1+ Vacation Rentals Near Highland Pines |
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Pirate Cove Cottages - Vacation Rentals in Highland Pines

Plantation Cottage From US $1,147
         

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Cottage
Plantation Cottage
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Luxury Places to Stay in Highland Pines

Over 518+ Luxury Places to Stay in or Near Highland Pines
Magnificent Mediterranean-style Estate From US $2,178
         

10.0 (1 Review)
House
Magnificent Mediterranean-style Estate
  • Air Conditioner
  • Pool
  • TV

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Grand Elegant Old-Florida Estate, Pool, Sleeps 18 From US $1,782
         

10.0 (1 Review)
House
Grand Elegant Old-Florida Estate, Pool, Sleeps 18
  • Air Conditioner
  • Parking
  • Pet Friendly

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Elevated Modern Living coupled with first-class amenities. From US $1,027
         

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House
Elevated Modern Living coupled with first-class amenities.
  • Air Conditioner
  • Pet Friendly
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ELEGANT PRIVATE OLD SOUTH FLORIDA ESTATE NEW SLEEPS 18 TO 20 LARGE FAMILIES RETREAT WEDDINGS REUNIONS NANNY QUARTERS From US $987
         

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New
House
ELEGANT PRIVATE OLD SOUTH FLORIDA ESTATE NEW SLEEPS 18 TO 20 LARGE FAMILIES RETREAT WEDDINGS REUNIONS NANNY QUARTERS
  • Air Conditioner
  • Parking
  • Pet Friendly

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4-Bed 4 bath 2 kitchens - Pool, Lanai, BBQ From US $933
         

10.0 (1 Review)
House
4-Bed 4 bath 2 kitchens - Pool, Lanai, BBQ
  • Air Conditioner
  • Parking
  • Pet Friendly

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Family-Friendly Suite w/Kitchen Near Six Mile Cypress Preserve | 4 Units From US $758
         

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Hotel
Family-Friendly Suite w/Kitchen Near Six Mile Cypress Preserve | 4 Units
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  • Pool

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Family & Friends Getaway! 4 Comfortable Units, Close to CenturyLink Sports Complex! From US $719
         

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Apartment
Family & Friends Getaway! 4 Comfortable Units, Close to CenturyLink Sports Complex!
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  • Pet Friendly

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Enjoy Free Breakfast and Parking! 4 Classy Units, Steps to Bell Tower Shops! From US $719
         

New
Apartment
Enjoy Free Breakfast and Parking! 4 Classy Units, Steps to Bell Tower Shops!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Top-Rated Vacation Rentals with a Pool in Highland Pines

Over 373+ Top-Rated Vacation Rentals with a Pool in or Near Highland Pines
Fabulous penthouse condo with golf&lake view, modern furnishings! From US $149
         

10.0 (36 Reviews)
Condo
Fabulous penthouse condo with golf&lake view, modern furnishings!
  • Air Conditioner
  • Parking
  • Pool

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Perfect for family and friends; Fully Renovated, 2 Master Suites From US $88
         

10.0 (28 Reviews)
Condo
Perfect for family and friends; Fully Renovated, 2 Master Suites
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  • Parking
  • Pool

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Beautiful 3 BR 2.5 Bath Paseo Townhome in a Quad From US $133
         

10.0 (16 Reviews)
Condo
Beautiful 3 BR 2.5 Bath Paseo Townhome in a Quad
  • Air Conditioner
  • Parking
  • Pool

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Resort Style Development w/Pool Tiki Bar - Sleeps 6 From US $201
         

10.0 (14 Reviews)
Condo
Resort Style Development w/Pool Tiki Bar - Sleeps 6
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  • Pool

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Beautiful Townhome with private patio/swimming pool and pet friendly ! From US $162
         

10.0 (14 Reviews)
House
Beautiful Townhome with private patio/swimming pool and pet friendly !
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  • Parking
  • Pet Friendly

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Cheers to Paradise: Pool, Tiki Bar, & Endless Fun! From US $448
         

10.0 (12 Reviews)
Villa
Cheers to Paradise: Pool, Tiki Bar, & Endless Fun!
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  • Pool

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Heritage Palms Country Club Condo - Golf Course & Lake Views. Ground floor. From US $159
         

10.0 (11 Reviews)
Condo
Heritage Palms Country Club Condo - Golf Course & Lake Views. Ground floor.
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Heritage Palms Golf & Country Club/Fort Myers, FL From US $156
         

10.0 (9 Reviews)
Condo
Heritage Palms Golf & Country Club/Fort Myers, FL
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  • Pool

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Pet-Friendly Vacation Rentals in Highland Pines

Over 109+ Pet-Friendly Vacation Rentals in or Near Highland Pines
Hidden Gem in Ft. Myers w/Heated Pool. Perfect for Family Getaway. Pet-friendly From US $478
         

10.0 (4 Reviews)
House
Hidden Gem in Ft. Myers w/Heated Pool. Perfect for Family Getaway. Pet-friendly
  • Air Conditioner
  • Parking
  • Pet Friendly

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

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10.0 (2 Reviews)
House
Catalina Cabana - self checkin - pool - parking
  • Air Conditioner
  • Parking
  • Pet Friendly

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Extended Stay America Premier Suites - Fort Myers - Airport From US $96
         

8.8 (763 Reviews)
Hotel
Extended Stay America Premier Suites - Fort Myers - Airport
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THE VILLAS BEST From US $411
         

10.0 (3 Reviews)
House
THE VILLAS BEST
  • Air Conditioner
  • Parking
  • Pet Friendly

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Just What You Were Looking For! 3 Comfortable Units, Pool From US $540
         

10.0 (1 Review)
Apartment
Just What You Were Looking For! 3 Comfortable Units, Pool
  • Air Conditioner
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  • Pet Friendly

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Warm and exciting Floridian getaway. Near the beach, downtown, and all the fun! From US $347
         

10.0 (1 Review)
House
Warm and exciting Floridian getaway. Near the beach, downtown, and all the fun!
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  • Parking
  • Pet Friendly

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Perfect for big family reunions, sport teams! From US $371
         

9.8 (123 Reviews)
House
Perfect for big family reunions, sport teams!
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  • Parking
  • Pet Friendly

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Modern dream house vacation gateway From US $259
         

9.6 (69 Reviews)
House
Modern dream house vacation gateway
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Highland Pines

Over 44+ Large Vacation Homes & Villas in or Near Highland Pines
Resort Living at its Finest in Fort Myers! From US $276
         

10.0 (2 Reviews)
Villa
Resort Living at its Finest in Fort Myers!
  • Air Conditioner
  • Parking
  • Pool

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Whiskey Creek Casa From US $305
         

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8.0 (3 Reviews)
House
Whiskey Creek Casa
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RESORT STYLE POOLS, TIKI BAR, TENNIS COURTS, MOVIE THEATER, GYM & MORE! From US $249
         

10.0 (1 Review)
House
RESORT STYLE POOLS, TIKI BAR, TENNIS COURTS, MOVIE THEATER, GYM & MORE!
  • Air Conditioner
  • Parking
  • Pool

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Family Vacation Home in Fort Myers From US $395
         

8.8 (3 Reviews)
House
Family Vacation Home in Fort Myers
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Peacock Villa * in luxury resort-style Paseo From US $436
         

8.0 (2 Reviews)
Villa
Peacock Villa * in luxury resort-style Paseo
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  • Parking
  • Pool

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Relax & Unwind! 3 Spacious Units, FREE Parking, Minutes to Lakes Regional Park! From US $540
         

New
Apartment
Relax & Unwind! 3 Spacious Units, FREE Parking, Minutes to Lakes Regional Park!
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  • Pet Friendly

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Vacation Starts Here! 3 Great Units, BBQ Facilities, Near Eagle Ridge Golf Club! From US $540
         

New
Apartment
Vacation Starts Here! 3 Great Units, BBQ Facilities, Near Eagle Ridge Golf Club!
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  • Pet Friendly

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Three Convenient Room | Close to Gulf Coast Town Center | Enjoy Free Parking From US $479
         

New
House
Three Convenient Room | Close to Gulf Coast Town Center | Enjoy Free Parking
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Wheelchair Accessible Vacation Homes in Highland Pines

Over 92+ Wheelchair Accessible Vacation Homes in or Near Highland Pines
Golf Cross Creek! NICE condo in the heart of Fort Myers. From US $161
         

10.0 (3 Reviews)
Condo
Golf Cross Creek! NICE condo in the heart of Fort Myers.
  • Air Conditioner
  • Parking
  • Pool

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Satin Gold Retreat From US $192
         

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7.0 (1 Review)
House
Satin Gold Retreat
  • Air Conditioner
  • Parking
  • Pet Friendly

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Hampton Inn & Suites Fort Myers - Colonial Blvd From US $124
         

9.4 (1005 Reviews)
Hotel
Hampton Inn & Suites Fort Myers - Colonial Blvd
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  • Parking
  • Pool

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Fort Myers Condo w/Resort Pools - Near Golf! From US $132
         

10.0 (2 Reviews)
Condo
Fort Myers Condo w/Resort Pools - Near Golf!
  • Air Conditioner
  • Parking
  • Pool

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Newly updated 2br2br+Den golf course property near airport 90-day min stay From US $110
         

10.0 (1 Review)
Condo
Newly updated 2br2br+Den golf course property near airport 90-day min stay
  • Air Conditioner
  • Parking
  • Pool

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Elegant 1 Bedroom Ft. Myers Condo w/swimming pool (long term rents available) From US $82
         

9.0 (10 Reviews)
Condo
Elegant 1 Bedroom Ft. Myers Condo w/swimming pool (long term rents available)
  • Air Conditioner
  • Parking
  • Pool

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Happy Ours Hideaway -Ft Myers 2bd 2ba condo Non Smoking No Pets 10miles to beach From US $153
         

8.0 (4 Reviews)
Condo
Happy Ours Hideaway -Ft Myers 2bd 2ba condo Non Smoking No Pets 10miles to beach
  • Air Conditioner
  • Parking
  • Pool

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Relax & Unwind! 2 Spacious Units, FREE Parking, Minutes to Lakes Regional Park! From US $578
         

6.0 (1 Review)
Apartment
Relax & Unwind! 2 Spacious Units, FREE Parking, Minutes to Lakes Regional Park!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Highland Pines Varoom and Airbnb Places to Stay Under $200

Over 299+ Highland Pines Varoom and Airbnb Places to Stay Under $200
Looking for a Resort Feel? Waterfront Property! From US $177
         

10.0 (6 Reviews)
House
Looking for a Resort Feel? Waterfront Property!
  • Air Conditioner
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  • Pool

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Beautiful two master bedroom condo in Fort Myers, Venetian Palms condominium From US $182
         

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New
Apartment
Beautiful two master bedroom condo in Fort Myers, Venetian Palms condominium
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Home2 Suites by Hilton Fort Myers Colonial Blvd From US $120
         

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9.4 (558 Reviews)
Hotel
Home2 Suites by Hilton Fort Myers Colonial Blvd
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Beautiful Townhouse in Paseo ~ Enjoy the Resort Lifestyle From US $182
         

10.0 (5 Reviews)
House
Beautiful Townhouse in Paseo ~ Enjoy the Resort Lifestyle
  • Air Conditioner
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  • Pool

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Luxury Condo Located In Heritage Palms Gated Golf Community From US $115
         

10.0 (5 Reviews)
House
Luxury Condo Located In Heritage Palms Gated Golf Community
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  • Pool

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Central Quiet Location, only 12 Miles to Ft. Myers Beach From US $153
         

10.0 (4 Reviews)
House
Central Quiet Location, only 12 Miles to Ft. Myers Beach
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Stunning Paseo Resort Lifestyle! Townhome w/Private Pool Access! Over $125 Free Daily Activities! From US $177
         

10.0 (2 Reviews)
Condo
Stunning Paseo Resort Lifestyle! Townhome w/Private Pool Access! Over $125 Free Daily Activities!
  • Air Conditioner
  • Pool
  • TV

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Awesome Condo in Beautiful Ft. Myers From US $190
         

10.0 (1 Review)
Condo
Awesome Condo in Beautiful Ft. Myers
  • Air Conditioner
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  • Pool

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Instantly Bookable Vacation Homes in Highland Pines

Over 194+ Instantly Bookable Vacation Homes in or Near Highland Pines
Charming Three Bedroom Townhome in an Award-Winning Community From US $312
         

New
House
Charming Three Bedroom Townhome in an Award-Winning Community
  • Air Conditioner
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Fort Myers Bungalow - 12 Miles to the Beach! From US $222
         

10.0 (64 Reviews)
House
Fort Myers Bungalow - 12 Miles to the Beach!
  • Air Conditioner
  • Parking
  • TV

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Beautiful Resort Condo - Minutes from the beach! From US $261
         

10.0 (5 Reviews)
Condo
Beautiful Resort Condo - Minutes from the beach!
  • Air Conditioner
  • Parking
  • Pool

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Paradise Awaits! Luxury Townhouse in Paseo-Resort Style Amenities! From US $342
         

10.0 (3 Reviews)
Condo
Paradise Awaits! Luxury Townhouse in Paseo-Resort Style Amenities!
  • Air Conditioner
  • Parking
  • Pool

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3-bed house in fabulous Fort Myers with WiFi, AC, 6 miles from the Airport. From US $263
         

10.0 (3 Reviews)
House
3-bed house in fabulous Fort Myers with WiFi, AC, 6 miles from the Airport.
  • Air Conditioner
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Perfect location close to the main club, activity center and neighborhood pool From US $237
         

10.0 (3 Reviews)
Condo
Perfect location close to the main club, activity center and neighborhood pool
  • Air Conditioner
  • Parking
  • Pool

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Beautiful Townhouse in Paseo From US $297
         

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

10.0 (1 Review)
House
Hot tub, Gazebo, Firepit Table Getaway Oasis House!
  • Air Conditioner
  • Parking
  • Pool

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About Highland Pines Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Piratecovecottages 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 with prices averaging $1,147 a night.

Piratecovecottages 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
Cottages 1

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

★ Pro Tip: Piratecovecottages makes it easy to compare the best listings on Piratecovecottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Piratecovecottages 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