118+ Private Villas and Holiday Rentals in Port Pine Heights |
Port Pine Heights Holiday Rentals
New
House
- Big Pine Key
- ·
- Port Pine Heights
- 0.43 mi to center
2 Bedrooms
3 Baths
6 Guests
Fireplace/Heating
Air Conditioner
Internet
Child Friendly
R6,378/Night
7 Nights - R44,644
House
- Big Pine Key
- ·
- Port Pine Heights
- 0.13 mi to center
1 Bedroom
2 Baths
6 Guests
957.99 ft²
- Fireplace/Heating
Balcony/Terrace- Air Conditioner
- Child Friendly
R4,252/Night
7 Nights - R29,762
House
- Florida
- ·
- Little Torch Key
- 0.84 mi to center
8.0Excellent
(4 Reviews)
8 Bedrooms
8 Baths
16 Guests
Private Pool
Pool- Balcony/Terrace
Kitchen
R35,034/Night
7 Nights - R245,235
House
- Florida
- ·
- Big Torch Key
- 2.04 mi to center
10.0Exceptional
(51 Reviews)
2 Bedrooms
2 Baths
6 Guests
1296 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
View
R8,646/Night
7 Nights - R60,514
House
- Big Pine Key
- ·
- Eden Pines
- 0.17 mi to center
2 Bedrooms
2 Baths
6 Guests
839.58 ft²
- Internet
- Child Friendly
Laundry
Barbecue/Outdoor Cooking
R2,703/Night
7 Nights - R18,919
House
- Big Pine Key
- ·
- Doctor's Arm
- 0.25 mi to center
10.0Exceptional
(23 Reviews)
2 Bedrooms
2 Baths
6 Guests
1152 ft²
- Private Pool
Oceanfront- Fireplace/Heating
- Pool
R4,255/Night
7 Nights - R29,779
House
- Big Pine Key
- ·
- Eden Pines
- 0.43 mi to center
10.0Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
R3,117/Night
7 Nights - R21,819
House
- Big Pine Key
- ·
- Doctor's Arm
- 0.16 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
7 Guests
Hot Tub- Balcony/Terrace
- Kitchen
Parking
R3,881/Night
7 Nights - R27,175
House
- Florida
- ·
- Big Torch Key
- 1.29 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
992 ft²
- Balcony/Terrace
- View
- Kitchen
- Parking
R2,929/Night
7 Nights - R20,501
Luxury Holiday Rentals in Port Pine Heights
Over 109+ Luxury Holiday Rentals in or Near Port Pine Heights
House
- Florida
- ·
- Little Torch Key
- 0.84 mi to center
8.0Excellent
(4 Reviews)
8 Bedrooms
8 Baths
16 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R39,028/Night
7 Nights - R273,202
New
House
- Florida
- ·
- Little Torch Key
- 1.31 mi to center
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R10,382/Night
7 Nights - R72,676
House
- Florida
- ·
- Big Torch Key
- 1.42 mi to center
9.6Exceptional
(5 Reviews)
6 Bedrooms
6 Baths
14 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
R9,286/Night
7 Nights - R64,996
House
- Florida
- ·
- Big Pine Key
- 1.96 mi to center
9.8Exceptional
(26 Reviews)
3 Bedrooms
2 Baths
6 Guests
1650 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R8,806/Night
7 Nights - R61,651
House
- Florida
- ·
- Big Torch Key
- 2.18 mi to center
9.6Exceptional
(62 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R8,152/Night
7 Nights - R57,069
Bed & Breakfast
- Big Pine Key
- ·
- Eden Pines
- 0.23 mi to center
3 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Air Conditioner
- Internet
- Child Friendly
R8,107/Night
7 Nights - R56,756
House
2 Bedrooms
2 Baths
11 Guests
1302.43 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
R7,812/Night
7 Nights - R54,680
House
- Big Pine Key
- ·
- Doctor's Arm
- 0.21 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
8 Guests
1600 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R6,856/Night
7 Nights - R47,989
House
- Big Pine Key
- ·
- Eden Pines
- 0.03 mi to center
10.0Exceptional
(4 Reviews)
5 Bedrooms
3 Baths
12 Guests
2448 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Pet Friendly
R6,668/Night
7 Nights - R46,671
Top-Rated Holiday Rentals with a Pool in Port Pine Heights
Over 30+ The Best Private Villas and Holiday Rentals in Port Pine Heights with a Pool
House
- Big Pine Key
- ·
- Eden Pines
- 0.22 mi to center
10.0Exceptional
(6 Reviews)
3 Bedrooms
2 Baths
6 Guests
1150 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
R4,668/Night
7 Nights - R32,679
House
- Big Pine Key
- ·
- Doctor's Arm
- 0.11 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
2000 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
R5,139/Night
7 Nights - R35,975
House
- Big Pine Key
- ·
- Eden Pines
- 0.48 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1500 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
R3,561/Night
7 Nights - R24,934
House
- Big Pine Key
- ·
- Eden Pines
- 0.13 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
960 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R3,780/Night
7 Nights - R26,467
House
- Big Pine Key
- ·
- Eden Pines
- 0.29 mi to center
9.8Exceptional
(17 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
R5,562/Night
7 Nights - R38,942
House
- Big Pine Key
- ·
- Port Pine Heights
- 0.35 mi to center
9.2Exceptional
(5 Reviews)
4 Bedrooms
2 Baths
12 Guests
1200 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R6,249/Night
7 Nights - R43,737
House
Slice of Paradise: Captivating Open Water Views, Deep Canal, Dockage, Heated Pool, and Pet-Friendly!
- Big Pine Key
- ·
- Eden Pines
- 0.58 mi to center
9.2Exceptional
(5 Reviews)
3 Bedrooms
3 Baths
8 Guests
1808 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
R5,764/Night
7 Nights - R40,342
House
- Big Pine Key
- ·
- Port Pine Heights
- 0.31 mi to center
8.8Fabulous
(16 Reviews)
3 Bedrooms
2 Baths
6 Guests
1440 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R5,368/Night
7 Nights - R37,574
House
- Florida
- ·
- Big Pine Key
- 3.66 mi to center
4 Bedrooms
2 Baths
10 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
R6,598/Night
7 Nights - R46,193
Pet-Friendly Holiday Rentals in Port Pine Heights
Over 45+ Pet-Friendly Holiday Rentals in or Near Port Pine Heights
House
- Big Pine Key
- ·
- Port Pine Heights
- 0.15 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R4,325/Night
7 Nights - R30,273
House
- Big Pine Key
- ·
- Port Pine Heights
- 0.19 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R2,297/Night
7 Nights - R16,084
House
- Florida
- ·
- Big Pine Key
- 3.38 mi to center
9.2Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
1142 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
R2,667/Night
7 Nights - R18,672
House
- Big Pine Key
- ·
- Eden Pines
- 0.40 mi to center
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
R4,694/Night
7 Nights - R32,861
Villa
- Big Pine Key
- ·
- Eden Pines
- 0.16 mi to center
2 Bedrooms
1 Bath
4 Guests
850 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R2,944/Night
7 Nights - R20,616
House
- Big Pine Key
- ·
- Eden Pines
- 0.33 mi to center
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R2,698/Night
7 Nights - R18,886
House
- Big Pine Key
- ·
- Port Pine Heights
- 0.17 mi to center
10.0Exceptional
(12 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Hot Tub
- View
- Pet Friendly
- Kitchen
R4,827/Night
7 Nights - R33,784
House
- Florida
- ·
- Little Torch Key
- 1.25 mi to center
10.0Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R3,765/Night
7 Nights - R26,351
House
- Florida
- ·
- Big Pine Key
- 4.93 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
R3,708/Night
7 Nights - R25,956
Large Holiday Rentals and Private Villas in Port Pine Heights
Over 7+ Large Holiday Rentals and Private Villas in or Near Port Pine Heights
House
- Big Pine Key
- ·
- Port Pine Heights
- 0.17 mi to center
3 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
R4,405/Night
7 Nights - R30,834
House
Blue Fish Point: Tranquil, Luxurious Waterfront Oasis, Amazing Sunsets, Pool, Tikis, Dock & Dogs OK!
- Florida
- ·
- Big Torch Key
- 0.94 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
3 Baths
12 Guests
3100 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
R6,032/Night
7 Nights - R42,221
House
- Big Pine Key
- ·
- Eden Pines
- 0.35 mi to center
5.0Average
(2 Reviews)
3 Bedrooms
2 Baths
14 Guests
- Kitchen
- Air Conditioner
- Internet
- Laundry
R4,746/Night
7 Nights - R33,223
House
- Florida
- ·
- Big Pine Key
- 3.25 mi to center
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- View
- Pet Friendly
- Air Conditioner
R11,414/Night
7 Nights - R79,894
House
- Florida
- ·
- Big Pine Key
- 3.40 mi to center
3 Bedrooms
3 Baths
10 Guests
- Private Pool
- Pool
- Pet Friendly
- Air Conditioner
R9,888/Night
7 Nights - R69,215
House
- Florida
- ·
- Big Pine Key
- 5.48 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
R4,207/Night
7 Nights - R29,449
House
- Big Pine Key
- ·
- Eden Pines
- 0.28 mi to center
3 Bedrooms
2 Baths
10 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
R5,877/Night
7 Nights - R41,134
Wheelchair Accessible Holiday Homes in Port Pine Heights
Over 1+ Wheelchair Accessible Holiday Homes in or Near Port Pine Heights
House
- Big Pine Key
- ·
- Doctor's Arm
- 0.21 mi to center
3 Bedrooms
3 Baths
8 Guests
1600 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
R6,665/Night
7 Nights - R46,654
Port Pine Heights Private Villas and Holiday Homes Under $200
Over 30+ Port Pine Heights Private Villas and Holiday Homes Under $200
House
- Big Pine Key
- ·
- Eden Pines
- 0.15 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
5 Guests
1000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R2,493/Night
7 Nights - R17,452
House
- Florida
- ·
- Little Torch Key
- 1.20 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R2,151/Night
7 Nights - R15,063
House
- Florida
- ·
- Little Torch Key
- 1.29 mi to center
6.0Good
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
R2,397/Night
7 Nights - R16,776
House
- Big Pine Key
- ·
- Port Pine Heights
- 0.05 mi to center
2 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
R2,935/Night
7 Nights - R20,550
R2,289/Night
7 Nights - R16,018
House
- Big Pine Key
- ·
- Port Pine Heights
- 0.15 mi to center
10.0Exceptional
(17 Reviews)
3 Bedrooms
2 Baths
6 Guests
1500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R2,631/Night
7 Nights - R18,408
House
- Florida
- ·
- Little Torch Key
- 1.21 mi to center
9.4Exceptional
(11 Reviews)
3 Bedrooms
2 Baths
6 Guests
929 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R2,295/Night
7 Nights - R16,068
House
- Big Pine Key
- ·
- Eden Pines
- 0.35 mi to center
9.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R3,282/Night
7 Nights - R22,973
House
- Big Pine Key
- ·
- Port Pine Heights
- 0.14 mi to center
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Pool
- Pet Friendly
- Kitchen
R3,038/Night
7 Nights - R21,259
Instantly Bookable Holiday Homes in Port Pine Heights
Over 40+ Instantly Bookable Holiday Homes in or Near Port Pine Heights
House
- Big Pine Key
- ·
- Eden Pines
- 0.16 mi to center
2 Bedrooms
2 Baths
6 Guests
840 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
R3,932/Night
7 Nights - R27,521
House
- Florida
- ·
- Big Pine Key
- 2.10 mi to center
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
R3,841/Night
7 Nights - R26,879
House
- Big Pine Key
- ·
- Port Pine Heights
- 0.17 mi to center
2 Bedrooms
1 Bath
4 Guests
768 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R3,490/Night
7 Nights - R24,423
House
- Big Pine Key
- ·
- Doctor's Arm
- 0.06 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
1400 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R5,786/Night
7 Nights - R40,507
House
- Big Pine Key
- ·
- Eden Pines
- 0.39 mi to center
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
R5,750/Night
7 Nights - R40,260
House
- Big Pine Key
- ·
- Eden Pines
- 0.45 mi to center
4 Bedrooms
3 Baths
1 Guest
- Air Conditioner
- Internet
- Child Friendly
Security/Safety
R5,568/Night
7 Nights - R38,975
House
- Big Pine Key
- ·
- Port Pine Heights
- 0.31 mi to center
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
R5,253/Night
7 Nights - R36,766
New
House
- Big Pine Key
- ·
- Port Pine Heights
- 0.13 mi to center
2 Bedrooms
2 Baths
6 Guests
960 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R5,485/Night
7 Nights - R38,398
House
- Florida
- ·
- Little Torch Key
- 1.18 mi to center
2.0Average
(1 Review)
3 Bedrooms
1 Bath
6 Guests
- Child Friendly
R2,043/Night
7 Nights - R14,304
Book a Last Minute Place to Stay in Port Pine Heights
About Casai's Private Villas and Holiday Rentals in Port Pine Heights
Discover more than 118 vacation rentals available in Port Pine Heights. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Port Pine Heights.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Port Pine Heights, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Port Pine Heights. On average, places to stay near Port Pine Heights offer 607.56 ft², with nightly prices averaging R4,996.
With Casai, finding and comparing holiday rentals in Port Pine Heights is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Port Pine Heights
| Type | Count |
|---|---|
| Vacation Homes | 114 |
| Cottages | 2 |
| Villas | 1 |
Use these Quick Filters to Find a Holiday Rental in Port Pine Heights
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Port Pine Heights.
Weather in Port Pine Heights, FL
View the weather forecast for Port Pine Heights before booking your Port Pine Heights 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 Port Pine Heights?
What are the top holiday rentals in Port Pine Heights?
With numerous options available in Port Pine Heights, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Port Pine Heights:
- Beachside @ Torchview Waterfront Retreat
- SPCL FALL RATES THREE LOTS WITH POOL AND DOCK! SECLUDED LOWER KEYS RETREAT
- Fisherman’s Paradise - Ocean & Gulf Access! Key Deer Preserve. TIME TO FISH!
- "Canal-Front Paradise in Big Pine Key-Relax &Explore the keys"
- Canal Front Paradise! Just a few yards from open water!
- Waterfront Paradise in Florida Keys. Free use of Kayaks, and more!
- Canal Front Home in Big Pine Key with Pool
- Dates available Oct, Nov, Dec 2023
- The Hideaway: Lose Yourself At This Recently Decorated Canal Front Home on Big Torch Key, Dockage!
- Tropical 5BR Paradise, Private Pool, Hot Tub, Canal Access – Sleeps 12
How many holiday rentals have private pools in Port Pine Heights?
Discover a selection of holiday rentals with private pools near Port Pine Heights with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- The Pineapple Cottage: Live Your Best Keys Life, 3BR Canal Front Home, Dockage & Pet-Friendly Bliss!
- PADGETT PARADISE with Two Boat Slips with Filet Table. POOL
- Casa Cielo
- Yellowstone by the Sea
Which holiday homes in Port Pine Heights are best for families?
If you're searching for a family-friendly holiday home in Port Pine Heights, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Port Pine Heights:
- Newly Remodeled Corner House on the Water
- Amazing Paradise House Canal Front with access to Atlantic and Gulf.
- Sunset Hideaway, Pool home on canal
How many Casai.co.za holiday rentals are available in Port Pine Heights?
As of 2026, Casai boasts over 118 properties listed in the Port Pine Heights area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Port Pine Heights.
People Also Ask
Finding the best prices in Port Pine Heights
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