Oakes Estates Vacation Rentals & Ski-in/Ski-out Homes
New
House
3 Bedrooms
2 Baths
9 Guests
1582 ft²
Parking
Pool
Balcony/Terrace
Kitchen
US $297/Night
7 Nights - US $2,076
House
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
10 Guests
32291.73 ft²
Oceanfront
Hot Tub- Parking
- Pool
US $695/Night
7 Nights - US $4,865
Hotel
9.4Exceptional
(949 Reviews)
1 Bath
Breakfast- Parking
- Pool
- Balcony/Terrace
US $109/Night
7 Nights - US $762
House
- Naples
- ·
- Willoughby Acres
- 0.22 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
7 Guests
1829.86 ft²
- Oceanfront
- Parking
- Pool
Ocean View
US $445/Night
7 Nights - US $3,113
Apartment
2 Bedrooms
2 Baths
6 Guests
Air Conditioner
Internet
Pet Friendly
Child Friendly
US $109/Night
7 Nights - US $765
Apartment
- Naples
- ·
- Oakes Estates
- 0.61 mi to center
10.0Exceptional
(87 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
View
US $213/Night
7 Nights - US $1,494
House
- Naples
- ·
- Oakes Estates
- 0.59 mi to center
10.0Exceptional
(53 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $326/Night
7 Nights - US $2,280
Apartment
- Naples
- ·
- Oakes Estates
- 0.62 mi to center
10.0Exceptional
(18 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $301/Night
7 Nights - US $2,110
Luxury Places to Stay in Oakes Estates
Over 611+ Luxury Places to Stay in or Near Oakes Estates
House
- Naples
- ·
- Indigo Lakes
- 0.17 mi to center
3 Bedrooms
3 Baths
6 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
Unlock the Best Price
House
10.0Exceptional
(7 Reviews)
11 Bedrooms
8 Baths
30 Guests
12500 ft²
Private Pool- Oceanfront
- Hot Tub
- Parking
US $3,408/Night
7 Nights - US $23,854
Apartment
8.7Fabulous
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
1280.91 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $3,000/Night
7 Nights - US $21,000
Apartment
8.0Excellent
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1227.09 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $2,550/Night
7 Nights - US $17,850
House
- Naples
- ·
- Willoughby Acres
- 0.37 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
7 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $2,408/Night
7 Nights - US $16,854
House
10.0Exceptional
(7 Reviews)
8 Bedrooms
6 Baths
20 Guests
9500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $2,229/Night
7 Nights - US $15,601
House
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,397/Night
7 Nights - US $9,777
New
House
- Naples
- ·
- Willoughby Acres
- 0.23 mi to center
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,369/Night
7 Nights - US $9,585
Apartment
- Naples
- ·
- Rural Estates
- 6.62 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
4 Baths
16 Guests
2685 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,298/Night
7 Nights - US $9,089
Top-Rated Vacation Rentals with a Pool in Oakes Estates
Over 412+ Top-Rated Vacation Rentals with a Pool in or Near Oakes Estates
House
- Naples
- ·
- Willoughby Acres
- 0.19 mi to center
10.0Exceptional
(38 Reviews)
4 Bedrooms
3 Baths
12 Guests
2150 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $616/Night
7 Nights - US $4,311
House
- Naples
- ·
- Oakes Estates
- 0.82 mi to center
10.0Exceptional
(22 Reviews)
6 Bedrooms
4 Baths
16 Guests
4000 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,180/Night
7 Nights - US $8,262
House
- Naples
- ·
- Willoughby Acres
- 0.24 mi to center
10.0Exceptional
(17 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $307/Night
7 Nights - US $2,147
House
- Naples
- ·
- Willoughby Acres
- 0.24 mi to center
10.0Exceptional
(15 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $600/Night
7 Nights - US $4,201
House
10.0Exceptional
(14 Reviews)
3 Bedrooms
2 Baths
5 Guests
2080 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $411/Night
7 Nights - US $2,877
Apartment
10.0Exceptional
(14 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $159/Night
7 Nights - US $1,111
Condo
10.0Exceptional
(14 Reviews)
2 Bedrooms
2 Baths
6 Guests
1700 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $147/Night
7 Nights - US $1,028
House
- Naples
- ·
- Willoughby Acres
- 0.41 mi to center
10.0Exceptional
(13 Reviews)
3 Bedrooms
2 Baths
6 Guests
1825 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $832/Night
7 Nights - US $5,826
House
- Naples
- ·
- North Naples
- 2.31 mi to center
10.0Exceptional
(13 Reviews)
4 Bedrooms
3 Baths
8 Guests
2975 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $452/Night
7 Nights - US $3,167
Pet-Friendly Vacation Rentals in Oakes Estates
Over 135+ Pet-Friendly Vacation Rentals in or Near Oakes Estates
Resort
- Naples
- ·
- North Naples
- 2.36 mi to center
9.4Exceptional
(29 Reviews)
16 Baths
79 Guests
558.74 ft²
Private Beach- Oceanfront
- Hot Tub
- Breakfast
US $411/Night
7 Nights - US $2,877
House
- Naples
- ·
- Oakes Estates
- 0.92 mi to center
1 Bedroom
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $575/Night
7 Nights - US $4,027
Condo
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $255/Night
7 Nights - US $1,788
House
- Naples
- ·
- Willoughby Acres
- 0.15 mi to center
9.0Exceptional
(4 Reviews)
5 Bedrooms
3 Baths
10 Guests
2497.23 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $547/Night
7 Nights - US $3,832
Condo
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $186/Night
7 Nights - US $1,303
Condo
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1449 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $381/Night
7 Nights - US $2,665
Apartment
- Naples
- ·
- Rural Estates
- 6.62 mi to center
9.8Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
6 Guests
1150 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $679/Night
7 Nights - US $4,752
House
- Naples
- ·
- Oakes Estates
- 0.06 mi to center
9.6Exceptional
(39 Reviews)
1 Bedroom
1 Bath
3 Guests
800 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $213/Night
7 Nights - US $1,489
House
- Naples
- ·
- Oakes Estates
- 0.28 mi to center
9.4Exceptional
(25 Reviews)
1 Bedroom
1 Bath
2 Guests
900 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $212/Night
7 Nights - US $1,482
Large Vacation Homes & Villas in Oakes Estates
Over 70+ Large Vacation Homes & Villas in or Near Oakes Estates
House
4.0Average
(1 Review)
5 Bedrooms
4 Baths
9 Guests
4305.56 ft²
- Hot Tub
- Parking
- Pool
Spa
US $700/Night
7 Nights - US $4,900
Villa
- Naples
- ·
- North Naples
- 3.72 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $133/Night
7 Nights - US $934
House
4 Bedrooms
3 Baths
13 Guests
2163.55 ft²
- Oceanfront
- Hot Tub
EV Charge Station- Parking
US $1,084/Night
7 Nights - US $7,585
Villa
9.4Exceptional
(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $154/Night
7 Nights - US $1,079
Villa
- Naples
- ·
- North Naples
- 2.83 mi to center
9.4Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $162/Night
7 Nights - US $1,132
Villa
2 Bedrooms
2 Baths
6 Guests
2050 ft²
- Pool
- Spa
- Kitchen
- Air Conditioner
US $288/Night
7 Nights - US $2,015
Villa
- Naples
- ·
- Village Walk
- 0.23 mi to center
2 Bedrooms
2 Baths
4 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $286/Night
7 Nights - US $2,003
Villa
- Naples
- ·
- Village Walk
- 0.20 mi to center
2 Bedrooms
2 Baths
4 Guests
1680 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $283/Night
7 Nights - US $1,983
Villa
2 Bedrooms
1 Bath
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $231/Night
7 Nights - US $1,617
Wheelchair Accessible Vacation Homes in Oakes Estates
Over 48+ Wheelchair Accessible Vacation Homes in or Near Oakes Estates
Hotel
8.9Fabulous
(492 Reviews)
6 Baths
361.93 ft²
- Oceanfront
- Breakfast
- EV Charge Station
- Parking
US $170/Night
7 Nights - US $1,190
Hotel
- Naples
- ·
- North Naples
- 2.39 mi to center
9.4Exceptional
(654 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Spa
US $509/Night
7 Nights - US $3,562
Condo
10.0Exceptional
(6 Reviews)
2 Bedrooms
3 Baths
4 Guests
2300 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $706/Night
7 Nights - US $4,945
Hotel
8.5Fabulous
(193 Reviews)
1 Bath
301.39 ft²
- Oceanfront
- EV Charge Station
- Parking
- Pool
US $98/Night
7 Nights - US $685
Condo
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1250 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $96/Night
7 Nights - US $670
Condo
- Naples
- ·
- North Naples
- 1.68 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $173/Night
7 Nights - US $1,211
Condo
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1294 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $246/Night
7 Nights - US $1,720
Condo
- Naples
- ·
- North Naples
- 2.52 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
4 Guests
1120 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $257/Night
7 Nights - US $1,800
Condo
- Naples
- ·
- Tarpon Bay
- 0.27 mi to center
9.6Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
1350 ft²
- Hot Tub
- Parking
- Pool
- Kitchen
US $522/Night
7 Nights - US $3,655
Oakes Estates Resorts and Airbnb Homes Under $200
Over 180+ Oakes Estates Resorts and Airbnb Homes Under $200
House
2 Bedrooms
2 Baths
6 Guests
1377.78 ft²
- Hot Tub
- Parking
- Pool
- Internet
US $124/Night
7 Nights - US $868
Hotel
9.0Exceptional
(1007 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $99/Night
7 Nights - US $694
Condo
- Naples
- ·
- North Naples
- 1.63 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $131/Night
7 Nights - US $914
Condo
- Naples
- ·
- North Naples
- 2.57 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $193/Night
7 Nights - US $1,348
Condo
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
1207 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $156/Night
7 Nights - US $1,095
Condo
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $138/Night
7 Nights - US $965
Condo
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $169/Night
7 Nights - US $1,181
Condo
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $148/Night
7 Nights - US $1,039
Condo
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
1377 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $117/Night
7 Nights - US $818
Instantly Bookable Vacation Homes in Oakes Estates
Over 262+ Instantly Bookable Vacation Homes in or Near Oakes Estates
Condo
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
1250 ft²
- Hot Tub
- Parking
- Pool
- Kitchen
US $410/Night
7 Nights - US $2,872
Condo
- Naples
- ·
- North Naples
- 3.19 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $223/Night
7 Nights - US $1,560
House
- Naples
- ·
- Willoughby Acres
- 0.19 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1741 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $656/Night
7 Nights - US $4,591
Condo
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $253/Night
7 Nights - US $1,769
Apartment
- Naples
- ·
- Rural Estates
- 6.70 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
818 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $205/Night
7 Nights - US $1,438
Condo
- Naples
- ·
- Tarpon Bay
- 0.07 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $186/Night
7 Nights - US $1,300
Apartment
9.8Exceptional
(26 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $56/Night
7 Nights - US $395
Condo
9.8Exceptional
(16 Reviews)
2 Bedrooms
2 Baths
4 Guests
1150 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $125/Night
7 Nights - US $873
Condo
9.8Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
1807 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $552/Night
7 Nights - US $3,865
Book a Last Minute Place to Stay in Oakes Estates
About Oakes Estates Vacation Rentals
Explore over 620 vacation rentals in Oakes Estates with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Oakes Estates for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Oakes Estates. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Oakes Estates tailored to your preferences. On average, these rentals offer 994.78 ft² of space, and are priced at an average of US $371 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Oakes Estates at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
Show more
Show less
Top Types of Ski Accommodations in Oakes Estates
| Type | Count |
|---|---|
| Vacation Homes | 287 |
| Holiday Apartments | 54 |
| Villas | 30 |
| Cottages | 3 |
| Unique Vacation Rentals | 1 |
Use these Quick Filters to Find a Vacation Rental in Oakes Estates
★ Pro Tip: Discover Your Ideal Vacation Rental in Oakes Estates with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Oakes Estates, FL
View the weather forecast for Oakes Estates before booking your Oakes Estates Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Frequently Asked Questions About Oakes Estates?
What are the top vacation rentals in Oakes Estates?
When organizing your trip to Oakes Estates, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Oakes Estates. Peruse our collection of highly-rated properties and secure your reservation today.
- Private Suite on 3 Acres in North Naples!
- Modern North Naples Villa on 3 Acres!
- NEW Naples Modern Farmhouse w/Heated Pool, Sleep 10
- Spacious Family Retreat with Pool Gym Sauna Pickleball and Guest Suite SLEEPS 16
- Villa Mango
- Lux Naples! Heated Pool ~ Fenced Yard ~ Near Beach
- Two Master Suites, Fully Stocked Home w/Heated Pool & Spa Close to Everything
- MODERN ELEGANT LUXURY HOME - Airy, uncluttered, clean & peaceful
- The Secret Garden
- Naples Beach , Golf and Country Club Naples Florida
How many vacation rentals have private pools in Oakes Estates?
Uncover 104 vacation rentals boasting private pools near Oakes Estates. Explore top-rated RBO homes offering access to a swimming pool:
- Orchid Estates
- Paradise Awaits! Country Club Living, Private Golf Course, beaches, 1st Floor!
- Palm River Estates - Courtwood
- ESPLANADE GOLF/5 Star🌟LUXURY Private Home/Pool/Spa + beaches 8-10 miles!
Which vacation homes or resorts in Oakes Estates are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Oakes Estates. Enjoy great views, locations and save money with SunSki Resorts.™
- Peaceful Naples Retreat Pool and Spa Haven
- Paradise away from Home! Home and neighborhood was not affected by hurricane
- Paradise Awaits! Country Club Living, Private Golf Course, beaches, 1st Floor!
How many SunSkiResorts vacation rentals or resorts are available in Oakes Estates?
Discover the ideal vacation rental in Oakes Estates with SunSki Resorts™. We provide an extensive selection of over 620 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Oakes Estates.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Tarpon Bay Vacation Rentals in Naples, Florida | 685 |
People Also Ask
Map
