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Vacation rentals with a pool in Estero Bay

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Estero Bay

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

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Condo in Bonita Springs

4.95 out of 5 average rating, 85 reviews

Ken & Gina's Beach Condo (#2301)

***Due to hurricane Ian, no amenities are available (pool, tennis, etc)*** Studio condo across the street from Bonita Beach. 3rd floor unit offering partial views of the gulf. Being able to walk to the beach (2 mins) and 3 restaurants while centrally located between Ft. Myers and Naples makes this a great location. Atmosphere is very relaxing and residents are very friendly. Local bike rental shops offer delivery of bicycles. Bonita beach offers jet ski, paddle board and catamaran rental.

Jun 20 – 27

ﺩ.ﺇ383 per night

Guesthouse in Fort Myers

4.98 out of 5 average rating, 620 reviews

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.

Jul 17 – 24

ﺩ.ﺇ496 per night

Home in Cape Coral

4.87 out of 5 average rating, 178 reviews

Recently Renovated Home with Pool in SW Cape Coral

The perfect getaway for families at our recently renovated house with pool and grill! Half an hour by car from famous beaches. Create lasting memories. Relax in the comfortable living area, and unwind in well-appointed bedrooms. Outside, make a splash in the refreshing pool or sizzle up a feast on the grill. Explore beaches, dine at charming restaurants, and enjoy outdoor activities. We ensure a memorable stay. Book now for an unforgettable family vacation! Pool heater from November to March.

Oct 14 – 21

ﺩ.ﺇ550 per night

Guest suite in Matlacha Isles-Matlacha Shores

4.84 out of 5 average rating, 315 reviews

Moon Shell Hideaway

Private entrance to your one bedroom plus den (with queen size sleeper/sofa) apartment attached to main house. Direct access to the Gulf of Mexico. Bedroom has a queen size bed and the den has a queen size sleeper/sofa. The den doubles as your kitchenette and sitting area with double sliding glass doors that open up to the shared pool and dock area. Gas grill and microwave for cooking (no stove). Boat to five restaurants. Visit the Matlacha Art Galleries. Fish off the dock. WELCOME!

Dec 15 – 22

ﺩ.ﺇ340 per night

Apartment in Bonita Springs

4.94 out of 5 average rating, 18 reviews

Heated Pool•7min->Beach•King•WD•SmartTV

• 2.1 miles to beach. 6 minute drive, 12 min bike ride • 700 sqft, 1st floor, 1 bedroom/1 bath • Safe & quiet neighborhood • Equipped kitchen, stocked w/essentials • Screened-in pool • On-site parking (1 vehicle) • Smart TV • On-site laundry • Fast internet • Backyard garden • Firepit • Bikes, beach equipment • Grill • Neighborhood boat ramp Minutes from: • Multiple Beaches • State parks • Restaurants • World class golf courses • Fishing/boating • Nightlife • Naples shopping & spas

Jun 25 – Jul 2

ﺩ.ﺇ450 per night

Guesthouse in Naples

4.93 out of 5 average rating, 113 reviews

Private & Spacious Studio 1 mile fr 5th Ave w/Pool

Welcome to Kevin's Newly Renovated Air BNB in Naples, featuring a private swimming pool, patio w/sun shade, parking, luxury sheets, fully stocked kitchen, full size W/D, and more! This uber-quiet and private space is located just over 1 mile from 5th Avenue/downtown Naples, & 2 miles from the beach. 5 minute walk to Naples Bay Resort, coffee shops & restaurants. Walk or use complimentary bikes to check out nearby Celebration Park, a brewery, Market 360, & pickleball courts!

Jun 28 – Jul 3

ﺩ.ﺇ543 per night

Apartment in Fort Myers Beach

4.9 out of 5 average rating, 193 reviews

Mermaid Oasis

Ft Myers beach Bonita Mermaid Oasis’s dream getaway! 1 bedroom King bed , full kitchen, spacious living room, sofa sleeper couch, beautiful balcony. Bathroom with a Jacuzzi tub, walk-in shower, private toilet area. The beautiful bay and pool invite you to come play. Flippers 5-star restaurant on the property. You can enjoy water sports long walks on Lovers Key Beach across the street. Only minutes to Bonita Naples and Ft. Myers beach, reviews say it all!

Sep 24 – Oct 1

ﺩ.ﺇ865 per night

Home in Fort Myers

4.92 out of 5 average rating, 202 reviews

*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

Sep 9 – 16

ﺩ.ﺇ584 per night

Home in Cape Coral

4.97 out of 5 average rating, 242 reviews

Dolphin beach house

* fantastic pool home located in the most desirable section of Cape Coral * Steps from the Yacht Club beach * Fishing and boating community * Home features a large paver patio for sunning and a screened Lanai with a private pool * This beach home has a grill outside for those who like to cook outdoors and a fully equipped kitchen inside * This home away from home has a Washer & Dryer * WiFi & Local TV * No Pets Please *

Sep 12 – 19

ﺩ.ﺇ543 per night

Apartment in Cape Coral

4.91 out of 5 average rating, 148 reviews

Private Apartment with sunny pool

One-bedroom plus den apartment attached to the main house with private entrance. The apartment has a small kitchenette for basic meal preparation. A large pool is right outside your door! Come relax by the pool & cool off on a hot day. The pool is for your private use. We have a gas BBQ grill located in the fenced yard for your use. Ft. Myers Beach 35 min away Sanibel Beach 45 min away Naples Beaches 60 min away

Jan 10 – 17

ﺩ.ﺇ476 per night

Home in Fort Myers

4.94 out of 5 average rating, 107 reviews

Private Heated Pool and Spa

Retreat to paradise in this extra clean and beautifully renovated home centralized to all major Southwest Florida attractions. Splash and play in your private, year-round heated pool or relax and unwind in the bubbles of the jacuzzi. Heating included in price! Less than a 10 minute drive gets you to RSW airport, tons of excellent restaurants, three supermarkets and 4 major shopping malls.

Nov 24 – Dec 1

ﺩ.ﺇ974 per night

Cottage in North Fort Myers

4.94 out of 5 average rating, 172 reviews

Cozy Private Pool Cottage

This is a small separate guest house with a large pool just steps from the door. Located in a very safe and quiet secluded neighborhood with only 18 homes, all retirees and famous artists along the caloosahatchee with some Riverfront views from pool deck. Only 1.2 miles to Historic Downtown Fort Myers and Edison Museum, along with numerous downtown events, restaurants and nightlife.

Jul 14 – 21

ﺩ.ﺇ517 per night

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Popular amenities for Estero Bay rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Fort Myers

4.94 out of 5 average rating, 270 reviews

Whole cozy house

Sep 15 – 22

ﺩ.ﺇ684 per night

Home in Cape Coral

4.96 out of 5 average rating, 108 reviews

Cozy in the Cape, Water views & private salt pool.

Oct 17 – 24

ﺩ.ﺇ612 per night

Home in Captiva

4.97 out of 5 average rating, 106 reviews

The Pearl Beach House, North Captiva Island,FL

Oct 30 – Nov 6

ﺩ.ﺇ2,505 per night

Home in Fort Myers

4.82 out of 5 average rating, 45 reviews

Mermaid Cottage minutes away from awesome beaches

Jan 15 – 22

ﺩ.ﺇ604 per night

Home in Cape Coral

4.96 out of 5 average rating, 24 reviews

Heated Pool; Elegant & Cozy Home

Aug 26 – Sep 2

ﺩ.ﺇ501 per night

Home in Fort Myers

5.0 out of 5 average rating, 13 reviews

Seashell Sanctuary

Aug 28 – Sep 4

ﺩ.ﺇ795 per night

Home in Fort Myers

4.97 out of 5 average rating, 35 reviews

Blue Bird Villa Fort Myers

May 18 – 25

ﺩ.ﺇ541 per night

Home in Bonita Springs

4.96 out of 5 average rating, 67 reviews

3BR w/HUGE 2k sq ft Lanai & Seasonally Heated Pool

May 21 – 28

ﺩ.ﺇ841 per night

Condo rentals with a pool

Condo in Naples

4.85 out of 5 average rating, 156 reviews

Ground Floor, A+ Location Club Membership Included

Oct 3 – 10

ﺩ.ﺇ396 per night

Condo in Naples

4.95 out of 5 average rating, 283 reviews

Lely Greenlinks Golf Resort Luxury Condo

May 14 – 21

ﺩ.ﺇ676 per night

Condo in Naples

4.87 out of 5 average rating, 218 reviews

Park Shore Walk to Beach!

Aug 24 – 31

ﺩ.ﺇ695 per night

Condo in Naples

4.91 out of 5 average rating, 146 reviews

Park Shore Resort Modern Top Floor 2 Bed 2 Bath

Oct 15 – 22

ﺩ.ﺇ869 per night

Condo in Cape Coral

4.92 out of 5 average rating, 111 reviews

Penthouse Suite in the heart of SW Cape Coral, FL

Jul 3 – 10

ﺩ.ﺇ607 per night

Condo in Fort Myers

4.78 out of 5 average rating, 203 reviews

2 Bed | 2 Bath | 'Home Away From Home'

Aug 26 – Sep 2

ﺩ.ﺇ544 per night

Condo in Naples

4.93 out of 5 average rating, 123 reviews

Lely Resort Luxury Condo-1 Spectacular Pool/Golf

Aug 16 – 23

ﺩ.ﺇ671 per night

Condo in Naples

4.91 out of 5 average rating, 108 reviews

Beautiful Pool 5m to the Beach Downtown & Shopping

Apr 5 – 12

ﺩ.ﺇ1,711 per night

Home rentals with a private pool

Home in Cape Coral

4.92 out of 5 average rating, 72 reviews

Luxury Waterfront Home with Pool

Dec 21 – 28

ﺩ.ﺇ1,953 per night

Home in Cape Coral

5.0 out of 5 average rating, 16 reviews

Awesome Location W/boat Dock, Pool, & Kayaks!

Oct 4 – 11

ﺩ.ﺇ1,210 per night

Home in Cape Coral

5.0 out of 5 average rating, 3 reviews

Blue Oasis

Nov 8 – 15

ﺩ.ﺇ834 per night

Home in Fort Myers Beach

147 Curlew St

May 3 – 10

ﺩ.ﺇ1,631 per night

Home in Bonita Springs

New place to stay

Coastal Waterfront Home W/pool-Tiki-Dock

Aug 13 – 20

ﺩ.ﺇ1,780 per night

Destinations to explore