Find hotels with pools in Tradewinds, Sanibel from $99

Start date: Check-in selected.
To Date
End date: Check-out

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Tradewinds Hotels with a Pool

Our top choices for Tradewinds hotels with a pool

Outdoor pool, open 7:00 AM to 7:00 PM, pool umbrellas, sun loungers
Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort
3.5 star property
Fort Myers Beach
9.0 out of 10, Wonderful, (1008)
"Clean rooms, friendly staff, so much to do there and nearby "
United States
Lisa R
$149 nightly
The price is $167
Dec 16 - Dec 17
Total with taxes and fees
Lani Kai Beachfront Resort
Lounge
Residence Inn by Marriott Fort Myers Sanibel

Residence Inn by Marriott Fort Myers Sanibel

Residence Inn by Marriott Fort Myers Sanibel
3.0 star property
Fort Myers
8.6 out of 10, Excellent, (1001)
"Clean room, wonderful staff, and nice breakfast. "
United States
Danielle
$95 nightly
The price is $106
Dec 14 - Dec 15
Total with taxes and fees
Residence Inn by Marriott Fort Myers Sanibel
Outdoor pool
Holiday Inn Express & Suites Ft Myers Beach-Sanibel Gateway by IHG

Holiday Inn Express & Suites Ft Myers Beach-Sanibel Gateway by IHG

Holiday Inn Express & Suites Ft Myers Beach-Sanibel Gateway by IHG
2.5 star property
Fort Myers Beach
9.4 out of 10, Exceptional, (1000)
"Great rooms, good staff"
United States
Dedan
$97 nightly
The price is $108
Dec 16 - Dec 17
Total with taxes and fees
Holiday Inn Express & Suites Ft Myers Beach-Sanibel Gateway by IHG
Outdoor pool
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina
3.0 star property
Fort Myers Beach
9.2 out of 10, Wonderful, (1006)
"Was great location "
United States
Jose
$135 nightly
The price is $148
Dec 14 - Dec 15
Total with taxes and fees
Matanzas Inn Bayside Resort and Marina
Sundeck
Latitude 26 Waterfront Boutique Resort - Fort Myers Beach

Latitude 26 Waterfront Boutique Resort - Fort Myers Beach

Latitude 26 Waterfront Boutique Resort - Fort Myers Beach
2.5 star property
Siesta Isle
8.8 out of 10, Excellent, (1004)
"Great Place to Stay!"
United States
JUDY
$96 nightly
The price is $107
Dec 14 - Dec 15
Total with taxes and fees
Latitude 26 Waterfront Boutique Resort - Fort Myers Beach
Outdoor pool, open 8:00 AM to 10:00 PM, cabanas (surcharge)
The Westin Cape Coral Resort At Marina Village

The Westin Cape Coral Resort At Marina Village

The Westin Cape Coral Resort At Marina Village
4.0 star property
Pelican
9.0 out of 10, Wonderful, (1003)
"Excellent stay over Thanksgiving holiday!"
United States
Nicole
$180 nightly
The price is $201
Dec 21 - Dec 22
Total with taxes and fees
The Westin Cape Coral Resort At Marina Village
Aerial view
Casa Ybel Resort

Casa Ybel Resort

Casa Ybel Resort
2.5 star property
Mid Island
8.8 out of 10, Excellent, (290)
"Room was amazing! Their video on their site is pre Hurricane Ian so don’t expect it to be like that ! Lots of devistation but they are working to bring it back. Most staff was nice , the front office staff were snotty and not helpful at !! Location on the beach is amazing! Sanibel / Captiva have captured my heart and I can’t wait to return. I’d stay there again . "
United States
Arra
$289 nightly
The price is $322
Dec 14 - Dec 15
Total with taxes and fees
Casa Ybel Resort
Outdoor pool, pool umbrellas, sun loungers
Pointe Estero Beach Resort

Pointe Estero Beach Resort

Pointe Estero Beach Resort
2.0 star property
South Island
9.2 out of 10, Wonderful, (1001)
"Could not beat the ocean view!!"
United States
BETH
$466 nightly
The price is $512
Dec 15 - Dec 16
Total with taxes and fees
Pointe Estero Beach Resort
Outdoor pool, open 7 AM to 10 PM, pool umbrellas
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers
3.0 star property
Villas
8.8 out of 10, Excellent, (1009)
"Great amenities, pool and spa, clean room, beautiful lobby and good on site restaurant "
United States
Aleksandar
$112 nightly
The price is $125
Dec 21 - Dec 22
Total with taxes and fees
Hilton Garden Inn Ft Myers
Outdoor pool, pool umbrellas, sun loungers
Fairfield Inn & Suites by Marriott Ft. Myers/Cape Coral

Fairfield Inn & Suites by Marriott Ft. Myers/Cape Coral

Fairfield Inn & Suites by Marriott Ft. Myers/Cape Coral
3.0 star property
Villas
8.6 out of 10, Excellent, (782)
"Clean room and very nice staff "
United States
Michael
$89 nightly
The price is $99
Dec 22 - Dec 23
Total with taxes and fees
Fairfield Inn & Suites by Marriott Ft. Myers/Cape Coral
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Tradewinds Hotel Reviews

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

10/10 Excellent
"Friendly and accommodating staff, great breakfast selection, nicely-maintained pool, located across the street from many good local restaurants."
Brendan Michael 10-night trip
Posted 2 days ago
Holiday Inn Express Cape Coral-Fort Myers Area by IHG

Frequently asked questions

What are some accommodations with pools in Tradewinds?
Margaritaville Beach Resort Fort Myers: Hotel located near Key West Express. Features 4 restaurants, an outdoor pool, and a full-service spa. Lani Kai Beachfront Resort: Hotel located near Key West Express. Offers 3 restaurants, an outdoor pool, and 3 beach bars. Holiday Inn Express Cape Coral-Fort Myers Area by IHG: Provides a snack bar/deli, an outdoor pool, and buffet. Sanibel Island Beach Resort: Hotel, 5-minute walk from Sanibel Island Southern Beach. Features free self parking, an outdoor pool, and sun loungers. DiamondHead Beach Resort: Resort located near Key West Express. Offers 2 hot tubs, an outdoor pool, and free self parking.
What is there to see and do in Tradewinds?
Explore places like Key West Express while you're in the area. Take in the natural beauty with a stop at J. N. Ding Darling National Wildlife Refuge.
When is the best time to book a hotel with a pool in Tradewinds?
You may want to consider an accommodation that offers an outdoor swimming pool if you're planning to visit Sanibel in the driest months of February, December, or March when the average rainfall is 2 inches. Lodging with an indoor pool may be what you want if you are visiting during the rainiest months of August, September, and July when the average rainfall is is 9 inches.

Explore a world of travel with Expedia