Tradewinds Pet Friendly Vacation Rentals
House
- Fort Myers
- ·
- Gulf Pines
- 0.05 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
5 Guests
1920 ft²
Oceanfront
Parking
Pool
Ocean View
US $180/Night
7 Nights - US $1,258
House
- Fort Myers
- ·
- Gulf Pines
- 0.07 mi to center
2 Bedrooms
2 Baths
6 Guests
2002.09 ft²
- Oceanfront
- Parking
- Ocean View
View
US $491/Night
7 Nights - US $3,437
US $362/Night
7 Nights - US $2,533
House
- Fort Myers
- ·
- Gulf Pines
- 0.07 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
2000 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $211/Night
7 Nights - US $1,475
House
- Fort Myers
- ·
- East Rocks
- 0.04 mi to center
3 Bedrooms
2 Baths
6 Guests
1797.57 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $409/Night
7 Nights - US $2,863
Condo
- Fort Myers
- ·
- Sanibel
- 1.25 mi to center
9.4Exceptional
(23 Reviews)
2 Bedrooms
2 Baths
6 Guests
1440 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $224/Night
7 Nights - US $1,568
Cottage
- Fort Myers
- ·
- Sanibel
- 3.13 mi to center
9.2Exceptional
(35 Reviews)
2 Bedrooms
2 Baths
4 Guests
1060 ft²
- Oceanfront
- Parking
- Ocean View
- View
US $396/Night
7 Nights - US $2,772
House
- Fort Myers
- ·
- Sanibel
- 1.86 mi to center
8.0Excellent
(1 Review)
2 Bedrooms
2 Baths
6 Guests
1338 ft²
- Oceanfront
- Parking
- Ocean View
- View
US $247/Night
7 Nights - US $1,727
House
- Fort Myers
- ·
- Sanctuary
- 0.17 mi to center
2 Bedrooms
2 Baths
4 Guests
Air Conditioner
Internet
Pet Friendly
Child Friendly
US $432/Night
7 Nights - US $3,021
Pet-Friendly Vacation Rentals in Tradewinds
Over 131+ Pet-Friendly Vacation Rentals in or Near Tradewinds
House
- Fort Myers
- ·
- Tradewinds
- 0.09 mi to center
2 Bedrooms
2 Baths
6 Guests
Private Pool- Oceanfront
- Parking
- Pool
US $229/Night
7 Nights - US $1,605
House
- Fort Myers
- ·
- Sanibel
- 1.25 mi to center
2 Bedrooms
2 Baths
6 Guests
1345.49 ft²
Breakfast- Parking
- Pool
- View
US $248/Night
7 Nights - US $1,736
US $595/Night
7 Nights - US $4,166
House
- Fort Myers
- ·
- Tradewinds
- 0.02 mi to center
2 Bedrooms
2 Baths
4 Guests
1118 ft²
- Oceanfront
- Ocean View
Balcony/Terrace- View
US $223/Night
7 Nights - US $1,563
House
- Fort Myers
- ·
- Murex Lakes
- 0.10 mi to center
3 Bedrooms
3 Baths
6 Guests
1797.57 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $223/Night
7 Nights - US $1,561
House
- Fort Myers
- ·
- Gulf Pines
- 0.08 mi to center
2 Bedrooms
2 Baths
6 Guests
1103 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $197/Night
7 Nights - US $1,381
House
- Fort Myers
- ·
- Belle Meade
- 0.10 mi to center
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $168/Night
7 Nights - US $1,178
New
Apartment
- Fort Myers
- ·
- Belle Meade
- 0.11 mi to center
1 Bedroom
1 Bath
4 Guests
797 ft²
- Parking
- Balcony/Terrace
Kitchen- Air Conditioner
US $72/Night
7 Nights - US $503
House
- Fort Myers
- ·
- Sanibel
- 1.72 mi to center
10.0Exceptional
(30 Reviews)
3 Bedrooms
2 Baths
6 Guests
1813 ft²
- Private Pool
- Oceanfront
Hot Tub- Parking
US $804/Night
7 Nights - US $5,628
Luxury Places to Stay in Tradewinds
Over 122+ Luxury Places to Stay in or Near Tradewinds
House
- Fort Myers
- ·
- Sanibel
- 1.78 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
6 Guests
2100 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
US $1,256/Night
7 Nights - US $8,791
House
- Fort Myers
- ·
- Sanctuary
- 0.53 mi to center
5 Bedrooms
8 Baths
12 Guests
- Private Pool
- Hot Tub
- Pool
- Ocean View
US $1,073/Night
7 Nights - US $7,513
House
- Fort Myers
- ·
- Del Sega
- 0.24 mi to center
3 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
- Air Conditioner
- Internet
US $661/Night
7 Nights - US $4,627
House
- Fort Myers
- ·
- East Rocks
- 0.23 mi to center
3 Bedrooms
3 Baths
6 Guests
1915 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $488/Night
7 Nights - US $3,416
House
- Fort Myers
- ·
- Murex Lakes
- 0.14 mi to center
4 Bedrooms
3 Baths
8 Guests
3500 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $483/Night
7 Nights - US $3,379
House
- Fort Myers
- ·
- Del Sega
- 0.24 mi to center
3 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $479/Night
7 Nights - US $3,353
House
- Fort Myers
- ·
- Sanibel
- 2.61 mi to center
4.8Average
(3 Reviews)
3 Bedrooms
4 Baths
8 Guests
2700 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $449/Night
7 Nights - US $3,142
New
House
- Fort Myers
- ·
- Sanibel
- 2.15 mi to center
5 Bedrooms
4 Baths
22 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $425/Night
7 Nights - US $2,975
House
- Fort Myers
- ·
- Sanibel
- 1.20 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
8 Guests
1668 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $416/Night
7 Nights - US $2,909
Top-Rated Vacation Rentals with a Pool in Tradewinds
Over 85+ Top-Rated Vacation Rentals with a Pool in or Near Tradewinds
House
- Fort Myers
- ·
- Chateaux Sur Mer
- 0.34 mi to center
10.0Exceptional
(7 Reviews)
6 Bedrooms
3 Baths
12 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $396/Night
7 Nights - US $2,773
House
- Fort Myers
- ·
- Murex Lakes
- 0.08 mi to center
10.0Exceptional
(6 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Pool
- Air Conditioner
- Internet
US $348/Night
7 Nights - US $2,434
House
- Fort Myers
- ·
- Tradewinds
- 0.1 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $352/Night
7 Nights - US $2,463
House
- Fort Myers
- ·
- East Rocks
- 0.18 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $349/Night
7 Nights - US $2,441
House
- Fort Myers
- ·
- Chateaux Sur Mer
- 0.24 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
3 Baths
11 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $299/Night
7 Nights - US $2,090
House
- Fort Myers
- ·
- Del Sega
- 0.15 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
4 Baths
7 Guests
1804 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $389/Night
7 Nights - US $2,720
House
- Fort Myers
- ·
- Sanibel
- 3.92 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $285/Night
7 Nights - US $1,995
House
- Fort Myers
- ·
- Heron's Landing
- 0.09 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $280/Night
7 Nights - US $1,963
Villa
- Fort Myers
- ·
- Chateaux Sur Mer
- 0.18 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
14 Guests
4500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $339/Night
7 Nights - US $2,372
Large Vacation Homes & Villas in Tradewinds
Over 18+ Large Vacation Homes & Villas in or Near Tradewinds
House
- Fort Myers
- ·
- Sanibel
- 3.71 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $338/Night
7 Nights - US $2,367
House
- Fort Myers
- ·
- Heron's Landing
- 0.29 mi to center
8.6Fabulous
(7 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $254/Night
7 Nights - US $1,780
House
- Fort Myers
- ·
- West Rocks
- 0.06 mi to center
8.0Excellent
(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $262/Night
7 Nights - US $1,833
House
- Fort Myers
- ·
- Bright Water
- 0.12 mi to center
4 Bedrooms
3 Baths
11 Guests
2500 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $388/Night
7 Nights - US $2,715
House
- Fort Myers
- ·
- Gulf Pines
- 0.11 mi to center
3 Bedrooms
2 Baths
10 Guests
1986 ft²
- Parking
- Pool
Spa- Ocean View
US $366/Night
7 Nights - US $2,564
House
- Fort Myers
- ·
- Sanibel
- 4.96 mi to center
3 Bedrooms
2 Baths
12 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $301/Night
7 Nights - US $2,104
House
- Fort Myers
- ·
- Sanibel
- 1.84 mi to center
4 Bedrooms
3 Baths
10 Guests
2000 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $290/Night
7 Nights - US $2,030
House
- Fort Myers
- ·
- Bright Water
- 0.03 mi to center
3 Bedrooms
2 Baths
10 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $254/Night
7 Nights - US $1,780
House
- Fort Myers
- ·
- Murex Lakes
- 0.15 mi to center
3 Bedrooms
2 Baths
10 Guests
1500 ft²
- Oceanfront
- Parking
- Ocean View
- View
US $242/Night
7 Nights - US $1,697
Wheelchair Accessible Vacation Homes in Tradewinds
Over 10+ Wheelchair Accessible Vacation Homes in or Near Tradewinds
House
- Fort Myers
- ·
- Bright Water
- 0.12 mi to center
3 Bedrooms
2 Baths
8 Guests
1798 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $269/Night
7 Nights - US $1,885
House
- Fort Myers
- ·
- Gulf Pines
- 0.08 mi to center
3 Bedrooms
2 Baths
8 Guests
1600 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $218/Night
7 Nights - US $1,525
House
- Fort Myers
- ·
- East Rocks
- 0.15 mi to center
4.8Average
(8 Reviews)
4 Bedrooms
3 Baths
2400 ft²
- Private Pool
- Pool
- Kitchen
- Air Conditioner
US $130/Night
7 Nights - US $910
House
- Fort Myers
- ·
- Bright Water
- 0.03 mi to center
4.0Average
(9 Reviews)
4 Bedrooms
3 Baths
8 Guests
2300 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $399/Night
7 Nights - US $2,793
Condo
- Fort Myers
- ·
- Sanibel
- 1.83 mi to center
3 Bedrooms
3 Baths
7 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $669/Night
7 Nights - US $4,680
House
- Fort Myers
- ·
- Murex Lakes
- 0.21 mi to center
3 Bedrooms
3 Baths
8 Guests
1934 ft²
- Private Pool
- Pool
- Kitchen
- Air Conditioner
US $204/Night
7 Nights - US $1,428
House
- Fort Myers
- ·
- Sanibel
- 2.00 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $555/Night
7 Nights - US $3,885
Villa
- Fort Myers
- ·
- Sanibel
- 2.30 mi to center
5 Bedrooms
4 Baths
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $1,740/Night
7 Nights - US $12,178
House
- Fort Myers
- ·
- West Rocks
- 0.11 mi to center
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,171/Night
7 Nights - US $8,199
Tradewinds Petfriendly and Airbnb Homes Under $200
Over 9+ Tradewinds Petfriendly and Airbnb Homes Under $200
House
- Fort Myers
- ·
- Murex Lakes
- 0.22 mi to center
8.0Excellent
(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
1934 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $182/Night
7 Nights - US $1,272
House
- Fort Myers
- ·
- Sanibel
- 1.72 mi to center
3 Bedrooms
2 Baths
6 Guests
1937.5 ft²
- Breakfast
- Parking
- View
- Internet
US $173/Night
7 Nights - US $1,211
House
- Fort Myers
- ·
- Gulf Pines
- 0.08 mi to center
3 Bedrooms
3 Baths
6 Guests
1851 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $196/Night
7 Nights - US $1,370
House
- Fort Myers
- ·
- Sanibel
- 1.70 mi to center
3 Bedrooms
2 Baths
6 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $198/Night
7 Nights - US $1,383
Hotel
- Fort Myers
- ·
- Tradewinds
- 0.10 mi to center
8.0Excellent
(297 Reviews)
9 Baths
486.23 ft²
Private Beach- Breakfast
- Parking
- Pool
US $163/Night
7 Nights - US $1,141
House
- Fort Myers
- ·
- Tradewinds
- 0.10 mi to center
3 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $146/Night
7 Nights - US $1,019
House
- Fort Myers
- ·
- Gulf Pines
- 0.08 mi to center
3 Bedrooms
3 Baths
6 Guests
1851 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $133/Night
7 Nights - US $930
House
- Fort Myers
- ·
- Tradewinds
- 0.02 mi to center
2 Bedrooms
2 Baths
4 Guests
1118 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $171/Night
7 Nights - US $1,199
House
- Fort Myers
- ·
- Sanibel
- 1.27 mi to center
3 Bedrooms
2 Baths
7 Guests
2222 ft²
- Oceanfront
- Parking
- Ocean View
- View
US $165/Night
7 Nights - US $1,157
Instantly Bookable Vacation Homes in Tradewinds
Over 67+ Instantly Bookable Vacation Homes in or Near Tradewinds
House
- Fort Myers
- ·
- Sanibel
- 1.14 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
2000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $292/Night
7 Nights - US $2,046
House
- Fort Myers
- ·
- East Rocks
- 0.18 mi to center
1 Bedroom
1 Bath
- Private Pool
- Oceanfront
- Parking
- Pool
US $370/Night
7 Nights - US $2,588
House
- Fort Myers
- ·
- Chateaux Sur Mer
- 0.07 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $313/Night
7 Nights - US $2,191
House
- Fort Myers
- ·
- Sanibel
- 1.69 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $309/Night
7 Nights - US $2,164
New
House
- Fort Myers
- ·
- Sanctuary
- 0.46 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
4 Baths
8 Guests
4046 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $286/Night
7 Nights - US $2,004
House
- Fort Myers
- ·
- Murex Lakes
- 0.15 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $254/Night
7 Nights - US $1,780
House
- Fort Myers
- ·
- Heron's Landing
- 0.01 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
6 Guests
2100 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $200/Night
7 Nights - US $1,400
House
- Fort Myers
- ·
- East Rocks
- 0.20 mi to center
9.8Exceptional
(11 Reviews)
3 Bedrooms
2 Baths
6 Guests
1306 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $295/Night
7 Nights - US $2,065
House
- Fort Myers
- ·
- Sanibel
- 1.86 mi to center
9.8Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $277/Night
7 Nights - US $1,940
Book a Last Minute Place to Stay in Tradewinds
About Tradewinds Vacation Rentals
There are more than 332 places to stay in Tradewinds and many that are available that welcome pets. These options include dog-friendly hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many pet-friendly places to stay in Tradewinds.
Are you seeking a last-minute pets-allowed hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With PetFriendly Tradewinds, you can quickly compare different options to find the hottest deals with a single click. Looking for pet travel at a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Tradewinds. Places to stay near Tradewinds are 787.4 ft² on average, with prices averaging US $355 a night.
PetFriendly makes it easy to find and compare hotels, resorts, and holiday rentals in Tradewinds with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your pet-friendly place to stay today.
Show more
Show less
Top Dog Hotels, Pet-Friendly Vacation Rentals, and Places to Stay in Tradewinds
| Type | Count |
|---|---|
| Vacation Homes | 213 |
| Cottages | 7 |
| Villas | 3 |
| Holiday Apartments | 2 |
Use these Quick Filters to Find a Vacation Rental in Tradewinds
★ Pro Tip: PetFriendly™ has the best results when it comes to finding places to stay that accept pets anywhere around the world. Travelers can find and compare over 10 million listings from all over the world. Use the intelligent Filter feature to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, inns, resorts, and more. Enjoy Pet Travel without Hassle in Tradewinds.
Weather in Tradewinds, FL
View the weather forecast for Tradewinds before booking your hotel or rental.
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
Frequently Asked Questions About Tradewinds?
What are the top vacation rentals in Tradewinds?
Find the best options in or near Tradewinds for pet-friendly travel. If you are planning a trip or vacation in Tradewinds, consider a week or two at exciting pets-allowed hotels, resorts, or other suggested properties best known as Top Vacation Rentals and Places to Stay in Tradewinds:
- 3 min walk to shells&sand-great escape Fully restored Sanibel Island
- Coconut Palm Hideaway, Private Pool home, close to Beach, 6 bedroom
- Island time. 10 min walk to beach, heated pool, wide water views. Pet friendly!
- Spacious Single Family Home "Breaking Away" Steps from the Beach
- Sooner Beach Escape: Cute Pool Home in East Rocks
- Paradise Palms: Gorgeous Home on Sanibel Island!
- Honu Dream luxurious retreat near the beach! NEW!
- SANIBEL ISLAND HOME IN PRIVATE BEACH COMMUNITY
- Bring Your Boat! 3br/3ba Santiva pool home, dock/lift. Pet Friendly.
- Dockside Dream at Ding Darling: Pool Home w Dock!
How many vacation rentals have private pools in Tradewinds?
We have found 40 accommodation options with private pools in or near Tradewinds, many of which accept and welcome pets. Top-rated hotels, resorts,and places to stay that have access to a swimming pool include:
- Palm Whisper: Private Pool Home by Bowmans Beach!
- Island Dreams: Remodeled West Gulf Drive Pool Home
- Sandy Cheeks- Gorgeous Newly Renovated Pool Home with Bikes
- Whimsea: West End, Pets OK, Pool Home on Canal!
Which vacation homes in Tradewinds are best for families?
Are you looking for a family-friendly and pet-friendly hotel, resort, or vacation home in Tradewinds? Check these highly-rated pet accommodations and places to stay with excellent reviews for families or groups staying in Tradewinds:
- Palm Whisper: Private Pool Home by Bowmans Beach!
- Down Time
- Island Dreams: Remodeled West Gulf Drive Pool Home
How many PetFriendly vacation rentals are available in Tradewinds?
PetFriendly™ updates its properties regularly to bring you a great selection of places to stay with their pet policies clearly spelled out. At present, the total number of active properties listed by PetFriendly in 2026 is over 332 in the Tradewinds area, and still growing every day. When we combine listings from multiple websites and travel providers, PetFriendly can provide you with a huge selection of the best places to stay that welcome pets in Tradewinds.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| Chateaux Sur Mer Pet Friendly Hotels and Vacation Rentals in Fort Myers, Florida | 344 |
| Sea Spray Pet Friendly Hotels and Vacation Rentals in Fort Myers, Florida | 312 |
Map
