Holiday rentals with a pool in Estero Island

Find and book unique homes with a pool on Airbnb

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Popular amenities for Estero Island rentals with a pool

House rentals with a pool

Top Guest favourite
Home in Cape Coral
4.99 out of 5 average rating, 71 reviews

Cape Eternal Paradise

MalachiRating, 5 stars2 weeks ago
Loved our stay at Joeldys place, beautiful view of the canal in the back and plenty of wildlife, couldn’t have asked for more :)
Top Guest favourite
Home in Cape Coral
4.96 out of 5 average rating, 92 reviews

***Relaxation Awaits*** Heated Saltwater Pool Home

ChrisRating, 5 stars2 days ago
I booked this home to celebrate my wife’s birthday. It was amazing. Private house with an enclosed pool. My wife did not want to get out of the pool. The house was immaculate and everything was handy and accessible. Will definitely look into staying here again if and when we travel to Cape Coral again.
Guest favourite
Home in Cape Coral
5 out of 5 average rating, 11 reviews

Waterfront Cape Coral Oasis+ Heated Pool | Kayaks

EllaRating, 5 stars2 days ago
This was our favorite Airbnb yet. The house and grounds were beautiful. There was something for everyone from 2 years old to 72. It was spotless and had everything we needed. Romy was proactive and checked on us but the setup was so well executed we wanted for nothing. We saw iguanas, owls, and bunnies. Sunsets were beautiful. The pool area had space for all. We will be back!
Guest favourite
Home in Fort Myers Beach
5 out of 5 average rating, 13 reviews

NEW! Across from BEACH! Private Heated Pool!

MeganRating, 5 stars3 days ago
I loved this place! It was absolutely beautiful, gorgeous outside area to hang out, and a short walk to the beach! Since the area is still rebuilding there are empty lots on all sides, but even if there wasn’t there is a nice privacy fence all around. We packed all of our beach things, just to find out they had beach chairs, boards, toys, a cart, an umbrella, the whole 9 yards! And a bunch of beach towels. It was truly one of those places you just need to show up with some clothes and could pretty much be set for the week! If we decide to go back to the area, I will definitely be trying to get this place again. Aaron was also great and very responsive any time I messaged him. Highly recommend!
Top Guest favourite
Home in Fort Myers Beach
5 out of 5 average rating, 22 reviews

Luxury Urban Oasis just steps from the beach!

MelissaRating, 5 stars1 month ago
We booked a couples getaway and this Airbnb was perfect!! Kelley was super responsive and flexible with the check in time. The amenties in the house were amazing. The kitchen had everything we needed....coffee machine, plates/utencils, even and air fryer! The beach was a 5 minute walk (loved that chairs, umbrell and a wagon were provided as well!) and a 15 minute walk to the Times Square area. The interior design of the home was amazing and the details really made it a trip to remember.
Guest favourite
Home in Cape Coral
5 out of 5 average rating, 6 reviews

Morning Glory - Walking Distance to Surfside Shops

PatriciaRating, 5 stars2 weeks ago
The house was beautiful! Very peaceful and comfy. My family and I really enjoyed our stay.
Top Guest favourite
Home in Cape Coral
4.92 out of 5 average rating, 61 reviews

Bougee Waterfront with Salt Water Pool/Spa/Game Rm

DonnaRating, 5 stars1 week ago
We would definitely stay again! Everything we needed was available. The house was nicely stocked with necessities. Super responsive host. Well thought out space inside and out. Peaceful and designed for relaxation. Thank you Jayme!
Guest favourite
Home in Fort Myers Beach
4.74 out of 5 average rating, 23 reviews

Beachside Oasis

AlexRating, 5 stars3 weeks ago
Loved this Airbnb! The location was amazing and had plenty of space for our family.

Condo rentals with a pool

Guest favourite
Condo in Fort Myers Beach
4.89 out of 5 average rating, 63 reviews

3BR BeachCondo | Gulfside Pool | Hot tub | Sleep 8

JillRating, 5 stars1 week ago
Great place to go with your family! Our 4 and 7 year old had the best time of their lives! I would stay here again!
Guest favourite
Condo in Fort Myers Beach
4.9 out of 5 average rating, 79 reviews

Boutique condo on the bay, short walk to the beach

ChelseaRating, 5 stars2 weeks ago
It was a great quiet getaway for my friends and I. It is a little bit of a quiet town, but that was perfect for us! If you are looking for a simple, peaceful beach getaway then this is the place for you.
Superhost
Condo in Fort Myers Beach
4.92 out of 5 average rating, 198 reviews

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

RobinRating, 5 stars1 month ago
Lover’s Key is a lovely low key and private place to stay! This is our 4th anniversary here in Ft Meyers. Our time here never disappoints. John’s place has what you need but we always bring extra TP, dishwasher cubes and laundry cubes. Just makes it easier… Flipper’s restaurant is right outside the door. Good food and good drinks! Key Lime Colada was delish! Lastly, please remember that Ft Meyers is still in a rebuilding phase, it’s taken a couple of years to get the bridge re built. There are plenty of things to do downtown and surrounding areas. We look forward to next year!
Top Guest favourite
Condo in Fort Myers Beach
5 out of 5 average rating, 10 reviews

GullWing 1006: Gulf View, Beach Front, Pool & Spa!

JaneRating, 5 stars2 weeks ago
This place was absolutely amazing! All the kitchen accessories, bedroom amenities, and beach stuff provided was top notch. The location right on the beach provided a cool breeze even on the hot days. Sunset views and so many shells. Gulf and pool water were the perfect temperature. We used the bikes and there were plenty to choose from. Gorgeous spot all around!
Superhost
Condo in Fort Myers Beach
4.92 out of 5 average rating, 101 reviews

Summer Savings Lovers Key Beach Club Private Beach

RebeccaRating, 5 stars1 month ago
Condo was very nice, clean, and updated. It had everything we needed. The bed was very comfortable! We were a little bummed that the balcony didn’t face the water, it faces the parking lot but we still were able to see from the side. The beach was great, private and we saw a lot of manatees and dolphins very close up. The bridge that is being built was interesting to watch and once completed, the views will be even better! Definitely a cute little place to stay! Owners were great and very responsive! Overall, it was a very fun 2 weeks!!
Guest favourite
Condo in Fort Myers Beach
5 out of 5 average rating, 10 reviews

Pleasant Paradise At Estero Beach & Tennis Club

ColeenRating, 5 stars4 months ago
This unit is wonderfully located, with a beautiful view of the shore. We usually prepare our b-fast & lunch in, then dinner out. The kitchen was very well equipped. It was great to have all the extras for the beach, chairs, cooler, toys, and umbrellas. We are grateful for a host with perfect communication skills, Thank you for that.
Top Guest favourite
Condo in Bonita Springs
4.98 out of 5 average rating, 129 reviews

Casa Bonita - Relax @ The Beach (Newly Remodeled)

EmilyRating, 5 stars1 week ago
The unit was exactly as described—clean, comfortable, and well-equipped. The location was excellent, and it had everything I needed to make breakfast each morning. While the grounds are still recovering from the hurricane, with some visible damage, the pools are open and fully functional. Overall, it didn’t detract from an enjoyable stay.
Superhost
Condo in Fort Myers Beach
4.94 out of 5 average rating, 33 reviews

Newly Renovated Second Floor 1 Bedroom Condo

TraceyRating, 5 stars33 months ago
The condo is very well stocked with everything you need for a beach vacation! Umbrellas, chairs, towels..all there! So nice! No problem checking in. You have your own parking spot so if you have you own vehicle there’s no additional charge for parking it on the property. We walked to Times Square for dinner a few nights and started our morning with a walk to the pier and back. The location is perfect if you are looking for something that is more on the quiet side. You walk right onto the beach which is what my husband and I wanted. I didn’t want to cross a street or walk two blocks to the beach access so the condos own beach access was great! Pool is very nice and refreshing! I highly suggest this condo for your relaxing beach vacation!

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