Holiday rentals with a pool in Estero Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Estero Island
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Estero Island rentals with a pool
House rentals with a pool
Home in Fort Myers Beach
4.94 out of 5 average rating, 107 reviewsLuxury Waterfront Escape Near The Beach C1
21–28 Jan
Home in Cape Coral
4.89 out of 5 average rating, 139 reviews*Gulf Access Pool Home with Private Office*
1–8 May
Home in Matlacha
5.0 out of 5 average rating, 142 reviewsThe Secret Island Retreat HeatedPool/4b/open water
30 May – 6 Jun
Home in Fort Myers
4.94 out of 5 average rating, 108 reviewsPrivate Heated Pool and Spa
15–22 Apr
Home in Captiva
4.97 out of 5 average rating, 107 reviewsThe Pearl Beach House, North Captiva Island,FL
31 Oct – 7 Nov
Home in Cape Coral
4.98 out of 5 average rating, 195 reviewsDolphin beach house 2
3–10 Dec
Home in Fort Myers Beach
5.0 out of 5 average rating, 7 reviewsCrain's Perch will WOW you!
19–26 Jun
Home in Fort Myers Beach
5.0 out of 5 average rating, 7 reviewsLuxury Urban Oasis just steps from the beach!
24 Sep – 1 Oct
Condo rentals with a pool
Condo in Naples
4.85 out of 5 average rating, 156 reviewsGround Floor, A+ Location Club Membership Included
2–9 Aug
Condo in Fort Myers
4.78 out of 5 average rating, 203 reviews2 Bed | 2 Bath | 'Home Away From Home'
4–11 Oct
Condo in Cape Coral
4.92 out of 5 average rating, 111 reviewsPenthouse Suite in the heart of SW Cape Coral, FL
12–19 Jun
Condo in Naples
4.87 out of 5 average rating, 218 reviewsPark Shore Walk to Beach!
3–10 Aug
Condo in Fort Myers
4.96 out of 5 average rating, 101 reviewsFort Myers 2nd Flr Lakefront 3/2 Resort Condo
15–22 Apr
Condo in Naples
4.91 out of 5 average rating, 146 reviewsPark Shore Resort Modern Top Floor 2 Bed 2 Bath
17–24 Dec
Condo in Fort Myers Beach
4.89 out of 5 average rating, 79 reviewsLovers Key / Stunning water and sanctuary views
17–24 Jan
Condo in Fort Myers Beach
5.0 out of 5 average rating, 32 reviewsFMBSteps away from Gulf, pool Fabulous 2B/2B condo
3–10 Aug
Home rentals with a private pool
Home in Cape Coral
4.92 out of 5 average rating, 72 reviewsLuxury Waterfront Home with Pool
21–28 Dec
Home in Cape Coral
5.0 out of 5 average rating, 16 reviewsAwesome Location W/boat Dock, Pool, & Kayaks!
29 Nov – 6 Dec
Home in Cape Coral
5.0 out of 5 average rating, 3 reviewsBlue Oasis
14–21 Jan
Home in Bonita Springs
New place to stayCoastal Waterfront Home W/pool-Tiki-Dock
1–8 Oct
Home in Fort Myers Beach
147 Curlew St
15–22 May
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