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St. Petersburg Luxury Holiday Homes

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    Travellers to St. Petersburg are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    26 Matching Rentals in St. PetersburgView all 174 rentals
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Tierra Verde Waterfront Mansion1 / 35
    (3)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • DVD Player
    • Washer
    • Ocean Views
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kick off your shoes, relax by the pool and enjoy the stunning views from the private sandy beach and our little piece of heaven!. We’re located within the St Petersburg/Gulfport region, only 5 minutes from St Pete Beach and just 25 minutes away from Tampa Bay International Airport, 15 minutes from...
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    St. Petersburg, Florida 33711
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    St.Petersburg Waterfront Mansion/ Wedding Venue/ Vacation 8 bedroom/7 bath1 / 46
    (33)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 21 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Patio
    • Private Outdoor Pool (Heated)
    • Washer
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 March 2018
    The Petro Mansion was a great place to stay for my large gathering of friends seeking a warm weather getaway. The house is very spacious and could easily accommodate our group...
    Reviewed 16 March 2018
    The Picture alone sold me and when we arrived we were NOT disappointed. It was amazing !! Beautiful home perfect for a large family we had 17 of us from 1 to 65 teens included...
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    About this property
    The Petro Waterfront Mansion is the largest private waterfront home in St. Petersburg that allows Intimate Weddings & private events of all kinds! IF YOUR EVENT OR STAY REQUIRES 7 OR MORE NIGHTS KINDLY ASK ME FOR A DISCOUNT! I WILL BE HAPPY TO DISCOUNT THE PUBLISHED RATE THAT SHOWS UP ON THIS...
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    St. Petersburg, Florida 33705
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 21
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    5 Bedrooms, 6 Bathrooms, Sleeps 15 Quick View
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    • Patio
    • Hot Tub
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    8000 SF, 5 BEDROOMS, 6 BATHS, GORGEOUS SECURED ESTATE WITH LARGE POOL DECK The pictures speak for themselves, no other property in the area rivals this house for elegance, space and entertainment. Perfect for family reunions, corporate retreats, local events, the house features a gorgeous pool...
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    St. Petersburg, Florida 33701
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 15
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are looking for a unique vacation stay on a Cruise Ready Luxurious Yacht with the most living space available……you are looking at the right boat located in PARADISE! This spacious designer power yacht is appointed w/innovative hand crafted interior design elements is compelling. The...
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    St. Petersburg, Florida 33706
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    B & B's Winter Getaway1 / 17
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
    • Internet Access
    • Patio
    • Hot Tub
    • Grill
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 December 2016
    The rental was perfect for us to entertain our parents and grown children over the week of Thanksgiving. Plenty of cozy places in the home to gather and have morning coffee or a...
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    About this property
    B & B’s getaway has the charm of old with convenience of new. You will feel at home here. Great location for events at the Mahaffey Theater, Tropicana Field, St. Pete Sailing Centre and more. Featuring lots of comfortable living space it is just around the corner is the lovely Crescent Lake Park in...
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    St. Petersburg, Florida 33701
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Central Heating
    • Ocean Views
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tiny Home with a loft bedroom will be dropped off and picked up at either Fort Desoto camp grounds or Bay Pines Marina KOA. Experience a tiny home in a camping environment. Enjoy paddle boarding, relaxing in a hammock and beautiful beach views or with the convenience of family friendly amenities....
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    Location Information
    St. Petersburg, Florida 33713
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Waterfront
    • Washer
    • Central Heating
    • DVD Player
    • Hot Tub
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to The Seahorse! A beautiful open-water home in the popular and quiet Arrowhead Estates neighborhood in St. Petersburg, FL -- minutes from downtown St. Petersburg, restaurants, museums, and the beaches. The property views the Weedon Island preserve and the famous 'shallow spot' where boats...
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    Location Information
    St. Petersburg, Florida 33703
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Luxury house in Downtown St Petersburg1 / 6
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 March 2018
    The place was very nice, a coworker and I were in town for work and the place was simple but had everything we needed. Within walking distance of downtown and a lot of nice...
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    About this property
    Designed with the flow and functionality of a five star boutique hotel. Soaring ceilings, massive kitchen and Luxury bathrooms. The 1st floor unit is over 1,300sqft and features a massive living area with a Grand kitchen featuring an enormous kitchen island carved from a single over sized slab of...
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    Location Information
    St. Petersburg, Florida 33705
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Internet Access
    • Patio
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely remodeled 3024 sq ft, 4 bedroom 3 bath pool house. New appliances with granite counter tops. Fully furnished with pillow top beds. Bella Vista offers a screened pool with patio, large yard, and is just a 10 min walk to the beach, restaurants & stores. Located in a quiet neighborhood and...
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    Location Information
    St. Petersburg, Florida 33706
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Jungle Shores House1 / 63
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Wi-Fi
    • Patio
    • DVD Player
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 March 2016
    We stayed at Jungle shores, St Petersburg, FL , 2/21/2016 to 2/27/2016 . When we arrived and went in it was amazing , everything we imagined and more . The property had a...
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    About this property
    Just a few minutes drive over to Treasure Island, this stunning executive bay-front home will have you relaxing in style! The home is situated in an exclusive neighborhood of St. Petersburg, just a short drive over the Treasure Island causeway to the beaches. The back yard is the Boca Ciega Bay,...
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    Location Information
    St. Petersburg, Florida 33710
    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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    • Patio
    • Porch
    • Internet Access
    • Cable/satellite TV
    • Grill
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in 2004, this gorgeous 3BR, 2.5BA has beautiful, quality upgrades throughout. Enjoy all of the modern conveniences a newer home provides: cathedral ceilings, arched doorways, hardwood floors, large master bed & bath, kitchen & family room combination, formal living & dining rooms, split...
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    St. Petersburg, Florida 33711
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Patio
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home was built in 1926 by Thomas Rowe, the developer of the famous Don Cesar Beachfront Hotel located on one of the most beautiful beaches on the west coast of Florida. This very exclusive to St. Pete Beach home offers 2 stories and plenty of nooks and crannies ordinary to an Historic Home....
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    Location Information
    St. Petersburg, Florida 33706
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *TeemingVR presents Vista Verde North 6115 or VVN6115 in Isla Del Sol* *All reservations must fall within a Sat-Sat window. Please note that this property requires paperwork to be completed 14 days prior to arrival. if less than 7 days from arrival please call us to rush the application.* If you...
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    Location Information
    St. Petersburg, Florida 33715
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Wi-Fi
    • Patio
    • DVD Player
    • Grill
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get ready for fun in the sun at this 3BR home - called 'The Castaway' - that boasts a fenced yard with a sparkling pool and waterfall. Belly up to the tiki bar with outdoor 22” flat screen TV and grab a cold beverage. The paver patio has plenty of lounge chairs for relaxing. There’s lots of fun...
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    Location Information
    St. Petersburg, Florida 33710
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Balcony
    • Grill
    • Central Heating
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This two bedroom 2 bath condo its the perfect place to relax and enjoy the magnificent water views from the balcony. The master bedroom has a queen sizes bed and a bathroom with a shower. The second bedroom has two twin sizes beds and there is a guess full bathroom with a tub. Upgraded kitchen with...
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    Location Information
    St. Petersburg, Florida 33705
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It's a 2016 Airstream International Signature. We rent it to residents of the Tampa Bay area for their short-term overnight visitors. It is fully appointed with a premium queen bed, linens, pillows and towels as well as a TV, bathroom, digital thermostat, refrigerator and microwave. Of course there...
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    Location Information
    St. Petersburg, Florida 33703
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Parking
    • Ocean Views
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Waterfront
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious 36ft yacht is right in the heart of thriving St Petersburg! 40in TV (HDMI ports to plug in devices - waiting on Satellite TV installation,) A/C, refrigerator / freezer, WiFi, microwave, oven, stove, and more! Sailing is available upon request and availability, Our 36ft sailing...
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    Location Information
    St. Petersburg, Florida 33701
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Washer
    • Terrace
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Plan your next coastal getaway to this recently remodeled 3-bedroom, 2-bathroom vacation rental house in Shore Acres! This charming 1,500-square-foot abode offers a gourmet kitchen with stainless steel appliances, granite countertops, a front porch, and a backyard with a picnic table. Catch...
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    Location Information
    St. Petersburg, Florida 33703
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This two bedroom guest house is in a great location in the old northeast just 3 blocks from the Vinoy Hotel and the vibrant downtown with its restaurants, museums and night life. Short walk to the waterfront. Just blocks to Vinoy Park where so many special events are held. One private parking space...
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    Location Information
    St. Petersburg, Florida 33701
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Gulfport Arts District is known for its offbeat casual vibe. Celebrating diversity and community, it is a rare bird for the state of Florida. This charming 1925 Spanish Bungalow has been restored to its original sparkle- chispa. with a queen bed, two singles and a sofa bed, and the cutest gas...
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    Location Information
    St. Petersburg, Florida 33705
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 2400 sq ft. home located in the charming Broadwater community in south St. Pete just minutes from everything. House has just completed total renovation to totally new condition. New porcelain tile and carpet floors, new entertainment kitchen with stainless appliances and granite counter...
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    St. Petersburg, Florida 33711
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our 1920’s apartment is located in the quiet, historic Old Northeast neighborhood of downtown St. Pete. The apartment is part of a historical triplex and has just been remodeled featuring a new bathroom and kitchen. You enter the apartment building with your private keyless electronic door lock...
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    Location Information
    St. Petersburg, Florida 33704
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    House w/Pool & Hot Tub, 15 Mins to St. Pete Beach!1 / 25
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 weeks ago
    A very comfortable clean place that became our home for 5 days. Walking distance to Tropicana Field and close to many food places. Convenient to stay without a rental car...
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    About this property
    Experience a rejuvenating Florida retreat without ever leaving this 3-bedroom, 2-bathroom St. Petersburg vacation rental house, featuring a luxurious in-ground pool, hot tub, and furnished screened-in porch! Additionally, this newly renovated home, brimming with essential amenities, provides up to...
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    Location Information
    St. Petersburg, Florida 33713
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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