Coffee Hawaii - Vacation Rentals in Tradewinds

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 (1 Review)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Downtown Getaway for Two! From US $160
         

10.0 (66 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Seabird Shack: Dog Friendly, Downtown Pensacola! From US $140
         

9.4 (80 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Tradewinds

Over 966+ Luxury Places to Stay in or Near Tradewinds
Cozy Downtown Cottage 10 Mins to Pcola Beach From US $604
         

2.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Large Historical Home for Groups Walk to Downtown! From US $600
         

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10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • View
Romana Hideaway & Juliet Haven -Family Friendly, Downtown Pensacola! From US $561
         

8.0 (1 Review)
House
  • Parking
  • Security/Safety
  • Barbecue/Outdoor Cooking
Urban Vista & Flat - Family Friendly, Downtown Pensacola From US $549
         

Top-Rated Vacation Rentals with a Pool in Tradewinds

Over 75+ Top-Rated Vacation Rentals with a Pool in or Near Tradewinds
Modern Pensacola Vacation Home w/Private Pool! From US $240
         

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

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10.0 (2 Reviews)
House
  • Parking
  • Pool
  • Accessibility
Downtown Pensacola Luxe Home From US $226
         

9.6 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Tradewinds

Over 331+ Pet-Friendly Vacation Rentals in or Near Tradewinds
Winter Warmup Private Pensacola Cottage For A Relaxing New Year From US $104
         

Pet-friendly Pensacola House Rental: 3 Mi to Beach From US $95
         

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5.0 (2 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Walking distance to downtown, 15 min to Pensacola Beach From US $215
         

10.0 (55 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Downtown Oasis From US $169
         

10.0 (33 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Robins Nest - Dog Friendly - Walk to Bay Center From US $155
         

10.0 (33 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Tradewinds

Over 70+ Large Vacation Homes & Villas in or Near Tradewinds
Celestine Bed and Breakfast From US $319
         

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9.7 (16 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Luxe Historic 2 BR Palafox Balcony Overlook ~ Fabu Posh A From US $493
         

2 for 1❗️2 separate houses From US $458
         

10.0 (2 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Urban Vista | 4 Bed, 2.5 Bath From US $356
         

10.0 (1 Review)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Pensacola Breeze/Downtown From US $263
         

9.6 (10 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Romana Hideaway | 3 Bed, 4 Bath From US $312
         

9.6 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Urban Vista & Flat | Family Friendly From US $402
         

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

Wheelchair Accessible Vacation Homes in Tradewinds

Over 53+ Wheelchair Accessible Vacation Homes in or Near Tradewinds
Cotton, Silk, and Linen at the Brent Lofts From US $334
         

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

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10.0 (1 Review)
House
  • Parking
  • Wheelchair Accessible
  • Child Friendly
Lily Hall- A Boutique Hotel From US $284
         

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9.6 (196 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Historic Charm w/Innovation! From US $298
         

10.0 (24 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Brand New 2/2 condo loft in the middle of Everything ! From US $513
         

Modern Loft, Historic Streets- 2 bed/2 bath From US $428
         

10.0 (11 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Celebrate in Luxury in this stunning 2/2! From US $311
         

10.0 (11 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Elevate your escape! From US $351
         

10.0 (10 Reviews)
Condo
  • Air Conditioner
  • TV
  • View

Tradewinds Varoom and Airbnb Places to Stay Under $200

Over 517+ Tradewinds Varoom and Airbnb Places to Stay Under $200
Premier Downtown Loft Building, Just Opened From US $198
         

Chalet De Reus From US $127
         

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

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9.2 (435 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Perfect Pensacola Location & Private Yard! From US $190
         

Instantly Bookable Vacation Homes in Tradewinds

Over 545+ Instantly Bookable Vacation Homes in or Near Tradewinds
HEART OF DOWNTOWN Palafox Loft, sleeps 6 From US $352
         

10.0 (94 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Cheerful 3BR close to downtown + double balcony From US $340
         

Downtown home + bay views + seafood market From US $226
         

Palafox Loft 122, sleeps 2 From US $242
         

10.0 (39 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

About Tradewinds Vacation Rentals

With more than 975 Tradewinds vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Coffeeshawaii 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 Tradewinds.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Coffeeshawaii Tradewinds, 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 Tradewinds. Places to stay near Tradewinds are 720.2 ft² on average, with prices averaging $218 a night.

Coffeeshawaii makes it easy and safe to find and compare vacation rentals in Tradewinds 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 Tradewinds

Type Count
Vacation Homes 697
Holiday Apartments 122
Cottages 70
Hotels with Suites 33
Villas 8
Others 4
B&B 3

Use these Quick Filters to Find a Vacation Rental in Tradewinds

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

Weather in Tradewinds

View the weather forecast for Tradewinds before booking your Tradewinds 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