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

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  2. Oceanfront Rentals
  3.  USA

  4.  Florida
  5.  Pensacola
  6.  Tradewinds

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239 Best Oceanfront Rentals in Tradewinds (Starting from $103)

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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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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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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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
Check Availability
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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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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Pensacola Paradise Downtown
Pensacola Paradise Downtown
House
Pensacola, FL, USA
2.2k from Tradewinds center

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

3 Bedrooms8 Guests
New to Booking
$398
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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A Poolside Paradise
A Poolside Paradise
House
Pensacola, FL, USA
2.3k from Tradewinds center

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

3 Bedrooms8 Guests
New to Booking
$225
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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Beach House
Beach House
House
Pensacola, FL, USA
2.5k from Tradewinds center

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

2 Bedrooms4 Guests
New to Booking
$255
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
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Pet-Friendly Pensacola Home with Patio and Yard!
Pet-Friendly Pensacola Home with Patio and Yard!
House
Pensacola, FL, USA
2.8k from Tradewinds center

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

2 Bedrooms6 Guests
New to Booking
$177
Average price / night
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Seabird Shack: Dog Friendly, Downtown Pensacola!
Seabird Shack: Dog Friendly, Downtown Pensacola!
House
Pensacola, FL, 32502, United States
1.6k from Tradewinds center

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

3 Bedrooms6 Guests
9.4

Superb

85 reviews

$151
Average price / night
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Walk Downtown, Private Parking, Short Drive to Beach & NAS
Walk Downtown, Private Parking, Short Drive to Beach & NAS
House
Pensacola, FL, USA
2.8k from Tradewinds center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$248
Average price / night
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Luna Bungalow - Downtown Pensacola
Luna Bungalow - Downtown Pensacola
Cottage
Pensacola, FL, 32502, United States
1.8k from Tradewinds center

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

3 Bedrooms6 Guests
9.8

Exceptional

22 reviews

$186
Average price / night
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1 Mi to Dtwn Home with Furnished Patio in Pensacola
1 Mi to Dtwn Home with Furnished Patio in Pensacola
House
Pensacola, FL, USA
2.8k from Tradewinds center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$177
Average price / night
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Cozy 2Bd/1Ba Cottage Minutes to Downtown and NAS!
Cozy 2Bd/1Ba Cottage Minutes to Downtown and NAS!
Cottage
Pensacola, FL, 32507, United States
1.8k from Tradewinds center

AC, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space, TV

2 Bedrooms6 Guests
New to Booking
$195
Average price / night
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Cozy Downtown Cottage 10 Mins to Pcola Beach
Cozy Downtown Cottage 10 Mins to Pcola Beach
House
Pensacola, FL, USA
3.0k from Tradewinds center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family, Self-catering

4 Bedrooms8 Guests
8.4

Very Good

5 reviews

$269
Average price / night
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Deep Sea Dreams
Deep Sea Dreams
House
Pensacola, FL, USA
3.3k from Tradewinds center

Ocean View, Security/Safety, Oceanfront, View, Pet Friendly, Internet, Child Friendly

3 Bedrooms6 Guests
New to Booking
$103
Average price / night
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Fantastic new building! Pensacola center !!
Fantastic new building! Pensacola center !!
House
Pensacola, FL, 32502, United States
1.9k from Tradewinds center

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

3 Bedrooms6 Guests
9.6

Exceptional

9 reviews

$493
Average price / night
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Family, friends, downtown, hot tub, spabath, beach
Family, friends, downtown, hot tub, spabath, beach
House
Pensacola, FL, 32502, United States
2.0k from Tradewinds center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms9 Guests
10.0

Exceptional

2 reviews

$421
Average price / night
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New Listing- The Jazzy Junction- Downtown and Bruce Beach just Minutes Away!
New Listing- The Jazzy Junction- Downtown and Bruce Beach just Minutes Away!
House
Pensacola, FL, 32502, United States
2.0k from Tradewinds center

Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
New to Booking
$530
Average price / night
Check Availability
2 bedrooms - King bed - close to beaches - beautiful deck with outdoor seating.
2 bedrooms - King bed - close to beaches - beautiful deck with outdoor seating.
Cottage
Pensacola, FL, 32507, United States
2.0k from Tradewinds center

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

2 Bedrooms7 Guests
10.0

Exceptional

19 reviews

$222
Average price / night
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Pensacola Vacation Rental w/ Community Pool!
Pensacola Vacation Rental w/ Community Pool!
House
Pensacola, FL, 32502, United States
2.1k from Tradewinds center

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

3 Bedrooms6 Guests
9.4

Superb

22 reviews

$315
Average price / night
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Two-story townhome near the beach with WiFi, washer and dryer
Two-story townhome near the beach with WiFi, washer and dryer
House
Pensacola, FL, 32502, United States
2.1k from Tradewinds center

AC, Balcony, Barbecue, Dryer, Heater, Internet, Kitchen, Microwave, No Smoking

3 Bedrooms6 Guests
New to Booking
$290
Average price / night
Check Availability
Olivers Oasis
Olivers Oasis
House
Pensacola, FL, 32502, United States
2.1k from Tradewinds center

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

3 Bedrooms6 Guests
10.0

Exceptional

22 reviews

$391
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 Oceanfront Rentals in Tradewinds.

Stay Near Tradewinds's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Tradewinds Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 239 verified oceanfront rentals in Tradewinds. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Tradewinds vary depending on the property size, exact beachfront location, and season. Rates typically start from around $103 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Tradewinds offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Tradewinds welcome pets. Currently, 36 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Tradewinds often include features designed for a comfortable coastal stay, such as Oceanfront, Ocean View, and View. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.