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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.
    27 Matching Rentals in EsteroView all 38 rentals
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    Villa with pool on lake1 / 18
    (12)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Estero Florida, Fabulous 2 Bedroom Condo1 / 9
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    1 Bedroom, 2 Bathrooms, Sleeps 3 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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    • Air Conditioning
    • Washer
    • DVD Player
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly Furnished, Uniquely Decorated 2 Bed and 2 Bath First Floor Condo In The Award Winning Stoneybrook Golf Community in Estero, Florida Great view from the screened in lanai which overlook the 11th tee box. Permanently installed Hurricane Shutters that roll up or down at the touch of a switch....
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    Estero, Southwest Gulf Coast 33928
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    • Waterfront
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lover's Key Resort Fresh ocean air, warm waves, and soft sands all await you at this cushy condo in Lover's Key. Perks like a shared pool and hot tub let you unwind after long days exploring the beach and nearby town, while a great location puts you right on the warm waters of Estero Bay. The...
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    Estero, Southwest Gulf Coast 33931
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Shared Outdoor Pool (Unheated)
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Be one of the first guests to enjoy the luxury and distinctive design of this BRAND NEW Creekside Preserve Carriage Home! No detail has been overlooked in the decor of this beautiful 1,600 sq ft 3 bedroom, 2 bath home that sleeps 8. Property Details: Meticulously decorated in a fresh, modern style...
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    Estero, Southwest Gulf Coast 33908
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Cozy Condo Bask in the balmy Florida weather on the lanai of this cozy condo in Fort Myers, where you can sip your morning coffee overlooking the lake or spot a bird or two sunning on its perch. Enjoy such on-site perks as a shared swimming pool and fitness center, and take morning walks or jogs...
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    Estero, Southwest Gulf Coast 33908
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Serene & Attractive Pool Home Near Gulf Beaches1 / 26
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • 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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    Location Information
    Estero, Southwest Gulf Coast 33928
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1 Bedroom, 3 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • 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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    Estero, Southwest Gulf Coast 33913
    Private Room - 1 Bedroom, 3 Bathrooms, Sleeps 4
    Paradise in Bella Terra - Amazing Vacation Condo!1 / 34
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Hot Tub
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 June 2018
    We had an amazing visit to Florida, and a good part of our comfort and enjoyment was due to our stay in this wonderful condo! The beds were very comfortable, and the neighbors...
    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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    Location Information
    Estero, Southwest Gulf Coast 33928
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Cable/satellite TV
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • Terrace
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book your Gulf Coast getaway to this luxurious 1-bed, 1-bath vacation rental condo inside the Lovers Key Resort! This quaint unit offers 4 beachgoers a newly furnished interior with hardwood flooring, modern decor, private balcony with tropical views, and access to all of the top-notch community...
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    Location Information
    Estero, Southwest Gulf Coast 33931
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    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
    • Cable/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
    Stoneybrook Golf Course1 / 14
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Hot Tub
    • DVD Player
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    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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    Estero, Southwest Gulf Coast 33928
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    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
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    2BR/2BA+DEN - Largest carriage model in Spring Run, AVAILABLE NOW Lovely 2nd floor spacious Cormorant with looming vaulted ceilings & open floor plan. Relax in peaceful tranquility nestled by the preserves with the 12th fairway/lake to the N-E. Play golf at Spring Run, you'll be a member for...
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    Location Information
    Estero, Southwest Gulf Coast 34135
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    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
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Seasonal Vacation Rental in Estero, FL. - $4,500 Monthly Pelican Sound located in Estero Florida is a gorgeous community perfectly located between Naples to the south, and Fort Myers to the north. You will love being close to everything from great shopping and dining to being only minutes to the...
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    Location Information
    Estero, Southwest Gulf Coast 33928
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Balcony
    • Terrace
    • Patio
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Offering a luxurious, well decorated Spring Run condo with water and golf course western views in gated community. Beautiful Par 72 Audobon certified course.Well equipped kitchen with new appliances. First floor, no steps. Large lanai with sliding doors. The master bedroom has beautiful views, a...
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    Estero, Southwest Gulf Coast 34135
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
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    • Hot Tub
    • Children's Pool
    Suitability
    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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    Location Information
    Estero, Southwest Gulf Coast 33928
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Patio
    • Washer
    • Private Outdoor Pool (Unheated)
    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 4 Quick View
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    Smoking allowed
    About this property
    This gorgeous townhouse is sure to be the perfect place for your stay. Welcoming, friendly and relaxed, this wonderful property with panoramic golf course views will have you thinking about extending your stay indefinitely. This spacious home has upgraded tile in the open areas and lush carpet in...
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    Estero, Southwest Gulf Coast 34135
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    **Note: currently accepting only 4-month or longer rental applications... Will accept 3-month rental applications as of 10/1/2018** Miromar Lakes, FL -- voted the #1 Residential Community in the entire United States for 2011, 2014 Silver award One of the best views in Miromar Lakes. This 3...
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    Location Information
    Estero, Southwest Gulf Coast 33913
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Private Garden
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    About this property
    Fully furnished and equipped seasonal rental townhouse 3 bedroom plus den and 2 1/2 bath townhome in secure gated community close to beaches and around the corner from major shopping, restaurants, etc. Community pool and amenities. Community application, and security deposit required. Across...
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    Estero, Southwest Gulf Coast 33967
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Secure Parking
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    • Private Outdoor Pool (Heated)
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 bedroom, 3 bath, 2 car garage villa home with screened in pool in Wildcat Country Club- an amazing golf course- Arnold Palmer's signature course. Newly furnished in last 3 yrs. 3 flat screens, internet and cable. Kitchen fully appointed as is house with towels and bed linens. Set on lake with...
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    Estero, Southwest Gulf Coast 33928
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    Happiness will be found here! YOUR DREAM PRIVATE 5,259 Sq. Ft VACATION Villa IN THE HEART OF ESTERO FLORIDA!!! Located in the heart of Estero between Naples and Fort Myers, just minutes away from Coconut Mall, Multiple High End Restaurants, Miramar Outlets, SWFL International Airport, Barefoot...
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    Estero, Southwest Gulf Coast 33928
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Smoking allowed
    About this property
    An unforgettable stay in the Sunshine state awaits at this 4-bedroom, 3-bathroom vacation rental home in Estero. Located in the acclaimed Corkscrew community, this newly updated Smart home offers access to a slew of resort amenities including a pool, hot tub, and on-site dining. The property is...
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    Estero, Southwest Gulf Coast 33928
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    23640 Walden Center Drive, unit 201, Bonita Spring, Florida, USA - 2 Bedrooms, 2 bath, 1,200 Sf, 2nd floor unit, (staircase) satTV, Internet, Dishwasher/Dryer, Large pool, Walking distance to Coconut Mall, one of the biggest malls in USA, fine dining and shopping, 15 minutes drive to beaches, must...
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    Location Information
    Estero, Southwest Gulf Coast 34134
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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