Select Vacation Villas - Vacation Rentals in Tradewinds

Island Dreams: Remodeled West Gulf Drive Pool Home From US $472
         

9.2 (25 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Bright & Beautiful Near-Beach Pet Friendly Home! From US $356
         

10.0 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Short Walk to The Beach! Anhinga House at Sea Oats From US $294
         

8.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Sanibel Dreamin' E101 From US $494
         

9.8 (6 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Tradewinds

Over 244+ Luxury Places to Stay in or Near Tradewinds
Sandals Unit A From US $1,563
         

New
Apartment
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  • Pool

Top-Rated Vacation Rentals with a Pool in Tradewinds

Over 178+ Top-Rated Vacation Rentals with a Pool in or Near Tradewinds
3 min walk to shells&sand-great escape Fully restored Sanibel Island From US $742
         

Quiet paradise awaits From US $546
         

10.0 (16 Reviews)
House
  • Air Conditioner
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  • Pet Friendly
4 bedroom, 4 bathroom beach front town home From US $714
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Tradewinds

Over 113+ Pet-Friendly Vacation Rentals in or Near Tradewinds
Sanibel Island Private Vacation Home - Dog Friendly From US $320
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Sanibel Sunrise From US $661
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Wild Lime Home - West end home with heated pool From US $362
         

Island time.walk to beach, heated pool, wide water views. Pet friendly! From US $412
         

Shimmering Shells: Island Oasis Nestled in Bayou! From US $444
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious Single Family Home "Breaking Away" Steps from the Beach From US $353
         

Honu Dream luxurious retreat near the beach! NEW! From US $348
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Wild Lime Home - West end home with heated pool From US $345
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Tradewinds

Over 22+ Large Vacation Homes & Villas in or Near Tradewinds
Gulf House with heated pool and ping pong table. From US $555
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa Belle Mer- Executive Pool Residence From US $414
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Gorgeous Near Beach Pool Home in West Rocks From US $325
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pelican's Perch: Gorgeous West Gulf Pool Home. WOW From US $399
         

9.8 (28 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Tradewinds

Over 13+ Wheelchair Accessible Vacation Homes in or Near Tradewinds
Island Beach Club #P1A – Coastal Comfort on Sanibel Island From US $517
         

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9.6 (21 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Sanibel Shells at Sea Bell From US $230
         

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New
Apartment
  • Air Conditioner
  • Pool
  • View
Lazy Ray in Sanibel, FL From US $638
         

New
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Exclusive and upscale. Sanibel's most private spot From US $399
         

4.0 (9 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Pool

Tradewinds Varoom and Airbnb Places to Stay Under $200

Over 23+ Tradewinds Varoom and Airbnb Places to Stay Under $200
Sea Oats: Your Tranquil Sanibel Island Retreat From US $191
         

Calinda South Home From US $173
         

New
House
  • Parking
  • Pet Friendly
  • Pool
Treetops - Gulf Pines Home on Sanibel Island From US $196
         

Treetops - Gulf Pines Home on Sanibel Island From US $193
         

Enjoy sunsets at spacious condo by Bowman's Beach B105 From US $154
         

5.0 (7 Reviews)
Condo
  • Air Conditioner
  • Pool
  • Bedding/Linens
Quiet condo within walking distance to Bowman's Beach B102 From US $154
         

Instantly Bookable Vacation Homes in Tradewinds

Over 143+ Instantly Bookable Vacation Homes in or Near Tradewinds
Blind Pass - ground floor luxury & beach access! From US $495
         

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10.0 (1 Review)
Condo
  • Air Conditioner
  • Parking
  • Pool
Sandy Feet Retreat: Cozy, Coastal Retreat. Pets OK From US $454
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Newly Renovated Vacation Home On Sanibel - The Magic Blue Home From US $363
         

Five Palms: Coastal Retreat w Private Pool on Lake From US $334
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

About Tradewinds Vacation Rentals

With more than 253 Tradewinds vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Selectvacationvillas 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 Selectvacationvillas 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 921.17 ft² on average, with prices averaging $439 a night.

Selectvacationvillas 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 195
Cottages 15
Holiday Apartments 3
Villas 3
Hostels 1
Hotels with Suites 1

Use these Quick Filters to Find a Vacation Rental in Tradewinds

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