Oakes Estates Vacation Rentals & Ski-in/Ski-out Homes
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 $217/Night
7 Nights - US $1,518
House
- Naples
- ·
- Willoughby Acres
- 0.50 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
2 Baths
8 Guests
1905.21 ft²
- Parking
Pool- View
Air Conditioner
US $305/Night
7 Nights - US $2,135
Hotel
9.4Exceptional
(1014 Reviews)
1 Bath
Breakfast- Parking
- Pool
- Balcony/Terrace
US $124/Night
7 Nights - US $867
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 $323/Night
7 Nights - US $2,259
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
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 $228/Night
7 Nights - US $1,595
Apartment
10.0Exceptional
(14 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $160/Night
7 Nights - US $1,118
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 $1,030
House
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $681/Night
7 Nights - US $4,764
Luxury Places to Stay in Oakes Estates
Over 616+ Luxury Places to Stay in or Near Oakes Estates
House
10.0Exceptional
(7 Reviews)
11 Bedrooms
8 Baths
30 Guests
12500 ft²
Private Pool- Oceanfront
- Hot Tub
- Parking
US $3,757/Night
7 Nights - US $26,298
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 $2,476/Night
7 Nights - US $17,334
House
10.0Exceptional
(8 Reviews)
8 Bedrooms
6 Baths
20 Guests
9500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $2,444/Night
7 Nights - US $17,109
House
- Naples
- ·
- Oakes Estates
- 0.92 mi to center
1 Bedroom
5 Baths
14 Guests
3003.13 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,908/Night
7 Nights - US $13,357
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 $1,623/Night
7 Nights - US $11,361
New
House
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
13 Guests
2331 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $1,377/Night
7 Nights - US $9,639
House
- Naples
- ·
- Willoughby Acres
- 0.23 mi to center
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,371/Night
7 Nights - US $9,597
Top-Rated Vacation Rentals with a Pool in Oakes Estates
Over 403+ Top-Rated Vacation Rentals with a Pool in or Near Oakes Estates
House
- Naples
- ·
- Willoughby Acres
- 0.19 mi to center
10.0Exceptional
(39 Reviews)
4 Bedrooms
3 Baths
12 Guests
2150 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $585/Night
7 Nights - US $4,097
House
- Naples
- ·
- Willoughby Acres
- 0.24 mi to center
10.0Exceptional
(18 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $284/Night
7 Nights - US $1,990
House
- Naples
- ·
- North Naples
- 2.31 mi to center
10.0Exceptional
(17 Reviews)
4 Bedrooms
3 Baths
8 Guests
2975 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $373/Night
7 Nights - US $2,611
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 $584/Night
7 Nights - US $4,085
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 $513/Night
7 Nights - US $3,594
Apartment
- Naples
- ·
- Rural Estates
- 6.62 mi to center
10.0Exceptional
(12 Reviews)
3 Bedrooms
2 Baths
10 Guests
1535 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $682/Night
7 Nights - US $4,776
House
10.0Exceptional
(10 Reviews)
3 Bedrooms
3 Baths
8 Guests
4262 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $866/Night
7 Nights - US $6,065
House
10.0Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
7 Guests
1787 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $242/Night
7 Nights - US $1,695
House
10.0Exceptional
(6 Reviews)
3 Bedrooms
3 Baths
6 Guests
2500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $799/Night
7 Nights - US $5,590
Pet-Friendly Vacation Rentals in Oakes Estates
Over 142+ Pet-Friendly Vacation Rentals in or Near Oakes Estates
Condo
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $284/Night
7 Nights - US $1,988
Resort
- Naples
- ·
- North Naples
- 2.36 mi to center
8.4Excellent
(36 Reviews)
36 Baths
107 Guests
586.63 ft²
Private Beach- Oceanfront
- Hot Tub
- Breakfast
US $515/Night
7 Nights - US $3,605
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
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $197/Night
7 Nights - US $1,377
House
- Naples
- ·
- Willoughby Acres
- 0.19 mi to center
1.0Average
(1 Review)
3 Bedrooms
2 Baths
8 Guests
1754.52 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $356/Night
7 Nights - US $2,492
Condo
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1449 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $304/Night
7 Nights - US $2,129
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 $655/Night
7 Nights - US $4,583
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 $218/Night
7 Nights - US $1,528
Cottage
- Naples
- ·
- Oakes Estates
- 0.36 mi to center
9.4Exceptional
(15 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $217/Night
7 Nights - US $1,522
Large Vacation Homes & Villas in Oakes Estates
Over 71+ Large Vacation Homes & Villas in or Near Oakes Estates
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 $136/Night
7 Nights - US $953
House
4.0Average
(1 Review)
5 Bedrooms
4 Baths
9 Guests
4305.56 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $596/Night
7 Nights - US $4,172
Villa
- Naples
- ·
- Village Walk
- 0.20 mi to center
2 Bedrooms
2 Baths
4 Guests
1680 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $422/Night
7 Nights - US $2,951
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
- 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 $1,999
Villa
2 Bedrooms
1 Bath
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $233/Night
7 Nights - US $1,629
Villa
- Naples
- ·
- Palm River Estates
- 0.31 mi to center
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $158/Night
7 Nights - US $1,105
Villa
- Naples
- ·
- North Naples
- 3.30 mi to center
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $109/Night
7 Nights - US $760
House
10.0Exceptional
(6 Reviews)
3 Bedrooms
3 Baths
10 Guests
2165 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $493/Night
7 Nights - US $3,451
Wheelchair Accessible Vacation Homes in Oakes Estates
Over 45+ Wheelchair Accessible Vacation Homes in or Near Oakes Estates
Condo
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1250 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $94/Night
7 Nights - US $661
Hotel
8.9Fabulous
(462 Reviews)
6 Baths
361.93 ft²
- Oceanfront
- Breakfast
- EV Charge Station
- Parking
US $229/Night
7 Nights - US $1,600
Hotel
- Naples
- ·
- North Naples
- 2.39 mi to center
9.2Exceptional
(682 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
Spa
US $604/Night
7 Nights - US $4,231
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 $185/Night
7 Nights - US $1,296
Hotel
8.5Fabulous
(193 Reviews)
1 Bath
301.39 ft²
- Oceanfront
- EV Charge Station
- Parking
- Pool
US $155/Night
7 Nights - US $1,085
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 $3,651
Apartment
- Naples
- ·
- Rural Estates
- 6.51 mi to center
9.2Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
1150 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $326/Night
7 Nights - US $2,279
Apartment
- Naples
- ·
- Rural Estates
- 6.51 mi to center
9.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1150 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $656/Night
7 Nights - US $4,590
Oakes Estates Resorts and Airbnb Homes Under $200
Over 179+ Oakes Estates Resorts and Airbnb Homes Under $200
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 $195/Night
7 Nights - US $1,364
New
Apartment
1 Bedroom
1 Bath
4 Guests
947.22 ft²
- Parking
- Pool
- Balcony/Terrace
- Air Conditioner
US $146/Night
7 Nights - US $1,021
Hotel
9.0Exceptional
(1007 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $99/Night
7 Nights - US $694
Condo
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
1207 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $182/Night
7 Nights - US $1,271
House
2 Bedrooms
2 Baths
6 Guests
1377.78 ft²
- Hot Tub
- Parking
- Pool
- Internet
US $124/Night
7 Nights - US $868
Condo
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $171/Night
7 Nights - US $1,200
Condo
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $149/Night
7 Nights - US $1,043
Condo
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
1377 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $115/Night
7 Nights - US $808
Condo
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $200/Night
7 Nights - US $1,397
Instantly Bookable Vacation Homes in Oakes Estates
Over 268+ 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 $413/Night
7 Nights - US $2,893
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 $1,561
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 $649/Night
7 Nights - US $4,546
Condo
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $255/Night
7 Nights - US $1,787
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 $1,437
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 $187/Night
7 Nights - US $1,309
Apartment
9.8Exceptional
(26 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $69/Night
7 Nights - US $480
Condo
9.8Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
1807 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $515/Night
7 Nights - US $3,607
Condo
9.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $120/Night
7 Nights - US $842
Book a Last Minute Place to Stay in Oakes Estates
About Oakes Estates Vacation Rentals
Explore over 625 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 980.55 ft² of space, and are priced at an average of US $378 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.
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Top Types of Ski Accommodations in Oakes Estates
| Type | Count |
|---|---|
| Vacation Homes | 287 |
| Holiday Apartments | 65 |
| Villas | 29 |
| 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
- Lux Naples! Heated Pool ~ Fenced Yard ~ Near Beach
- Villa Mango
- Relax on 1 acre in Heart of Naples, Privacy, Gym, Pool, Hot Tub, Fireplace
- Two Master Suites, Fully Stocked Home w/Heated Pool & Spa Close to Everything
- The Secret Garden
- Naples Beach , Golf and Country Club Naples Florida
How many vacation rentals have private pools in Oakes Estates?
Uncover 101 vacation rentals boasting private pools near Oakes Estates. Explore top-rated RBO homes offering access to a swimming pool:
- Paradise Awaits! Country Club Living, Private Golf Course, beaches, 1st Floor!
- Heron House at Logan Woods. Bright & spacious fully renovated home with pool!
- Huge 5BR Heated Pool, BBQ, 3 Suites Nr Beaches,Pets OK
- Home with Private Pool
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.™
- Paradise Awaits! Country Club Living, Private Golf Course, beaches, 1st Floor!
- Single house with a heated pool in North Naples
- Coastal Condo in Naples. Newly updated and ready to host your stay in paradise!
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 625 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 |
Map
