Short-Term Rentals in Tradewinds, FL: Compare 10+ Sites & Save

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1816 Best Short-Term Rentals in Tradewinds (Starting from $160)

Down Time
Down Time
House
Sanibel, FL, USA
0.2k from Tradewinds center

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

3 Bedrooms6 Guests
New to Booking
$387
Average price / night
Check Availability
Coastal Cottage walking distance to the beach, internet and washer and dryer
Coastal Cottage walking distance to the beach, internet and washer and dryer
House
Sanibel, FL, 33957, United States
0.0k from Tradewinds center

AC, Dryer, Free Parking, Kitchen, Living Area, Microwave, No Smoking, Patio, TV

2 Bedrooms4 Guests
New to Booking
$171
Average price / night
Check Availability
Blind Pass #G102
Blind Pass #G102
House
Sanibel, FL, USA
1.3k from Tradewinds center

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

2 Bedrooms4 Guests
New to Booking
$283
Average price / night
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Sleeps 10 - Available Year Round -  Huge Private Home
Sleeps 10 - Available Year Round - Huge Private Home
House
Sanibel, FL, 33957, United States
0.0k from Tradewinds center

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

4 Bedrooms10 Guests
9.8

Exceptional

117 reviews

$442
Average price / night
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Sanibel Shells at Sea Bell
Sanibel Shells at Sea Bell
Apartment
FL, USA
1.4k from Tradewinds center

Apartments, Accommodations, Pools, Lodgings, Places to stay, Accessible hotels

2 Bedrooms6 Guests
New to Booking
$230
Average price / night
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Peace, Love & Shells: Cute Beach Cottage Near Gulf
Peace, Love & Shells: Cute Beach Cottage Near Gulf
House
Sanibel, FL, 33957, United States
0.1k from Tradewinds center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$277
Average price / night
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Blind Pass A205
Blind Pass A205
House
Sanibel, FL, USA
1.4k from Tradewinds center

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

1 Bedroom6 Guests
New to Booking
$271
Average price / night
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Tahitian Waters: Pet-Friendly Pool Home Just Steps to the Beach!
Tahitian Waters: Pet-Friendly Pool Home Just Steps to the Beach!
House
Sanibel, FL, 33957, United States
0.1k from Tradewinds center

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

2 Bedrooms6 Guests
New to Booking
$270
Average price / night
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Colonel's Cottage- Sanibel Beach Retreat Fantastic Amenities
Colonel's Cottage- Sanibel Beach Retreat Fantastic Amenities
House
Sanibel, FL, USA
1.5k from Tradewinds center

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

2 Bedrooms6 Guests
New to Booking
$491
Average price / night
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New Rebuild - Tiki Too
New Rebuild - Tiki Too
Cottage
Sanibel, FL, 33957, United States
0.1k from Tradewinds center

AC, Dryer, Free Parking, Kitchen, Living Area, Microwave, No Smoking, TV, Washer

2 Bedrooms4 Guests
9.2

Superb

30 reviews

$328
Average price / night
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5294 Umbrella Pool Rd home
5294 Umbrella Pool Rd home
House
Sanibel, FL, USA
1.9k from Tradewinds center

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

3 Bedrooms8 Guests
New to Booking
$508
Average price / night
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West End Paradise Unit Scallop 5 - One bedroom suite w/water views
West End Paradise Unit Scallop 5 - One bedroom suite w/water views
Condo
Sanibel, FL, 33957, United States
0.1k from Tradewinds center

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

1 Bedroom4 Guests
9.0

Fabulous

14 reviews

$228
Average price / night
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Island Beach Club #P1A
Island Beach Club #P1A
House
Tradewinds, Sanibel, Florida, USA
3.1k from Tradewinds center

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

2 Bedrooms6 Guests
New to Booking
$248
Average price / night
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West End Paradise Unit Coral 4 - One bedroom efficiency suite
West End Paradise Unit Coral 4 - One bedroom efficiency suite
Condo
Sanibel, FL, 33957, United States
0.1k from Tradewinds center

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

1 Bedroom4 Guests
9.4

Superb

33 reviews

$196
Average price / night
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On the Rocks- Gorgeous Newly Renovated Pool Home
On the Rocks- Gorgeous Newly Renovated Pool Home
House
Sanibel, FL, USA
3.3k from Tradewinds center

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

3 Bedrooms6 Guests
New to Booking
$409
Average price / night
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West End Paradise Unit Fish 6 - One bedroom suite w/water views
West End Paradise Unit Fish 6 - One bedroom suite w/water views
Condo
Sanibel, FL, 33957, United States
0.1k from Tradewinds center

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

1 Bedroom4 Guests
9.2

Superb

27 reviews

$217
Average price / night
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Deja Blue
Deja Blue
House
Sanibel, FL, USA
3.5k from Tradewinds center

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

3 Bedrooms8 Guests
New to Booking
$371
Average price / night
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Down Time- Sanibel Home, private pool and beach access!
Down Time- Sanibel Home, private pool and beach access!
House
Sanibel, FL, 33957, United States
0.2k from Tradewinds center

Balcony, Free Parking, Internet, Kitchen, Laundry, Living Area, No Smoking, Outdoor Space, Pool

3 Bedrooms6 Guests
New to Booking
$326
Average price / night
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Beach Please
Beach Please
House
Sanibel, FL, USA
3.6k from Tradewinds center

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

3 Bedrooms6 Guests
New to Booking
$371
Average price / night
Check Availability
Heron Rest: Newly Built Home Near Beach! Pets OK!
Heron Rest: Newly Built Home Near Beach! Pets OK!
House
Sanibel, FL, 33957, United States
0.2k from Tradewinds center

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

3 Bedrooms6 Guests
New to Booking
$260
Average price / night
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Great Location! Secluded House with Pool near Beach
Great Location! Secluded House with Pool near Beach
House
Sanibel, FL, 33957, United States
0.2k from Tradewinds center

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

3 Bedrooms6 Guests
9.8

Exceptional

12 reviews

$200
Average price / night
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Gorgeous Newly Renovated Coastal Cottage \"Egret\" Minutes to the beach and free bikes!! JULY SAVINGS!
Gorgeous Newly Renovated Coastal Cottage \"Egret\" Minutes to the beach and free bikes!! JULY SAVINGS!
Cottage
Sanibel, FL, 33957, United States
0.2k from Tradewinds center

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

1 Bedroom4 Guests
8.6

Fabulous

26 reviews

$516
Average price / night
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West End Paradise Unit Seahorse 3 - two bedroom suite w/water views
West End Paradise Unit Seahorse 3 - two bedroom suite w/water views
Condo
Sanibel, FL, 33957, United States
0.2k from Tradewinds center

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

2 Bedrooms6 Guests
9.6

Exceptional

25 reviews

$337
Average price / night
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West End Paradise Starfish 1 - Quaint Hotel Style Room near the Beach
West End Paradise Starfish 1 - Quaint Hotel Style Room near the Beach
Condo
Sanibel, FL, 33957, United States
0.2k from Tradewinds center

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

1 Bedroom2 Guests
8.8

Fabulous

14 reviews

$163
Average price / night
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West End Paradise Unit Turtle 2 - One bedroom suite w/water views
West End Paradise Unit Turtle 2 - One bedroom suite w/water views
Condo
Sanibel, FL, 33957, United States
0.2k from Tradewinds center

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

1 Bedroom4 Guests
9.2

Superb

19 reviews

$239
Average price / night
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West End Paradise Sanddollar 7 - Quaint Hotel Style Room near the Beach
West End Paradise Sanddollar 7 - Quaint Hotel Style Room near the Beach
Condo
Sanibel, FL, 33957, United States
0.2k from Tradewinds center

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

1 Bedroom2 Guests
8.8

Fabulous

16 reviews

$160
Average price / night
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Spacious Single Family Home \"Breaking Away\" Steps from the Beach
Spacious Single Family Home \"Breaking Away\" Steps from the Beach
House
Sanibel, FL, 33957, United States
0.2k from Tradewinds center

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

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$389
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 Short-Term Rentals in Tradewinds.

Stay Near Tradewinds's Top Attractions

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Tradewinds Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 1816 verified short-term rentals in Tradewinds, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Tradewinds vary depending on location, property size, and travel dates. Rates typically start from around $160 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Tradewinds include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Tradewinds, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Tradewinds often include amenities such as View, Internet, and Fireplace/Heating, providing a comfortable and convenient stay.

Short-term rentals in Tradewinds are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.