Vacation rentals with a pool in Gateway

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Gateway

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Guest favourite
Guesthouse in Fort Myers
Hints of Key West in Fort Myers' Historic District
Tucked away in tranquil Dean Park Historic District. Built in 1925, this carriage house has been completely renovated in 2016. It is over a garage, there are stairs. Stroll to downtown Fort Myers River District, and enjoy the restaurants, nightlife, and cultural events. Take advantage of all the activities the area has to offer, and at the end of the day come back to this peaceful oasis. Our place can accommodate couples, older child (twin air mattress available), business travelers. No pets.
Feb. 8 – 15
$247 CAD per night
4.98 out of 5 average rating, 611 reviews
Guest favourite
Home in Fort Myers
Entire Centrally Located Beautiful Pool Home
Enjoy everything that SW Florida has to offer from this centrally located, beautiful heated pool home, including 3 bd + den/2 ba, that comfortably sleeps 10. If you plan to have a party or event this place is NOT for you. The neighbors are very strict in terms of noise and large groups of people. It is close to popular attractions, shopping, dining, it's 3 miles from Bell Tower, and outdoor recreation including the wonderful Lakes Regional Park where you can hike, kayak, picnic and much more!
Jul. 19 – 26
$409 CAD per night
4.94 out of 5 average rating, 107 reviews
Guest favourite
Home in Fort Myers
*Unique Pyramid Home for an amazing vacation
*Great location for exploring all of southwest Florida *Refreshing spring water lake for all guests to enjoy *located approximately 15 miles from most beaches *easy access to FGCU, shopping, sightseeing, RSW airport *self check in with lock box *Private and relaxing community *each pyramid has two private patios with private gas grill *free wifi/ roku tv, beach gear * superhost with 12 total properties *Fully stocked unit with all the amenities of home
Jun. 5 – 12
$259 CAD per night
4.92 out of 5 average rating, 196 reviews

Popular amenities for Gateway rentals with a pool

House rentals with a pool

Guest favourite
Home in Fort Myers
Whole cozy house
Jul. 9 – 16
$381 CAD per night
4.94 out of 5 average rating, 257 reviews
Guest favourite
Home in Fort Myers
Paradise on Estero Bay
Jul. 30 – Aug. 6
$578 CAD per night
4.95 out of 5 average rating, 114 reviews
Guest favourite
Home in Captiva
The Pearl Beach House, North Captiva Island,FL
Oct. 17 – 24
$1,113 CAD per night
4.98 out of 5 average rating, 104 reviews
Guest favourite
Home in Cape Coral
LUX Villa w/ Private Salt Water Pool, Lanai, Canal
Oct. 7 – 14
$785 CAD per night
4.99 out of 5 average rating, 172 reviews
Guest favourite
Home in Fort Myers
Blue Beach Bungalow
Oct. 7 – 14
$689 CAD per night
4.83 out of 5 average rating, 116 reviews
Guest favourite
Home in Cape Coral
*Gulf Access Pool Home with Private Office*
Jun. 19 – 26
$189 CAD per night
4.89 out of 5 average rating, 132 reviews
Guest favourite
Home in Cape Coral
Recently Renovated Home with Pool in SW Cape Coral
Aug. 3 – 10
$258 CAD per night
4.87 out of 5 average rating, 173 reviews
Guest favourite
Home in Lehigh Acres
Secluded Pool Home
Oct. 1 – 8
$217 CAD per night
4.94 out of 5 average rating, 69 reviews
Guest favourite
Home in Fort Myers
Heated Pool Home with Extras! Soak in the Sun!
Jul. 12 – 19
$578 CAD per night
4.98 out of 5 average rating, 60 reviews
Superhost
Home in Lehigh Acres
3 bed home & community pool, close to fort myers
Apr. 13 – 20
$265 CAD per night
4.94 out of 5 average rating, 18 reviews
Guest favourite
Home in Fort Myers
Fairview Getaway
Sep. 22 – 29
$573 CAD per night
4.93 out of 5 average rating, 15 reviews
Guest favourite
Home in Fort Myers
Heated Pool W/Huge Backyard B/T Naples& FT. Myers
May 31 – Jun. 7
$326 CAD per night
5.0 out of 5 average rating, 7 reviews

Condo rentals with a pool

Guest favourite
Condo in Naples
Ground Floor, A+ Location Club Membership Included
Jul. 18 – 25
$182 CAD per night
4.85 out of 5 average rating, 151 reviews
Guest favourite
Condo in Cape Coral
Penthouse Suite in the heart of SW Cape Coral, FL
Jun. 5 – 12
$280 CAD per night
4.93 out of 5 average rating, 107 reviews
Superhost
Condo in Fort Myers Beach
Lovers Key Resort, Fort Myers Beach - Awesome
Jul. 24 – 31
$310 CAD per night
4.81 out of 5 average rating, 155 reviews
Superhost
Condo in Fort Myers
2 Bed | 2 Bath | 'Home Away From Home'
Aug. 13 – 20
$241 CAD per night
4.78 out of 5 average rating, 198 reviews
Guest favourite
Condo in Naples
558 Sea Glass Cottage | New Pool | Mins 2 Beaches
Dec. 22 – 29
$836 CAD per night
4.95 out of 5 average rating, 107 reviews
Guest favourite
Condo in Naples
Park Shore Resort Modern Top Floor 2 Bed 2 Bath
Jun. 22 – 29
$468 CAD per night
4.91 out of 5 average rating, 146 reviews
Guest favourite
Condo in Naples
Park Shore Walk to Beach!
Aug. 5 – 12
$302 CAD per night
4.86 out of 5 average rating, 212 reviews
Guest favourite
Condo in Naples
2 Beds 2 Baths Pool 5m Beach Downtown & Shopping
Dec. 23 – 30
$848 CAD per night
4.91 out of 5 average rating, 102 reviews
Superhost
Condo in Lehigh Acres
Sunset
Apr. 20 – 27
$187 CAD per night
4.82 out of 5 average rating, 11 reviews
Guest favourite
Condo in Fort Myers
Glamorous Fort Myers Getaway! Condo Resort Style!
Nov. 28 – Dec. 5
$216 CAD per night
5.0 out of 5 average rating, 14 reviews
Superhost
Condo in Punta Gorda
Burnt Store Marina Harbor Towers 2 Bdrm Condo
Sep. 24 – Oct. 1
$251 CAD per night
5.0 out of 5 average rating, 21 reviews
Guest favourite
Condo in Fort Myers
Fort Myers 2nd Flr Lakefront 3/2 Resort Condo
Aug. 30 – Sep. 6
$359 CAD per night
4.97 out of 5 average rating, 99 reviews

Home rentals with a private pool

Guest favourite
Home in Cape Coral
Awesome Location W/boat Dock, Pool, & Kayaks!
Sep. 22 – 29
$508 CAD per night
5.0 out of 5 average rating, 11 reviews
Guest favourite
Villa in Cape Coral
Gorgeous Villa In Cape Coral, Florida's Gulf Coast
Jul. 28 – Aug. 4
$396 CAD per night
4.94 out of 5 average rating, 51 reviews
Guest favourite
Home in Cape Coral
Luxury Waterfront Home with Pool
Sep. 21 – 28
$350 CAD per night
4.92 out of 5 average rating, 72 reviews
Home in Cape Coral
Blue Oasis
Apr. 29 – May 6
$383 CAD per night
New place to stay
Home in Fort Myers Beach
147 Curlew St
Apr. 21 – 28
$641 CAD per night
New place to stay

Quick stats about vacation rentals with a pool in Gateway

Total rentals

40 properties

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

50 reviews

Nightly prices starting at

$54 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Lee County
  5. Gateway
  6. Rentals with pools