Vacation Rentals with Pool in Pine Woods, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Naples
  6.  Pine Woods

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2384 Best Vacation Rentals with Pool in Pine Woods (Starting from $99)

Lovely Naples Vacation Rental with Shared Pools!
Lovely Naples Vacation Rental with Shared Pools!
Apartment
Naples, FL, USA
0.7k from Pine Woods center

Apartments, Accommodations, Pools, Parking, Spa, Lodgings, Vacation rentals, Hot tubs, Places to stay

2 Bedrooms4 Guests
New to Booking
$138
Average price / night
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immaculate 2B 2B Condo at the World Tennis Club
immaculate 2B 2B Condo at the World Tennis Club
Condo
Naples, FL, 34105, United States
0.4k from Pine Woods center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
9.8

Exceptional

24 reviews

$262
Average price / night
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Naples Luxury Condo, Pool, Tennis, Minutes from the Beach
Naples Luxury Condo, Pool, Tennis, Minutes from the Beach
Apartment
Naples, FL, USA
0.7k from Pine Woods center

Apartments, Luxury, Cheap, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay

1 Bedroom4 Guests
6.0

Review score

3 reviews

$250
Average price / night
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204E Pinewoods Condo
204E Pinewoods Condo
Condo
Naples, FL, 34105, United States
0.4k from Pine Woods center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$120
Average price / night
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Chic Naples Getaway - Tennis Pool Comfort
Chic Naples Getaway - Tennis Pool Comfort
House
Naples, FL, USA
0.7k from Pine Woods center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$131
Average price / night
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Ultimate Tennis Condo at World Tennis Center
Ultimate Tennis Condo at World Tennis Center
Condo
Naples, FL, 34105, United States
0.5k from Pine Woods center

AC, Balcony, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms4 Guests
10.0

Exceptional

11 reviews

$116
Average price / night
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Naples Dream at WTC with Heated Pool SPA Sauna 7 bicycles and 3 mls to beach
Naples Dream at WTC with Heated Pool SPA Sauna 7 bicycles and 3 mls to beach
Apartment
Naples, FL, USA
0.7k from Pine Woods center

Apartments, Cheap, Accommodations, Pools, Parking, Spa, Lodgings, Vacation rentals, Hot tubs

2 Bedrooms6 Guests
9.6

Exceptional

45 reviews

$449
Average price / night
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Lakeview Coach Home Near Naples Beaches
Lakeview Coach Home Near Naples Beaches
Condo
Naples, FL, 34105, United States
0.5k from Pine Woods center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
7.0

Good

2 reviews

$201
Average price / night
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Awesome Apartment near the Beach
Awesome Apartment near the Beach
Apartment
Naples, FL, USA
1.0k from Pine Woods center

Apartments, Cheap, Accommodations, Pools, Parking, Spa, Lodgings, Vacation rentals, Jacuzzis

2 Bedrooms6 Guests
9.0

Fabulous

13 reviews

$173
Average price / night
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Naples Lake House, Views! 5bd, Privacy
Naples Lake House, Views! 5bd, Privacy
House
Naples, FL, 34105, United States
0.5k from Pine Woods center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

5 Bedrooms10 Guests
New to Booking
$1022
Average price / night
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Coastal Getaway w/Private Pool
Coastal Getaway w/Private Pool
House
Naples, FL, USA
1.2k from Pine Woods center

Ocean View, Guest Services, Barbecue/Outdoor Cooking, Security/Safety, Oceanfront, Entertainment, Pool

3 Bedrooms6 Guests
New to Booking
$376
Average price / night
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Fairways at Emerald Greens - Very Nice and Spacious 2BR Condo! Central Location
Fairways at Emerald Greens - Very Nice and Spacious 2BR Condo! Central Location
Condo
Naples, FL, 34105, United States
0.6k from Pine Woods center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms4 Guests
10.0

Exceptional

7 reviews

$144
Average price / night
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4 BDR Pool Tropical Naples Oasis
4 BDR Pool Tropical Naples Oasis
House
FL, USA
1.2k from Pine Woods center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

2 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$599
Average price / night
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Naples Finest - 30-day min. - Safe and clean community.
Naples Finest - 30-day min. - Safe and clean community.
Condo
Naples, FL, 34105, United States
0.6k from Pine Woods center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
New to Booking
$112
Average price / night
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Luxury pool dog friendly central to Naples and Marco Island by Sky Run Naples
Luxury pool dog friendly central to Naples and Marco Island by Sky Run Naples
House
Naples, FL, USA
1.2k from Pine Woods center

Luxury, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom6 Guests
New to Booking
$355
Average price / night
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Naples -Fairways at Emerald Greens Condo, Golf Course views, South West Exposure
Naples -Fairways at Emerald Greens Condo, Golf Course views, South West Exposure
Condo
Naples, FL, 34105, United States
0.6k from Pine Woods center

AC, Balcony, Dryer, Elevator, Free Parking, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$206
Average price / night
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Custom Naples Pool Oasis 3BDR
Custom Naples Pool Oasis 3BDR
House
FL, USA
1.3k from Pine Woods center

Pool, Pet Friendly, Parking, Internet, Security/Safety, Air Conditioner, Child Friendly

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$266
Average price / night
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Peaceful, 3 bedroom condo in Central Naples Location
Peaceful, 3 bedroom condo in Central Naples Location
Condo
Naples, FL, 34105, United States
0.6k from Pine Woods center

AC, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
New to Booking
$170
Average price / night
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Spacious Naples House Sleeps 10 with Pool Gazebo and Outdoor Grill
Spacious Naples House Sleeps 10 with Pool Gazebo and Outdoor Grill
House
Naples, FL, USA
1.3k from Pine Woods center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms10 Guests
5.2

Review score

4 reviews

$230
Average price / night
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Tranquil Retreat ~ Private Pool, Close to Beaches, Downtown 5th Ave & Golf!
Tranquil Retreat ~ Private Pool, Close to Beaches, Downtown 5th Ave & Golf!
House
Naples, FL, 34105, United States
0.7k from Pine Woods center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$371
Average price / night
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Welcome to Bolero Oasis - In the heart if Naples - Close to Beaches and Restaurants
Welcome to Bolero Oasis - In the heart if Naples - Close to Beaches and Restaurants
House
Naples, FL, USA
1.3k from Pine Woods center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms7 Guests
7.0

Good

1 reviews

$368
Average price / night
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World Tennis Club Condo, Lake View Gated Community
World Tennis Club Condo, Lake View Gated Community
Condo
Naples, FL, 34105, United States
0.7k from Pine Woods center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Kitchen, Laundry, Living Area

3 Bedrooms5 Guests
8.4

Very Good

20 reviews

$168
Average price / night
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Tennis courts just outside your patio
Tennis courts just outside your patio
Condo
Naples, FL, 34105, United States
0.7k from Pine Woods center

AC, Free Parking, Internet, Kitchen, Microwave, No Smoking, Outdoor Space, Patio, Pool

2 Bedrooms4 Guests
9.0

Fabulous

7 reviews

$99
Average price / night
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Beach 4ml/ World Tennis Club/ Pickleball / Heated Pools/ Hot Tub/ Sauna/ 1st Flr
Beach 4ml/ World Tennis Club/ Pickleball / Heated Pools/ Hot Tub/ Sauna/ 1st Flr
Condo
Naples, FL, 34105, United States
0.7k from Pine Woods center

AC, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

27 reviews

$753
Average price / night
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Beach, Golf and  So Much More!
Beach, Golf and So Much More!
Condo
Naples, FL, 34105, United States
0.7k from Pine Woods center

AC, Balcony, Free Parking, Internet, Kitchen, Microwave, No Smoking, Pool, TV

1 Bedroom2 Guests
10.0

Exceptional

6 reviews

$249
Average price / night
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85\" TV•World Tennis Club•Beach 4mi•Sauna•2 Heated Pools•Hot Tub•Pickleball
85\" TV•World Tennis Club•Beach 4mi•Sauna•2 Heated Pools•Hot Tub•Pickleball
Condo
Naples, FL, 34105, United States
0.8k from Pine Woods center

AC, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$603
Average price / night
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Hot Tub Pool 5m-Beach & Downtwn Tennis/Pickleball
Hot Tub Pool 5m-Beach & Downtwn Tennis/Pickleball
Condo
Naples, FL, 34105, United States
0.8k from Pine Woods center

AC, Balcony, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

9.6

Exceptional

34 reviews

$318
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Pool in Pine Woods.

Stay Near Pine Woods's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Pine Woods Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 2384 verified vacation rentals with a pool in Pine Woods. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Pine Woods vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $99 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Pine Woods offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Pine Woods welcome pets. Currently, 19 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Pine Woods often include additional outdoor features such as Pool, View, and Fireplace/Heating. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Pine Woods offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.