Chicago\92s Best Vacation Rentals - Vacation Rentals in Highland Pines

Catalina Cabana - self checkin - pool - parking From US $350
         

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10.0 (2 Reviews)
House
  • Air Conditioner
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  • Pet Friendly
Hampton Inn & Suites Fort Myers - Colonial Blvd From US $120
         

9.4 (1011 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Fort Myers Bungalow - 12 Miles to the Beach! From US $189
         

10.0 (68 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Beautiful Townhome with private patio/swimming pool and pet friendly ! From US $130
         

Beautiful 3 BR 2.5 Bath Paseo Townhome in a Quad From US $129
         

10.0 (16 Reviews)
Condo
  • Air Conditioner
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Resort Style Development w/Pool Tiki Bar - Sleeps 6 From US $133
         

10.0 (15 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Cheers to Paradise: Pool, Tiki Bar, & Endless Fun! From US $267
         

10.0 (14 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Highland Pines

Over 563+ Luxury Places to Stay in or Near Highland Pines
Magnificent Mediterranean-style Estate From US $2,178
         

10.0 (1 Review)
House
  • Air Conditioner
  • Pool
  • TV
Elevated Modern Living coupled with first-class amenities. From US $1,027
         

New
House
  • Air Conditioner
  • Pet Friendly
  • Designated Smoking Area
Grand Elegant Old-Florida Estate, Pool, Sleeps 18 From US $795
         

4.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Fort Myers Home, Lanai & Private, Heated Pool From US $538
         

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10.0 (3 Reviews)
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  • Parking
  • Pet Friendly
  • Pool
Family Vacation Home in Fort Myers From US $506
         

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10.0 (1 Review)
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  • Parking
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Paseo 4107 From US $484
         

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New
Apartment
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Top-Rated Vacation Rentals with a Pool in Highland Pines

Over 391+ Top-Rated Vacation Rentals with a Pool in or Near Highland Pines
Villa w Relaxing Resort Amenities From US $173
         

10.0 (10 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Heritage Palms Golf & Country Club/Fort Myers, FL From US $144
         

Paradise awaits you in this beautiful 3br waterfront condo From US $225
         

Very Nice and Large 1500+square Ft Riverwalk Condo Top Floor From US $138
         

Looking for a Resort Feel? Waterfront Property! From US $142
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Highland Pines

Over 127+ Pet-Friendly Vacation Rentals in or Near Highland Pines
Extended Stay America Premier Suites - Fort Myers - Airport From US $74
         

8.8 (973 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy 1-Bedroom Loft Apartment in the Heart of Fort Myers! From US $141
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Tropical pool home/Tiki bar/near Fort Myers beach, Sanibel From US $238
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Perfect for big family reunions, sport teams! From US $291
         

9.6 (127 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Highland Pines

Over 54+ Large Vacation Homes & Villas in or Near Highland Pines
Resort Living at its Finest in Fort Myers! From US $202
         

10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Whiskey Creek Casa From US $305
         

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8.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Family Vacation Home in Fort Myers From US $342
         

9.4 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Blue Beach Bungalow From US $309
         

8.8 (46 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Peacock Villa * in luxury resort-style Paseo From US $322
         

8.0 (2 Reviews)
Villa
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  • Parking
  • Pool
Private Pool Home Near Beaches & Downtown w/Spacious yard From US $297
         

New
House
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  • Pet Friendly
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Wheelchair Accessible Vacation Homes in Highland Pines

Over 104+ Wheelchair Accessible Vacation Homes in or Near Highland Pines
Golf Cross Creek! NICE condo in the heart of Fort Myers. From US $174
         

Whiskey Creek From US $362
         

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New
House
  • Air Conditioner
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  • Wheelchair Accessible
Home2 Suites by Hilton Fort Myers Colonial Blvd From US $136
         

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9.4 (715 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Fort Myers Condo w/Resort Pools - Near Golf! From US $190
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Highland Pines Vacation Rentals and Airbnb Places to Stay Under $200

Over 350+ Highland Pines Vacation Rentals and Airbnb Places to Stay Under $200
GpL 5544 Cozy Getaway with Bright Colors & Full Kitchen From US $75
         

3.8 (10 Reviews)
Apartment
  • Parking
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  • Security/Safety
Homewood Suites by Hilton - Fort Myers From US $155
         

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9.2 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Highland Pines

Over 225+ Instantly Bookable Vacation Homes in or Near Highland Pines
Paseo Grande 3 Bedroom Resort Oasis From US $368
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Amazing Paseo Resort Condo - Minutes from the beach! From US $234
         

10.0 (5 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Beautiful Townhouse in Paseo From US $297
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Hot tub, Gazebo, Firepit Table Getaway Oasis House! From US $357
         

3BR Home w/Pool in heart of Fort Myers From US $227
         

10.0 (1 Review)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

About Highland Pines Vacation Rentals

With more than 572 Highland Pines vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Chicagosbestvacationrentals and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Highland Pines.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Chicagosbestvacationrentals Highland Pines, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Highland Pines. Places to stay near Highland Pines are 742.39 ft² on average, with prices averaging US $209 a night.

Chicagosbestvacationrentals makes it easy and safe to find and compare vacation rentals in Highland Pines with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Highland Pines

Type Count
Vacation Homes 195
Holiday Apartments 82
Hotels 60
Villas 20
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Highland Pines

Pro Tip: Chicagosbestvacationrentals makes it easy to compare the best listings on Chicagosbestvacationrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Chicagosbestvacationrentals homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Highland Pines.

Weather in Highland Pines

View the weather forecast for Highland Pines before booking your Highland Pines 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

Highland Pines Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Highland Pines?
How many vacation rentals are available in Highland Pines?

Currently, the total number of properties listed in 2026 is over 572 in the Highland Pines area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Highland Pines.