
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
Get the amount of space that is right for you
Popular amenities for Estero Island rentals with a pool
House rentals with a pool

Cape Eternal Paradise
Loved our stay at Joeldys place, beautiful view of the canal in the back and plenty of wildlife, couldn’t have asked for more :)

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

Waterfront Cape Coral Oasis+ Heated Pool | Kayaks
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!

NEW! Across from BEACH! Private Heated Pool!
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!

Luxury Urban Oasis just steps from the beach!
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.

Morning Glory - Walking Distance to Surfside Shops
The house was beautiful! Very peaceful and comfy. My family and I really enjoyed our stay.

Bougee Waterfront with Salt Water Pool/Spa/Game Rm
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!

Beachside Oasis
Loved this Airbnb! The location was amazing and had plenty of space for our family.
Condo rentals with a pool

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

Boutique condo on the bay, short walk to the beach
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.

Ft Myers Beach & Lovers Key State Park- FANTASTIC!
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!

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

Summer Savings Lovers Key Beach Club Private Beach
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!!

Pleasant Paradise At Estero Beach & Tennis Club
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.

Casa Bonita - Relax @ The Beach (Newly Remodeled)
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.

Newly Renovated Second Floor 1 Bedroom Condo
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!
Destinations to explore
- Tampa Bay Holiday rentals
- St Petersburg Holiday rentals
- Tampa Holiday rentals
- Seminole Holiday rentals
- Fort Lauderdale Holiday rentals
- Central Florida Holiday rentals
- Gold Coast Holiday rentals
- Miami Holiday rentals
- Miami Beach Holiday rentals
- Key West Holiday rentals
- Florida Keys Holiday rentals
- Four Corners Holiday rentals
- Rentals with a washing machine and dryer Estero Island
- Apartment rentals Estero Island
- Rentals with a kayak Estero Island
- Pet-friendly rentals Estero Island
- Kid-friendly rentals Estero Island
- Beachfront rentals Estero Island
- Villa rentals Estero Island
- Beach condo rentals Estero Island
- Condo rentals Estero Island
- Fitness-friendly rentals Estero Island
- Rentals with outdoor seating Estero Island
- Rentals with an EV charger Estero Island
- Rentals with beach access Estero Island
- House rentals Estero Island
- Rentals with a fire pit Estero Island
- Rentals with a hot tub Estero Island
- Rentals with a fireplace Estero Island
- Rentals with lake access Estero Island
- Waterfront rentals Estero Island
- Beach house rentals Estero Island
- Family-friendly rentals Estero Island
- Rentals with a patio Estero Island
- Rentals with pools Fort Myers Beach
- Rentals with pools Lee County
- Rentals with pools Florida
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Naples Beach
- Captiva Island
- Clam Pass Park
- Barefoot beach Bonita Springs,FL
- Lovers Key Beach
- Tigertail Beach
- The Club at The Strand
- Worthington Country Club
- Seagate Beach Club
- Panther Run Golf Club
- Delnor-Wiggins Pass State Park
- Englewood Beach
- Bonita National Golf & Country Club
- Morgan Beach
- Heritage Bay Golf & Country Club
- LaPlaya Golf Club
- Gasparilla Island State Park
- Stump Pass Beach State Park
- Boca Grande Pass
- Cypress Woods Golf & Country Club
- The Quarry Golf Club Naples
- Talis Park Golf Club
- Sanibel Island Northern Beach
- Blind Pass Beach