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

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Fort Myers
  6.  Tradewinds

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1342 Best Vacation Rentals with Pool in Tradewinds (Starting from $173)

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
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
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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Villa Belle Mer- Executive Pool Residence
Villa Belle Mer- Executive Pool Residence
Villa
Sanibel, FL, 33957, United States
0.2k from Tradewinds center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Hot Tub

4 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$386
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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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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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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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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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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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
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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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Coconut Palm Hideaway, \nPrivate Pool home, close to Beach, 6 bedroom
Coconut Palm Hideaway, \nPrivate Pool home, close to Beach, 6 bedroom
House
Sanibel, FL, 33957, United States
0.3k from Tradewinds center

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

6 Bedrooms12 Guests
10.0

Exceptional

6 reviews

$408
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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Architectural 3-bedroom pool house w/private beach access in brilliant Sanibel
Architectural 3-bedroom pool house w/private beach access in brilliant Sanibel
House
Sanibel, FL, 33957, United States
0.4k from Tradewinds center

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

3 Bedrooms8 Guests
New to Booking
$689
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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Angel’s Nest – Gulf-Front with Private Pool in Sanibel’s Chateaux Sur Mer
Angel’s Nest – Gulf-Front with Private Pool in Sanibel’s Chateaux Sur Mer
House
Sanibel, FL, 33957, United States
0.4k from Tradewinds center

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

3 Bedrooms6 Guests
New to Booking
$697
Average price / night
Check Availability
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
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Stunning Gulf Front Sanibel Home
Stunning Gulf Front Sanibel Home
House
Sanibel, FL, 33957, United States
0.5k from Tradewinds center

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

3 Bedrooms8 Guests
New to Booking
$749
Average price / night
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Calinda South Home
Calinda South Home
House
Tradewinds, Sanibel, Florida, USA
4.1k from Tradewinds center

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

1 Bedroom6 Guests
New to Booking
$173
Average price / night
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Book your stay now and experience the magic of Waters Edge!
Book your stay now and experience the magic of Waters Edge!
House
Sanibel, FL, 33927, United States
1.1k from Tradewinds center

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

3 Bedrooms7 Guests
New to Booking
$632
Average price / night
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Welcoming 2-bedroom 2-bathroom condo in a secluded section of Sanibel Island
Welcoming 2-bedroom 2-bathroom condo in a secluded section of Sanibel Island
Condo
Sanibel, FL, 33957, United States
1.2k from Tradewinds center

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

2 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$318
Average price / night
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Ground Floor Luxury on Bowman's Beach-Pool, Pickleball, Kayaks & Paddleboards
Ground Floor Luxury on Bowman's Beach-Pool, Pickleball, Kayaks & Paddleboards
Condo
Sanibel, FL, 33957, United States
1.3k from Tradewinds center

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

2 Bedrooms4 Guests
10.0

Exceptional

38 reviews

$306
Average price / night
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Blind Pass Condos at Bowman's Beach E108 on beautiful Sanibel Island
Blind Pass Condos at Bowman's Beach E108 on beautiful Sanibel Island
Condo
Sanibel, FL, 33957, United States
1.3k from Tradewinds center

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

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$351
Average price / night
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Blind Pass Condos at Bowman's Beach C108 on beautiful Sanibel Island
Blind Pass Condos at Bowman's Beach C108 on beautiful Sanibel Island
Condo
Sanibel Island, FL, 33957, United States
1.4k from Tradewinds center

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

3 Bedrooms8 Guests
9.4

Superb

11 reviews

$429
Average price / night
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Blind Pass Condos at Bowman's Beach C109 on beautiful Sanibel Island
Blind Pass Condos at Bowman's Beach C109 on beautiful Sanibel Island
Condo
Sanibel, FL, 33957, United States
1.4k from Tradewinds center

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

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$337
Average price / night
Check Availability
Blind Pass Condos at Bowman's Beach A203 on beautiful Sanibel Island
Blind Pass Condos at Bowman's Beach A203 on beautiful Sanibel Island
Condo
Sanibel Island, FL, 33957, United States
1.4k from Tradewinds center

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

3 Bedrooms8 Guests
9.4

Superb

6 reviews

$325
Average price / night
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Blind Pass Condos at Bowman's Beach F103 on beautiful Sanibel Island
Blind Pass Condos at Bowman's Beach F103 on beautiful Sanibel Island
Condo
Sanibel Island, FL, 33957, United States
1.4k from Tradewinds center

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

3 Bedrooms8 Guests
7.8

Good

6 reviews

$353
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 with Pool 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 Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 1342 verified vacation rentals with a pool in Tradewinds. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Tradewinds vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $173 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Tradewinds offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Tradewinds welcome pets. Currently, 19 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Tradewinds often include additional outdoor features such as Pool, Fireplace/Heating, and View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Tradewinds offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.