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Holiday Rentals in Gulfport

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    Travellers to Gulfport are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 26 Rentals in Gulfport
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    A little piece of PARADISE1 / 20
    (6)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Blue Arbor Guest Cottage1 / 15
    (26)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    The Lovely Guesthouse1 / 17
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    NEW - Desirable Art District1 / 40
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Porch
    • Grill
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 2017
    Thank you so much for the perfect house/cottage in beautiful downtown Gulfport. The house/cottage was super clean and cozy. Plenty of air conditioners. Everything we needed was...
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    About this property
    Completely Renovated and new to the rental market! This home has all new furniture and appliances throughout! There's plenty of living space - between two furnished seating areas outside, a large living room and an extra bonus room separated by french doors (makes for the perfect reading spot or...
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    Gulfport, Florida 33707
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Beach House with Fabulous View1 / 33
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Reviewed 9 July 2018
    We had an amazing time the view is incredible. Coffee in the morning and adult beverages in the evening as we were sharing stories. The accommodations and hospitality was...
    Reviewed 26 March 2018
    Everything was perfect! The place, the host & the view! I loved the restaurants that were especially on the same block! Will def visit again!! - One of the pics during sunset!
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    About this property
    Prime Location With Fabulous Beach View! Wonderful beach rental in beautiful building. Huge private wrap-around covered balcony. Enjoy the entire top level with incredible view of Gulfport Beach. This comfortable unit is perfect for couples, business travelers and families. Even pets are...
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    Gulfport, Florida 33707
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Dolphin House at Gulfport's Pier1 / 19
    (10)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
    • Porch
    • Patio
    • Internet Access
    • Grill
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2017
    We had a lovely reunion, enhanced by the comfort and spaciousness of this charming cottage. It is nicely laid out, very clean with a well stocked kitchen. The beds were...
    Reviewed 10 September 2016
    We were only here for a short time but would surely go back again. The house is very well equipped. The kitchen, especially, better equipped than mine at home. This was a...
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    About this property
    We can’t explain why guests say they relax the minute they enter Dolphin House. Maybe it’s because the cheerful coastal vibe reminds them that they’ve finally made their escape to the beach. Or because comfortable furnishings and sun-filled spaces make this rental truly feel like home. Or because...
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    Gulfport, Florida 33707
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Flamingo Cottage: Romantic Tropical Retreat in Gulfport Waterfront District1 / 21
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Grill
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    • DVD Player
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2018
    Had a great stay at the Flamingo Cottage. It is located within walking distance to restaurants and shops. The cottage was clean, well decorated and the kitchen was fully stocked...
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    About this property
    From the moment you step into this cheerful, tropical 1BR, 1BA getaway, you’ll be whisked away from the hustle and bustle of the everyday. Leave chilly mornings and hum-drum afternoons behind for a romantic retreat in balmy Gulfport, where the charms of Old Florida meet world-class dining, art, and...
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    Location Information
    Gulfport, Florida 33707
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Palm Cottage:Vintage Tropical Hideaway in the Waterfront District1 / 25
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
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    • Porch
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    • Patio
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 February 2015
    Palm cottage is an older home with an excellent location, one block from the beach and 3 blocks from downtown. The beds were comfortable although one is only a double...
    Reviewed 29 July 2014
    We were very happy with our stay at Palm Cottage. The cottage was beautiful and filled all our needs. The kitchen was better equipped than mine at home. We were within a short...
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    About this property
    Sunny Palm Cottage, located in the first block from the beach, is an ideal location for any season whether you are looking for winter sun or a summer seaside escape. Relax in this clean, quiet and relaxing cottage in a convenient location. Just like the town of Gulfport itself, Palm Cottage...
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    Location Information
    Gulfport, Florida 33707
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Charming Gulfport Guest Cottage1 / 28
    (22)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Washer
    • Hot Tub
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    • Air Conditioning
    • Porch
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This gem in its quaint neighborhood is definitely like your home away from home. Relaxing, comfortable furnishings feel like your own little nest in Gulfport. You feel welcome...
    Reviewed 4 weeks ago
    Everything--from first contact with owner Daniel to our last day at the cottage--was fantastic. Peaceful, spotlessly clean, spacious home away from home for four wonderful...
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    About this property
    Welcome to Gulfport Guest Cottage, a cute and comfortable guest house in the quaint and quirky village of Gulfport, Florida. Imagine lovely old oaks covered in Spanish moss, brick-paved streets and cute little colorful cottages. Our Gulfport cottage is approximately 1000 square feet, and has two...
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    Location Information
    Gulfport, Florida 33707
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    The Sand Dollar: Historic Charm Meets Beach Chic in the Waterfront District1 / 12
    (1)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Cable/satellite TV
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    • Air Conditioning
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    • DVD Player
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Classic charm meets modern beach breeziness at The Sand Dollar, a chic, second-story 1BR/1.5BA apartment in the heart of Gulfport’s vibrant Waterfront District. With a parlor-style living space and private, tropical patio, there’s no shortage of spaces to relax. And you’ll do so in style:...
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    Gulfport, Florida 33707
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Resort Style Living1 / 15
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Private Outdoor Pool (Unheated)
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2018
    This home had the most beautiful view of the bay and high rises of St. Pete in the distance. We thoroughly enjoyed use of the dock and pool. Home is under renovations and the...
    Reviewed 8 July 2018
    This was our main house for entertaining family during our reunion. We had two other homes at the same time. This house had fantastic views, plentry of room inside and out...
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    About this property
    Resort style residence on Boca Ciega Bay with Southern facing view. Sunrise in the morning and sunset in the evening. Only two story on the North side of the Bay...views views views. Lounge by the pool or a 9 minute walk to the restaurants in downtown Gulfport. An elevator is available to the...
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    Location Information
    Gulfport, Florida 33711
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gulfport Waterfront Mid-Century Modern Masterpiece1 / 21
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Porch
    • Private Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 April 2017
    I would highly recommend Gulfport as a base in this part of Tampa Bay. I would consider it to be better than staying at the beaches themselves. I didn't know anything about it...
    Reviewed 12 April 2017
    Excellent home. Neighborhood is just ok but the back of the home facing the bay is beautiful. Would stay again!
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    About this property
    Take a break from your everyday routine and spend your vacation in this beautifully upgraded mid-century modern ranch in charming and unique Gulfport, FL. This property sleeps six people in its three bedrooms, and has two full baths, a nicely appointed, completely modern kitchen, and a laundry room...
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    Gulfport, Florida 39501
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beach Cottage, Old-Florida Style!1 / 5
    (1)Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
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    • DVD Player
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    • Patio
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 February 2014
    Location wonderful. Walk to everything. Pet friendly. Quiet. Furniture sparse and uncomfortable. Clean.
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    About this property
    Tyn & Marty's is the quintessential old-Florida summer cottage sited on a corner lot in Gulfport's Waterfront District. Lovely wood floors in the living area, bedrooms and hallway. Tile floor in the bath. Large windows with blinds in the living room and bedrooms to let as much (or as little!) sun...
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    Gulfport, Florida 33707
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Harbor Mist: Fresh & Friendly in Marina District + Private Outdoor Oasis1 / 14
    (3)Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2016
    Once again, Harbor Mist was the perfect place for a relaxing getaway! The house was perfect- very clean and had everything you could need or want. Quiet neighborhood close to...
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    About this property
    Bright, clean, and thoughtfully appointed, Harbor Mist brings new meaning to home-away-from-home. This Gulfport gem is tucked in one of the town’s friendliest neighborhoods—home to smiling locals who gather and relax at the marina just down the street. Bring your pup along and you’re both...
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    Gulfport, Florida 33711
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Washer
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a newly renovated two story townhouse located in the Exclusive Bermuda Bay Racquet Club - a Lush 12 acre Secure Gated Community on the edge of Boca Ceiga Bay close To Gulf Of Mexico`s Finest Beaches. A Private Beach In The Club, 2 Heated Pools, Hot Tub, Racquetball & Tennis Courts, Putting...
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    Gulfport, Florida 33711
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Enjoy a stay in our newly renovated 1925 historical 2-beroom 2-bathroom beach house with beautiful views to the Boca Ciega Bay in the quaint coastal community of Gulfport / St Petersburg, Florida. Stay in our fully furnished 2-bedroom / 2-bathroom house and enjoy the charming town of Gulfport,...
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    Gulfport, Florida 33707
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This charming classic Cape Cod style home with an oversize fenced yard is waiting for you and your family. Located in the heart of the quaint town of Gulfport, you can walk to the beach or to the Arts district, with a Farmers Market, live music, picnics, volleyball, and fun cool gift shops. Six...
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    Gulfport, Florida 00000
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Recently renovated, large one bedroom, second floor condo with great shady treetop garden views. Steps away from the most amazing Boca Ciega Bay Sunsets! This gated community on the bay has it all... 2 pools, hot tub, putting green, tennis courts, racquetball, shuffle board, picnic areas, and...
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    Gulfport, Florida 33711
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
    About this property
    Unwind amidst lush tropical greenery at Fish Camp, a charming 1BR/1BA ideal for your next sweethearts’ getaway. Soak up Florida sunshine, or curl up with a good book and a glass of lemonade. Stroll around Gulfport and visit local art galleries and restaurants, or plan a day in the waves of Boca...
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    Gulfport, Florida 33707
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    This is a single family home with three bedrooms and two bathrooms that has a split floor plan. This house has two living spaces as well as a dining room. A brand new kitchen with stainless steel appliances and granite counter tops. Refrigerator has an ice maker and kitchen has a small dishwasher....
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    Gulfport, Florida 33707
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New listing! Make yourself at home in a comfy retro 50's bungalow. Bright and spacious two bedroom with queen beds and a great set up for entertaining. Well appointed eat-in kitchen adjacent to full size dining room, with a large private covered deck outside. Kick back after your day at beautiful...
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    Gulfport, Florida 33707
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Relaxation is easy at this 2BR/2BA cottage—affectionately known as the Gulfport Beach House Getaway. Located on a charming brick lined street, there’s plenty of room for six guests. Enjoy a private patio and wooden decks, complete with a gas grill, open-air dining, and swaying hammocks. The...
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    Gulfport, Florida 33707
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    With the beach 2 blocks from your door and downtown Gulfport galleries and boutiques a quick stroll away, this bright and beachy 3BR/2BA home promises a memorable Florida vacation. New upgrades include a modern kitchen and beautifully tiled baths, plus a custom wood-paneled wall in the master...
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    Gulfport, Florida 33707
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Housekeeping Included
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax poolside by Boca Ciega Bay in the secure and friendly gated community of Bermuda Bay. This main floor unit with new laminate wood flooring means no stairs to contend with. Freshly painted, with a gourmet kitchen, eats & sleeps up to 4 people comfortably. Why go elsewhere when you can have...
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    Gulfport, Florida 33711
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great set-up for families or couples traveling together. Two bedrooms are in the front of the house, along with the larger of the two bathrooms. The master has the King Sleep Number bed. The second bedroom has a bunk/full/trundle bed set up, idea for kids or singles or one couple. The...
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    Gulfport, Florida 33707
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    This adorable 2BR/1BA bungalow is steps from the beach, the fishing pier, and all of Gulfport's unique shops and eateries. Relax on your private back patio with homemade cocktails or lemonade before heading out to the local dance hall. Gulfport Municipal Marina is 8 blocks from your door — take...
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    Gulfport, Florida 33707
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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