo
3 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $333/Night
7 Nights - US $2,331
Gleneagles Luxury Rentals
Condo
1 Bedroom
1 Bath
2 Guests
- Pool
- Ocean View
Balcony/Terrace- View
US $5,662/Night
7 Nights - US $39,635
House
4 Bedrooms
4 Baths
8 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Laundry
US $3,349/Night
7 Nights - US $23,444
Villa
10.0(1 Review)
7 Bedrooms
4 Baths
20 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,593/Night
7 Nights - US $11,150
House
10.0(6 Reviews)
4 Bedrooms
3 Baths
17 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,469/Night
7 Nights - US $10,280
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Private Pool
- Fireplace/Heating
- Pool
Pet Friendly
US $1,340/Night
7 Nights - US $9,380
House
10.0(15 Reviews)
7 Bedrooms
4 Baths
18 Guests
3900 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $1,310/Night
7 Nights - US $9,172
House
1 Bedroom
5 Baths
11 Guests
3799.66 ft²
- Pool
- Balcony/Terrace
Parking- Air Conditioner
US $1,264/Night
7 Nights - US $8,849
Condo
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
Kitchen
US $1,125/Night
7 Nights - US $7,873
Gleneagles Pet Friendly Vacation Rentals
Cottage
2 Bedrooms
1 Bath
4 Guests
400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $108/Night
7 Nights - US $756
Villa
10.0(5 Reviews)
3 Bedrooms
2 Baths
8 Guests
2303.48 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $828/Night
7 Nights - US $5,796
House
6.0(1 Review)
1 Bedroom
1 Bath
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $887/Night
7 Nights - US $6,209
Apartment
10.0(53 Reviews)
2 Bedrooms
2 Baths
5 Guests
1250 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $196/Night
7 Nights - US $1,374
Villa
10.0(2 Reviews)
3 Bedrooms
3 Baths
8 Guests
1603.82 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $316/Night
7 Nights - US $2,212
House
10.0(33 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $181/Night
7 Nights - US $1,264
Condo
10.0(28 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $193/Night
7 Nights - US $1,354
Condo
10.0(17 Reviews)
2 Bedrooms
2 Baths
6 Guests
1244 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $210/Night
7 Nights - US $1,470
Gleneagles Large Vacation Homes
Villa
10.0(38 Reviews)
2 Bedrooms
2 Baths
6 Guests
1538 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $203/Night
7 Nights - US $1,420
Villa
10.0(2 Reviews)
2 Bedrooms
3 Baths
8 Guests
1603.82 ft²
- Balcony/Terrace
- Pet Friendly
- Parking
- Air Conditioner
US $316/Night
7 Nights - US $2,212
Villa
10.0(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
1470 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $233/Night
7 Nights - US $1,630
Villa
9.8(57 Reviews)
2 Bedrooms
2 Baths
6 Guests
1399.31 ft²
- Oceanfront
- Hot Tub
Spa- Fireplace/Heating
US $278/Night
7 Nights - US $1,946
Villa
10.0(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
1530 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $398/Night
7 Nights - US $2,789
Villa
10.0(5 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $212/Night
7 Nights - US $1,481
Villa
10.0(5 Reviews)
1 Bedroom
1 Bath
2 Guests
576 ft²
- Pool
- Kitchen
- Parking
- Air Conditioner
US $100/Night
7 Nights - US $702
Villa
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $262/Night
7 Nights - US $1,831
Why Choose Rent By Owner for your Gleneagles Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Gleneagles Vacation Rentals
Where are the best neighborhoods to stay in Gleneagles?
When choosing a neighborhood to stay in Gleneagles, Naples, Florida, you’ll find a variety of options that suit different preferences and lifestyles. This charming area offers a peaceful atmosphere with easy access to nearby amenities, making it an ideal spot for your next vacation rental. Whether you're seeking a quiet retreat or a more active environment, exploring the neighborhoods within Gleneagles will help you find the perfect place to relax and enjoy your time in Naples. With its convenient location and inviting community settings, staying here ensures a memorable and comfortable visit to Florida’s Gulf Coast.
Lely Golf Estates
Situated within the region, this neighborhood offers easy access to premier golf courses and scenic surroundings, making it an ideal choice for those seeking a relaxed yet active lifestyle. Here, you can enjoy comfortable vacation rentals that provide a peaceful retreat in the heart of Naples.
View 38+ Rentals in Lely Golf EstatesBest Times to Visit Gleneagles
When should you plan your Vacation Rentals stay?
Choosing the ideal time to vacation here can enhance your experience, as the best seasons in Naples, Florida, offer pleasant weather and optimal conditions for enjoying this beautiful region.
Peak Season Highlights
Winter (December to February)
During this time, the area experiences warm and pleasant weather, making it ideal for enjoying outdoor activities and relaxing by the water. It's the busiest season for visitors seeking a sunny escape.
Average Temperature Daytime: 75°F - Nighttime: 60°F
Spring (March to May)
Spring brings mild temperatures and blooming landscapes, attracting travelers looking for comfortable weather and scenic views. It’s a popular period for those wanting to explore comfortably.
Average Temperature Daytime: 80°F - Nighttime: 65°F
Off-Season Highlights
Summer (June to August)
While summer offers warmer temperatures, it is considered less busy as many visitors prefer cooler destinations. This is an excellent opportunity to enjoy quieter surroundings with lower rates.
Average Temperature Daytime: 88°F - Nighttime: 75°F
Fall (September to November)
Autumn features cooler, comfortable weather and fewer tourists, providing a peaceful setting for your stay. It’s a great time to find deals on vacation rentals in this region.
Average Temperature Daytime: 78°F - Nighttime: 63°F
Weekly Weather Forecast for Gleneagles
How to Book Your Gleneagles Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Gleneagles
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy swimming and relaxing in your private outdoor pool, perfect for warm days in the region.
- Take advantage of a spacious outdoor patio or deck area for al fresco dining and gatherings.
- Maintain an active lifestyle with access to tennis courts or other sports facilities nearby.
- Unwind in beautifully landscaped gardens or lush green spaces that surround your rental.
- Benefit from outdoor grilling stations or barbecue areas to enjoy Florida-style cookouts.
- Make the most of scenic walking or biking paths within the community or nearby parks.
- Experience tranquil water features such as lakes or ponds that add to the area's serene atmosphere.
Top Attractions Around Gleneagles
What attractions are nearby?
During your stay in this desirable area, you can explore a variety of outdoor activities, golf courses, and scenic beaches that offer the perfect setting for relaxation and recreation here in Naples, Florida.
Family Activities
- Gulf Coast Explorer Tour: Discover the stunning Gulf Coast waters on a family-friendly boat tour that offers scenic views and wildlife sightings unique to this part of Florida.
- Clam Pass Park: Spend a relaxing day at this popular beach spot, where you can enjoy picnicking, gentle walks along the nature trail, and swimming in calm waters.
- Corkscrew Swamp Sanctuary: Encounter Florida’s natural beauty here with guided walks through lush wetlands teeming with diverse birdlife and alligators.
- Naples Zoo at Caribbean Gardens: Experience an engaging day with exotic animals and interactive exhibits suitable for children and adults alike, right in the heart of the region.
Adult Activities
- Golfing at the Gleneagles Golf Club: Experience world-class golf on meticulously maintained courses, perfect for a relaxing day on the greens.
- Exploring the nearby Naples Botanical Garden: Discover lush landscapes and vibrant plant collections, offering a tranquil escape within the region.
- Sailing and fishing along the Gulf of Mexico: Take advantage of the area's rich waters with boating excursions or deep-sea fishing adventures.
- Dining at upscale restaurants in Naples: Indulge in exquisite cuisine at some of Florida’s finest eateries, just a short drive from your rental.
Gleneagles Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take advantage of the area's renowned culinary scene by trying local restaurants and fresh seafood to enhance your beachside experience.
- Visit the Nearby Beaches: Make time for relaxing days at the region’s beautiful beaches, ensuring you soak up the sun and enjoy the tranquil ocean views.
- Plan Outdoor Activities: Discover outdoor pursuits such as boating, fishing, or nature walks that highlight the natural beauty of this destination.
- Choose the Right Vacation Rental: Select a well-located property that offers easy access to attractions and amenities for a seamless stay in the area.
Transportation Options
- Car Rentals: Renting a car here offers the flexibility to explore the scenic region at your own pace, making it ideal for visiting nearby beaches and attractions.
- Local Shuttle Services: Convenient shuttle options operate within the area, providing easy transportation to key destinations without the hassle of driving.
- Taxi and Ride-Sharing Services: Taxis and ride-sharing apps are readily available, offering quick and reliable transportation around this popular destination.
- Public Transit: The regional bus system connects various neighborhoods and points of interest, making it a budget-friendly choice for getting around the region.
Local Customs Options
- Southern Hospitality: You will notice a warm welcoming atmosphere as locals here often greet visitors with friendly smiles and courteous behavior, reflecting the region’s Southern charm.
- Golf Etiquette: Playing at local courses or observing players, you'll find that there is a strong emphasis on proper golf etiquette, emphasizing respect and sportsmanship in this destination’s renowned golf community.
- Environmental Respect: As you explore the area, you'll see residents valuing environmental preservation, with practices such as recycling and conservation playing a key role in daily life.
- Community Events: Engaging with nearby gatherings and festivals, you'll experience the local customs of participating actively in community celebrations, highlighting the area's vibrant social fabric.
Gleneagles Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Gleneagles?
There are a lot of options in Gleneagles. If you plan on staying in the Gleneagles area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Gleneagles:
- New Updates Lely Resort, 3 bed, golf course home Includes Players Club and Spa
- Villa on Golf Course with Heated Saltwater Pool
- Purple Orchid -Luxury Fully Renovated Modern 1st floor 3bdr Resort Villa
- Lely Resort Masters Reserve Naples Home on Private Lake in Gated Community
- Naples Lely Resort- Quiet Villa Home with Oversized Pool
- Lovely 2-Bedroom + Den Condo in Greenlinks Resort
- TWO MASTER SUITES Heated Pool+Spa BEACH Home Private Comm IN NAPLES, Walk to
- VILLA BELLY :-) heated pool. free WIFI, very private, Garage, BBQ, Kings Lake
- Enjoy Players Club Access in this Luxurious Naples Golf Course Home.
- Generously sized updated lanai showcasing a prime mid-water south view.
2. How many vacation rentals have private pools in Gleneagles?
There are 385 vacation rentals with private pools near Gleneagles. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Gleneagles are best for families?
If you are looking for a family-friendly vacation home in Gleneagles, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Gleneagles:
4. How many Rentbyowner vacation rentals are available in Gleneagles?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1825 in the Gleneagles area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Gleneagles.
5. What is the cancellation policy for vacation rentals in Gleneagles, Naples?
Cancellation policies vary by property; please review the specific listing details or contact the owner directly to understand the terms and any potential fees.
6. How do I secure my reservation at a vacation rental in Gleneagles, Naples?
Reservations are typically confirmed through the listing platform once you complete the booking process and payment. For additional assurance, reach out to the property owner if you have questions before confirming.
7. Are there minimum stay requirements for vacation rentals here?
Minimum stay requirements depend on the individual property. Check the listing details or contact the owner to confirm any specific stay duration before making your reservation.
8. What amenities should I expect from vacation rentals in Gleneagles, Naples?
Amenities can include anything from private pools to fully equipped kitchens. Review each listing carefully to see what features are included, or ask the owner for specific details about the property.
9. Is it safe to book vacation rentals in this area during peak season?
Yes, trusted listings are verified for safety and quality. To ensure a smooth experience, read reviews and communicate with the owner directly if you have any concerns before booking.
Gleneagles Top Rated Vacation Rentals
House
10.0(146 Reviews)
3 Bedrooms
2 Baths
6 Guests
1800 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Spa
US $256/Night
7 Nights - US $1,794
House
10.0(122 Reviews)
2 Bedrooms
2 Baths
6 Guests
1600 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $246/Night
7 Nights - US $1,721
Condo
10.0(119 Reviews)
3 Bedrooms
2 Baths
6 Guests
1400 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $193/Night
7 Nights - US $1,352
House
10.0(103 Reviews)
3 Bedrooms
2 Baths
8 Guests
2200 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $400/Night
7 Nights - US $2,803
House
10.0(80 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $213/Night
7 Nights - US $1,493
Apartment
10.0(76 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $151/Night
7 Nights - US $1,058
House
10.0(75 Reviews)
4 Bedrooms
3 Baths
7 Guests
3200 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $211/Night
7 Nights - US $1,478
House
10.0(64 Reviews)
2 Bedrooms
2 Baths
4 Guests
1567 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $424/Night
7 Nights - US $2,968
