Vacation Rentals in Tradewinds, FL: Compare 10+ Sites & Save

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828 Best Vacation Rentals in Tradewinds (Starting from $131)

Kaylee's Place
Kaylee's Place
House
Red Oak, FL, USA
0.1k from Tradewinds center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms9 Guests
New to Booking
$290
Average price / night
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Bring the pup!  Historic 2 bed, 2.5 bath waterfront town-home.
Bring the pup! Historic 2 bed, 2.5 bath waterfront town-home.
House
Pensacola, FL, 32507, United States
0.5k from Tradewinds center

AC, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, TV, Washer

2 Bedrooms4 Guests
New to Booking
$327
Average price / night
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Hello Sunshine
Hello Sunshine
House
Pensacola, FL, USA
0.1k from Tradewinds center

Parking, Security/Safety, Fireplace/Heating, Internet, Guest Services, Laundry, Child Friendly

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$244
Average price / night
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Pet-Friendly Pensacola Home ~ 2 Mi to Bruce Beach!
Pet-Friendly Pensacola Home ~ 2 Mi to Bruce Beach!
House
Pensacola, FL, 32507, United States
0.7k from Tradewinds center

AC, Barbecue, Dryer, Free Parking, Heater, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$196
Average price / night
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Stay Awhile
Stay Awhile
Apartment
Pensacola, FL, USA
0.1k from Tradewinds center

Apartments, Accommodations, Parking, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$178
Average price / night
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Little Gem |Reduced Rates |Extended Stays Accepted |5 Min to NAS & Downtown Pensacola |Fenced Yard
Little Gem |Reduced Rates |Extended Stays Accepted |5 Min to NAS & Downtown Pensacola |Fenced Yard
House
Pensacola, FL, 32507, United States
0.8k from Tradewinds center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

3 Bedrooms8 Guests
9.8

Exceptional

27 reviews

$236
Average price / night
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Pet-Friendly Pensacola Home about 2 Mi to Bruce Beach!
Pet-Friendly Pensacola Home about 2 Mi to Bruce Beach!
House
Pensacola, FL, USA
0.7k from Tradewinds center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$190
Average price / night
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Renovated Bungalow near Downtown Pensacola with King Bed!
Renovated Bungalow near Downtown Pensacola with King Bed!
House
Pensacola, FL, 32502, United States
0.8k from Tradewinds center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

29 reviews

$188
Average price / night
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Little Gem
Little Gem
House
Pensacola, FL, USA
0.8k from Tradewinds center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom8 Guests
9.0

Fabulous

2 reviews

$131
Average price / night
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* New In-ground pool<br>* Dog Friendly!<br>* 4 miles to NAS, 10 miles to Pensacola Beach<br>* 3 Bedrooms- King, Queen & Full Bed<br>* Astro Turfed Yard<br>* Washer & Dryer <br>* Smart TVs in Living Room & Primary Bedroom<br>* Outdoor Grill<br>* 3 Car
8.6

Fabulous

10 reviews

$395
Average price / night
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Cypress St Bungalow
Cypress St Bungalow
House
Tradewinds, Pensacola, Florida, USA
1.1k from Tradewinds center

Parking, Air Conditioner, Internet, Child Friendly

1 Bedroom2 Guests
New to Booking
$347
Average price / night
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Coastal Getaway near Pensacola beach, Downtown & NAS + walk to bayou & marinas
Coastal Getaway near Pensacola beach, Downtown & NAS + walk to bayou & marinas
House
Pensacola, FL, 32507, United States
0.9k from Tradewinds center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
10.0

Exceptional

16 reviews

$228
Average price / night
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Lone Oak House
Lone Oak House
House
Pensacola, FL, USA
1.6k from Tradewinds center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom8 Guests
9.7

Exceptional

3 reviews

$153
Average price / night
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Country Club Estate close to NAS - EV charger
Country Club Estate close to NAS - EV charger
House
Pensacola, FL, 32507, United States
0.9k from Tradewinds center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

18 reviews

$305
Average price / night
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Charming Coastal Pensacola Home 1 Mi to Palafox St
Charming Coastal Pensacola Home 1 Mi to Palafox St
House
Pensacola, FL, USA
1.9k from Tradewinds center

Cheap, Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings

3 Bedrooms6 Guests
8.0

Good

1 reviews

$266
Average price / night
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Practically Perfect Place in Every Way
Practically Perfect Place in Every Way
House
Pensacola, FL, 32502, United States
0.9k from Tradewinds center

AC, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
8.0

Good

19 reviews

$326
Average price / night
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1 Mi to Dtwn Pet-Friendly Pensacola Getaway!
1 Mi to Dtwn Pet-Friendly Pensacola Getaway!
House
Pensacola, FL, USA
1.9k from Tradewinds center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$232
Average price / night
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Perfect Centralized Location!!
Perfect Centralized Location!!
House
Pensacola, FL, 32502, United States
1.0k from Tradewinds center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms5 Guests
10.0

Exceptional

9 reviews

$189
Average price / night
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1204 W Government St
1204 W Government St
House
Pensacola, FL, USA
2.0k from Tradewinds center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom6 Guests
New to Booking
$136
Average price / night
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Cozy Cottage Near the Sea!
Cozy Cottage Near the Sea!
House
Pensacola, FL, 32507, United States
1.0k from Tradewinds center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom4 Guests
New to Booking
$149
Average price / night
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Pensacola Vacation Rental with Community Pool!
Pensacola Vacation Rental with Community Pool!
House
Pensacola, FL, USA
2.1k from Tradewinds center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$285
Average price / night
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Back to home
Back to home
House
Pensacola, FL, 32507, United States
1.0k from Tradewinds center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms11 Guests
7.6

Good

5 reviews

$175
Average price / night
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Downtown Dream- Relaxing Escape In Downtown Pensacola
Downtown Dream- Relaxing Escape In Downtown Pensacola
House
Pensacola, FL, USA
2.1k from Tradewinds center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms7 Guests
9.6

Exceptional

19 reviews

$299
Average price / night
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BAY HOUSE - Steps to its own Private Beach - Amazing Sunsets on the Water
BAY HOUSE - Steps to its own Private Beach - Amazing Sunsets on the Water
House
Pensacola, FL, 32502, United States
1.3k from Tradewinds center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

73 reviews

$471
Average price / night
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\"Pensacola Pearl\" cottage near downtown, NAS & the beach!
\"Pensacola Pearl\" cottage near downtown, NAS & the beach!
House
Pensacola, FL, 32507, United States
1.3k from Tradewinds center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$175
Average price / night
Check Availability
Charming 3-bedroom Barrancas Bungalow in Pensacola with AC
Charming 3-bedroom Barrancas Bungalow in Pensacola with AC
House
Pensacola, FL, 32502, United States
1.4k from Tradewinds center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Patio

3 Bedrooms6 Guests
New to Booking
$552
Average price / night
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Quaint Bay Cottage close to Downtown and NAS!
Quaint Bay Cottage close to Downtown and NAS!
House
Pensacola, FL, 32502, United States
1.4k from Tradewinds center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
8.6

Fabulous

24 reviews

$256
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Tradewinds.

Stay Near Tradewinds's Top Attractions

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Frequently Asked Questions

You can explore 828 verified vacation rentals in Tradewinds. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Tradewinds vary depending on the season, property size, and location. Rates typically start from around $131 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Tradewinds include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Tradewinds welcome pets. Currently, 32 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Tradewinds often include amenities such as Fireplace/Heating, Internet, and Laundry. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.