Hollywood Beach Villas - Vacation Rentals in Westerly Heights

Cypress St Bungalow From US $347
         

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New
House
  • Air Conditioner
  • Parking
  • Child Friendly
Pet-friendly Pensacola Home w/Patio & Yard! From US $196
         

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10.0 (2 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Seabird Shack: Dog Friendly, Downtown Pensacola! From US $135
         

9.4 (85 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cheerful 3BR close to downtown + double balcony From US $341
         

Luxury Places to Stay in Westerly Heights

Over 942+ Luxury Places to Stay in or Near Westerly Heights
6-unit retreat w/fire pit & backyard From US $1,909
         

Waterfront Retreat w/Outdoor Oasis in Pensacola From US $812
         

Downtown + Sleeps 15 + 18 Min to Beach! + Unit B&C From US $705
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • View
Large Historical Home for Groups Walk to Downtown! From US $600
         

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10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • View

Top-Rated Vacation Rentals with a Pool in Westerly Heights

Over 70+ Top-Rated Vacation Rentals with a Pool in or Near Westerly Heights
Modern Pensacola Vacation Home w/Private Pool! From US $306
         

10.0 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Modern Pensacola Vacation Home w/Private Pool! From US $448
         

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10.0 (2 Reviews)
House
  • Parking
  • Pool
  • Security/Safety
Townhome in Downtown Pensacola w/POOL From US $320
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
SEA-Bound STR From US $298
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Westerly Heights

Over 351+ Pet-Friendly Vacation Rentals in or Near Westerly Heights
Escape by Beaches & Blue Angels From US $242
         

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10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Motel 6 Pensacola, FL - NAS From US $101
         

6.4 (515 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Downtown Oasis From US $254
         

10.0 (36 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Walk to Downtown Fun, Short Drive to Beach & NAS From US $285
         

10.0 (30 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Lemon Zest Cottagen(Paws Welcome) From US $230
         

10.0 (20 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
The Pensacola Retreat- Luxurious, Pet-friendly home From US $427
         

10.0 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Westerly Heights

Over 77+ Large Vacation Homes & Villas in or Near Westerly Heights
2 for 1❗️2 separate houses From US $464
         

10.0 (2 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Celestine Bed and Breakfast From US $319
         

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9.7 (16 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
The Bungalow. Walk to Bayou! Backyard Family Fun! From US $345
         

9.8 (34 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pensacola Breeze/Downtown From US $263
         

9.6 (10 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Romana Hideaway | 3 Bed, 4 Bath From US $495
         

9.6 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Close to Downtown, Beaches and Naval Base. From US $263
         

9.4 (8 Reviews)
House
  • Air Conditioner
  • TV
  • Security/Safety
Urban Vista & Flat | Family Friendly From US $538
         

9.4 (3 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace

Wheelchair Accessible Vacation Homes in Westerly Heights

Over 44+ Wheelchair Accessible Vacation Homes in or Near Westerly Heights
Cotton, Silk, and Linen at the Brent Lofts From US $271
         

10.0 (26 Reviews)
Condo
  • Parking
  • TV
  • Wheelchair Accessible
Charming Pensacola Cottage - 4 Mi to Downtown From US $322
         

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10.0 (1 Review)
House
  • Parking
  • Wheelchair Accessible
  • Child Friendly
Extended Stay Premier Suites - Pensacola- Nas Corry Station From US $144
         

9.0 (624 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Historic Charm Southern Exposure From US $339
         

10.0 (24 Reviews)
Condo
  • Parking
  • TV
  • Wheelchair Accessible
Southern Comfort 318 From US $358
         

10.0 (12 Reviews)
Condo
  • Parking
  • TV
  • Wheelchair Accessible
To Geaux Cups Luxury in this stunning From US $349
         

10.0 (12 Reviews)
Condo
  • Parking
  • TV
  • Wheelchair Accessible
Palafox Oasis at the Brent Lofts From US $338
         

10.0 (12 Reviews)
Condo
  • Parking
  • TV
  • Wheelchair Accessible
Modern Loft, Historic Streets- 2 bed/2 bath From US $456
         

10.0 (11 Reviews)
Condo
  • Parking
  • TV
  • Wheelchair Accessible

Westerly Heights Vacation Rentals and Airbnb Places to Stay Under $200

Over 445+ Westerly Heights Vacation Rentals and Airbnb Places to Stay Under $200
Chalet De Reus From US $127
         

New
House
  • Child Friendly
  • Internet
Pensacola Victorian B&B From US $129
         

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9.2 (448 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Sunny Pensacola Studio Near Beach & Downtown From US $155
         

10.0 (11 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Groovy Cottage in Downtown Pensacola, Pet Friendly From US $187
         

10.0 (5 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Fishing Retreat Unit B From US $125
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety

Instantly Bookable Vacation Homes in Westerly Heights

Over 530+ Instantly Bookable Vacation Homes in or Near Westerly Heights
Walk to downtown + seafood market. *Bay views* From US $309
         

10.0 (33 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Charming Apartment Sleeps 4 From US $129
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Experience Downtown Charm and Modern Comfort at Your Perfect VRBO Getaway! From US $313
         

10.0 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Perfect Pensacola Location & Private Yard! From US $330
         

Bright & open/walk to downtown! From US $341
         

10.0 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Westerly Heights Vacation Rentals

With more than 951 Westerly Heights vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Hollywoodbeachvillas 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 Westerly Heights.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Hollywoodbeachvillas Westerly Heights, 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 Westerly Heights. Places to stay near Westerly Heights are 731.4 ft² on average, with prices averaging US $237 a night.

Hollywoodbeachvillas makes it easy and safe to find and compare vacation rentals in Westerly Heights 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 Westerly Heights

Type Count
Vacation Homes 694
Holiday Apartments 124
Cottages 67
Hotels 22
Villas 8
B&B 4
Others 3

Use these Quick Filters to Find a Vacation Rental in Westerly Heights

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

Weather in Westerly Heights

View the weather forecast for Westerly Heights before booking your Westerly 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

Westerly Heights Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Westerly Heights?
How many vacation rentals have private pools in Westerly Heights?
How many vacation rentals are available in Westerly Heights?

Currently, the total number of properties listed in 2026 is over 951 in the Westerly Heights area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Westerly Heights.