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Holiday Rentals with Pools in Estero

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    Travellers to Estero are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    23 Matching Rentals in EsteroView all 28 rentals
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    Estero Florida, Fabulous 2 Bedroom Condo1 / 9
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2 Bed 2 Bath First Floor Condo in Estero, Florida1 / 26
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Villa with pool on lake1 / 17
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Serene & Attractive Pool Home Near Gulf Beaches1 / 13
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This serene and attractive home is ideally located between Naples and Ft Myers near the beautiful Gulf beaches of SW Florida in a private, gated community West of Hwy 41and 15 minutes south of Ft Myers Intl Airport; near Barefoot Beach and Ft Myers Beach; near Coconut Point Mall; and within easy...
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    Estero, Southwest Gulf Coast 33928
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Air Conditioning
    • Washer
    • Waterfront
    • DVD Player
    • Children's Pool
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Everyone dreams of this experience. Located in a gated golf community, Spring Run CC in Bonita Springs is perfectly placed between Naples and Ft Myers. The amenities don't stop. Close proximity to the areas attractions including a short drive to Sanibel/Captiva Islands and eight miles from the...
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    Estero, Southwest Gulf Coast 34135
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Paradise in Bella Terra - Amazing Vacation Condo!1 / 34
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Hot Tub
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 October 2016
    We very much enjoyed our visit to this secure, comfortable, quiet, well equipped property. The amenities on the property make it hard to leave. A small pool is within walking...
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    About this property
    You'll only need your toothbrush and suitcase in this fantastic rental! Immaculate two bedroom, two bath, second floor condo in the amazing Bella Terra community! Brand new furnishings and premium linens, towels, and amenities (including basic cable and Internet) welcome you to this freshly...
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    Estero, Southwest Gulf Coast 33928
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Internet Access
    • Air Conditioning
    • Washer
    • Satellite TV
    • Grill
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay for a month or longer at our beautifully renovated ground floor condo located in the Island Sound section of Pelican Sound. With our location in Estero, Florida, you are just minutes away from everything. Coconut Point, Miromar Outlets, Gulf Coast Town Center, Bonita Springs, Naples, Fort...
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    Estero, Southwest Gulf Coast 33928
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Satellite TV
    • Wi-Fi
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1,800 square foot condo overlooks a lake with waterfall. All the amenities, 2 pools, hot to, fitness room. Walk to Mall with dining and all shopping necessities. Coconut Point Mall is a favorite destination. You are only 25 min. from the Beach and 20 min from the airport. Best location...
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    Estero, Southwest Gulf Coast 33928
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Waterfront
    • Internet Access
    • Satellite TV
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elevate your next Gulf Coast experience with this 3-bedroom, 3-bathroom Estero vacation rental house that comfortably sleeps 6. This Florida home boasts nearly 2,000 square feet of luxurious living space, as well as a spacious, covered backyard with lounge chairs and a private pool. Whether you’re...
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    Estero, Southwest Gulf Coast 33928
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Stoneybrook Golf Course1 / 14
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Hot Tub
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2017
    This condo unit was lovely with a quiet neighborhood, great location, and friendly people. The owners are exceedingly considerate and responsible. We are returning next year!
    Reviewed 3 February 2015
    My husband and I rented this condo in Stoneybrook for the month of Jan., 2015. We had a really nice time. Catherine, our landlord, was great. Any questions we had were...
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    About this property
    Stoneybrook is a 24 hour manned GATED community that offers bike and walking paths, soccer field, basketball and tennis courts, a roller hockey rink, playground, softball diamond, fitness center, and three large community pools. Stoneybrook offers reasonable rates on a "pay as you golf" course with...
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    Location Information
    Estero, Southwest Gulf Coast 33928
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Washer
    • Air Conditioning
    • Patio
    • Secure Parking
    • Satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This two story 1,820 sqft. townhouse offers attached living with the convenience of a condo but the living area and feel of a single family home. This beautifully appointed and meticulously maintained home includes three bedrooms, two and a half baths plus a one car garage, a screened lanai and...
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    Estero, Southwest Gulf Coast 33928
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Stylish 4-bedroom condo at Miromar Lakes Community1 / 28
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Children's Pool
    • DVD Player
    • Waterfront
    • Wi-Fi
    • Sauna
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 October 2016
    We were staying for 3 month over the season.Everything was perfect, thank you Eleana for your flexibility and help with moving in. This Condo is well thought through and feels...
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    About this property
    This stylish 3-Bedroom+Den Condo situated at Miromar Beach&Golf Club - Number One Community in Florida. 5 minutes walk from private beach on the lake Como, infinity swimming pool, luxury spa, boat and golf club facilities. Fully furnished spacious turnkey condo at 2nd floor with private lake...
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    Location Information
    Estero, Southwest Gulf Coast 33913
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Patio
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Plan your Sunshine State escape in Estero with this brand new 2-bedroom, 2-bathroom vacation rental home, which boasts high-end furnishings. Sleeping 4 guests, this beautiful home has a private pool overlooking the lake and is perfect for couples or a family. You won't soon forget your retreat to...
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    Estero, Southwest Gulf Coast 33928
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Balcony
    • Waterfront
    • Air Conditioning
    • Hot Tub
    • Porch
    • Internet Access
    • Washer
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the Italian Riviera in Southwest Florida. Our luxury condominium available for seasonal rentals in RAPALLO At Coconut Pt., Estero... 2 large bedrooms, 2 large baths, , Lanai overlooking water... 1966 sq. feet of living space, 2 car garage, fully stocked kitchen & more. 15 minutes to Gulf...
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    Location Information
    Estero, Southwest Gulf Coast 33928
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Sun, Fun, Golf, Beach!!!! Fountain Lakes Community1 / 13
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Washer
    • Balcony
    • Waterfront
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 March 2015
    We loved this condo as it was very comfortable and cozy. It was literally across the street from a wonderful mall if shopping is your thing, close to beaches, close to Naples...
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    About this property
    White sand beaches and jewel blue water in beautiful Estero, Florida. Estero is nestled halfway between Fort Myers and Naples. Some of the best public golf courses in southwest Florida are close at hand including Bonita Fairways Golf Club, Villages of Country Creek Golf Club, Stoneybrook Golf...
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    Location Information
    Estero, Southwest Gulf Coast 33928
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    • Grill
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The grand Estero Manor overlooks the fairways at Club of Grandezza through floor to ceiling windows and is complete with a pool table, formal dining room, a large master suite, and a screened in heated pool and hot tub. Located in a gated community, Estero Manor is only a short drive to Lovers...
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    Location Information
    Estero, Southwest Gulf Coast 33928
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully appointed single family home with 3 bedrooms/3 baths and solar heated pool. Located in the Village of Estero. Your well behaved pet is welcome! Sport club membership transfer available at Estero Country Club$ 300 mo, $108 per round (green fees + cart) up to 20 rounds of golf per month....
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    Location Information
    Estero, Southwest Gulf Coast 33967
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This luxury high rise condominium is elegant and inviting! New furnishings summer of 2013. Views from every room to the East and West!! King bed in the master with flat screen tv, walk in closet with, spacious bath with roman tub. 2nd bedroom has been furnished with twim beds, has it's own...
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    Location Information
    Estero, Southwest Gulf Coast 33928
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 3 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Washer
    • Waterfront
    • Sauna
    • Children's Pool
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shared basis. Private room. 2 spare bedrooms are available. We are a young working couple therefore we are barely home. We will be happy to offer 2 spare bedrooms at our professionally decorated 3 bedroom + den Condo. Both Bedrooms available on daily basis. Nightly rate of $150 is given per...
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    Location Information
    Estero, Southwest Gulf Coast 33913
    Private Room - 1 Bedroom, 3 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nicely furnished first floor coach home with an amazing lake view! Inviting clubhouse with pro shop, formal and casual dining, bar and grille room. tennis center with six har-tru courts. Newly renovated River Club is a casual eatery with indoor/outdoor dining overlooking the Estero River. Enjoy...
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    Estero, Southwest Gulf Coast 33928
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the relaxing palm tree sound in this lovely appointed three bedroom two bath corner, first floor unit in the sought after gated community of Pelican Sound Golf and River Club in Estero. Bountiful activities from sun up to sundown. Start you day with refreshing morning coffee on the serene...
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    Estero, Southwest Gulf Coast 33928
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    • Shared Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nicely furnished first floor 2 BR + Den coach home with an amazing lake view! Inviting clubhouse with pro shop, formal and casual dining, bar and grille room. tennis center with six har-tru courts. Newly renovated River Club is a casual eatery with indoor/outdoor dining overlooking the Estero...
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    Estero, Southwest Gulf Coast 33928
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Sauna
    • Hot Tub
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Note: currently accepting only 3-month or longer rental applications... Miromar Lakes, FL -- voted the #1 Residential Community in the entire United States for 2011. One of the best views in Miromar Lakes. Newly furnished. This 3 bedroom, 2.5 bathroom top-floor penthouse unit offers panoramic...
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    Estero, Southwest Gulf Coast 33913
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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